EP0470177A1 - Fungicidal oxime carbamates - Google Patents
Fungicidal oxime carbamatesInfo
- Publication number
- EP0470177A1 EP0470177A1 EP90907790A EP90907790A EP0470177A1 EP 0470177 A1 EP0470177 A1 EP 0470177A1 EP 90907790 A EP90907790 A EP 90907790A EP 90907790 A EP90907790 A EP 90907790A EP 0470177 A1 EP0470177 A1 EP 0470177A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- substituted
- phenyl
- halogen
- alkyl
- dimethylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 oxime carbamates Chemical class 0.000 title claims description 76
- 230000000855 fungicidal effect Effects 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 241000233866 Fungi Species 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 94
- 150000002367 halogens Chemical group 0.000 claims description 94
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 69
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 61
- 239000007787 solid Substances 0.000 claims description 57
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 46
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 38
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 34
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 229910006095 SO2F Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- LAPHGNAXDKHTET-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] bis(2,2,2-trichloroethyl) phosphate Chemical compound CN(C)C(=O)C(Cl)=NOP(=O)(OCC(Cl)(Cl)Cl)OCC(Cl)(Cl)Cl LAPHGNAXDKHTET-UHFFFAOYSA-N 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- GYYAOFZHVGBHTI-UHFFFAOYSA-N [[1-chloro-2-(diethylamino)-2-oxoethylidene]amino] n-[(2-chlorophenyl)methyl]carbamate Chemical compound CCN(CC)C(=O)C(Cl)=NOC(=O)NCC1=CC=CC=C1Cl GYYAOFZHVGBHTI-UHFFFAOYSA-N 0.000 claims description 2
- BVIUYPWPAXRMDC-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] 4-phenylbenzoate Chemical compound C1=CC(C(=O)ON=C(Cl)C(=O)N(C)C)=CC=C1C1=CC=CC=C1 BVIUYPWPAXRMDC-UHFFFAOYSA-N 0.000 claims description 2
- OCKNRGSXAUMTRT-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] carbonochloridate Chemical compound CN(C)C(=O)C(Cl)=NOC(Cl)=O OCKNRGSXAUMTRT-UHFFFAOYSA-N 0.000 claims description 2
- YYFAVLPXWFWRAI-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] n-(2,4,5-trichlorophenyl)carbamate Chemical compound CN(C)C(=O)C(Cl)=NOC(=O)NC1=CC(Cl)=C(Cl)C=C1Cl YYFAVLPXWFWRAI-UHFFFAOYSA-N 0.000 claims description 2
- WUVGCPREYYWXQD-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] n-(2,6-dichlorophenyl)carbamate Chemical compound CN(C)C(=O)C(Cl)=NOC(=O)NC1=C(Cl)C=CC=C1Cl WUVGCPREYYWXQD-UHFFFAOYSA-N 0.000 claims description 2
- JTKZBDULMZPPNE-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] n-[3,5-bis(trifluoromethyl)phenyl]carbamate Chemical compound CN(C)C(=O)C(Cl)=NOC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JTKZBDULMZPPNE-UHFFFAOYSA-N 0.000 claims description 2
- ZFEUWZCHSBKPNK-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)ON=C(Cl)C(=O)N(C)C ZFEUWZCHSBKPNK-UHFFFAOYSA-N 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- OFIYXBCPTNPIKP-UHFFFAOYSA-N benzyl [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] carbonate Chemical compound CN(C)C(=O)C(Cl)=NOC(=O)OCC1=CC=CC=C1 OFIYXBCPTNPIKP-UHFFFAOYSA-N 0.000 claims description 2
- 229910005948 SO2Cl Inorganic materials 0.000 claims 1
- FGXMSMGLWRYQOX-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] n-(3,5-dichlorophenyl)carbamate Chemical compound CN(C)C(=O)C(Cl)=NOC(=O)NC1=CC(Cl)=CC(Cl)=C1 FGXMSMGLWRYQOX-UHFFFAOYSA-N 0.000 claims 1
- ALKQRVIHQQTFSW-UHFFFAOYSA-N [[1-chloro-2-(dimethylamino)-2-oxoethylidene]amino] naphthalene-2-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)ON=C(Cl)C(=O)N(C)C)=CC=C21 ALKQRVIHQQTFSW-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 28
- 239000000725 suspension Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- XREBYUVOZCUOES-UHFFFAOYSA-N 2-(dimethylamino)-n-hydroxy-2-oxoethanimidoyl chloride Chemical compound CN(C)C(=O)C(Cl)=NO XREBYUVOZCUOES-UHFFFAOYSA-N 0.000 description 14
- 239000012298 atmosphere Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000003828 vacuum filtration Methods 0.000 description 11
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000012677 causal agent Substances 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000008213 purified water Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 150000005846 sugar alcohols Polymers 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- TZUYFNORLRBWLP-UHFFFAOYSA-N ethanimidoyl chloride Chemical compound CC(Cl)=N TZUYFNORLRBWLP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 6
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000002923 oximes Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 2
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- WPQCGHSYJYAFEL-UHFFFAOYSA-N 2-(dimethylamino)-2-oxoethanimidoyl chloride Chemical compound CN(C)C(=O)C(Cl)=N WPQCGHSYJYAFEL-UHFFFAOYSA-N 0.000 description 2
- OFNRXVWPXRJPOR-UHFFFAOYSA-N 2-oxoethanimidoyl chloride Chemical compound ClC(=N)C=O OFNRXVWPXRJPOR-UHFFFAOYSA-N 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- 241000530549 Cercospora beticola Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical group ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
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- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
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- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
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- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
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- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
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- 230000001376 precipitating effect Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
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- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
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- 239000004546 suspension concentrate Substances 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
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- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 239000011031 topaz Substances 0.000 description 1
- 229910052853 topaz Inorganic materials 0.000 description 1
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
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Classifications
-
- 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
- C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- 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
-
- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Definitions
- Hubele CH 66-16,259 claims compounds of Formula ii as fungicides for crop protection.
- EP 293 667 A as fungicides for crop protection.
- fungus comprising the application of an effective amount of a compound of Formula I to the locus to be protected.
- Q and Q 1 are independently oxygen, NR 8 or a
- X is C1 or Br; provided that when X is Br, A is
- L is O or S
- n 0, 1 or 2;
- R is C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, or C 3 -C 7 cycloalkyl, each
- halogen optionally substituted with halogen, C 1 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl, C 1 -C 6 alkylthio, C 3 -C 6 cycloalkyl, CN, or with a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy, provided that when A is
- R is not C 2 alkenyl or C 2 alkynyl; R is a phenyl ring or a C 10 -C 14 fused
- SO 2 NR 14 R 15 2-, 3-, or 4-pyridyl, or phenyl substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino or amino;
- R can additionally be a heterocyclic ring
- R can additionally be a heteroaromatic or fused heteroaromatic ring system, ring-carbonlinked to the carbonyl group when A is
- heteroatoms comprise 1-3 nitrogen atoms, or 1-2 nitrogen atoms and one oxygen or sulfur atom, or 1-2 oxygen or sulfur atoms, these rings being substituted with 0-1
- R 1 is C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 3 -C 20
- alkynyl or C 1 -C 8 alkyl, C 3 -C 8 alkenyl or
- alkoxyalkyl C 1 -C 6 alkylthio, C 3 -C 6
- cycloalkyl CN or with a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy; provided that, if R 1 is alkenyl or alkynyl, the unsaturated carbons are not bonded directly to the oxygen atom of
- R 2 and R 3 are independently selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, benzyl or phenyl; R 4 is H or C 1 -C 4 alkyl;
- R 5 is C 1 -C 4 alkyl substituted with 0-3 halogen, or R 5 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 ,
- R 6 is H, C 1 -C 4 alkyl substituted with 0-3
- halogen or R6 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
- R 7 is H or C 1 -C 4 alkyl substituted with 0-3
- halogen or R 6 and R 7 taken together with the nitrogen atom to which they are attached can be piperidine, pyrrolidine or
- R 8 is H or C 1 -C 4 alkyl
- R 9 is C 1 -C 8 alkyl substituted with 0-3 halogen, or R 9 is phenyl substituted with 0-2
- R 10 and R 11 are independently H, C 1 -C 4 alkyl
- R 12 is C 1 -C 12 alkyl or haloalkyl, or benzyl substituted with 0-2 halogen, CH 3 , C F3 , CH 3 O or CN;
- R 13 is C 1 -C 4 alkyl, haloalkyl or C 2 -C 4
- alkoxyalkyl C 3 -C 4 alkenyl, haloalkenyl. alkynyl or haloalkynyl, or benzyl or phenyl, said benzyl or phenyl rings being
- R 14 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or
- R 15 is H or C 1 -C 4 alkyl
- R 16 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, or benzyl substituted with 0-2 halogen, methyl, trifluoromethyl, nitro or methoxy; and p is 1 or 2.
- Q and Q 1 are independently oxygen, NR 8 or a
- L is O or S
- n 0, 1 or 2;
- R is C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20
- alkynyl ⁇ 3 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, or C 3 -C 7 cycloalkyl, each optionally substituted with halogen, C 1 -C 6 alkoxy, C 2 -C 6 alkoxyalkyl, C 1 -C 6 alkylthio, C 3 -C 6 cycloalkyl, CN, or with a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy, provided that when A is
- R is not C 2 alkenyl or C 2 alkynyl
- R is a phenyl ring or a C 10 -C 14 fused
- carbocyclic aromatic ring systems wherein said rings are substituted with 0-4 halogen, and 0-1 groups selected from -CH 2 (CH 2 ) p CH 2 -, -O(CH 2 ) p CH 2 -, -S(CH 2 ) p CH 2 -, -O(CH 2 ) p O,
- SO 2 NR 14 R 15 2-, 3-, or 4-pyridyl, or phenyl substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino or amino;
- R can additionally be a heterocyclic ring
- heteroatoms comprise 1-3 nitrogen atoms, or 1-2 nitrogen atoms and one oxygen or sulfur atom, or 1-2 oxygen or sulfur atoms, these rings being substituted with 0-1
- R 1 is C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 3 -C 20
- alkynyl or C 1 -C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, each optionally substituted with halogen, C 1 -C 6 alkoxy, C 2 -C 6
- alkoxyalkyl C 1 -C 6 alkylthio, C 3 -C 6
- cycloalkyl CN or with a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy; provided that, if R 1 is alkenyl or alkynyl, the unsaturated carbons are not bonded directly to the oxygen atom of
- R 2 and R 3 are independently selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, benzyl or phenyl;
- R 4 is H or C 1 -C 4 alkyl
- R 5 is C 1 -C 4 alkyl substituted with 0-3 halogen, or R 5 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl,
- R 6 is H, C 1 -C 4 alkyl substituted with 0-3 halogen, or R6 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
- R 7 is H or C 1 -C 4 alkyl substituted with 0-3
- halogen or R 6 and R 7 taken together with the nitrogen atom to which they are attached can be piperidine, pyrrolidine or
- R 8 is H or C 1 -C 4 alkyl
- R 9 is C 1 -C 8 alkyl substituted with 0-3 halogen, or R 9 is phenyl substituted with 0-2
- R 10 and R 11 are independently H, CJL-C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, or benzyl or phenyl, said benzyl or phenyl rings being substituted with 0-2 halogen, CH 3 , CF 3 , CH 3 O or CN; or R 10 and R 11 , taken together with the nitrogen atom to which they are attached, can be azetidine,
- R 12 is C 1 -C 12 alkyl or haloalkyl, or benzyl
- R 13 is C 1 -C 4 alkyl, haloalkyl or C 2 -C 4
- alkoxyalkyl C 3 -C 4 alkenyl, haloalkenyl, alkynyl or haloalkynyl, or benzyl or phenyl, said benzyl or phenyl rings being
- R 14 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or
- R 15 is H or C 1 -C 4 alkyl
- R 16 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, or benzyl substituted with 0-2 halogen, methyl, trifluoromethyl, nitro or methoxy; and p is 1 or 2;
- X is Cl. 3.
- R is C 1 -C 2 alkyl substituted with a phenyl
- phenyl group being substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
- R is a phenyl or naphthyl ring, substituted
- R 10 and R 11 are independently H, C 1 -C 4 alkyl, haloalkyl or benzyl substituted with 0-2 halogen, CH 3 , CF 3 , CH 3 O or CN; or R 10 and R 11 , taken together with the nitrogen atom to which they are attached, can be
- R is C 1 -C 2 alkyl substituted with a phenyl
- phenyl group being substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
- R is a substituted phenyl or naphthyl ring, wherein the substituent is selected from: 0-3 halogen and 0-2 CH 3 , CF 3 , CH 3 O, CN,
- X is Cl. Also particularly preferred for ease of
- R is C 1 -C 2 alkyl substituted with a phenyl
- phenyl group being substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
- R is a substituted phenyl or naphthyl ring
- substituent is selected from: 0-3 halogen and 0-2 CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy; and
- compositions of the above-described compounds comprising a fungicidally active amount of said compound and at least one of the following:
- surfactant solid diluent or liquid diluent.
- the compounds of Formula I can be prepared from compounds of Formula III and an appropriate
- electrophilic reagent of Formula II in an inert solvent with or without a base used either as a catalyst or acid scavenger Suitable solvents include polar aprotic solvents such as acetonitrile, dimethylformamide, or dimethylsulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone;
- hydrocarbons such as toluene or benzene
- halocarbons such as dichloromethane or chloroform.
- Appropriate bases include alkali metal alkoxides such as sodium methoxide or potassium tert-butoxide, inorganic bases such as sodium hydride or potassium carbonate, or tertiary amines such as triethylamine, pyridine, 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU), or triethylenediamine (DABCO).
- alkali metal alkoxides such as sodium methoxide or potassium tert-butoxide
- inorganic bases such as sodium hydride or potassium carbonate
- tertiary amines such as triethylamine, pyridine, 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU), or triethylenediamine (DABCO).
- temperature can vary between 0°C and 150° for periods of 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates.
- a novel method of preparation of compounds of Formula Ia-c comprises sequential preparation of the novel chloroformate Ig. by reaction of compounds of
- Compounds of Formula Id can be prepared from compounds of Formula III and a carboxylic acid Ilg in the presence of a coupling auxiliary reagent such as, but not limited to, N,N-dicyclohexyl carbodiimide (DCC) or 2,2'-dipyridyldisulfide (DPDS).
- a coupling auxiliary reagent such as, but not limited to, N,N-dicyclohexyl carbodiimide (DCC) or 2,2'-dipyridyldisulfide (DPDS).
- hydroximoyl chlorides or bromides of Formulas Ia, b, d, e, f can be prepared from the corresponding aldoximes of Formula IV with halogens (see H. Metzger, Heinrich Oximen, Houben-Weyl, Methoden der or ⁇ anische Chemie. E.
- Hydroximoyl chlorides of Formula lb and Id can be prepared by the reaction of nitro compounds of Formula Ih with two equivalents of an organic base such as triethylamine and two equivalents of a chloroforraate of Formula lIb or an acid chloride of Formula lId (see T. Shinizer, Y. Hayashi,
- Formula I can be prepared from the carboxamide or ketone compounds, respectively, of Formula I by methods described elsewhere (see S. Scheibye,
- the ⁇ -chloroaldoximes of Formula III can be prepared by treating amines of Formula V with sodium nitrite and hydrochloric acid (see G. S. Skinner, J. Am. Chem. Soc., 1924, 46,731).
- ⁇ -chloroaldoximes of Formula III can also be prepared from aldoximes of Formula VI by treatment with N-chlorosuccinimide (see K. E. Larsen and K. B. G. Torsell, Tetrahedron. 1984, 40, 2985) or
- Some ⁇ -haloaldoximes of Formula III may be prepared from amide oximes VII by treatment with sodium nitrite in hydrohalic acid solution (see M. Kocevar, S. Polanc, M. Sollner, M. Tisler and B. Vercek, Synth. Comm., 1988, 18, 1427).
- ⁇ -haloaldoximes of Formula III can be prepared from trihalomethyl compounds of Formula VIII by basic hydrolysis in the presence of hydroxylamine (see A. P. Kozikowski and M. Adamczyk, J. Org. Chem., 1983, 48, 366).
- the ⁇ -haloaldoximes of Formula III can be prepared by the reaction of nitrile N-oxides of
- nitrile N-oxides of Formula IX can be prepared by several methods well known in the chemical art (for a summary of methods, see T. Shimizu,
- carboxamide and carboxylic acid ester compounds of Formula III can be prepared by the procedures taught in the U.S. Patents 3,557,089,
- the thiocarboxamide compounds of Formula III can be prepared from the trihalothioacetamides of Formula XI which are obained from the haloimmonium chlorides of Formula XII. See W. Walter and K. -D. Bode, Angew. Chem. Infcernat. Edit., 1966, 5, 447 for a review of the syntheses of thiocarboxamides.
- the cyano compound of Formula III can be
- the ketone compounds of Formula III can be prepared from halomethyl ketones of Formula XIII by treatment with an alkyl nitrite and hydrochloric acid (see N. Levin and W. H. Hartung, Org. Synthesis, 1944, 21, 25).
- the ketone compounds of Formula III can also be prepared from halomethyl ketones of Formula XIII by treatment with dimethyl sulfide to afford compounds of Formula XIV. which are then treated with sodium nitrite and hydrochloric acid (see Y. Ofsuji,
- the ketone compounds of Formula III can be prepared from ⁇ -ketosulfoxides of Formula XV by treatment with sodium nitrite in hydrohalic acid solution (see Y. Otsuji, Y. Tsujii, A. Yoshida and E. Imoto, Bull. Chem. Soc. Japan, 1971, 44, 219).
- the ketone compounds of Formula III can also be prepared from compounds of Formula VI by treatment with chlorine gas (see G. Casnati and A. Ricca, Tet. Letters. 1967, 327 and Y. H. Chiang, J. Org. Chem., 1971, 36 , 2146).
- the thioalkyl and thioaryl compounds of Formula III can be prepared from dihaloformaldoxime XVI (see D. Chiarino, M. Napoletano and A. Sala, Synth. Comm., 1988, 18, 1171 and D. M. Vyas, Y. Chiang and
- the sulfonylcarbohydroximoyl chlorides of Formula III can be prepared from
- compounds of Formula I are O-substituted oximes which can be of either the syn or anti form.
- the scope of the specification referring to compounds of Formula I includes both stereoisomeric oxime forms either as a specific steroisomer, a mixture of stereoisomers, or as any reciprocal mixture ratio of the two
- N,N-dimethylf ⁇ rmamide was added 2-biphenylcarboxylic acid (3.42 g), followed by N,N'-dicyclohexy1- carbodiimide (3.56 g) .
- chlorothiolformate (2.23 g) was added to the solution at room temperature.
- the solution was cooled to 10°C, then triethylamine was added to the solution.
- the reaction was allowed to warm to room temperature.
- the oil was dissolved in BuCl ( ⁇ 100 mL), diluted to the cloud point with hexane, and restripped to an oil, which solidified to a light-orange solid under a nitrogen stream.
- the solid was dissolved in 100 mL of hot cyclohexane, and the supernatant decanted from a little insoluble oil; the oil was extracted with 25 mL of hot cyclohexane, and the combined, hot, turbid extracts treated with MgSO 4 (6 g) to soak up some of the oil present, and filtered.
- the above was prepared by dissolving 23.7 mL of piperidine in 100 mL H 2 O. After cooling to 3°C, diketene was added dropwise over 10 minutes, causing an exotherm to 32°C. The mixture was stirred while cooling to 5°C for 10 minutes. 16.6 g of sodium nitrite was added in three portions, keeping the temperature less than 10°C whereupon the mixture was stirred for 30 minutes. Under a nitrogen blanket, 21 mL of concentrated HCI was added portionwise over 10 minutes, keeping the temperature ⁇ 35°C. After all of the acid had been added, the suspension was cooled to2°C and stirred at that temperature for 45 minutes. Vacuum filtration, followed by a cold water wash yielded an off-white solid which was partially dried by filtration suction. The material was used without further characterization in the above step.
- W-Z-A 1 of (Ii) is the same as A of (I).
- the compounds of this invention will generally be used in formulation with a liquid or solid diluent or with an organic solvent.
- Useful formulations of the compounds of Formula I can be prepared in
- formulations can be extended in suitable media and used at spray volumes of from about one to several hundred liters per hectare. High strength
- compositions are primarily used as intermediates for further formulation.
- the formulations broadly,
- surfactant(s) and b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following
- compositions Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are
- Emulsifiers Annual MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection
- compositions are well known. Solutions are prepared by simply mixing the ingredients . Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Water dispersible granules may be produced by agglomerating a fine powder composition (see, for example, B. Cross and H. Scher, "Pesticide Formulations", ACS Symposium Series 371, American Chemical Society, Washington, D. C, 1988, pp.
- Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084).
- Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning,
- the ingredients are blended, hammermilled, re-blended and packaged.
- the ingredients are blended and ground in a hammermill to produce a high strength
- the ingredients are combined and stirred to produce a solution, which can be used for low volume applications.
- the compounds of this invention are useful as plant disease control agents. They provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete. Ascomycete and
- Oomvcete classes are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal and fruit crops. These pathogens include, Plasmopora viticola. Phytophthora infestans, Peronospora
- the compounds of this invention can be mixed with fungicides, bactericides, acaricides,
- nei ⁇ aticides nei ⁇ aticides, insecticides, or other biologically active compounds in order to achieve desired results with a minimum expenditure of time, effort and material.
- Suitable agents of this type are wel1-known to those skilled in the art. Some are listed below:
- pre-infection to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs.
- the compound may also be applied to the seed, to protect the seed and seedling.
- Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions.
- Foliage can normally be protected when treated at a rate of from less than 10 g/ha to 10,000 g/ha of active ingredient. Seed and seedlings can normally be protected when seed is treated at a rate of from .1 to 10 g per kilogram of seed.
- test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on apple seedlings. The following day the seedlings were inoculated with a spore suspension of Venturia inaequalis (the causal agent of apple scab) and incubated in a saturated atmosphere at 20°C for 24 hr, and then moved to a growth chamber at 22°C for 11 days, after which disease ratings were made.
- a spore suspension of Venturia inaequalis the causal agent of apple scab
- Example B The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on peanut seedlings.
- Trem 014 polyhydric alcohol esters
- test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 hr, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made.
- Puccinia recondita the causal agent of wheat leaf rust
- Example D The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on rice seedlings.
- Trem 014 polyhydric alcohol esters
- test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on tomato seedlings. The following day the seedlings were inoculated with a spore suspension of Phvtophthora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 hr, and then moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
- Phvtophthora infestans the causal agent of potato and tomato late blight
- Example F The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on grape seedlings.
- Trem 014 polyhydric alcohol esters
- the seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 hr, moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 hr, after which disease ratings were made.
- Plasmopara viticola the causal agent of grape downy mildew
- test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on cucumber
- Example H The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on sugar beet
- Example I The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 1000 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on tobacco seedlings. The following day the seedlings were inoculated with a spore suspension of Peronospora tabacina (the causal agent of tobacco blue mold) and incubated in a
- Example J The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on cucumber
- Pseudoperonospora cubensis the causal agent of cucumber downy mildew
- incubated in a saturated atmosphere at 20°C for 24 hr moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 hr, after which disease ratings were made.
- Results for Examples A to J are given in Table A, B, and/or C.
- Data in Tables A and C are the average of three replicates.
- Data in Table B are from a single replicate.
- a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control relative to the carrier sprayed controls).
- NT indicates that no test was performed.
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Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US34287689A | 1989-04-25 | 1989-04-25 | |
US342876 | 1989-04-25 | ||
US39826689A | 1989-08-24 | 1989-08-24 | |
US398266 | 1989-08-24 |
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EP90304388A Withdrawn EP0397345A1 (en) | 1989-04-25 | 1990-04-24 | Fungicidal oxime carbamates |
EP90907790A Withdrawn EP0470177A1 (en) | 1989-04-25 | 1990-04-24 | Fungicidal oxime carbamates |
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EP90304388A Withdrawn EP0397345A1 (en) | 1989-04-25 | 1990-04-24 | Fungicidal oxime carbamates |
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EP (2) | EP0397345A1 (ko) |
JP (1) | JPH04505015A (ko) |
KR (1) | KR920701138A (ko) |
CN (1) | CN1047279A (ko) |
AU (1) | AU5556390A (ko) |
BR (1) | BR9007330A (ko) |
HU (1) | HUT59903A (ko) |
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AU8432291A (en) * | 1990-08-16 | 1992-03-17 | E.I. Du Pont De Nemours And Company | Fungicidal sulfoneoxime esters |
MY110439A (en) * | 1991-02-07 | 1998-05-30 | Ishihara Sangyo Kaisha | N-phenylcarbamate compound, process for preparing the same and biocidal composition for control of harmful organisms |
WO1995004809A1 (fr) * | 1993-08-09 | 1995-02-16 | Firmenich S.A. | Procede de parfumage de textiles |
JP2779905B2 (ja) * | 1993-10-28 | 1998-07-23 | 純正化學株式会社 | 工業用抗菌剤及びこれを含有した工業用抗菌剤組成物 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH490004A (de) * | 1967-10-31 | 1970-05-15 | Agripat Sa | Schädlingsbekämpfungsmittel und seine Verwendung |
FR2097552A5 (ko) * | 1970-07-10 | 1972-03-03 | Roussel Uclaf | |
FR2327984A1 (fr) * | 1973-03-15 | 1977-05-13 | Roussel Uclaf | Nouveaux derives substitues de l'o chlore o isonitrose acetophenone, procede de preparation et application comme pesticides |
DE2621102A1 (de) * | 1976-05-10 | 1977-11-24 | Schering Ag | Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
US4278613A (en) * | 1978-08-28 | 1981-07-14 | Ciba-Geigy Corporation | Sulfur-containing oxime compounds, processes for producing them, and their use for protecting cultivated plants |
AT365410B (de) * | 1978-08-31 | 1982-01-11 | Ciba Geigy Ag | Mittel zum schutz von kulturpflanzen vor aggressi-ven herbiziden |
US4272453A (en) * | 1980-07-24 | 1981-06-09 | Morton-Norwich Products, Inc. | 1-Chloro-1-p-methoxybenzoylformaldoxime-N-methylcarbamate |
-
1990
- 1990-04-23 IL IL94170A patent/IL94170A0/xx unknown
- 1990-04-24 CN CN90104263A patent/CN1047279A/zh active Pending
- 1990-04-24 HU HU904362A patent/HUT59903A/hu unknown
- 1990-04-24 AU AU55563/90A patent/AU5556390A/en not_active Abandoned
- 1990-04-24 BR BR909007330A patent/BR9007330A/pt unknown
- 1990-04-24 EP EP90304388A patent/EP0397345A1/en not_active Withdrawn
- 1990-04-24 EP EP90907790A patent/EP0470177A1/en not_active Withdrawn
- 1990-04-24 WO PCT/US1990/002124 patent/WO1990012784A1/en not_active Application Discontinuation
- 1990-04-24 JP JP2507082A patent/JPH04505015A/ja active Pending
- 1990-04-24 KR KR1019910701440A patent/KR920701138A/ko not_active Application Discontinuation
Non-Patent Citations (1)
Title |
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See references of WO9012784A1 * |
Also Published As
Publication number | Publication date |
---|---|
CN1047279A (zh) | 1990-11-28 |
AU5556390A (en) | 1990-11-16 |
WO1990012784A1 (en) | 1990-11-01 |
HUT59903A (en) | 1992-07-28 |
JPH04505015A (ja) | 1992-09-03 |
EP0397345A1 (en) | 1990-11-14 |
IL94170A0 (en) | 1991-01-31 |
KR920701138A (ko) | 1992-08-11 |
HU904362D0 (en) | 1992-02-28 |
BR9007330A (pt) | 1992-04-28 |
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