JP2669933B2 - 殺節足動物性カルボキシアニリド類 - Google Patents
殺節足動物性カルボキシアニリド類Info
- Publication number
- JP2669933B2 JP2669933B2 JP4502714A JP50271492A JP2669933B2 JP 2669933 B2 JP2669933 B2 JP 2669933B2 JP 4502714 A JP4502714 A JP 4502714A JP 50271492 A JP50271492 A JP 50271492A JP 2669933 B2 JP2669933 B2 JP 2669933B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- group
- haloalkyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 238000000034 method Methods 0.000 claims abstract description 35
- 241000238421 Arthropoda Species 0.000 claims abstract description 10
- -1 substituted Chemical class 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 9
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000006456 halo alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 32
- 238000006243 chemical reaction Methods 0.000 description 95
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 241000607479 Yersinia pestis Species 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- POLDJTZEHXQPTJ-UHFFFAOYSA-N 7-chloro-4a-(4-chlorophenyl)-n-[4-(trifluoromethyl)phenyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)N1N=C2C3=CC=C(Cl)C=C3CC2(C=2C=CC(Cl)=CC=2)OC1 POLDJTZEHXQPTJ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 150000002465 imidoyl halides Chemical class 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000256244 Heliothis virescens Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 241001414662 Macrosteles fascifrons Species 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 241000237096 Smicrornis brevirostris Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 229960000583 acetic acid Drugs 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 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
- 239000000969 carrier Substances 0.000 description 3
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- 150000004681 metal hydrides Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- QAUYVAQZPBDDJU-UHFFFAOYSA-N 3,4-dihydrooxadiazine-2-carboxamide Chemical compound NC(=O)N1NCC=CO1 QAUYVAQZPBDDJU-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- 238000005054 agglomeration Methods 0.000 description 2
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- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 238000005991 sulfenylation reaction Methods 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 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
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- 125000004001 thioalkyl 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
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
- C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63243890A | 1990-12-21 | 1990-12-21 | |
| US632,438 | 1990-12-21 | ||
| US71440191A | 1991-06-11 | 1991-06-11 | |
| US714,401 | 1991-06-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06504777A JPH06504777A (ja) | 1994-06-02 |
| JP2669933B2 true JP2669933B2 (ja) | 1997-10-29 |
Family
ID=27091627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4502714A Expired - Fee Related JP2669933B2 (ja) | 1990-12-21 | 1991-12-17 | 殺節足動物性カルボキシアニリド類 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5462938A (en:Method) |
| EP (1) | EP0565574B1 (en:Method) |
| JP (1) | JP2669933B2 (en:Method) |
| KR (1) | KR0178062B1 (en:Method) |
| CN (1) | CN1034468C (en:Method) |
| AT (1) | ATE125801T1 (en:Method) |
| AU (1) | AU659121B2 (en:Method) |
| BG (1) | BG61264B1 (en:Method) |
| BR (1) | BR9107246A (en:Method) |
| CA (1) | CA2098612C (en:Method) |
| DE (3) | DE69111827T2 (en:Method) |
| ES (1) | ES2077392T3 (en:Method) |
| GR (1) | GR3017869T3 (en:Method) |
| HU (1) | HU213635B (en:Method) |
| IL (1) | IL100429A (en:Method) |
| MY (1) | MY111387A (en:Method) |
| NZ (1) | NZ241072A (en:Method) |
| RU (1) | RU2096409C1 (en:Method) |
| TR (1) | TR25739A (en:Method) |
| TW (1) | TW203045B (en:Method) |
| WO (1) | WO1992011249A1 (en:Method) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5462938A (en) * | 1990-12-21 | 1995-10-31 | Annus; Gary D. | Arthropodicidal oxadiazinyl, thiadiazinyl and triazinyl carboxanilides |
| EP0586551A1 (en) * | 1991-05-24 | 1994-03-16 | E.I. Du Pont De Nemours And Company | Arthropodicidal anilides |
| ES2127270T3 (es) * | 1992-03-26 | 1999-04-16 | Du Pont | Amidas artropodicidas. |
| WO1993022311A1 (en) * | 1992-04-27 | 1993-11-11 | E.I. Du Pont De Nemours And Company | Fungicidal 1,3,4-oxadiazines and 1,3,4-thiadiazines |
| US5602126A (en) * | 1993-11-22 | 1997-02-11 | E. I. Du Pont De Nemours And Company | Arthropodicidal anilides |
| JPH09507081A (ja) * | 1993-12-29 | 1997-07-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺節足動物性オキサジアジン−、チアジアジン−又はトリアジン−カルボキシアニリド類 |
| CN101007763B (zh) | 1994-04-20 | 2012-10-10 | 纳幕尔杜邦公司 | 用于制备噁二嗪的中间体 |
| CZ306096A3 (en) * | 1994-04-20 | 1997-03-12 | Du Pont | Preparation of arthropodous oxadiazines |
| DE4444865A1 (de) * | 1994-12-16 | 1996-06-20 | Bayer Ag | 1,3,4-Oxadiazin-Derivate |
| US5510505A (en) * | 1995-04-06 | 1996-04-23 | E. I. Du Pont De Nemours And Company | Arthopodicidal oxadiazine intermediate |
| CN1072212C (zh) * | 1995-05-17 | 2001-10-03 | 尤尼罗亚尔化学公司 | 杀虫的噁二嗪 |
| WO1996036618A1 (en) * | 1995-05-17 | 1996-11-21 | Uniroyal Chemical Company, Inc. | Pesticidal oxadiazines |
| DE69700781T2 (de) * | 1996-03-15 | 2000-06-08 | E.I. Du Pont De Nemours And Co., Wilmington | Insektizide mischungen |
| USH1950H1 (en) | 1996-08-05 | 2001-03-06 | E. I. Du Pont De Nemours And Company | Processes for preparing indeno[1,2-E][1,3,4]oxadiazine-dicarboxylates |
| CA2278429C (en) * | 1997-02-26 | 2006-07-25 | Uniroyal Chemical Company, Inc. | Pesticidal thiadiazines |
| US6011034A (en) * | 1998-02-12 | 2000-01-04 | Uniroyal Chemical Company, Inc. | Insecticidal dihydrooxadiazine compounds |
| ES2203437T3 (es) * | 1999-03-12 | 2004-04-16 | Basf Aktiengesellschaft | Composiciones insecticidas sinergicas. |
| SK286647B6 (sk) | 1999-03-12 | 2009-03-05 | Basf Aktiengesellschaft | Synergické insekticídne kompozície, spôsob ničenia hmyzu a spôsob ochrany rastlín pred zamorením a napadnutím hmyzom |
| US6492357B1 (en) * | 1999-09-14 | 2002-12-10 | Aventis Cropscience, S.A. | Compositions and methods for controlling insects which damage rice and other crops |
| DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| WO2001036381A1 (fr) * | 1999-11-15 | 2001-05-25 | Nissan Chemical Industries, Ltd. | Composes hydrazone et pesticides |
| DE60105402T2 (de) * | 2000-03-29 | 2005-09-22 | E.I. Du Pont De Nemours And Co., Wilmington | Arthropodische carboxanilide |
| DE10018370A1 (de) * | 2000-04-14 | 2001-10-18 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10043610A1 (de) * | 2000-09-05 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| JP4359433B2 (ja) * | 2001-05-21 | 2009-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 非芳香族複素環式環を含有するジアミド無脊椎有害動物抑制剤 |
| DK1401575T3 (da) | 2001-06-29 | 2007-03-19 | Du Pont | Hydroxylering af beta-dicarbonyler med zirconiumkatalysatorer |
| MX258385B (es) * | 2002-01-22 | 2008-07-02 | Du Pont | Quinazolina(di)onas para control de plagas de invertebrados. |
| DE10207241A1 (de) * | 2002-02-21 | 2003-09-04 | Bayer Cropscience Ag | Synergistische insektizide Mischungen |
| DE10248257A1 (de) * | 2002-10-16 | 2004-04-29 | Bayer Cropscience Ag | Wirkstoffkombinationen im insektiziden und akariziden Eigenschaften |
| US7906128B2 (en) * | 2002-10-21 | 2011-03-15 | Wyeth Llc | Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals |
| PA8591801A1 (es) * | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
| US7144583B2 (en) * | 2003-03-05 | 2006-12-05 | Sumitomo Chemical Company, Limited | Pesticidal composition |
| TWI350728B (en) * | 2004-10-08 | 2011-10-21 | Wyeth Corp | Amitraz compositions |
| IN241255B (en:Method) * | 2005-05-02 | 2010-06-25 | ||
| TWI368505B (en) * | 2005-05-24 | 2012-07-21 | Wyeth Corp | Versatile high load concentrate compositions for control of ecto-parasites |
| US20080112993A1 (en) * | 2005-05-24 | 2008-05-15 | Wyeth | High-dose, long-lasting ectoparasiticide for extended control |
| CN101583278B (zh) | 2006-09-01 | 2013-07-10 | 杜邦公司 | 包含茚虫威的局部外用给药制剂 |
| TW200846029A (en) * | 2007-02-09 | 2008-12-01 | Wyeth Corp | High dose, long-acting ectoparasiticide for extended control |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2227951A1 (de) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| JP2011246436A (ja) | 2010-04-28 | 2011-12-08 | Sumitomo Chemical Co Ltd | 有害生物防除組成物 |
| MX2013014418A (es) | 2011-06-08 | 2014-01-20 | Intervet Int Bv | Combinacion parasiticida que comprende indoxacarb y deltametrin. |
| CN102391261A (zh) * | 2011-10-14 | 2012-03-28 | 上海交通大学 | 一种n-取代噁二嗪类化合物及其制备方法和应用 |
| CN102415394A (zh) * | 2011-12-06 | 2012-04-18 | 海利尔药业集团股份有限公司 | 含有茚虫威的高效杀虫组合物 |
| CN102630690A (zh) * | 2012-03-26 | 2012-08-15 | 中化蓝天集团有限公司 | 一种含茚虫威和zj3265的杀虫组合物 |
| CN102626103B (zh) * | 2012-03-28 | 2013-09-25 | 董志平 | 一种利用茚虫威防治二点委夜蛾的新用途 |
| CN102696665A (zh) * | 2012-05-15 | 2012-10-03 | 镇江市苏盾植保专业合作联社 | 含有茚虫威的杀虫剂组合物 |
| CN106928098B (zh) * | 2015-12-31 | 2019-02-26 | 江苏优嘉植物保护有限公司 | 一种茚虫威中间体缩胺基脲的合成方法 |
| CN105707107A (zh) * | 2016-03-31 | 2016-06-29 | 北京颖泰嘉和生物科技股份有限公司 | 一种杀虫剂组合物和制剂及其应用 |
| CN106397198A (zh) * | 2016-08-31 | 2017-02-15 | 京博农化科技股份有限公司 | 一种5‑氯‑2,3‑二氢‑2‑羟基‑1‑氧代‑1h‑茚‑2‑羧酸甲酯的制备方法 |
| US10961206B2 (en) * | 2017-03-29 | 2021-03-30 | Adama Makhteshim Ltd. | Catalytic system for scalable preparation of indoxacarb |
| CN108911980B (zh) * | 2018-08-24 | 2021-06-29 | 吉林大学 | 微反应条件或常规反应条件下对α-羟基-β-二羰基化合物对映体进行动力学拆分的方法 |
| CN111269194B (zh) * | 2020-03-18 | 2023-05-05 | 山东京博农化科技股份有限公司 | 一种茚虫威关键中间体的制备方法 |
| CN113607833B (zh) * | 2021-07-08 | 2023-10-31 | 山东京博农化科技股份有限公司 | 一种茚虫威中间体的含量分析方法 |
| CN117940402A (zh) | 2021-07-13 | 2024-04-26 | 安道麦马克西姆有限公司 | 制备杀节肢动物的噁二嗪中间体的方法 |
| CN118556052A (zh) | 2022-01-04 | 2024-08-27 | 安道麦马克西姆有限公司 | 茚虫威及其中间体的制备方法 |
| EP4472955A1 (en) | 2022-02-02 | 2024-12-11 | Adama Makhteshim Ltd. | Novel solid state forms of indoxacarb |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
| US4863947A (en) * | 1985-01-11 | 1989-09-05 | Rohm And Haas | N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides and methods of their production |
| DE3765782D1 (de) * | 1987-01-05 | 1990-11-29 | Du Pont | Pyrazolin mit insektizidischer aktivitaet. |
| US5091405A (en) * | 1987-01-05 | 1992-02-25 | E. I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| EP0362216A1 (en) * | 1987-04-09 | 1990-04-11 | E.I. Du Pont De Nemours And Company | Insecticidal substituted indazoles |
| DE3826058A1 (de) * | 1988-07-30 | 1990-02-08 | Bayer Ag | Mittel gegen fischparasiten |
| EP0437455A1 (en) * | 1988-09-22 | 1991-07-24 | E.I. Du Pont De Nemours And Company | Substituted indazole arthropodicides |
| JPH04500969A (ja) * | 1988-10-11 | 1992-02-20 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 殺節足動物剤としての置換インダゾール類 |
| AU632093B2 (en) * | 1988-12-27 | 1992-12-17 | E.I. Du Pont De Nemours And Company | Substituted semicarbazone arthropodicides |
| US5462938A (en) * | 1990-12-21 | 1995-10-31 | Annus; Gary D. | Arthropodicidal oxadiazinyl, thiadiazinyl and triazinyl carboxanilides |
| EP0586551A1 (en) * | 1991-05-24 | 1994-03-16 | E.I. Du Pont De Nemours And Company | Arthropodicidal anilides |
| US5514678A (en) * | 1992-03-26 | 1996-05-07 | E. I. Du Pont De Nemours And Company | Arthropodicidal 1,2,4-triazinyl amides |
-
1990
- 1990-12-21 US US08/075,534 patent/US5462938A/en not_active Expired - Lifetime
-
1991
- 1991-12-17 DE DE69111827T patent/DE69111827T2/de not_active Expired - Lifetime
- 1991-12-17 DE DE2001199048 patent/DE10199048I1/de active Pending
- 1991-12-17 JP JP4502714A patent/JP2669933B2/ja not_active Expired - Fee Related
- 1991-12-17 ES ES92902235T patent/ES2077392T3/es not_active Expired - Lifetime
- 1991-12-17 RU SU915011055A patent/RU2096409C1/ru active Protection Beyond IP Right Term
- 1991-12-17 DE DE201112100038 patent/DE122011100038I1/de active Pending
- 1991-12-17 AT AT92902235T patent/ATE125801T1/de not_active IP Right Cessation
- 1991-12-17 EP EP92902235A patent/EP0565574B1/en not_active Expired - Lifetime
- 1991-12-17 KR KR1019930701895A patent/KR0178062B1/ko not_active Expired - Lifetime
- 1991-12-17 HU HU9301808A patent/HU213635B/hu active Protection Beyond IP Right Term
- 1991-12-17 BR BR9107246A patent/BR9107246A/pt not_active Application Discontinuation
- 1991-12-17 CA CA002098612A patent/CA2098612C/en not_active Expired - Lifetime
- 1991-12-17 WO PCT/US1991/009164 patent/WO1992011249A1/en active IP Right Grant
- 1991-12-17 AU AU91270/91A patent/AU659121B2/en not_active Expired
- 1991-12-18 TW TW080109930A patent/TW203045B/zh not_active IP Right Cessation
- 1991-12-19 TR TR91/1166A patent/TR25739A/xx unknown
- 1991-12-19 IL IL10042991A patent/IL100429A/en not_active IP Right Cessation
- 1991-12-19 NZ NZ241072A patent/NZ241072A/xx not_active IP Right Cessation
- 1991-12-19 MY MYPI91002356A patent/MY111387A/en unknown
- 1991-12-21 CN CN91111730A patent/CN1034468C/zh not_active Expired - Lifetime
-
1993
- 1993-06-18 BG BG97888A patent/BG61264B1/bg unknown
-
1995
- 1995-05-23 US US08/448,086 patent/US5708170A/en not_active Expired - Fee Related
- 1995-10-25 GR GR950402973T patent/GR3017869T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL100429A (en) | 1996-01-19 |
| BR9107246A (pt) | 1994-06-14 |
| DE122011100038I1 (de) | 2011-11-10 |
| EP0565574A1 (en) | 1993-10-20 |
| IL100429A0 (en) | 1992-09-06 |
| ES2077392T3 (es) | 1995-11-16 |
| NZ241072A (en) | 1994-03-25 |
| AU9127091A (en) | 1992-07-22 |
| CN1062726A (zh) | 1992-07-15 |
| AU659121B2 (en) | 1995-05-11 |
| RU2096409C1 (ru) | 1997-11-20 |
| CA2098612C (en) | 2002-05-07 |
| TR25739A (tr) | 1993-09-01 |
| DE69111827T2 (de) | 1996-03-28 |
| JPH06504777A (ja) | 1994-06-02 |
| WO1992011249A1 (en) | 1992-07-09 |
| BG97888A (bg) | 1994-05-27 |
| DE69111827D1 (de) | 1995-09-07 |
| CA2098612A1 (en) | 1992-06-22 |
| EP0565574B1 (en) | 1995-08-02 |
| DE10199048I1 (de) | 2001-11-29 |
| BG61264B1 (en) | 1997-04-30 |
| HU9301808D0 (en) | 1993-09-28 |
| US5708170A (en) | 1998-01-13 |
| HU213635B (en) | 1997-08-28 |
| GR3017869T3 (en) | 1996-01-31 |
| MY111387A (en) | 2000-03-31 |
| KR0178062B1 (ko) | 1999-03-20 |
| US5462938A (en) | 1995-10-31 |
| HUT65223A (en) | 1994-05-02 |
| TW203045B (en:Method) | 1993-04-01 |
| CN1034468C (zh) | 1997-04-09 |
| ATE125801T1 (de) | 1995-08-15 |
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