KR20140051404A - N-티오-안트라닐아미드 화합물 및 살충제로서의 그의 용도 - Google Patents
N-티오-안트라닐아미드 화합물 및 살충제로서의 그의 용도 Download PDFInfo
- Publication number
- KR20140051404A KR20140051404A KR1020147006267A KR20147006267A KR20140051404A KR 20140051404 A KR20140051404 A KR 20140051404A KR 1020147006267 A KR1020147006267 A KR 1020147006267A KR 20147006267 A KR20147006267 A KR 20147006267A KR 20140051404 A KR20140051404 A KR 20140051404A
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- South Korea
- Prior art keywords
- compound
- alkyl
- alkoxy
- radicals
- group
- Prior art date
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- 239000000575 pesticide Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 350
- 239000000203 mixture Substances 0.000 claims abstract description 135
- 150000003839 salts Chemical class 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 64
- 241001465754 Metazoa Species 0.000 claims abstract description 57
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 49
- 239000000463 material Substances 0.000 claims abstract description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 46
- 244000045947 parasite Species 0.000 claims abstract description 45
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 42
- 150000002367 halogens Chemical class 0.000 claims abstract description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 36
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 30
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 14
- 208000015181 infectious disease Diseases 0.000 claims abstract description 13
- 125000004970 halomethyl group Chemical group 0.000 claims abstract description 11
- 206010061217 Infestation Diseases 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 4
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims description 477
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- 239000000460 chlorine Substances 0.000 claims description 82
- 125000001424 substituent group Chemical group 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 238000011282 treatment Methods 0.000 claims description 54
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- 229910052794 bromium Inorganic materials 0.000 claims description 49
- 241000244206 Nematoda Species 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 230000000749 insecticidal effect Effects 0.000 claims description 27
- 239000002689 soil Substances 0.000 claims description 26
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 15
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 15
- 239000002917 insecticide Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 241000239223 Arachnida Species 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 241000282414 Homo sapiens Species 0.000 claims description 11
- 239000004009 herbicide Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 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 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- 238000010899 nucleation Methods 0.000 claims description 7
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 239000005648 plant growth regulator Substances 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 25
- 238000002360 preparation method Methods 0.000 abstract description 15
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- 241000196324 Embryophyta Species 0.000 description 157
- 150000003254 radicals Chemical group 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 125000004432 carbon atom Chemical group C* 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 241000894007 species Species 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 28
- 239000003112 inhibitor Substances 0.000 description 27
- 229910052731 fluorine Inorganic materials 0.000 description 25
- 239000007921 spray Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 239000013543 active substance Substances 0.000 description 18
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 108090000623 proteins and genes Proteins 0.000 description 16
- 241000238876 Acari Species 0.000 description 15
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000010790 dilution Methods 0.000 description 15
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- 150000004665 fatty acids Chemical class 0.000 description 15
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 102000004169 proteins and genes Human genes 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
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- 150000001450 anions Chemical class 0.000 description 11
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- 241000254173 Coleoptera Species 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 9
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-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
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 229960004546 thiabendazole Drugs 0.000 description 1
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- 125000005458 thianyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 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
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-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
- 229930192474 thiophene Natural products 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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- 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
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 229940035339 tri-chlor Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-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
- YIXVXFVKVAPMDM-UHFFFAOYSA-N trimethyl-[2-(trimethylazaniumyl)ethyl]azanium Chemical compound C[N+](C)(C)CC[N+](C)(C)C YIXVXFVKVAPMDM-UHFFFAOYSA-N 0.000 description 1
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- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- 230000003612 virological effect Effects 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161522727P | 2011-08-12 | 2011-08-12 | |
| US61/522,727 | 2011-08-12 | ||
| PCT/EP2012/065651 WO2013024010A1 (en) | 2011-08-12 | 2012-08-10 | N-thio-anthranilamide compounds and their use as pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140051404A true KR20140051404A (ko) | 2014-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147006267A Withdrawn KR20140051404A (ko) | 2011-08-12 | 2012-08-10 | N-티오-안트라닐아미드 화합물 및 살충제로서의 그의 용도 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20140179519A1 (enExample) |
| EP (1) | EP2742036A1 (enExample) |
| JP (1) | JP2014522876A (enExample) |
| KR (1) | KR20140051404A (enExample) |
| CN (1) | CN103827103A (enExample) |
| BR (1) | BR112014003186A2 (enExample) |
| IN (1) | IN2014CN01025A (enExample) |
| WO (1) | WO2013024010A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200102449A (ko) * | 2017-12-21 | 2020-08-31 | 바스프 에스이 | 살충 화합물 |
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| ATE520681T1 (de) * | 2005-07-07 | 2011-09-15 | Basf Se | N-thioanthranilamidverbindungen und ihre verwendung als pestizide |
| KR20140064849A (ko) | 2011-08-12 | 2014-05-28 | 바스프 에스이 | 아닐린 유형 화합물 |
| JP5955961B2 (ja) | 2011-08-12 | 2016-07-20 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Ｎ−置換１ｈ−ピラゾール５−カルボニルクロリド化合物を製造するための方法 |
| IN2014CN00979A (enExample) | 2011-08-12 | 2015-04-10 | Basf Se | |
| IN2014CN03469A (enExample) | 2011-11-21 | 2015-07-03 | Basf Se | |
| AU2013255894A1 (en) | 2012-05-04 | 2014-11-13 | Basf Se | Substituted pyrazole-containing compounds and their use as pesticides |
| JP6242872B2 (ja) | 2012-05-24 | 2017-12-06 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Ｎ−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
| WO2014053403A1 (en) * | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling insecticide resistant insects |
| WO2014053402A1 (en) * | 2012-10-01 | 2014-04-10 | Basf Se | Method for controlling non-crop pests |
| WO2014053401A2 (en) * | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
| US20150250175A1 (en) * | 2012-10-01 | 2015-09-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
| WO2014053396A1 (en) * | 2012-10-01 | 2014-04-10 | Basf Se | Use of anthranilamide compounds in soil and seed treatment application methods |
| WO2014053407A1 (en) * | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| US20150237858A1 (en) * | 2012-10-01 | 2015-08-27 | Basf Se | Method of controlling ryanodine-modulator insecticide resistant insects |
| MX2015004175A (es) * | 2012-10-01 | 2015-06-10 | Basf Se | Uso de compuestos de n-tio-antranilamida en plantas cultivadas. |
| CN104768377A (zh) * | 2012-10-01 | 2015-07-08 | 巴斯夫欧洲公司 | 包含邻氨基苯甲酰胺类化合物的农药活性混合物 |
| WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
| WO2014082879A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4]triazole compounds |
| EP2928873A1 (en) | 2012-11-27 | 2015-10-14 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| US20150313229A1 (en) | 2012-11-27 | 2015-11-05 | Basf Se | Substituted [1,2,4] Triazole Compounds |
| WO2014082871A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| WO2014086850A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a fungicidal inhibitor of respiratory complex ii |
| WO2014086856A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a biopesticide |
| WO2014086854A1 (en) | 2012-12-04 | 2014-06-12 | Basf Agro B.V., Arnhem (Nl) | Compositions comprising a quillay extract and a plant growth regulator |
| CA2894023A1 (en) | 2012-12-14 | 2014-06-19 | Basf Se | Malononitrile compounds for controlling animal pests |
| US20150307460A1 (en) | 2012-12-19 | 2015-10-29 | Basf Se | Substituted Triazoles and Imidazoles and Their Use as Fungicides |
| EP2746266A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
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| EP2934147B1 (en) | 2012-12-20 | 2019-11-27 | BASF Agro B.V. | Compositions comprising a triazole compound |
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-
2012
- 2012-08-10 IN IN1025CHN2014 patent/IN2014CN01025A/en unknown
- 2012-08-10 EP EP12745865.1A patent/EP2742036A1/en not_active Withdrawn
- 2012-08-10 CN CN201280046780.2A patent/CN103827103A/zh active Pending
- 2012-08-10 WO PCT/EP2012/065651 patent/WO2013024010A1/en not_active Ceased
- 2012-08-10 JP JP2014524395A patent/JP2014522876A/ja active Pending
- 2012-08-10 US US14/236,351 patent/US20140179519A1/en not_active Abandoned
- 2012-08-10 KR KR1020147006267A patent/KR20140051404A/ko not_active Withdrawn
- 2012-08-10 BR BR112014003186A patent/BR112014003186A2/pt not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200102449A (ko) * | 2017-12-21 | 2020-08-31 | 바스프 에스이 | 살충 화합물 |
Also Published As
| Publication number | Publication date |
|---|---|
| IN2014CN01025A (enExample) | 2015-04-10 |
| EP2742036A1 (en) | 2014-06-18 |
| JP2014522876A (ja) | 2014-09-08 |
| US20140179519A1 (en) | 2014-06-26 |
| CN103827103A (zh) | 2014-05-28 |
| BR112014003186A2 (pt) | 2017-04-04 |
| WO2013024010A1 (en) | 2013-02-21 |
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