BR0212183B1 - composto de antranilamida substituída, seus n-óxidos e sais, método para o controle de uma praga invertebrada e composição para o controle de uma praga invertebrada - Google Patents
composto de antranilamida substituída, seus n-óxidos e sais, método para o controle de uma praga invertebrada e composição para o controle de uma praga invertebrada Download PDFInfo
- Publication number
- BR0212183B1 BR0212183B1 BRPI0212183-2A BR0212183A BR0212183B1 BR 0212183 B1 BR0212183 B1 BR 0212183B1 BR 0212183 A BR0212183 A BR 0212183A BR 0212183 B1 BR0212183 B1 BR 0212183B1
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- Prior art keywords
- alkyl
- formula
- independently
- halogen
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 290
- 239000000203 mixture Substances 0.000 title claims abstract description 99
- 238000000034 method Methods 0.000 title claims abstract description 82
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 63
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- -1 3-chloro-2-pyridinyl Chemical group 0.000 claims description 103
- 125000001424 substituent group Chemical group 0.000 claims description 100
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 150000002367 halogens Chemical class 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 24
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
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- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
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- 239000004094 surface-active agent Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 101150020251 NR13 gene Proteins 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- 206010035148 Plague Diseases 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 102220060025 rs141586345 Human genes 0.000 claims 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 abstract description 3
- 238000012360 testing method Methods 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- 239000002904 solvent Substances 0.000 description 43
- 239000002253 acid Substances 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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- 239000000047 product Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
- 239000002585 base Substances 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 230000009418 agronomic effect Effects 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 241000238631 Hexapoda Species 0.000 description 18
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 17
- 125000004414 alkyl thio group Chemical group 0.000 description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 16
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- 238000009472 formulation Methods 0.000 description 16
- 102220290611 rs765385264 Human genes 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 241001124076 Aphididae Species 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 125000004663 dialkyl amino group Chemical group 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 14
- 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 description 14
- 238000005507 spraying Methods 0.000 description 14
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 13
- 241000254032 Acrididae Species 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 241000238876 Acari Species 0.000 description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 11
- 240000001307 Myosotis scorpioides Species 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 230000008878 coupling Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- 125000001188 haloalkyl group Chemical group 0.000 description 11
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
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- 230000006378 damage Effects 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 241000238814 Orthoptera Species 0.000 description 9
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- 125000003282 alkyl amino group Chemical group 0.000 description 9
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- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 9
- 230000001276 controlling effect Effects 0.000 description 9
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- 235000013305 food Nutrition 0.000 description 9
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
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- 238000002425 crystallisation Methods 0.000 description 8
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- 239000000543 intermediate Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 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 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
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- 125000004122 cyclic group Chemical group 0.000 description 7
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- 229910052698 phosphorus Inorganic materials 0.000 description 7
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- 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 5
- 239000005660 Abamectin Substances 0.000 description 5
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- 125000003342 alkenyl group Chemical group 0.000 description 4
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- UJJDEOLXODWCGK-UHFFFAOYSA-N tert-butyl carbonochloridate Chemical compound CC(C)(C)OC(Cl)=O UJJDEOLXODWCGK-UHFFFAOYSA-N 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 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
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 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
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 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
- 150000007944 thiolates Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000012485 toluene extract Substances 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
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin 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
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 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
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- 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<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31268001P | 2001-08-16 | 2001-08-16 | |
| US60/312,680 | 2001-08-16 | ||
| PCT/US2002/026960 WO2003016284A1 (en) | 2001-08-16 | 2002-08-13 | Substituted anthranilamides for controlling invertebrate pests |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0212183A BR0212183A (pt) | 2004-08-24 |
| BR0212183B1 true BR0212183B1 (pt) | 2014-10-21 |
Family
ID=23212517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0212183-2A BR0212183B1 (pt) | 2001-08-16 | 2002-08-13 | composto de antranilamida substituída, seus n-óxidos e sais, método para o controle de uma praga invertebrada e composição para o controle de uma praga invertebrada |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7199138B2 (enExample) |
| EP (1) | EP1417176B1 (enExample) |
| JP (1) | JP4224397B2 (enExample) |
| KR (1) | KR100869002B1 (enExample) |
| CN (1) | CN100453532C (enExample) |
| AT (1) | ATE417829T1 (enExample) |
| AU (1) | AU2002326748B8 (enExample) |
| BR (1) | BR0212183B1 (enExample) |
| DE (1) | DE60230421D1 (enExample) |
| DK (1) | DK1417176T3 (enExample) |
| ES (1) | ES2319743T3 (enExample) |
| MX (1) | MXPA04001407A (enExample) |
| PT (1) | PT1417176E (enExample) |
| WO (1) | WO2003016284A1 (enExample) |
Families Citing this family (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040102324A1 (en) | 2002-02-28 | 2004-05-27 | Annis Gary David | Heterocyclic diamide invertebrate pest control agents |
| JP4448327B2 (ja) | 2001-08-13 | 2010-04-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 新規置換1h−ジヒドロピラゾール、それらの製造および使用 |
| TWI325302B (en) * | 2001-08-13 | 2010-06-01 | Du Pont | Benzoxazinone compounds |
| AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| US7288554B2 (en) | 2001-08-15 | 2007-10-30 | E.I. Du Pont De Nemours And Company | Ortho-substituted aryl amides for controlling invertebrate pests |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| EP1467988B1 (en) * | 2002-01-22 | 2013-07-17 | E.I. Du Pont De Nemours And Company | Quinazoline(di)ones for invertebrate pest control |
| JP4287816B2 (ja) * | 2002-06-13 | 2009-07-01 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ピラゾールカルボキサミド殺虫剤 |
| US7666882B2 (en) * | 2002-11-15 | 2010-02-23 | E.I. Du Pont De Nemours And Company | Anthranilamide insecticides |
| KR100921594B1 (ko) | 2003-01-28 | 2009-10-14 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 시아노 안트라닐아미드 살충제 |
| WO2004111030A1 (en) * | 2003-06-12 | 2004-12-23 | E.I. Dupont De Nemours And Company | Method for preparing fused oxazinones |
| DE10353281A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
| DE102004021564A1 (de) | 2003-11-14 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| WO2005053405A1 (de) | 2003-12-04 | 2005-06-16 | Bayer Cropscience Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften |
| DE102004021565A1 (de) * | 2003-12-04 | 2005-06-30 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| EP1691611A1 (de) * | 2003-12-04 | 2006-08-23 | Bayer CropScience Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden eigenschaften |
| DE10356550A1 (de) * | 2003-12-04 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| SI1717237T1 (sl) | 2004-02-18 | 2011-03-31 | Ishihara Sangyo Kaisha | Antranilamidi, postopek za njihovo proizvodnjo in sredstva za zatiranje škodljivcev, ki jih vsebujejo |
| AU2005213943B2 (en) | 2004-02-24 | 2010-06-24 | Sumitomo Chemical Company, Limited | Insecticide compositions |
| AR048669A1 (es) * | 2004-03-03 | 2006-05-17 | Syngenta Ltd | Derivados biciclicos de bisamida |
| RU2006139953A (ru) * | 2004-04-13 | 2008-05-20 | Е.И. Дюпон Де Немур Энд Компани (Us) | Антраниламидные инсектициды |
| DE102004031100A1 (de) * | 2004-06-28 | 2006-01-12 | Bayer Cropscience Ag | Anthranilamide |
| GT200500179BA (es) | 2004-07-01 | 2008-10-29 | Mezclas sinergistas de agentes de antranilamida para el control de plagas de invertebrados | |
| DE102004035134A1 (de) | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden oder Phthalsäurediamiden und Safenern |
| MY140912A (en) * | 2004-07-26 | 2010-01-29 | Du Pont | Mixtures of anthranilamide invertebrate pest control agents |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| GB0427008D0 (en) | 2004-12-09 | 2005-01-12 | Syngenta Participations Ag | Novel insecticides |
| ES2371356T3 (es) | 2005-07-07 | 2011-12-30 | Basf Se | Compuestos de n-tio-antranilamida y su uso como plaguicidas. |
| WO2007020877A1 (ja) * | 2005-08-12 | 2007-02-22 | Ishihara Sangyo Kaisha, Ltd. | アントラニルアミド系化合物、それらの製造方法及びそれらを含有する有害生物防除剤 |
| AU2006283181A1 (en) * | 2005-08-24 | 2007-03-01 | E. I. Du Pont De Nemours And Company | Anthranilamides for controlling invertebrate pests |
| DE102005044108A1 (de) | 2005-09-15 | 2007-03-29 | Bayer Cropscience Ag | Dioxazin- und Oxdiazin-substituierte Arylamide |
| KR101315574B1 (ko) | 2005-10-14 | 2013-10-08 | 스미또모 가가꾸 가부시끼가이샤 | 히드라지드 화합물 및 이의 살충 용도 |
| AR059035A1 (es) | 2006-01-16 | 2008-03-12 | Syngenta Participations Ag | Insecticidas derivados de antranilamida |
| DE102006032168A1 (de) | 2006-06-13 | 2007-12-20 | Bayer Cropscience Ag | Anthranilsäurediamid-Derivate mit heteroaromatischen Substituenten |
| JP2009001541A (ja) * | 2006-12-15 | 2009-01-08 | Ishihara Sangyo Kaisha Ltd | 新規ピラゾール化合物を中間体として用いるアントラニルアミド系化合物の製造方法 |
| JP5507045B2 (ja) * | 2006-12-15 | 2014-05-28 | 石原産業株式会社 | アントラニルアミド系化合物の製造方法 |
| CN104496901B (zh) * | 2006-12-15 | 2016-05-25 | 石原产业株式会社 | 邻氨基苯甲酰胺系化合物的制造方法 |
| JP2008280336A (ja) | 2007-04-11 | 2008-11-20 | Sumitomo Chemical Co Ltd | アミド化合物の製造方法 |
| JP2008280339A (ja) * | 2007-04-12 | 2008-11-20 | Sumitomo Chemical Co Ltd | ヒドラジド化合物及びそれを含有する有害節足動物防除剤 |
| JP2008280340A (ja) * | 2007-04-12 | 2008-11-20 | Sumitomo Chemical Co Ltd | ヒドラジド化合物及びそれを含有する有害節足動物防除剤 |
| WO2008134970A1 (fr) * | 2007-04-30 | 2008-11-13 | Sinochem Corporation | Composés anthranilamides et leur utilisation |
| JP5551371B2 (ja) * | 2008-03-24 | 2014-07-16 | 石原産業株式会社 | 有害生物防除用固形組成物 |
| WO2010069502A2 (de) | 2008-12-18 | 2010-06-24 | Bayer Cropscience Ag | Tetrazolsubstituierte anthranilsäureamide als pestizide |
| EP2533641B1 (de) | 2010-02-09 | 2016-07-13 | Bayer CropScience AG | Hydrazin-substituierte anthranilsäurederivate |
| KR20130052734A (ko) | 2010-04-16 | 2013-05-23 | 바이엘 크롭사이언스 아게 | 농약으로서의 트리아졸-치환된 안트라닐아미드 |
| PT2563149T (pt) | 2010-04-30 | 2016-11-15 | Syngenta Participations Ag | Um método para reduzir infecções virais transmitidas por insetos |
| MX339033B (es) | 2010-06-15 | 2016-05-05 | Bayer Ip Gmbh | Derivados de acido antranilico. |
| BR112012032259A2 (pt) | 2010-06-15 | 2015-09-15 | Bayer Ip Gmbh | "novos derivados de arilamida orto-substituída". |
| JP6046035B2 (ja) | 2010-06-15 | 2016-12-14 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 環状側鎖を有するアントラニル酸ジアミド誘導体 |
| KR20130089232A (ko) | 2010-06-15 | 2013-08-09 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 안트라닐산 디아미드 유도체 |
| CN103080102B (zh) | 2010-07-09 | 2016-08-24 | 拜耳知识产权有限责任公司 | 作为杀虫剂的邻氨基苯甲酰胺衍生物 |
| EP2668153B1 (en) * | 2011-01-28 | 2015-03-04 | E.I. Du Pont De Nemours And Company | Method for preparing 2-aminobenzamide derivatives |
| BR112014003220A2 (pt) * | 2011-08-12 | 2017-03-01 | Basf Se | composto de fórmula (i), processo para preparar um composto de fórmula i e v, uso do composto de fórmula i, método para controlar uma praga invertebrada, forma cristalina, uso das formas cristalinas e método para controlar uma praga invertebrada |
| AR087515A1 (es) * | 2011-08-12 | 2014-03-26 | Basf Se | Compuestos de n-tio-antranilamida y sus usos como plaguicidas |
| CN103874694B (zh) | 2011-08-12 | 2016-08-17 | 巴斯夫欧洲公司 | 制备n-取代的1h-吡唑-5-甲酰氯化合物的方法 |
| KR20140051404A (ko) | 2011-08-12 | 2014-04-30 | 바스프 에스이 | N-티오-안트라닐아미드 화합물 및 살충제로서의 그의 용도 |
| JP2014522873A (ja) | 2011-08-12 | 2014-09-08 | ビーエーエスエフ ソシエタス・ヨーロピア | アントラニルアミド化合物および殺虫剤としてのその使用 |
| BR112014003112A2 (pt) * | 2011-08-12 | 2017-02-21 | Basf Se | composto da fórmula geral (i), métodos para preparar um composto da fórmula (i), composição agrícola ou veterinária, método para combater ou controlar pragas invertebradas, método para proteger o cultivo de plantas, método para a proteção de sementes, semente, usos de um composto e método para tratar um animal |
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-
2002
- 2002-08-13 AT AT02761486T patent/ATE417829T1/de not_active IP Right Cessation
- 2002-08-13 EP EP02761486A patent/EP1417176B1/en not_active Expired - Lifetime
- 2002-08-13 DE DE60230421T patent/DE60230421D1/de not_active Expired - Lifetime
- 2002-08-13 DK DK02761486T patent/DK1417176T3/da active
- 2002-08-13 AU AU2002326748A patent/AU2002326748B8/en not_active Ceased
- 2002-08-13 US US10/486,312 patent/US7199138B2/en not_active Expired - Fee Related
- 2002-08-13 BR BRPI0212183-2A patent/BR0212183B1/pt not_active IP Right Cessation
- 2002-08-13 KR KR1020047002143A patent/KR100869002B1/ko not_active Expired - Fee Related
- 2002-08-13 JP JP2003521210A patent/JP4224397B2/ja not_active Expired - Fee Related
- 2002-08-13 CN CNB028160509A patent/CN100453532C/zh not_active Expired - Fee Related
- 2002-08-13 PT PT02761486T patent/PT1417176E/pt unknown
- 2002-08-13 WO PCT/US2002/026960 patent/WO2003016284A1/en not_active Ceased
- 2002-08-13 ES ES02761486T patent/ES2319743T3/es not_active Expired - Lifetime
- 2002-08-13 MX MXPA04001407A patent/MXPA04001407A/es active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| ATE417829T1 (de) | 2009-01-15 |
| ES2319743T3 (es) | 2009-05-12 |
| EP1417176A1 (en) | 2004-05-12 |
| US7541377B2 (en) | 2009-06-02 |
| CN100453532C (zh) | 2009-01-21 |
| EP1417176B1 (en) | 2008-12-17 |
| US20050282868A1 (en) | 2005-12-22 |
| WO2003016284A1 (en) | 2003-02-27 |
| AU2002326748B2 (en) | 2008-06-26 |
| JP2005503384A (ja) | 2005-02-03 |
| US20070203201A1 (en) | 2007-08-30 |
| DE60230421D1 (de) | 2009-01-29 |
| AU2002326748B8 (en) | 2008-07-10 |
| DK1417176T3 (da) | 2009-03-23 |
| KR20040029431A (ko) | 2004-04-06 |
| BR0212183A (pt) | 2004-08-24 |
| PT1417176E (pt) | 2009-02-26 |
| JP4224397B2 (ja) | 2009-02-12 |
| KR100869002B1 (ko) | 2008-11-17 |
| US7199138B2 (en) | 2007-04-03 |
| MXPA04001407A (es) | 2004-05-27 |
| CN1653051A (zh) | 2005-08-10 |
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