KR20080093045A - 비사이클릭 비스아미드 구조를 함유하는 살충제 - Google Patents
비사이클릭 비스아미드 구조를 함유하는 살충제 Download PDFInfo
- Publication number
- KR20080093045A KR20080093045A KR1020087019833A KR20087019833A KR20080093045A KR 20080093045 A KR20080093045 A KR 20080093045A KR 1020087019833 A KR1020087019833 A KR 1020087019833A KR 20087019833 A KR20087019833 A KR 20087019833A KR 20080093045 A KR20080093045 A KR 20080093045A
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- KR
- South Korea
- Prior art keywords
- alkyl
- spp
- formula
- chloro
- compounds
- 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.)
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- 239000000575 pesticide Substances 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 427
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 cyano, hydroxy Chemical group 0.000 claims description 349
- 239000000203 mixture Substances 0.000 claims description 131
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 115
- 239000004480 active ingredient Substances 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 51
- 241000196324 Embryophyta Species 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 241000607479 Yersinia pestis Species 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 241000894007 species Species 0.000 claims description 21
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 19
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 19
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 241000238876 Acari Species 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 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 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 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 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 241000219198 Brassica Species 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 235000011331 Brassica Nutrition 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 276
- 238000002360 preparation method Methods 0.000 description 116
- 239000000126 substance Substances 0.000 description 114
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 107
- 239000007787 solid Substances 0.000 description 97
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
- 230000000694 effects Effects 0.000 description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 239000000047 product Substances 0.000 description 55
- 238000003818 flash chromatography Methods 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 39
- 239000007858 starting material Substances 0.000 description 38
- 239000000725 suspension Substances 0.000 description 38
- 231100000765 toxin Toxicity 0.000 description 36
- 239000003053 toxin Substances 0.000 description 35
- 108700012359 toxins Proteins 0.000 description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 33
- 229910004298 SiO 2 Inorganic materials 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000012267 brine Substances 0.000 description 30
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 240000008042 Zea mays Species 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000011161 development Methods 0.000 description 26
- 230000018109 developmental process Effects 0.000 description 26
- 239000011734 sodium Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 22
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 21
- 235000005822 corn Nutrition 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- 150000002431 hydrogen Chemical class 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 18
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 239000012085 test solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 0 CC1=C(*)*(*)*=C1 Chemical compound CC1=C(*)*(*)*=C1 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 102000004169 proteins and genes Human genes 0.000 description 13
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 11
- 230000009261 transgenic effect Effects 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- AOPYBRLTXWCZAV-UHFFFAOYSA-N (1-cyclopropylcyclopropyl)azanium;chloride Chemical compound [Cl-].C1CC1C1([NH3+])CC1 AOPYBRLTXWCZAV-UHFFFAOYSA-N 0.000 description 9
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000193388 Bacillus thuringiensis Species 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 229940097012 bacillus thuringiensis Drugs 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- YNOFOVLFZVOJQP-UHFFFAOYSA-N 2-methyl-1-methylsulfanylpropan-2-amine Chemical compound CSCC(C)(C)N YNOFOVLFZVOJQP-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 8
- 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 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
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- 239000000706 filtrate Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 230000012010 growth Effects 0.000 description 8
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 241001124076 Aphididae Species 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 235000010582 Pisum sativum Nutrition 0.000 description 7
- 240000004713 Pisum sativum Species 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- 230000000361 pesticidal effect Effects 0.000 description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- 241000256836 Apis Species 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 230000001418 larval effect Effects 0.000 description 6
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- 235000013311 vegetables Nutrition 0.000 description 6
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 5
- SAWNFCCPPRARBZ-UHFFFAOYSA-N 6-amino-5-methyl-1h-indazole-7-carboxylic acid Chemical compound OC(=O)C1=C(N)C(C)=CC2=C1NN=C2 SAWNFCCPPRARBZ-UHFFFAOYSA-N 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- JXHWAIXXLWXEKS-UHFFFAOYSA-N N-propan-2-yl-1H-indazole-7-carboxamide Chemical compound C(C)(C)NC(=O)C=1C=CC=C2C=NNC=12 JXHWAIXXLWXEKS-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
- 239000000642 acaricide Substances 0.000 description 5
- GDZNYEZGJAFIKA-UHFFFAOYSA-N acetoprole Chemical compound NC1=C(S(C)=O)C(C(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GDZNYEZGJAFIKA-UHFFFAOYSA-N 0.000 description 5
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- 230000015572 biosynthetic process Effects 0.000 description 5
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- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 5
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 229940088597 hormone Drugs 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- MMJIKDUYHKCIKA-UHFFFAOYSA-N methyl 6-amino-5-bromo-1h-indazole-7-carboxylate Chemical compound COC(=O)C1=C(N)C(Br)=CC2=C1NN=C2 MMJIKDUYHKCIKA-UHFFFAOYSA-N 0.000 description 5
- 229940102396 methyl bromide Drugs 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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- 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
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 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
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- 230000002588 toxic effect Effects 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
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- UZKQTCBAMSWPJD-UQCOIBPSSA-N trans-Zeatin Natural products OCC(/C)=C\CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-UQCOIBPSSA-N 0.000 description 1
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- 238000012546 transfer Methods 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
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
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- 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
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-UHFFFAOYSA-N 0.000 description 1
- XBRCDWHXULVEFB-UHFFFAOYSA-N triphenyltin(1+) Chemical compound C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 XBRCDWHXULVEFB-UHFFFAOYSA-N 0.000 description 1
- MLFGIRNMAOXTHS-UHFFFAOYSA-N tris(2-methylaziridin-1-yl)-sulfanylidene-$l^{5}-phosphane Chemical compound CC1CN1P(=S)(N1C(C1)C)N1C(C)C1 MLFGIRNMAOXTHS-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- SPDZFJLQFWSJGA-UHFFFAOYSA-N uredepa Chemical compound C1CN1P(=O)(NC(=O)OCC)N1CC1 SPDZFJLQFWSJGA-UHFFFAOYSA-N 0.000 description 1
- 229950006929 uredepa Drugs 0.000 description 1
- FVECELJHCSPHKY-JLSHOZRYSA-N veratridine Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 FVECELJHCSPHKY-JLSHOZRYSA-N 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- AWSFICBXMUKWSK-UHFFFAOYSA-N ytterbium(3+) Chemical compound [Yb+3] AWSFICBXMUKWSK-UHFFFAOYSA-N 0.000 description 1
- 229940023877 zeatin Drugs 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 1
- WOAQZEHJXZOJCS-UHFFFAOYSA-N zinc;diisocyanate Chemical compound [Zn+2].[N-]=C=O.[N-]=C=O WOAQZEHJXZOJCS-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
- C07D401/14—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 three or more hetero rings
-
- 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
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06003094 | 2006-02-16 | ||
| EP06003094.7 | 2006-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080093045A true KR20080093045A (ko) | 2008-10-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020087019833A Ceased KR20080093045A (ko) | 2006-02-16 | 2007-02-14 | 비사이클릭 비스아미드 구조를 함유하는 살충제 |
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| US (1) | US8658801B2 (https=) |
| EP (1) | EP1984354B1 (https=) |
| JP (1) | JP2009526798A (https=) |
| KR (1) | KR20080093045A (https=) |
| CN (1) | CN101426779B (https=) |
| AR (1) | AR059494A1 (https=) |
| AT (1) | ATE438643T1 (https=) |
| AU (1) | AU2007214661B2 (https=) |
| BR (1) | BRPI0709555B1 (https=) |
| CA (1) | CA2640307A1 (https=) |
| DE (1) | DE602007001870D1 (https=) |
| EG (1) | EG25368A (https=) |
| ES (1) | ES2331437T3 (https=) |
| IL (1) | IL192930A0 (https=) |
| MA (1) | MA30262B1 (https=) |
| NZ (1) | NZ570099A (https=) |
| RU (1) | RU2437881C2 (https=) |
| TW (1) | TW200808766A (https=) |
| UA (1) | UA91406C2 (https=) |
| WO (1) | WO2007093402A1 (https=) |
| ZA (1) | ZA200806326B (https=) |
Families Citing this family (50)
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| RS52042B (sr) | 2007-04-25 | 2012-04-30 | Syngenta Participations Ag | Fungicidne smeše |
| WO2009010260A2 (en) | 2007-07-16 | 2009-01-22 | Syngenta Participations Ag | Condensed anthranilamide insecticides |
| WO2009021717A2 (en) * | 2007-08-14 | 2009-02-19 | Syngenta Participations Ag | Pesticidal formulation |
| GB0716414D0 (en) * | 2007-08-22 | 2007-10-03 | Syngenta Participations Ag | Novel insecticides |
| TWI411395B (zh) * | 2007-12-24 | 2013-10-11 | Syngenta Participations Ag | 殺蟲化合物 |
| CN102131789A (zh) * | 2008-08-22 | 2011-07-20 | 先正达参股股份有限公司 | 杀虫化合物 |
| EP2331536B1 (en) * | 2008-08-22 | 2013-08-21 | Syngenta Participations AG | Insecticidal compounds |
| WO2010025998A1 (en) * | 2008-09-04 | 2010-03-11 | Syngenta Participations Ag | Insecticidal compounds |
| GB2463318A (en) * | 2008-09-12 | 2010-03-17 | Syngenta Participations Ag | Preparation of anthranilamide derivatives containing a pyridinylpyrazole moiety |
| GB2463736A (en) * | 2008-09-30 | 2010-03-31 | Syngenta Participations Ag | Process for the preparation of ortho amino-substituted aromatic carboxylic acids |
| WO2010083199A1 (en) | 2009-01-19 | 2010-07-22 | Abbott Laboratories | Benzthiazole inhibitors of poly(adp-ribose)polymerase |
| JP5684802B2 (ja) * | 2009-06-22 | 2015-03-18 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫性化合物 |
| WO2011095461A1 (en) | 2010-02-04 | 2011-08-11 | Syngenta Participations Ag | Pyridazine derivatives, processes for their preparation and their use as fungicides |
| EP2539338A1 (en) | 2010-02-24 | 2013-01-02 | Syngenta Participations AG | Novel microbicides |
| WO2012001040A1 (en) | 2010-07-02 | 2012-01-05 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
| TW201211005A (en) | 2010-07-29 | 2012-03-16 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
| WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
| WO2012069652A2 (en) | 2010-11-26 | 2012-05-31 | Syngenta Participations Ag | Fungicide mixtures |
| WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
| EP2742036A1 (en) | 2011-08-12 | 2014-06-18 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| UY34279A (es) | 2011-08-23 | 2013-04-05 | Syngenta Participations Ag | Compuestos heterocíclicos activos como microbiocidas, intermediarios, composiciones y usos |
| WO2014128136A1 (en) | 2013-02-20 | 2014-08-28 | Basf Se | Anthranilamide compounds and their use as pesticides |
| BR112015020830A2 (pt) | 2013-03-06 | 2017-07-18 | Bayer Cropscience Ag | diamidas de ácido antranílico substituídas com alcoximino como pesticidas |
| JP6759514B2 (ja) | 2014-08-01 | 2020-09-23 | ヌエヴォリューション・アクティーゼルスカブＮｕｅｖｏｌｕｔｉｏｎ Ａ／Ｓ | ブロモドメインに対して活性な化合物 |
| JP6662901B2 (ja) | 2015-03-27 | 2020-03-11 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性二環式複素環式誘導体 |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
| CN115819417A (zh) | 2016-09-09 | 2023-03-21 | 因赛特公司 | 作为hpk1调节剂的吡唑并吡啶衍生物及其用于治疗癌症的用途 |
| US20180072741A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyrimidine compounds and uses thereof |
| WO2018152220A1 (en) | 2017-02-15 | 2018-08-23 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| US10722495B2 (en) | 2017-09-08 | 2020-07-28 | Incyte Corporation | Cyanoindazole compounds and uses thereof |
| BR112020012455B1 (pt) * | 2017-12-20 | 2024-04-30 | Pi Industries Ltd | Pirazolopiridina-diamidas, seu uso como inseticida e processos para sua preparação |
| WO2019123194A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Anthranilamides, their use as insecticide and processes for preparing the same. |
| JP7307079B2 (ja) | 2018-01-30 | 2023-07-11 | ピーアイ インダストリーズ リミテッド | 新規アントラニルアミド、殺虫剤としてのその使用およびその製造方法 |
| US10752635B2 (en) | 2018-02-20 | 2020-08-25 | Incyte Corporation | Indazole compounds and uses thereof |
| EP3755703B1 (en) | 2018-02-20 | 2022-05-04 | Incyte Corporation | N-(phenyl)-2-(phenyl)pyrimidine-4-carboxamide derivatives and related compounds as hpk1 inhibitors for treating cancer |
| US10745388B2 (en) | 2018-02-20 | 2020-08-18 | Incyte Corporation | Indazole compounds and uses thereof |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| US10899755B2 (en) | 2018-08-08 | 2021-01-26 | Incyte Corporation | Benzothiazole compounds and uses thereof |
| WO2020068729A1 (en) | 2018-09-25 | 2020-04-02 | Incyte Corporation | Pyrazolo[4,3-d]pyrimidine compounds as alk2 abd/or fgfr modulators |
| AU2020311940A1 (en) | 2019-07-11 | 2022-02-03 | ESCAPE Bio, Inc. | Indazoles and azaindazoles as LRRK2 inhibitors |
| JP7691974B2 (ja) * | 2019-07-25 | 2025-06-12 | キュラデブ ファーマ ピーブイティー． リミテッド | アセチル補酵素ａシンテターゼ短鎖２（ａｃｓｓ２）の小分子阻害剤 |
| BR112022002059A2 (pt) | 2019-08-06 | 2022-06-07 | Incyte Corp | Formas sólidas de um inibidor de hpk1 |
| CN110483403A (zh) * | 2019-09-02 | 2019-11-22 | 南通大学 | 一种5-溴-4-甲氧基-1h-吲唑的合成方法 |
| US11618751B1 (en) | 2022-03-25 | 2023-04-04 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives |
| US11319319B1 (en) | 2021-04-07 | 2022-05-03 | Ventus Therapeutics U.S., Inc. | Compounds for inhibiting NLRP3 and uses thereof |
| CN115572282B (zh) * | 2021-07-05 | 2024-07-09 | 华东理工大学 | 含芳杂环结构的吡唑酰胺类化合物及其制备方法和应用 |
| WO2023006634A1 (en) | 2021-07-27 | 2023-02-02 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
| EP4380363A1 (en) | 2021-08-05 | 2024-06-12 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
| IL309501A (en) | 2021-08-19 | 2024-02-01 | Syngenta Crop Protection Ag | Method for controlling pests resistant to diamide and compounds therefor |
| US12331048B2 (en) | 2022-10-31 | 2025-06-17 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors |
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| US674047A (en) * | 1900-04-19 | 1901-05-14 | Henry N Samstag | Engine. |
| RU2283840C2 (ru) * | 2001-08-13 | 2006-09-20 | Е.И.Дюпон Де Немур Энд Компани | Антраниламидное соединение, композиция для борьбы с насекомыми, композиция для борьбы с беспозвоночными вредителями, способы борьбы с насекомыми, промежуточные соединения |
| AR048669A1 (es) * | 2004-03-03 | 2006-05-17 | Syngenta Ltd | Derivados biciclicos de bisamida |
| GB0422556D0 (en) * | 2004-10-11 | 2004-11-10 | Syngenta Participations Ag | Novel insecticides |
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- 2007-02-14 AT AT07703468T patent/ATE438643T1/de not_active IP Right Cessation
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- 2007-02-14 AR ARP070100621A patent/AR059494A1/es not_active Application Discontinuation
- 2007-02-14 NZ NZ570099A patent/NZ570099A/en not_active IP Right Cessation
- 2007-02-14 UA UAA200811094A patent/UA91406C2/ru unknown
- 2007-02-14 BR BRPI0709555A patent/BRPI0709555B1/pt not_active IP Right Cessation
- 2007-02-14 KR KR1020087019833A patent/KR20080093045A/ko not_active Ceased
- 2007-02-14 TW TW096105429A patent/TW200808766A/zh unknown
- 2007-02-14 CA CA002640307A patent/CA2640307A1/en not_active Abandoned
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- 2008-09-05 MA MA31211A patent/MA30262B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200808766A (en) | 2008-02-16 |
| ZA200806326B (en) | 2009-07-29 |
| DE602007001870D1 (de) | 2009-09-17 |
| CN101426779A (zh) | 2009-05-06 |
| IL192930A0 (en) | 2009-02-11 |
| RU2437881C2 (ru) | 2011-12-27 |
| CA2640307A1 (en) | 2007-08-23 |
| ES2331437T3 (es) | 2010-01-04 |
| EP1984354B1 (en) | 2009-08-05 |
| UA91406C2 (ru) | 2010-07-26 |
| BRPI0709555B1 (pt) | 2015-11-03 |
| WO2007093402A1 (en) | 2007-08-23 |
| RU2008136750A (ru) | 2010-03-27 |
| ATE438643T1 (de) | 2009-08-15 |
| AU2007214661B2 (en) | 2012-05-17 |
| US8658801B2 (en) | 2014-02-25 |
| EG25368A (en) | 2011-12-20 |
| NZ570099A (en) | 2010-08-27 |
| BRPI0709555A2 (pt) | 2011-07-19 |
| US20090298816A1 (en) | 2009-12-03 |
| MA30262B1 (fr) | 2009-03-02 |
| JP2009526798A (ja) | 2009-07-23 |
| CN101426779B (zh) | 2013-08-21 |
| AU2007214661A1 (en) | 2007-08-23 |
| AR059494A1 (es) | 2008-04-09 |
| EP1984354A1 (en) | 2008-10-29 |
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