JP2023515979A - 殺有害生物的に活性なジアジン－ビスアミド化合物 - Google Patents
殺有害生物的に活性なジアジン－ビスアミド化合物 Download PDFInfo
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- 230000000361 pesticidal effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 732
- -1 stereoisomers Chemical class 0.000 claims abstract description 268
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 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 abstract description 9
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 193
- 125000001424 substituent group Chemical group 0.000 claims description 160
- 229910052736 halogen Inorganic materials 0.000 claims description 111
- 150000002367 halogens Chemical class 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 150000002431 hydrogen Chemical class 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 59
- 239000000460 chlorine Substances 0.000 claims description 56
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- 241000607479 Yersinia pestis Species 0.000 claims description 47
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 43
- 229910052801 chlorine Inorganic materials 0.000 claims description 43
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 241001465754 Metazoa Species 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 26
- 241000238631 Hexapoda Species 0.000 claims description 23
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 22
- 241000244206 Nematoda Species 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 244000045947 parasite Species 0.000 claims description 18
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 17
- 241000238876 Acari Species 0.000 claims description 17
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- 125000003566 oxetanyl group Chemical group 0.000 claims description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 11
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 230000000749 insecticidal effect Effects 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 11
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 241000237852 Mollusca Species 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 5
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 198
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- 241000196324 Embryophyta Species 0.000 description 45
- 238000002360 preparation method Methods 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- JTBBRGSSVACAJM-UHFFFAOYSA-N (2-methyl-2,3-dihydro-1-benzofuran-7-yl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)C2 JTBBRGSSVACAJM-UHFFFAOYSA-N 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 36
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 36
- 239000007787 solid Substances 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 34
- 239000003053 toxin Substances 0.000 description 34
- 231100000765 toxin Toxicity 0.000 description 34
- 108700012359 toxins Proteins 0.000 description 34
- 230000014759 maintenance of location Effects 0.000 description 33
- 125000004043 oxo group Chemical group O=* 0.000 description 33
- 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 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 229910052731 fluorine Inorganic materials 0.000 description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 30
- 230000002829 reductive effect Effects 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 27
- 239000011737 fluorine Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 23
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- 239000002585 base Substances 0.000 description 22
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 241000894007 species Species 0.000 description 21
- 125000001188 haloalkyl group Chemical group 0.000 description 20
- 240000008042 Zea mays Species 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 16
- 229910052740 iodine Inorganic materials 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 235000013311 vegetables Nutrition 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 239000013058 crude material Substances 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
- 235000005822 corn Nutrition 0.000 description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 230000009261 transgenic effect Effects 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 11
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 11
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 11
- 241000500437 Plutella xylostella Species 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- OUNSASXJZHBGAI-UHFFFAOYSA-N Salithion Chemical compound C1=CC=C2OP(OC)(=S)OCC2=C1 OUNSASXJZHBGAI-UHFFFAOYSA-N 0.000 description 10
- 241000700605 Viruses Species 0.000 description 10
- 239000002671 adjuvant Substances 0.000 description 10
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- DHUNBQDZUVRCMJ-UHFFFAOYSA-N 1-cyclopropyl-8-(difluoromethoxy)-6-fluoro-7-[4-(2-methoxyphenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=CC=CC=C1N1CCN(C=2C(=C3C(C(C(C(O)=O)=CN3C3CC3)=O)=CC=2F)OC(F)F)CC1 DHUNBQDZUVRCMJ-UHFFFAOYSA-N 0.000 description 9
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- 241001635274 Cydia pomonella Species 0.000 description 9
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000255925 Diptera Species 0.000 description 8
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
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- YXABZCRJGRKZEL-UHFFFAOYSA-N N-[1-(3-chloropyrazin-2-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide Chemical compound ClC=1C(=NC=CN=1)C(C)NC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O YXABZCRJGRKZEL-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 239000002131 composite material Substances 0.000 description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 description 8
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
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- 229940097012 bacillus thuringiensis Drugs 0.000 description 7
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 6
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
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- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| IN202011008381 | 2020-02-27 | ||
| IN202011008381 | 2020-02-27 | ||
| IN202011041550 | 2020-09-24 | ||
| IN202011041550 | 2020-09-24 | ||
| PCT/EP2021/055072 WO2021170881A1 (en) | 2020-02-27 | 2021-03-01 | Pesticidally active diazine-bisamide compounds |
Publications (2)
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| JP2023515979A true JP2023515979A (ja) | 2023-04-17 |
| JP2023515979A5 JP2023515979A5 (enExample) | 2024-03-11 |
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| JP2022551689A Abandoned JP2023515979A (ja) | 2020-02-27 | 2021-03-01 | 殺有害生物的に活性なジアジン－ビスアミド化合物 |
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| BR (1) | BR112022017093A2 (enExample) |
| WO (1) | WO2021170881A1 (enExample) |
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| WO2022233777A1 (en) | 2021-05-06 | 2022-11-10 | Bayer Aktiengesellschaft | Alkylamide substituted, annulated imidazoles and use thereof as insecticides |
| EP4140986A1 (en) * | 2021-08-23 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
| US20250107528A1 (en) * | 2021-08-23 | 2025-04-03 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
| MX2024002386A (es) | 2021-08-25 | 2024-03-14 | Bayer Ag | Nuevos compuestos de pirazinil-triazol como pesticidas. |
| US20250042875A1 (en) | 2021-10-27 | 2025-02-06 | Syngenta Crop Protection Ag | Pesticidally active pyridazinone compounds |
| US20250049033A1 (en) | 2021-12-10 | 2025-02-13 | Syngenta Crop Protection Ag | Pesticidally active pyridazinone compounds |
| WO2024110554A1 (en) | 2022-11-23 | 2024-05-30 | Syngenta Crop Protection Ag | N-[(1 -[2-[6-(pyridazin-3-yl]-1,2,4-triazol-3-yl]ethyl]-quinazolin-4-amine and n-[1-[3-(6-(pyridazin-3-yl)pyrazin-2-yl]ethyl]-8-quinazolin-4-amine derivatives as pesticides |
| WO2024133551A1 (en) | 2022-12-21 | 2024-06-27 | Syngenta Crop Protection Ag | Pesticidally active pyridazine compounds |
| EP4389210A1 (en) | 2022-12-21 | 2024-06-26 | Basf Se | Heteroaryl compounds for the control of invertebrate pests |
| KR20250127064A (ko) | 2022-12-21 | 2025-08-26 | 바스프 에스이 | 무척추동물 해충의 방제를 위한 헤테로아릴 화합물 |
| IL330217A (en) | 2023-12-22 | 2026-08-01 | Basf Se | Diazinon compounds for controlling invertebrate pests |
| EP4574819A1 (en) | 2023-12-22 | 2025-06-25 | Basf Se | Diazinone compounds for the control of invertebrate pests |
| WO2025186065A1 (en) | 2024-03-05 | 2025-09-12 | Bayer Aktiengesellschaft | Heteroaryl-substituted (aza)quinoxaline derivatives as pesticides |
| WO2026162563A1 (en) | 2025-01-30 | 2026-08-06 | Basf Agricultural Solutions Deutschland Gmbh | Diazinone derivatives for the control of invertebrate pests |
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| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| CA1340685C (en) | 1988-07-29 | 1999-07-27 | Frederick Meins | Dna sequences encoding polypeptides having beta-1,3-glucanase activity |
| US5169629A (en) | 1988-11-01 | 1992-12-08 | Mycogen Corporation | Process of controlling lepidopteran pests, using bacillus thuringiensis isolate denoted b.t ps81gg |
| CA2005658A1 (en) | 1988-12-19 | 1990-06-19 | Eliahu Zlotkin | Insecticidal toxins, genes encoding these toxins, antibodies binding to them and transgenic plant cells and plants expressing these toxins |
| ES2199931T3 (es) | 1989-03-24 | 2004-03-01 | Syngenta Participations Ag | Plantas transgenicas resistentes a enfermedades. |
| GB8910624D0 (en) | 1989-05-09 | 1989-06-21 | Ici Plc | Bacterial strains |
| CA2015951A1 (en) | 1989-05-18 | 1990-11-18 | Mycogen Corporation | Novel bacillus thuringiensis isolates active against lepidopteran pests, and genes encoding novel lepidopteran-active toxins |
| EP0427529B1 (en) | 1989-11-07 | 1995-04-19 | Pioneer Hi-Bred International, Inc. | Larvicidal lectins and plant insect resistance based thereon |
| US5639949A (en) | 1990-08-20 | 1997-06-17 | Ciba-Geigy Corporation | Genes for the synthesis of antipathogenic substances |
| UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
| US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
| US5631072A (en) | 1995-03-10 | 1997-05-20 | Avondale Incorporated | Method and means for increasing efficacy and wash durability of insecticide treated fabric |
| EP1114030B1 (en) | 1998-09-15 | 2005-06-01 | Syngenta Participations AG | Pyridine ketones useful as herbicides |
| KR100581163B1 (ko) | 2000-08-25 | 2006-05-22 | 신젠타 파티서페이션즈 아게 | 하이브리드 바실러스 튜린지엔시스 독소, 이를 암호화하는 핵산 및 이를 사용한 해충의 방제방법 |
| DE10121003A1 (de) | 2001-04-28 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| AU2002345250A1 (en) | 2001-06-22 | 2003-01-08 | Syngenta Participations Ag | Plant disease resistance genes |
| US7230167B2 (en) | 2001-08-31 | 2007-06-12 | Syngenta Participations Ag | Modified Cry3A toxins and nucleic acid sequences coding therefor |
| EP1439752B1 (en) | 2001-10-25 | 2005-08-24 | Siamdutch Mosquito Netting Company Limited | Treatment of fabric materials with an insecticide |
| AU2002361696A1 (en) | 2001-12-17 | 2003-06-30 | Syngenta Participations Ag | Novel corn event |
| PL374845A1 (en) | 2002-07-22 | 2005-11-14 | Eli Lilly And Company | Selective estrogen receptor modulators containing a phenylsulfonyl group |
| US20050132500A1 (en) | 2003-12-22 | 2005-06-23 | Basf Aktiengesellschaft | Composition for impregnation of fibers, fabrics and nettings imparting a protective activity against pests |
| DE102004023894A1 (de) | 2004-05-12 | 2005-12-08 | Basf Ag | Verfahren zur Behandlung von flexiblen Substraten |
| AR053992A1 (es) | 2004-12-22 | 2007-05-30 | Astrazeneca Ab | Compuestos quimicos con actividad anticancerosa, un procedimiento para su preparacion, su uso en la preparacion de medicamentos y composicion farmaceutica. |
| US20060199828A1 (en) * | 2005-03-04 | 2006-09-07 | Georg Jaeschke | Pyrazine-2-carboxyamide derivatives |
| DE102005020889A1 (de) | 2005-05-04 | 2006-11-09 | Fritz Blanke Gmbh & Co.Kg | Verfahren zur antimikrobiellen Ausrüstung von textilen Flächengebilden |
| KR20080018934A (ko) | 2005-06-03 | 2008-02-28 | 바스프 악티엔게젤샤프트 | 해충에 대한 보호 활성을 제공하는 섬유, 직물 및 네팅함침용 조성물 |
| WO2007090739A1 (de) | 2006-02-03 | 2007-08-16 | Basf Se | Verfahren zum behandeln von substraten |
| EP2158354B1 (en) | 2007-06-12 | 2012-04-04 | Basf Se | Aqueous formulation and process for the impregnation of non-living-materials imparting a protective activity against pests |
| AR075869A1 (es) | 2009-03-19 | 2011-05-04 | Sanofi Aventis | Sintesis de azaindoles |
| KR20130065663A (ko) | 2010-05-06 | 2013-06-19 | 바이엘 크롭사이언스 아게 | 디티인 테트라카복시디이미드의 제조방법 |
| JO2998B1 (ar) | 2010-06-04 | 2016-09-05 | Amgen Inc | مشتقات بيبيريدينون كمثبطات mdm2 لعلاج السرطان |
| EP2511263A1 (en) | 2011-04-14 | 2012-10-17 | Phenex Pharmaceuticals AG | Pyrrolo sulfonamide compounds for modulation of orphan nuclear receptor RAR-related orphan receptor-gamma (RORgamma, NR1F3) activity and for the treatment of chronic inflammatory and autoimmune diseases |
| WO2014006945A1 (ja) | 2012-07-04 | 2014-01-09 | アグロカネショウ株式会社 | 2-アミノニコチン酸エステル誘導体およびこれを有効成分とする殺菌剤 |
| MX2015007710A (es) | 2012-12-19 | 2015-09-23 | Bayer Cropscience Ag | Indanilcarboxamidas difluorometil-nicotinicas. |
| BR112016023016B1 (pt) | 2014-04-11 | 2021-09-21 | Syngenta Participations Ag | Compostos derivados de n'-[2-metil-6-[2-alcoxi-etoxi]-3-piridil]-n-alquil-formamidina, composição compreendendo os referidos compostos e método de controle ou prevenção de doenças fitopatogênicas |
| UA120960C2 (uk) | 2015-03-27 | 2020-03-10 | Сінгента Партісіпейшнс Аг | Мікробіоцидні гетеробіциклічні похідні |
| EP3277666A1 (en) | 2015-04-02 | 2018-02-07 | Bayer CropScience Aktiengesellschaft | Novel 5-substituted imidazole derivatives |
| HRP20202011T1 (hr) | 2015-06-15 | 2021-04-02 | Syngenta Crop Protection Ag | Halogen-supstituirani fenoksifenilamidini i njihova upotreba kao fungicidi |
| EA035584B1 (ru) | 2015-08-12 | 2020-07-10 | Зингента Партисипейшнс Аг | Микробиоцидные гетеробициклические производные |
| CN108137538B (zh) | 2015-08-14 | 2021-02-26 | 拜耳作物科学股份公司 | 三唑衍生物、其中间体及其作为杀真菌剂的用途 |
| US10501425B2 (en) | 2015-10-02 | 2019-12-10 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| PL3356358T3 (pl) | 2015-10-02 | 2020-11-02 | Syngenta Participations Ag | Mikrobiocydowe pochodne oksadiazolowe |
| CN108289448B (zh) | 2015-12-02 | 2021-10-22 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
| UY37062A (es) | 2016-01-08 | 2017-08-31 | Syngenta Participations Ag | Derivados de aryl oxadiazol fungicidas |
| DK3426032T3 (da) | 2016-03-10 | 2020-10-19 | Syngenta Participations Ag | Mikrobiocide quinolin(thio)carboxamidderivater |
| AR108222A1 (es) * | 2016-05-05 | 2018-08-01 | Elanco Tiergesundheit Ag | Compuestos heteroaril-1,2,4-triazol y heteroaril-tetrazol |
| AR108745A1 (es) | 2016-06-21 | 2018-09-19 | Syngenta Participations Ag | Derivados de oxadiazol microbiocidas |
| PL3522715T3 (pl) | 2016-10-06 | 2021-06-28 | Syngenta Participations Ag | Mikrobiocydowe pochodne oksadiazolowe |
| WO2018153707A1 (en) | 2017-02-22 | 2018-08-30 | Basf Se | Crystalline forms of a strobilurin type compound for combating phytopathogenic fungi |
| UY37623A (es) | 2017-03-03 | 2018-09-28 | Syngenta Participations Ag | Derivados de oxadiazol tiofeno fungicidas |
| EA201992550A1 (ru) | 2017-05-02 | 2020-04-14 | Басф Се | Фунгицидные смеси, содержащие замещенные 3-фенил-5-(трифторметил)-1,2,4-оксадиазолы |
| EP3638032A1 (en) | 2017-06-14 | 2020-04-22 | Syngenta Participations AG | Fungicidal compositions |
| CN111433192A (zh) | 2017-12-04 | 2020-07-17 | 先正达参股股份有限公司 | 杀微生物的苯基脒衍生物 |
| PY1980182A (es) * | 2018-10-02 | 2020-08-21 | Syngenta Participations Ag | Compuestos de benceno y azina-amida activos como plaguicidas |
| WO2020208036A1 (en) * | 2019-04-11 | 2020-10-15 | Syngenta Crop Protection Ag | Pesticidally active diazine-amide compounds |
| JP2022545266A (ja) * | 2019-08-23 | 2022-10-26 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物的に活性なピラジン－アミド化合物 |
-
2021
- 2021-03-01 WO PCT/EP2021/055072 patent/WO2021170881A1/en not_active Ceased
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- 2021-03-01 BR BR112022017093A patent/BR112022017093A2/pt not_active IP Right Cessation
- 2021-03-01 EP EP21709395.4A patent/EP4110766A1/en not_active Withdrawn
- 2021-03-01 CN CN202180017514.6A patent/CN115244036A/zh active Pending
- 2021-03-01 US US17/802,665 patent/US20230143596A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
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| US20230143596A1 (en) | 2023-05-11 |
| EP4110766A1 (en) | 2023-01-04 |
| CN115244036A (zh) | 2022-10-25 |
| BR112022017093A2 (pt) | 2023-02-14 |
| WO2021170881A1 (en) | 2021-09-02 |
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