WO2012029672A1 - 有害生物防除剤 - Google Patents
有害生物防除剤 Download PDFInfo
- Publication number
- WO2012029672A1 WO2012029672A1 PCT/JP2011/069352 JP2011069352W WO2012029672A1 WO 2012029672 A1 WO2012029672 A1 WO 2012029672A1 JP 2011069352 W JP2011069352 W JP 2011069352W WO 2012029672 A1 WO2012029672 A1 WO 2012029672A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- halogen atom
- optionally substituted
- substituted
- alkyl
- Prior art date
Links
- 230000001473 noxious effect Effects 0.000 title abstract 2
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 133
- 239000000126 substance Substances 0.000 claims abstract description 120
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 90
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 68
- 150000001412 amines Chemical class 0.000 claims abstract description 35
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 26
- 230000000694 effects Effects 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- -1 COOR5 Proteins 0.000 claims description 252
- 150000001875 compounds Chemical class 0.000 claims description 248
- 125000005843 halogen group Chemical group 0.000 claims description 243
- 241000238631 Hexapoda Species 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 65
- 241000238876 Acari Species 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- DHQKLWKZSFCKTA-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]pyridin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1C=CC=CN1CC1=CC=C(Cl)N=C1 DHQKLWKZSFCKTA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 25
- 229940079593 drug Drugs 0.000 claims description 23
- 241001465754 Metazoa Species 0.000 claims description 22
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 22
- 239000002689 soil Substances 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
- 150000002367 halogens Chemical group 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 241000254173 Coleoptera Species 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
- 241000255925 Diptera Species 0.000 claims description 13
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 230000003071 parasitic effect Effects 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 230000001276 controlling effect Effects 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 241001414989 Thysanoptera Species 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000004419 alkynylene group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- YYELCPZJQRYUSB-UHFFFAOYSA-N n-[1-[(6-bromopyridin-3-yl)methyl]pyridin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1C=CC=CN1CC1=CC=C(Br)N=C1 YYELCPZJQRYUSB-UHFFFAOYSA-N 0.000 claims description 7
- YMDDUFGMFWBOIM-UHFFFAOYSA-N n-[1-[(6-chloro-5-fluoropyridin-3-yl)methyl]pyridin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound N1=C(Cl)C(F)=CC(CN2C(C=CC=C2)=NC(=O)C(F)(F)F)=C1 YMDDUFGMFWBOIM-UHFFFAOYSA-N 0.000 claims description 7
- DOYIIGHUVNZMAL-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]pyridin-2-ylidene]-2,2-difluoroacetamide Chemical compound FC(F)C(=O)N=C1C=CC=CN1CC1=CC=C(Cl)N=C1 DOYIIGHUVNZMAL-UHFFFAOYSA-N 0.000 claims description 7
- 235000015097 nutrients Nutrition 0.000 claims description 7
- XWHQQWVKDTVEEJ-UHFFFAOYSA-N 2-chloro-n-[1-[(6-chloropyridin-3-yl)methyl]pyridin-2-ylidene]-2,2-difluoroacetamide Chemical compound FC(F)(Cl)C(=O)N=C1C=CC=CN1CC1=CC=C(Cl)N=C1 XWHQQWVKDTVEEJ-UHFFFAOYSA-N 0.000 claims description 6
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 6
- 101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- YFSUKTJZKJIUTM-UHFFFAOYSA-N n-[1-[(2-chloropyrimidin-5-yl)methyl]pyridin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1C=CC=CN1CC1=CN=C(Cl)N=C1 YFSUKTJZKJIUTM-UHFFFAOYSA-N 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 5
- ABFADXMVCUMADD-UHFFFAOYSA-N 2,2,2-trifluoro-n-[1-[(6-fluoropyridin-3-yl)methyl]pyridin-2-ylidene]acetamide Chemical compound C1=NC(F)=CC=C1CN1C(=NC(=O)C(F)(F)F)C=CC=C1 ABFADXMVCUMADD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- SAILTMJFUSTICR-UHFFFAOYSA-N n-[1-[1-(6-chloropyridin-3-yl)ethyl]pyridin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound C1=CC=CC(=NC(=O)C(F)(F)F)N1C(C)C1=CC=C(Cl)N=C1 SAILTMJFUSTICR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 5
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical group O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims description 2
- 239000003501 hydroponics Substances 0.000 claims description 2
- 239000012466 permeate Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 186
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 186
- 238000006243 chemical reaction Methods 0.000 description 162
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 152
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 123
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 120
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 94
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
- 238000012360 testing method Methods 0.000 description 85
- 239000000243 solution Substances 0.000 description 84
- 239000002904 solvent Substances 0.000 description 79
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 74
- 239000000203 mixture Substances 0.000 description 70
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 69
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000002585 base Substances 0.000 description 56
- 230000015572 biosynthetic process Effects 0.000 description 55
- 238000003786 synthesis reaction Methods 0.000 description 53
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 52
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 52
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 51
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 49
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 44
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 44
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 38
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 229910000027 potassium carbonate Inorganic materials 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- 230000000749 insecticidal effect Effects 0.000 description 29
- 150000002170 ethers Chemical class 0.000 description 28
- 229910000104 sodium hydride Inorganic materials 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
- 239000013078 crystal Substances 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 206010021033 Hypomenorrhoea Diseases 0.000 description 24
- 239000000843 powder Substances 0.000 description 24
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 23
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 23
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 23
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 23
- 150000001408 amides Chemical class 0.000 description 23
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 23
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 23
- 229930195733 hydrocarbon Natural products 0.000 description 23
- 150000002576 ketones Chemical class 0.000 description 23
- 150000002825 nitriles Chemical class 0.000 description 23
- 239000012312 sodium hydride Substances 0.000 description 23
- 239000008096 xylene Substances 0.000 description 23
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 22
- 229940117389 dichlorobenzene Drugs 0.000 description 22
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 22
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 22
- 150000003462 sulfoxides Chemical class 0.000 description 22
- 150000001298 alcohols Chemical class 0.000 description 21
- 238000001914 filtration Methods 0.000 description 21
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 20
- 150000008046 alkali metal hydrides Chemical class 0.000 description 20
- 150000003512 tertiary amines Chemical class 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- 238000010898 silica gel chromatography Methods 0.000 description 19
- 229910000029 sodium carbonate Inorganic materials 0.000 description 19
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 18
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 18
- 150000003222 pyridines Chemical class 0.000 description 18
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 18
- 241001414720 Cicadellidae Species 0.000 description 17
- 239000007788 liquid Substances 0.000 description 17
- 240000007594 Oryza sativa Species 0.000 description 16
- 235000007164 Oryza sativa Nutrition 0.000 description 16
- 229920001213 Polysorbate 20 Polymers 0.000 description 16
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 16
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 16
- 235000009566 rice Nutrition 0.000 description 16
- 238000007605 air drying Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 150000004820 halides Chemical class 0.000 description 15
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 14
- 239000005906 Imidacloprid Substances 0.000 description 14
- 229940056881 imidacloprid Drugs 0.000 description 14
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 14
- 241001124076 Aphididae Species 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- YMIPTEDANARMCB-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]-2-methylsulfanylethanamine Chemical compound CSCCNCC1=CC=C(Cl)N=C1 YMIPTEDANARMCB-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 241000258937 Hemiptera Species 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 239000004927 clay Substances 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000003973 irrigation Methods 0.000 description 7
- 230000002262 irrigation Effects 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241001600408 Aphis gossypii Species 0.000 description 6
- 241001498622 Cixius wagneri Species 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
- 241001674048 Phthiraptera Species 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- ISVPLFUDYVCXHM-UHFFFAOYSA-N 1-[(6-chloropyridin-3-yl)methyl]pyridin-2-imine;hydrochloride Chemical compound Cl.C1=NC(Cl)=CC=C1CN1C(=N)C=CC=C1 ISVPLFUDYVCXHM-UHFFFAOYSA-N 0.000 description 5
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 5
- 241001466042 Fulgoromorpha Species 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 5
- 235000020637 scallop Nutrition 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- AFEAKGRUQYCVME-UHFFFAOYSA-N (6-chloropyridin-3-yl)methylcyanamide Chemical compound ClC1=CC=C(CNC#N)C=N1 AFEAKGRUQYCVME-UHFFFAOYSA-N 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- 241000207199 Citrus Species 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 241000256602 Isoptera Species 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 241001556089 Nilaparvata lugens Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000237503 Pectinidae Species 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 241000258242 Siphonaptera Species 0.000 description 4
- 241000254152 Sitophilus oryzae Species 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 241000270666 Testudines Species 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 235000013330 chicken meat Nutrition 0.000 description 4
- 235000020971 citrus fruits Nutrition 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 238000003892 spreading Methods 0.000 description 4
- 230000007480 spreading Effects 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- IIQBZHSAQAFGND-UHFFFAOYSA-N 1,1,1-trifluoro-4,4-bis(methylsulfanyl)but-3-en-2-one Chemical compound CSC(SC)=CC(=O)C(F)(F)F IIQBZHSAQAFGND-UHFFFAOYSA-N 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000256593 Brachycaudus schwartzi Species 0.000 description 3
- 241000282465 Canis Species 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005899 Fipronil Substances 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 241000257226 Muscidae Species 0.000 description 3
- 241000320508 Pentatomidae Species 0.000 description 3
- 241000009328 Perro Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 241001454295 Tetranychidae Species 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229940013764 fipronil Drugs 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 230000004899 motility Effects 0.000 description 3
- HKSZSGAPTPXYTI-UHFFFAOYSA-N n'-[(6-chloropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=C(Cl)N=C1 HKSZSGAPTPXYTI-UHFFFAOYSA-N 0.000 description 3
- HUAISZZSFFNQFQ-UHFFFAOYSA-N n-[bis(methylsulfanyl)methylidene]-2,2,2-trifluoroacetamide Chemical compound CSC(SC)=NC(=O)C(F)(F)F HUAISZZSFFNQFQ-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 230000017448 oviposition Effects 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000008057 potassium phosphate buffer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 206010039766 scrub typhus Diseases 0.000 description 3
- 150000003461 sulfonyl halides Chemical class 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- 239000000230 xanthan gum Substances 0.000 description 3
- 229920001285 xanthan gum Polymers 0.000 description 3
- 235000010493 xanthan gum Nutrition 0.000 description 3
- 229940082509 xanthan gum Drugs 0.000 description 3
- CUKQNVRFLCHODH-UHFFFAOYSA-N 1,1,1-trifluoro-3-(1,3-thiazolidin-2-ylidene)propan-2-one Chemical compound FC(F)(F)C(=O)C=C1NCCS1 CUKQNVRFLCHODH-UHFFFAOYSA-N 0.000 description 2
- AWKBXXMENHCBFR-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)-n-ethylethanamine Chemical compound CCNC(C)C1=CC=C(Cl)N=C1 AWKBXXMENHCBFR-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KVHVZNYXQMHZJS-UHFFFAOYSA-N 2,2-dibromo-n-[1-[(6-chloropyridin-3-yl)methyl]pyridin-2-ylidene]acetamide Chemical compound C1=NC(Cl)=CC=C1CN1C(=NC(=O)C(Br)Br)C=CC=C1 KVHVZNYXQMHZJS-UHFFFAOYSA-N 0.000 description 2
- DSJPCYWXUGROQW-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)ethanamine Chemical compound NCCC1=CC=C(Cl)N=C1 DSJPCYWXUGROQW-UHFFFAOYSA-N 0.000 description 2
- CRRMIKBAPPOPNW-UHFFFAOYSA-N 2-bromo-5-(bromomethyl)pyridine Chemical compound BrCC1=CC=C(Br)N=C1 CRRMIKBAPPOPNW-UHFFFAOYSA-N 0.000 description 2
- UDKXPYYVQQQFBR-UHFFFAOYSA-N 3-[1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-ylidene]-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)C=C1NCCN1CC1=CC=C(Cl)N=C1 UDKXPYYVQQQFBR-UHFFFAOYSA-N 0.000 description 2
- JIHHGLWJEUIQOP-UHFFFAOYSA-N 5-(bromomethyl)-2-chloro-3-fluoropyridine Chemical compound FC1=CC(CBr)=CN=C1Cl JIHHGLWJEUIQOP-UHFFFAOYSA-N 0.000 description 2
- YJOULMMJZAADRY-UHFFFAOYSA-N 5-(bromomethyl)-2-chloropyridine Chemical compound ClC1=CC=C(CBr)C=N1 YJOULMMJZAADRY-UHFFFAOYSA-N 0.000 description 2
- IUJPAAPIEURDEZ-UHFFFAOYSA-N 5-(bromomethyl)-2-fluoropyridine Chemical compound FC1=CC=C(CBr)C=N1 IUJPAAPIEURDEZ-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- 241000238421 Arthropoda Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010004194 Bed bug infestation Diseases 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 241000244203 Caenorhabditis elegans Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000223782 Ciliophora Species 0.000 description 2
- 241001414835 Cimicidae Species 0.000 description 2
- 241000254171 Curculionidae Species 0.000 description 2
- 239000005889 Cyantraniliprole Substances 0.000 description 2
- 239000005946 Cypermethrin Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 239000005900 Flonicamid Substances 0.000 description 2
- 239000005780 Fluazinam Substances 0.000 description 2
- 108010010803 Gelatin Chemical class 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000005907 Indoxacarb Substances 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000131077 Lucanidae Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000005926 Pyridalyl Substances 0.000 description 2
- 239000005927 Pyriproxyfen Substances 0.000 description 2
- 241000343234 Scirtothrips citri Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000005665 Spiromesifen Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005938 Teflubenzuron Substances 0.000 description 2
- 241000243774 Trichinella Species 0.000 description 2
- 241000256856 Vespidae Species 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound 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](O)[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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- VKEVYOIDTOPARM-UHFFFAOYSA-N benzenesulfonylformonitrile Chemical class N#CS(=O)(=O)C1=CC=CC=C1 VKEVYOIDTOPARM-UHFFFAOYSA-N 0.000 description 2
- JPUHPGALPBINPO-UHFFFAOYSA-N benzotriazole-1-carbonitrile Chemical compound C1=CC=C2N(C#N)N=NC2=C1 JPUHPGALPBINPO-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical class NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- WPBXOELOQKLBDF-UHFFFAOYSA-N cyanogen iodide Chemical compound IC#N WPBXOELOQKLBDF-UHFFFAOYSA-N 0.000 description 2
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229960005424 cypermethrin Drugs 0.000 description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 2
- SIEILFNCEFEENQ-UHFFFAOYSA-N dibromoacetic acid Chemical compound OC(=O)C(Br)Br SIEILFNCEFEENQ-UHFFFAOYSA-N 0.000 description 2
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 244000013123 dwarf bean Species 0.000 description 2
- 244000078703 ectoparasite Species 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 244000079386 endoparasite Species 0.000 description 2
- XDUKCSCITZQGGB-UHFFFAOYSA-N ethanamine;methanol Chemical compound OC.CCN XDUKCSCITZQGGB-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000004503 fine granule Substances 0.000 description 2
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 description 2
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 2
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000003958 fumigation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000008273 gelatin Chemical class 0.000 description 2
- 229920000159 gelatin Chemical class 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000003054 hormonal effect Effects 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- SLPWXZZHNSOZPX-UHFFFAOYSA-N imidazole-1-carbonitrile Chemical compound N#CN1C=CN=C1 SLPWXZZHNSOZPX-UHFFFAOYSA-N 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 2
- 125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000007096 poisonous effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 2
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000010455 vermiculite Substances 0.000 description 2
- 229910052902 vermiculite Inorganic materials 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- XPARFBOWIYMLMY-UHFFFAOYSA-N (6-chloropyridin-3-yl)methanamine Chemical compound NCC1=CC=C(Cl)N=C1 XPARFBOWIYMLMY-UHFFFAOYSA-N 0.000 description 1
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 1
- 0 **N(*)C(*)* Chemical compound **N(*)C(*)* 0.000 description 1
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- UXSNZYGTQTXRAD-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)N=C1 UXSNZYGTQTXRAD-UHFFFAOYSA-N 0.000 description 1
- UGXYEGHYZXFICM-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)ethyl 4-methylbenzenesulfonate Chemical compound C=1C=C(Cl)N=CC=1C(C)OS(=O)(=O)C1=CC=C(C)C=C1 UGXYEGHYZXFICM-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical group [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical class S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
- 125000006411 1-propenylene group Chemical group [H]\C(*)=C(\[H])C([H])([H])[H] 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- LZIPBJBQQPZLOR-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyloxyethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOS(=O)(=O)C1=CC=C(C)C=C1 LZIPBJBQQPZLOR-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
- YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 1
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 description 1
- XZJURWKNRAGMCG-UHFFFAOYSA-N 2-chloro-3-fluoro-5-methylpyridine Chemical compound CC1=CN=C(Cl)C(F)=C1 XZJURWKNRAGMCG-UHFFFAOYSA-N 0.000 description 1
- ZGSJLGPYKKQJDE-UHFFFAOYSA-N 2-chloro-5-(2H-pyridin-1-ylmethyl)pyridine Chemical compound ClC1=CC=C(C=N1)CN1CC=CC=C1 ZGSJLGPYKKQJDE-UHFFFAOYSA-N 0.000 description 1
- APRMCBSTMFKLEI-UHFFFAOYSA-N 2-chloro-5-methylpyrimidine Chemical compound CC1=CN=C(Cl)N=C1 APRMCBSTMFKLEI-UHFFFAOYSA-N 0.000 description 1
- AOSOZARHUJMBLZ-UHFFFAOYSA-N 2-fluoro-5-methylpyridine Chemical compound CC1=CC=C(F)N=C1 AOSOZARHUJMBLZ-UHFFFAOYSA-N 0.000 description 1
- AWSZRJQNBMEZOI-UHFFFAOYSA-N 2-methoxyethyl 2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate Chemical compound C=1C=C(C(C)(C)C)C=CC=1C(C#N)(C(=O)OCCOC)C(=O)C1=CC=CC=C1C(F)(F)F AWSZRJQNBMEZOI-UHFFFAOYSA-N 0.000 description 1
- 125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
- CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- WJLMZDWUGGHQEH-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-imine Chemical compound C1=NC(Cl)=CC=C1CN1C(=N)SCC1 WJLMZDWUGGHQEH-UHFFFAOYSA-N 0.000 description 1
- RRTIBEYIUWKVJY-UHFFFAOYSA-N 3-[1-(6-chloropyridin-3-yl)ethylamino]propanenitrile Chemical compound N#CCCNC(C)C1=CC=C(Cl)N=C1 RRTIBEYIUWKVJY-UHFFFAOYSA-N 0.000 description 1
- YMJBGGDWKVPBMD-UHFFFAOYSA-N 3-[3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene]-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)C=C1SCCN1CC1=CC=C(Cl)N=C1 YMJBGGDWKVPBMD-UHFFFAOYSA-N 0.000 description 1
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 1
- AJZDHLHTTJRNQJ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(tetrazol-1-yl)ethyl]benzamide Chemical compound N1(N=NN=C1)CCNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O AJZDHLHTTJRNQJ-UHFFFAOYSA-N 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
- GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 1
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
- 239000005651 Acequinocyl Substances 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241001465979 Adelgidae Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000256173 Aedes albopictus Species 0.000 description 1
- 241001617418 Aelurostrongylus abstrusus Species 0.000 description 1
- 241000218473 Agrotis Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238682 Amblyomma americanum Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 241000244023 Anisakis Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000273311 Aphis spiraecola Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241000244188 Ascaris suum Species 0.000 description 1
- 241000968069 Asterolecaniidae Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- 241001302798 Bemisia argentifolii Species 0.000 description 1
- 239000005734 Benalaxyl Substances 0.000 description 1
- 239000005653 Bifenazate Substances 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 239000005740 Boscalid Substances 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- 241000243770 Bursaphelenchus Species 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- RJYFGQIOVOVPOR-DTQAZKPQSA-N CC(/N=C1/N(Cc(cn2)ccc2Cl)C=CC=C1)=O Chemical compound CC(/N=C1/N(Cc(cn2)ccc2Cl)C=CC=C1)=O RJYFGQIOVOVPOR-DTQAZKPQSA-N 0.000 description 1
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 description 1
- 241001313742 Callosobruchus chinensis Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001057794 Cerococcidae Species 0.000 description 1
- 241000258920 Chilopoda Species 0.000 description 1
- 241000237515 Chlamys nipponensis Species 0.000 description 1
- 239000005886 Chlorantraniliprole Substances 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- 239000005887 Chromafenozide Substances 0.000 description 1
- 241000931705 Cicada Species 0.000 description 1
- XUDXFQKWCMCYAM-UHFFFAOYSA-N ClC1=NC=C(C=N1)CN1C(C=CC=C1)=NC(C(F)(F)F)=O.ClC(C(=O)N=C1N(C=CC=C1)CC=1C=NC(=CC1)Cl)(F)F Chemical compound ClC1=NC=C(C=N1)CN1C(C=CC=C1)=NC(C(F)(F)F)=O.ClC(C(=O)N=C1N(C=CC=C1)CC=1C=NC(=CC1)Cl)(F)F XUDXFQKWCMCYAM-UHFFFAOYSA-N 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000699662 Cricetomys gambianus Species 0.000 description 1
- 241000270722 Crocodylidae Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000258924 Ctenocephalides felis Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 239000005754 Cyazofamid Substances 0.000 description 1
- 239000005755 Cyflufenamid Substances 0.000 description 1
- 239000005655 Cyflumetofen Substances 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 241000252233 Cyprinus carpio Species 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 1
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 241001480793 Dermacentor variabilis Species 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 1
- 241000489947 Diabrotica virgifera virgifera Species 0.000 description 1
- 239000005759 Diethofencarb Substances 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 241000258963 Diplopoda Species 0.000 description 1
- 241001279823 Diuraphis noxia Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241001581006 Dysaphis plantaginea Species 0.000 description 1
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 1
- 241000738498 Epitrix pubescens Species 0.000 description 1
- 241000970939 Eriococcidae Species 0.000 description 1
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005896 Etofenprox Substances 0.000 description 1
- 239000005897 Etoxazole Substances 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 description 1
- 239000005777 Fenpropidin Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005902 Flupyradifurone Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 239000005959 Fosthiazate Substances 0.000 description 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 241000578422 Graphosoma lineatum Species 0.000 description 1
- 241000255990 Helicoverpa Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005797 Iprovalicarb Substances 0.000 description 1
- 241000052897 Ixodes hirsti Species 0.000 description 1
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001057668 Lecanodiaspididae Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000131091 Lucanus cervus Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 241001648788 Margarodidae Species 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- 239000005805 Mepanipyrim Substances 0.000 description 1
- 239000005914 Metaflumizone Substances 0.000 description 1
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000005811 Myclobutanil Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241001057671 Ortheziidae Species 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000223785 Paramecium Species 0.000 description 1
- 241000237509 Patinopecten sp. Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000517324 Pediculidae Species 0.000 description 1
- 241000517307 Pediculus humanus Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 241000048273 Periplaneta japonica Species 0.000 description 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000005923 Pirimicarb Substances 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241000718000 Pulex irritans Species 0.000 description 1
- 239000005925 Pymetrozine Substances 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- MWMQNVGAHVXSPE-UHFFFAOYSA-N Pyriprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SC(F)F)=C1NCC1=CC=CC=N1 MWMQNVGAHVXSPE-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- 241000167882 Rhopalosiphum maidis Species 0.000 description 1
- 241000700141 Rotifera Species 0.000 description 1
- 241000242677 Schistosoma japonicum Species 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 241000238371 Sepiidae Species 0.000 description 1
- 241000180219 Sitobion avenae Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 241000256011 Sphingidae Species 0.000 description 1
- 239000005929 Spinetoram Substances 0.000 description 1
- GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 description 1
- 239000005930 Spinosad Substances 0.000 description 1
- 239000005664 Spirodiclofen Substances 0.000 description 1
- 239000005931 Spirotetramat Substances 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- 239000005934 Sulfoxaflor Substances 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
- 241000255628 Tabanidae Species 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- 241000044038 Tenebroides mauritanicus Species 0.000 description 1
- 239000005940 Thiacloprid Substances 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005845 Tolclofos-methyl Substances 0.000 description 1
- 241000244030 Toxocara canis Species 0.000 description 1
- 241000244020 Toxocara cati Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- FMPFURNXXAKYNE-UHFFFAOYSA-N [2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]quinolin-4-yl] methyl carbonate Chemical compound C1=C2C(OC(=O)OC)=C(C)C(CC)=NC2=CC(C)=C1OC1=CC=C(OC(F)(F)F)C=C1 FMPFURNXXAKYNE-UHFFFAOYSA-N 0.000 description 1
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
- INISTDXBRIBGOC-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate 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-CGAIIQECSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- QDRXWCAVUNHOGA-UHFFFAOYSA-N acequinocyl Chemical group C1=CC=C2C(=O)C(CCCCCCCCCCCC)=C(OC(C)=O)C(=O)C2=C1 QDRXWCAVUNHOGA-UHFFFAOYSA-N 0.000 description 1
- KBVVMANFPYCWAO-UHFFFAOYSA-N acetamide;acetonitrile Chemical compound CC#N.CC(N)=O KBVVMANFPYCWAO-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229960002587 amitraz Drugs 0.000 description 1
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
- 150000008059 anilinopyrimidines Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- USRKFGIXLGKMKU-ABAIWWIYSA-N benthiavalicarb-isopropyl Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@H](C(C)C)NC(=O)OC(C)C)=NC2=C1 USRKFGIXLGKMKU-ABAIWWIYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229940118790 boscalid Drugs 0.000 description 1
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 235000021329 brown rice Nutrition 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005622 butynylene group Chemical group 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- RXDMAYSSBPYBFW-UHFFFAOYSA-N carpropamid Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1(CC)C(C)C1(Cl)Cl RXDMAYSSBPYBFW-UHFFFAOYSA-N 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- ZVTQWXCKQTUVPY-UHFFFAOYSA-N chloromethylcyclopropane Chemical compound ClCC1CC1 ZVTQWXCKQTUVPY-UHFFFAOYSA-N 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001916 cyano esters Chemical class 0.000 description 1
- 150000005245 cyanopyrroles Chemical class 0.000 description 1
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004980 cyclopropylene group Chemical group 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- APJLTUBHYCOZJI-VZCXRCSSSA-N cyenopyrafen Chemical compound CC1=NN(C)C(\C(OC(=O)C(C)(C)C)=C(/C#N)C=2C=CC(=CC=2)C(C)(C)C)=C1C APJLTUBHYCOZJI-VZCXRCSSSA-N 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- YEJGPFZQLRMXOI-PKEIRNPWSA-N diclocymet Chemical compound N#CC(C(C)(C)C)C(=O)N[C@H](C)C1=CC=C(Cl)C=C1Cl YEJGPFZQLRMXOI-PKEIRNPWSA-N 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000856 effect on pests Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000000967 entomopathogenic effect Effects 0.000 description 1
- YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical group C=CC1CC1 YIWFBNMYFYINAD-UHFFFAOYSA-N 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- HEZNVIYQEUHLNI-UHFFFAOYSA-N ethiofencarb Chemical compound CCSCC1=CC=CC=C1OC(=O)NC HEZNVIYQEUHLNI-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 1
- 229950005085 etofenprox Drugs 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- GOWLARCWZRESHU-AQTBWJFISA-N ferimzone Chemical compound C=1C=CC=C(C)C=1C(/C)=N\NC1=NC(C)=CC(C)=N1 GOWLARCWZRESHU-AQTBWJFISA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- MXWAGQASUDSFBG-RVDMUPIBSA-N fluacrypyrim Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C(F)(F)F)=NC(OC(C)C)=N1 MXWAGQASUDSFBG-RVDMUPIBSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
- QOIYTRGFOFZNKF-UHFFFAOYSA-N flupyradifurone Chemical compound C=1C(=O)OCC=1N(CC(F)F)CC1=CC=C(Cl)N=C1 QOIYTRGFOFZNKF-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 244000037671 genetically modified crops Species 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940045189 glucose-6-phosphate Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229940074076 glycerol formal Drugs 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- HICUREFSAIZXFQ-JOWPUVSESA-N i9z29i000j Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\[C@H](OC(=O)C(=N/OC)\C=1C=CC=CC=1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 HICUREFSAIZXFQ-JOWPUVSESA-N 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 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 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000028454 lice infestation Diseases 0.000 description 1
- 229920005610 lignin Chemical class 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- ZOTBXTZVPHCKPN-ZPHPHTNESA-N methyl (2z)-2-methoxyimino-2-[2-[(2-methylphenoxy)methyl]phenyl]acetate Chemical group CO\N=C(/C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-ZPHPHTNESA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- KFOHPCNQDRSVDQ-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-4,5-dihydroimidazol-2-yl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1NCCN1CC1=CC=C(Cl)N=C1 KFOHPCNQDRSVDQ-UHFFFAOYSA-N 0.000 description 1
- NWOFWGTYDVCXRD-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]pyridin-2-ylidene]-2,2,3,3,3-pentafluoropropanamide Chemical compound FC(F)(F)C(F)(F)C(=O)N=C1C=CC=CN1CC1=CC=C(Cl)N=C1 NWOFWGTYDVCXRD-UHFFFAOYSA-N 0.000 description 1
- DVBBNIYQXQOIFX-UHFFFAOYSA-N n-[3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N=C1SCCN1CC1=CC=C(Cl)N=C1 DVBBNIYQXQOIFX-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- DSOOGBGKEWZRIH-UHFFFAOYSA-N nereistoxin Chemical class CN(C)C1CSSC1 DSOOGBGKEWZRIH-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 230000004783 oxidative metabolism Effects 0.000 description 1
- 229960000321 oxolinic acid Drugs 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- FURYAADUZGZUGQ-UHFFFAOYSA-N phenoxybenzene;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 FURYAADUZGZUGQ-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Chemical class 0.000 description 1
- 239000005017 polysaccharide Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- WHMZYGMQWIBNOC-UHFFFAOYSA-N propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)C)C=C1OC WHMZYGMQWIBNOC-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical class [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- DDIQWGKUSJOETH-UHFFFAOYSA-N pyrafluprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SCF)=C1NCC1=CN=CC=N1 DDIQWGKUSJOETH-UHFFFAOYSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 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
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Images
Classifications
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues 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
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-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
- 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
- A01N47/02—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 no bond to a nitrogen atom
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/04—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 no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C261/00—Derivatives of cyanic acid
- C07C261/04—Cyanamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen 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
- C07D401/06—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 carbon chain containing only aliphatic 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
- 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
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Definitions
- the present invention relates to a novel amine derivative and a pest control agent using the same.
- Non-Patent Document 1 neonicotinoids represented by imidacloprid, and main insecticides including phenylpyrazoles represented by fipronil, etc.
- Patent Document 1 describes a monoalkylamine compound having a cyano group on the nitrogen atom, and its insecticidal activity against aphids, but the specific disclosure of the dialkylamine compound is not disclosed. There is no description about the control activity against pests other than aphids.
- Patent Document 2 describes an amine derivative having a 2,6-dichloro-4-pyridyl group and having a carboxyl group on the nitrogen atom, and its bactericidal and insecticidal activities. The ring is not disclosed.
- Non-Patent Document 2 and Non-Patent Document 3 disclose amine derivatives having a 6-chloro-3-pyridyl group and an acetyl group on the nitrogen atom as metabolites or reaction intermediates. Its pest control activity is not described.
- Non-Patent Document 4 discloses an amine derivative having a 6-chloro-3-pyridyl group and having an N-methylcarbamoyl group and an N-formylcarbamoyl group on the nitrogen atom. Is not described.
- Patent Document 3 discloses a plurality of compounds having the same ring structure as the compound represented by the formula (Ie), but its use is a herbicide and there is no description about pest control.
- Patent Document 4 discloses the structural formula of N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide. However, the production method thereof is not disclosed at all, and is not included in the list of compound groups in which pest control activity is recognized (No. 3 of Patent Document 4). Table 2, Table 3).
- Patent Document 5 discloses the structural formula of N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide. However, the production method thereof is not disclosed at all (Example 7 of Table 7 of Patent Document 5), and is not listed as an example of a compound having pest control activity in the Examples.
- Non-Patent Document 5 discloses a plurality of compounds having a ring structure similar to the compound represented by the formula (Ie) described later, but is only disclosed as a synthetic intermediate.
- Patent Document 6 discloses a plurality of compounds having a ring structure similar to the compound represented by the formula (Ie), but does not disclose or suggest a compound having a trifluoroacetic acid imino structure.
- One of the important problems in the present invention is that it has an excellent control effect on the green planthopper, white-spotted planthopper, and brown planthopper, which have become important pests in the field of rice in recent years. It is intended to provide a drug that exhibits high activity and that can be used safely by reducing the opportunity for workers to be exposed to the drug during soil treatment, seed treatment, seedling box treatment, and the like.
- the present inventors have found that the amine derivative represented by the chemical formula (I) has excellent activity as a pest control agent.
- a pest control agent comprising at least one compound represented by the following chemical formula (I) and a salt thereof.
- Ar represents an optionally substituted phenyl group or an optionally substituted 5- to 6-membered heterocycle
- R1 represents a hydrogen atom or a C1-6 alkyl group
- R2 represents a C1-6 alkylcarbonyl group in which the alkyl part may be substituted with a halogen atom, and C1 ⁇ in which the alkyl part may be substituted with a halogen atom.
- R3 is a C1-8 alkylene group optionally substituted by a halogen atom, a C2-8 alkenylene group optionally substituted by a halogen atom, a C2-8 alkynylene group optionally substituted by a halogen atom, substituted An optionally substituted phenylene group, or an optionally substituted 5- to 6-membered heterocyclic divalent group, R4 represents a hydrogen atom, a cyano group, an optionally substituted phenyl group, an optionally substituted 3- to 8-membered cyclic alkyl group, an optionally substituted 3- to 8
- R6 and R7 each independently represent a C1-6 alkyl group which may be substituted with a hydrogen atom or a halogen atom.
- R8 represents an optionally substituted C1-6 alkyl group, and the optionally substituted substituent is a halogen atom, a C1-4 alkyloxycarbonyl group, a C1-4 alkylcarbonyl group, a halogen atom or a halogen atom.
- a benzoyl group, a C1-4 alkyloxy group, and a C1-4 alkylthio group which may be substituted with an optionally substituted C1-4 alkyl group.
- R9 and R10 are independently of each other a hydrogen atom, a formyl group, a C1-6 alkyl group optionally substituted with a halogen, a C1-6 alkylcarbonyl group optionally substituted with a halogen atom, an alkyl moiety Is an optionally substituted C1-6 alkylcarbonyloxy group, an optionally substituted phenyl group (the optionally substituted substituent is a halogen atom or optionally substituted by a halogen atom) C1-4 alkyl group, C1-4 alkyloxy group which may be substituted with a halogen atom), benzyl group which may be substituted (optionally substituted substituents are substituted with halogen or halogen An optionally substituted C1-4 alkyl group, a C1-4 alkyloxy group optionally substituted by halogen), or R9 and R10 form a ring Or shows a 3-10 membered heterocycloalkyl group containing atom, or N, R9
- N, R2, R3, and R4 may be taken together to represent a group represented by the formula (E).
- Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-6 alkyl group optionally substituted by a halogen atom, a C1-6 alkyloxy group optionally substituted by a halogen atom, a cyano group, a formyl group, a nitro group
- R4e represents a C1-6 alkyl group substituted by halogen or a C1-6 alkyloxy group optionally substituted by halogen.
- R2 does not represent a C1-6 alkyloxycarbonyl group in which the alkyl moiety may be substituted with a halogen atom.
- Ar in chemical formula (I) is a 6-chloro-3-pyridyl group or a 5-chloro-3-thiazolyl group.
- R2 in the chemical formula (I) is a C1-6 alkylcarbonyl group in which the alkyl part may be substituted with a halogen atom, a C1-6 alkylsulfonyl group in which the alkyl part may be substituted with a halogen atom, or cyano
- the compound represented by the chemical formula (Ie) is N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroaceta N- [1-((6-chloro-5-fluoropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1- ((6-Fluoropyridin-3-yl) methyl) pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1-((6-bromopyridin-3-yl) Methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1- (1- (6-chloropyridin-3-yl) ethyl) pyridine-2 (1H)
- At least one insect species selected from the group consisting of lepidopterous insects, semilepidopterous insects, thrips insect pests, diptera insects, coleoptera insects, animal parasitic fleas and mites, and dog filamentous insects
- the pest control agent according to any one of (1) to (8), which has a control activity against.
- Ar represents an optionally substituted phenyl group or an optionally substituted 5- to 6-membered heterocycle
- R1 represents a hydrogen atom or a C1-6 alkyl group
- R2 represents a C1-6 alkylcarbonyl group in which the alkyl part may be substituted with a halogen atom, and C1 ⁇ in which the alkyl part may be substituted with a halogen atom.
- R3 is a C1-8 alkylene group optionally substituted by a halogen atom, a C2-8 alkenylene group optionally substituted by a halogen atom, a C2-8 alkynylene group optionally substituted by a halogen atom, substituted An optionally substituted phenylene group, or an optionally substituted 5- to 6-membered heterocyclic divalent group, R4 represents a hydrogen atom, a cyano group, an optionally substituted phenyl group, an optionally substituted 3- to 8-membered cyclic alkyl group, an optionally substituted 3- to 8
- R6 and R7 each independently represent a C1-6 alkyl group which may be substituted with a hydrogen atom or a halogen atom.
- R8 represents an optionally substituted C1-6 alkyl group, and the optionally substituted substituent is a halogen atom, a C1-4 alkyloxycarbonyl group, a C1-4 alkylcarbonyl group, a halogen atom or a halogen atom.
- a benzoyl group, a C1-4 alkyloxy group, and a C1-4 alkylthio group which may be substituted with an optionally substituted C1-4 alkyl group.
- R9 and R10 are independently of each other a hydrogen atom, a formyl group, a C1-6 alkyl group optionally substituted by a halogen atom, a C1-6 alkylcarbonyl group optionally substituted by a halogen atom, an alkyl A C1-6 alkylcarbonyloxy group in which the moiety may be substituted by a halogen atom, an optionally substituted phenyl group (the optionally substituted substituent may be a halogen atom or a halogen atom, A good C1-4 alkyl group, an optionally substituted C1-4 alkyloxy group), an optionally substituted benzyl group (optionally substituted substituents include halogen or halogen substituted) A C1-4 alkyl group which may be substituted, a C1-4 alkyloxy group which may be substituted by a halogen) or one or more of R9 and R10 forming a ring Or shows a 3-10 membered heterocycloalkyl group
- N, R2, R3, and R4 together may represent a group represented by the formula (E) .
- Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-6 alkyl group optionally substituted by halogen, a C1-6 alkyloxy group optionally substituted by a halogen atom, a cyano group, a formyl group, a nitro group.
- R4e represents a C1-6 alkyl group substituted by a halogen atom or a C1-6 alkyloxy group optionally substituted by a halogen atom.
- R2 does not represent a C1-6 alkyloxycarbonyl group in which the alkyl moiety may be substituted with a halogen atom
- Ar represents 6-chloro-3
- R 1 represents a pyridyl group
- R 1 represents a hydrogen atom
- Y represents a 5-methyl group
- R 4e does not represent CF 3] (13)
- R2 in the chemical formula (I) is a C1-6 alkylcarbonyl group in which the alkyl part may be substituted with a halogen atom, a C1-6 alkylsulfonyl group in which the alkyl part may be substituted with a halogen atom, or The amine derivative or salt thereof according to (12) or (13), which is a cyano group.
- Ar ′ represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group
- Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-6 alkyl group optionally substituted by a halogen atom, C1-6 alkyloxy group optionally substituted by a halogen atom, cyano group, formyl group, nitro group
- R4e is a C1-6 alkyl group substituted by halogen or C1-6 optionally substituted by halogen 6 represents an alkyloxy group.
- the compound represented by the above formula (Ie ′) is N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoro Loacetamide, N- [1-((6-chloro-5-fluoropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [ 1-((6-Fluoropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1-((6-bromopyridin-3- Yl) methyl) pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide, N- [1- (1- (6-chloropyridin-3-yl) ethyl) pyridine-2,
- At least one insect species selected from the group consisting of lepidopterous insects, semilepidopterous insects, thrips insect pests, diptera insects, coleoptera insects, animal parasitic fleas and mites, and dog filamentous insects
- the amine derivative or the salt thereof according to any one of (12) to (19), which has a controlling activity against.
- (21) A method for controlling pests using the pest control agent according to any one of (1) to (9) or the amine derivative or salt thereof according to any one of (12) to (20).
- N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide crystal powder prepared by the first production method It is a graph which shows the result of a X-ray crystal analysis. Difference in crystals of N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide prepared by the first production method It is a graph which shows the result of a scanning calorimetric analysis.
- N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide crystal powder prepared by the second production method It is a graph which shows the result of a X-ray crystal analysis. Differential of crystals of N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide prepared by the second production method It is a graph which shows the result of a scanning calorimetric analysis.
- Ar is an optionally substituted phenyl group, or an optionally substituted 5 to 6 membered member.
- substituents examples include a halogen atom, a C1-4 alkyl group that may be substituted with a halogen atom, an alkyloxy group that may be substituted with a halogen atom, a hydroxyl group, a cyano group, a nitro group, and the like.
- a halogen atom or a C1-4 alkyl group optionally substituted by a halogen atom.
- phenyl group examples include phenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3-nitrophenyl group, 4-nitrophenyl group.
- the optionally substituted 5- to 6-membered heterocycle include pyridine, thiazole, tetrahydrofuran, furan and the like, preferably a 3-pyridyl group and a 3-thiazolyl group, more preferably 6 -Chloro-3-pyridyl group, 5-chloro-3-thiazolyl group, 6-chloro-5-fluoro-3-pyridyl group, 6-bromo-3-pyridyl group, 6-fluoro-3-pyridyl group, 5, 6-dichloro-3-pyridyl group, 6-trifluoromethyl-3-pyridyl group, particularly preferably 6-chloro-3-pyridyl group, 6-fluoro-3-pyridyl group, 6-chloro-5-fluoro 3-pyridyl group and 6-bromo-3-pyridyl group.
- the “C1-6 alkyl group” represented by R1 is a chain, branched, cyclic, or a combination thereof having 1 to 6 carbon atoms. When it contains a branched or cyclic alkyl group, it is clear that the carbon number is 3 or more. Specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a cyclopropyl group, and a methyl group and an ethyl group are preferable.
- R2 is a C1-6 alkylcarbonyl group in which the alkyl part may be substituted with a halogen atom, a C1-6 alkyloxycarbonyl group in which the alkyl part may be substituted with a halogen atom, and the alkyl part is substituted with a halogen atom.
- R3 is a C1-8 alkylene group optionally substituted by a halogen atom, a C2-8 alkenylene group optionally substituted by a halogen atom, a C2-8 alkynylene group optionally substituted by a halogen atom, substituted A phenylene group which may be substituted, or a 5- to 6-membered heterocyclic divalent group which may be substituted, preferably a C1-8 alkylene group which may be substituted with a halogen atom.
- R4 represents a hydrogen atom, a cyano group, an optionally substituted phenyl group, an optionally substituted 3- to 8-membered cyclic alkyl group, an optionally substituted 3- to 8-membered heterocycle, a halogen atom, OR5, OCOR5, OCOOR5, COR5, COOR5, SR5, SOR5, SO 2 R5, N-CO-OR8, N-CO-SR8, N-CS-OR8, N-CS-SR8, NO-CO-R8, O- CO-R8, O-CO-OR8, O-CO-SR8, O-CS-OR8, O-CS-SR8, O-CS-SR8, S-CS-SR8, S-CO-SR8, S-CS-SR8, S-CO-SR8, S-CS-SR8, S-CO-SR8, S-CS-SR8, S-CO-SR8, S-CS-SR8, S-CO-SR8, S-CS-R8, S-CO-SR8, S-CS-R8, S-CO-SR8, S-CS-R8, S-
- R5 represents a C1-6 alkyl group which may be substituted with a halogen atom, an aryl group which may be substituted with a halogen atom, or an aralkyl group which may be substituted with a halogen atom.
- R6 and R7 each independently represent a C1-6 alkyl group which may be substituted with a hydrogen atom or a halogen atom.
- R8 represents an optionally substituted C1-6 alkyl group, and the optionally substituted substituent is a halogen atom, a C1-4 alkyloxycarbonyl group, a C1-4 alkylcarbonyl group, a halogen atom or a halogen atom.
- a benzoyl group, a C1-4 alkyloxy group, and a C1-4 alkylthio group which may be substituted with an optionally substituted C1-4 alkyl group.
- R9 and R10 are independently of each other a hydrogen atom, a formyl group, a C1-6 alkyl group optionally substituted by a halogen atom, a C1-6 alkylcarbonyl group optionally substituted by a halogen atom, an alkyl A C1-6 alkylcarbonyloxy group in which the moiety may be substituted by a halogen atom, an optionally substituted phenyl group (the optionally substituted substituent may be a halogen atom or a halogen atom, A good C1-4 alkyl group, an optionally substituted C1-4 alkyloxy group), an optionally substituted benzyl group (optionally substituted substituents include halogen or halogen substituted) A C1-4 alkyl group which may be substituted, a C1-4 alkyloxy group which may be substituted by a halogen) or one or more of R9 and R10 forming a ring Or shows a 3-10 membered heterocycloalkyl group
- the “C1-6 alkyl group optionally substituted by a halogen atom” represented by R5, R6, R7, R8, R9, and R10 is a chain, branched, cyclic, or a combination thereof having 1 to 6 carbon atoms.
- the upper limit of the number of halogen atoms that are alkyl groups and may be substituted is the number of hydrogen atoms that the alkyl group has. When it contains a branched or cyclic alkyl group, it is clear that the carbon number is 3 or more.
- C1-6 alkyl group optionally substituted by a halogen atom represented by R5 include a methyl group, an ethyl group, an n-propyl group, a difluoromethyl group, a trifluoromethyl group, a chloromethyl group, A 2-trifluoroethyl group is mentioned.
- C1-6 alkyl group optionally substituted by a halogen atom represented by R6 and R7 include a methyl group, an ethyl group, an n-propyl group, a difluoromethyl group, a trifluoromethyl group, and a chloromethyl group.
- R6 and R7 include a methyl group, an ethyl group, an n-propyl group, a difluoromethyl group, a trifluoromethyl group, and a chloromethyl group.
- 2-trifluoroethyl group 2-trifluoroethyl group.
- C1-6 alkyl group optionally substituted by a halogen atom represented by R8 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an n-pentyl group, A 2-trifluoroethyl group and a 2-chloroethyl group are exemplified, and a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and an n-pentyl group are preferable.
- C1-6 alkyl group optionally substituted by a halogen atom represented by R9 and R10 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and an n-pentyl group.
- Group, 2-trifluoroethyl group, and 2-chloroethyl group are preferable, and methyl group and ethyl group are preferable.
- C1-6 alkylcarbonyl group in which the alkyl moiety may be substituted with a halogen atom represented by R2, R9 and R10
- C1-6 alkyloxycarbonyl in which the alkyl moiety may be substituted with a halogen atom represented by R2 Group "
- the alkyl moiety in the “C1-6 alkylcarbonyloxy group in which the alkyl moiety may be substituted with a halogen atom” represented by R9 and R10 has 1 to 6 carbon atoms, and is linear, branched, cyclic, or their An alkyl group represented by a combination.
- the upper limit of the number of halogen atoms that may be substituted is the number of hydrogen
- the “C1-6 alkylcarbonyl group in which the alkyl moiety may be substituted with a halogen atom” represented by R2 is specifically an acetyl group, an ethylcarbonyl group, an n-propylcarbonyl group, a difluoroacetyl group, a trifluoroacetyl group.
- Group, pentafluoroacetyl group, chloroacetyl group, trichloroacetyl group, and trifluoroacetyl group is preferable.
- the “C1-6 alkyloxycarbonyl group in which the alkyl moiety may be substituted with a halogen atom” represented by R2 specifically includes a methyloxycarbonyl group, an ethyloxycarbonyl group, an n-propyloxycarbonyl group, a chloromethyl Examples thereof include an oxycarbonyl group and a 2-trifluoroethyloxycarbonyl group.
- the “C1-6 alkylsulfonyl group in which the alkyl moiety may be substituted with a halogen atom” represented by R2 is specifically a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, a difluoromethylsulfonyl group, a trifluoride group, Examples thereof include a fluoromethylsulfonyl group, a trichloromethylsulfonyl group, and a 2-trifluoromethylsulfonyl group, and a trifluoromethylsulfonyl group is preferable.
- C1-6 O, O′-alkylphosphoryl group in which the alkyl moiety may be substituted with a halogen atom” represented by R2 is specifically O, O′-dimethylphosphoryl group, O, O′-diethyl. A phosphoryl group is mentioned.
- the “C1-6 alkylcarbonyl group in which the alkyl moiety may be substituted with a halogen atom” represented by R5 is specifically an acetyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, 2-chloro An ethylcarbonyl group is mentioned.
- the “C1-6 alkylcarbonyl group in which the alkyl moiety may be substituted with a halogen atom” represented by R9 and R10 specifically includes a methyloxycarbonyl group, an ethyloxycarbonyl group, an n-propyloxycarbonyl group, isopropyl Examples thereof include an oxycarbonyl group and a 2-chloroethyloxycarbonyl group.
- the “C1-6 alkylcarbonyloxy group in which the alkyl moiety may be substituted with a halogen atom” represented by R9 and R10 specifically includes a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, Examples include isopropylcarbonyloxy group and 2-chloroethylcarbonyloxy group.
- the “C1-8 alkylene group optionally substituted by a halogen atom” represented by R3 is a C1-C8 alkylene group represented by a linear, branched, cyclic, or combination thereof, and is substituted.
- the upper limit of the number of halogen atoms that may be used is the number of hydrogen atoms of the alkyl group. When it contains a branched or cyclic alkyl group, it is clear that the carbon number is 3 or more.
- Specific examples include methylene group, ethylene group, propylene group, butylene group, fluoromethylene group, 1-chloroethylene group, 2-methylethylene group, cyclopropylene group, 2-cyclopropylethylene group, 1,3- A cyclopentylene group etc. are mentioned, Preferably they are a methylene group, ethylene group, and a propylene group, More preferably, it is an ethylene group.
- the “C2-8 alkenylene group optionally substituted by a halogen atom” represented by R3 is an alkenylene group having 2 to 8 carbon atoms represented by a linear, branched, cyclic or combination thereof, and is substituted.
- the upper limit of the number of halogen atoms that may be used is the number of hydrogen atoms of the alkyl group. When it contains a branched or cyclic alkyl group, it is clear that the carbon number is 3 or more. Specific examples include vinylene group, 1-propenylene group, 2-fluoro-1-propenylene group, 2-methyl-1-propenylene group, and 2-cyclohexene-1,4-ylene group.
- the “C2-8 alkynylene group optionally substituted by a halogen atom” represented by R3 is a C2-C8 alkynylene group represented by a straight chain, branched, cyclic, or a combination thereof, and is substituted.
- the upper limit of the number of halogen atoms that may be used is the number of hydrogen atoms of the alkyl group. When it contains a branched or cyclic alkyl group, it is clear that the carbon number is 3 or more. Specific examples include propynylene group and butynylene group, preferably 1-propynylene.
- the “optionally substituted phenylene” represented by R3 is a divalent group excluding the two hydrogen atoms of benzene, and examples of the substituent include a halogen atom and a C1 ⁇ 4Alkyl group, alkyloxy group optionally substituted by a halogen atom, hydroxyl group, cyano group, nitro group and the like can be mentioned. Specific examples include a phenylene group, a 4-fluorophenylene group, and a 2-methylphenylene group.
- the “optionally substituted 5- to 6-membered heterocyclic divalent group” represented by R3 is a divalent group excluding two hydrogen atoms of the 5- to 6-membered heterocyclic ring.
- a specific example is a 2-pyridinylene group.
- Examples of the substituent that may be substituted by the “optionally substituted pyridyl group” or “optionally substituted pyrimidyl group” represented by Ar ′ of the compound represented by the formula (Ie ′) include a halogen atom, halogen Examples thereof include a C1-4 alkyl group optionally substituted by an atom, an alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, a nitro group, and the like, and preferably a halogen atom.
- Preferred embodiments of Ar of the compound represented by the formula (Ie) and Ar ′ of the compound represented by the formula (Ie ′) include 3-pyridyl group, 6-chloro-3-pyridyl group, 5-chloro-3-thiazolyl Group, 6-chloro-5-fluoro-3-pyridyl group, 6-bromo-3-pyridyl group, 6-fluoro-3-pyridyl group, 5,6-dichloro-3-pyridyl group, 6-trifluoromethyl- 3-pyridyl group, 2-chloro-5-pyrimidyl group, more preferably 6-chloro-3-pyridyl group, 6-fluoro-3-pyridyl group, 6-chloro-5-fluoro-3-pyridyl group, 6-bromo-3-pyridyl group and 2-chloro-5-pyrimidyl group.
- Y in the compounds represented by the formulas (Ie) and (Ie ′) represents 1 to 3 substituents which may be the same or different.
- the “C1-6 alkyl group optionally substituted by a halogen atom” represented by Y in the compounds represented by formula (Ie) and (Ie ′) is a chain, branched, cyclic, or a combination thereof.
- the upper limit of the number of halogen atoms which are alkyl groups of 1 to 6 and may be substituted is the number of hydrogen atoms of the alkyl group. When it contains a branched or cyclic alkyl group, it is clear that the carbon number is 3 or more.
- a methyl group an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a trifluoromethyl group, and a 2-chloroethyl group, and a methyl group is preferable.
- C1-6 alkyloxy group optionally substituted with halogen represented by Y include a methoxy group, an ethoxy group, a trifluoromethyl group, and a difluoromethyl group.
- a hydrogen atom or a halogen is preferable, and a hydrogen atom is more preferable.
- the “C1-6 alkyl group substituted by a halogen atom” represented by R4e of the compounds represented by the formula (Ie) and the formula (Ie ′) is a chain, branched, cyclic, or a combination thereof having 1 to 6 is an alkyl group, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms of the alkyl group. When it contains a branched or cyclic alkyl group, it is clear that the carbon number is 3 or more.
- C1-6 alkyloxy group optionally substituted with halogen represented by R4e include a methoxy group, an ethoxy group, an isopropyloxy group, a trifluoromethoxy group, and the like.
- R4e is a C1-6 alkyl group optionally substituted by halogen, and more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group, or a pentafluoroethyl group.
- Examples of the salt of the amine derivative represented by the chemical formula (I), which is an active ingredient of the pest control agent provided by the present invention, are acid addition salts that are acceptable in agricultural and veterinary medicine, such as hydrochloride, nitrate, sulfuric acid. Examples thereof include salts, phosphates and acetates.
- Ar is 4-nitrophenyl group, 4-cyanophenyl group, 3,5-dibromophenyl group, 2,4-dibromophenyl group, 6-chloro-3-pyridyl group, 5-chloro-3-thiazolyl group, 6 -Chloro-5-fluoro-3-pyridyl group, 6-bromo-3-pyridyl group, 6-fluoro-3-pyridyl group, 5,6-dichloro-3-pyridyl group, or 6-trifluoromethyl-3- Represents a pyridyl group, R1 represents a hydrogen atom or a methyl group, R2 represents a C1-6 alkylcarbonyl group in which the alkyl moiety may be substituted with a halogen atom, a C1-6 alkylsulfonyl group in which the alkyl moiety may be substituted with a halogen atom, or a cyan
- Preferred examples of the compounds are the following compounds (i) to (iii).
- Ar is 4-cyanophenyl group, 4-nitrophenyl group, 3,5-dichlorophenyl group, 3,5-dibromophenyl group, 2,4-dibromophenyl group, 4-bromophenyl group, 3-nitro -5-bromophenyl group, 6-chloro-3-pyridyl group, 5-chloro-3-thiazolyl group, 6-chloro-5-fluoro-3-pyridyl group, 6-trifluoromethyl-3-pyridyl group , R1 represents a hydrogen atom, R2 represents a trifluoromethylsulfonyl group, R3 represents a methylene group, an ethylene group, or a 1-propynylene group, R4 is a compound showing a hydrogen atom or a cyano group, (Ii) Ar represents a 6-chloro-3-pyridyl group, a 5-chloro-3-thiazolyl group, or a 6-trifluoromethyl-3
- Ar is 4-cyanophenyl group, 4-nitrophenyl group, 3,5-dichlorophenyl group, 3,5-dibromophenyl group, 2,4-dibromophenyl group, 4-bromophenyl group, 3-nitro -5-bromophenyl group, 6-chloro-3-pyridyl group, 5-chloro-3-thiazolyl group, 6-chloro-5-fluoro-3-pyridyl group, 6-trifluoromethyl-3-pyridyl group , R1 represents a hydrogen atom, R2 represents a trifluoromethylsulfonyl group, R3 represents a methylene group, an ethylene group, or a 1-propynylene group, R4 is a compound showing a hydrogen atom, (Ii) Ar represents a 6-chloro-3-pyridyl group, a 5-chloro-3-thiazolyl group, or a 6-trifluoromethyl-3-pyridyl group
- the compound represented by the chemical formula (I) as an active ingredient of the pest control agent of the present invention is preferably 500 ppm for foliage treatment, 0.1 mg / seedling soil irrigation treatment, 2 ⁇ g / head topical application treatment, 50 ppm chemical solution It has a control activity (for example, death rate or morbidity rate of 30% or more, 50% or more, 80% or more, 100%) by immersion treatment in 200ppm and dry film treatment of 200ppm (test example of the present invention) checking). Further, it has a controlling activity (insecticidal effect) by 20 ⁇ g / plant seedling root treatment shown in Test Example 15 or motility evaluation under the culture condition of about 3 ppm shown in Test Example 21.
- a control activity for example, death rate or morbidity rate of 30% or more, 50% or more, 80% or more, 100%
- foliage treatment more preferably, it has a controlling activity at a concentration of less than 500 ppm (for example, 400 ppm, 300 ppm, 200 ppm, 100 ppm, 50 ppm, 30 ppm, 10 ppm, 5 ppm, 3 ppm, 1.5 ppm, 1.25 ppm, 1 ppm, 0.5 ppm). Is.
- 500 ppm for example, 400 ppm, 300 ppm, 200 ppm, 100 ppm, 50 ppm, 30 ppm, 10 ppm, 5 ppm, 3 ppm, 1.5 ppm, 1.25 ppm, 1 ppm, 0.5 ppm.
- the soil irrigation treatment has a controlling activity at a concentration of less than 0.1 mg / seedling (for example, 0.05 mg / seedling, 0.01 mg / seedling, 0.005 mg / seedling, 0.002 mg / seedling).
- the topical application treatment has a controlling activity at a concentration of less than 2 ⁇ g / head (for example, 1 ⁇ g / head, 0.5 ⁇ g / head, 0.2 ⁇ g / head).
- dry film treatment more preferably, it has a controlling activity at a concentration of less than 200 ppm (for example, 100 ppm, 50 ppm, 30 ppm, 10 ppm).
- ⁇ g / seedling for example, 10 ⁇ g / seedling, 5 ⁇ g / seedling, 2 ⁇ g / seedling, 1 ⁇ g / seedling, 0.5 ⁇ g / seedling, 0.1 ⁇ g / seedling, 0.05 ⁇ g / seedling, 0.03 ⁇ g / Seedling, 0.01 ⁇ g / seedling
- concentration for example, 10 ⁇ g / seedling, 5 ⁇ g / seedling, 2 ⁇ g / seedling, 1 ⁇ g / seedling, 0.5 ⁇ g / seedling, 0.1 ⁇ g / seedling, 0.05 ⁇ g / seedling, 0.03 ⁇ g / Seedling, 0.01 ⁇ g / seedling
- the most preferred compound is Compound No. 212: N- [1-((6-chloropyridin-3-yl) methyl) pyridine-2 (1H) -ylidene] -2,2,2 listed in Table 5 below.
- insect species in which a pest control agent containing at least one compound of the present invention represented by the chemical formula (I) exhibits a controlling effect are as follows.
- Agricultural and horticultural pests include lepidopterous pests (for example, Spodoptera litura, Coleoptera, Acayoto, Aomushi, Konaga, Shirouchimojiyoto, Nikameiga, Kofomomeiga, Futakoyaga, Sakigaiga, Sinkiga, Azalea, Agrotis p.
- lepidopterous pests for example, Spodoptera litura, Coleoptera, Acayoto, Aomushi, Konaga, Shirouchimojiyoto, Nikameiga, Kofomomeiga, Futakoyaga, Sakigaiga, Sinkiga, Azalea, Agrotis p.
- Hemiptera pests eg, peach aphids, cotton aphids, Aphisfabae, corn aphids, pea aphids, potato aphids, bean aphids, beetle aphids
- Macrosiphum avenae Methopolophium dirhodum
- wheat beetle aphids barley aphids
- radish aphids fake aphids
- snowy aphids Rosy apple aphid Aphids (Aphididae, Adelgidae, Phy11oxeridae) such as apple aphid, komikan aphid, citrus aphid
- leafhoppers such as leafhopper leafhopper, green-bellied leafhopper, leafhopper planter such as leafhopper, leafhopper, white-tailed leafhopper
- Coleopterous pests eg, rice weevil, azuki bean weevil, brown rice weevil, western corn root worm, southern corn root worm, dove squirrel, scallop, kissing flea beetle, cucumber potato beetle, mite beetle, mite beetle, stag beetle Eyes (eg, spider mites, spider mites, citrus spider mites), hymenoptera pests (eg, wasps), straight-eyed pests (eg, grasshoppers), diptera pests (eg, houseflies, leafhoppers), thrips pests (eg For example, southern blue thrips, citrus white thrips, etc.), plant parasitic nematodes (eg, root-knot nematodes, neptune nematodes, rice stag beetles, pine wood nematodes, etc.) and the like.
- insect pests eg, rice weevil, a
- Animal parasitic pests include ticks (eg, Lone star ticks, Gulf ticks, Rock ticks, Rocky forest ticks, West coast ticks, American dog ticks, Ticks, Ticks, Ticks, Ticks, Ticks, Westerns Black mite, shulze mite, sheep mite, black mite, oyster mite, mite mite), tsume mites (e.g., cat ticks, mites), mites (e.g., mites, mites), mites (e.g.
- Hymenid mites for example, oxenid mites, Inomi mite mites), Saulid mites (for example, avian mites), Spiders, Mites (for example, chickens) Mites, mites, mites), tsutsugamushi (e.g., pine tsutsugamushi, red tsutsugamushi), fleas (e.g., cat fleas, human fleas, keops mud mines, murines), lice (e.g., dog lice, chicken lice), lice (E.g., pig lice, dog lice, body lice, human lice, whiteflies, bed bugs), house flies, cow flies, cow flies, horse flies, fly flies (e.g., sand flies), tset flies, abs, cicada (e.g.
- Aedes aegypti cuttlefish (e.g., mosquitoes), anopheles, nuciferous, flyfish, sand turtles, houseworms, nematodes (e.g., nematodes, worms, roundworms (e.g.
- ciliate nematodes eg , metamorphosis (eg , Porcine pneumoniae, Cantonese schistosomiasis, cat lungworm), helminths, caecal worms (eg chicken roundworm), roundworms (eg anisakis nematode, pig roundworm, horse roundworm, dog roundworm, cat roundworm) , Gyrus nematodes (eg, burulae, spiny jaw-mouthed caterpillar, cat stomachworm, horoscope stomachworm, large-mouth horse stomachworm, chicken stomachworm, medinaworm), filamentous worms (eg, dog filamentous worms) , Lymphoid worms, rotifers, loar worms), nematodes, trichinidae (for example, Trichinella, Trichinella)), flukes (for example, Schistosoma japonicum, liver fluke), bald worms And crustaceans (for example, suspicious leaves (for example
- Sanitary pests, unpleasant pests, stored grain pests, stored food pests, and house pests include mosquitoes (for example, Aedes albopictus, Culex), cockroaches (for example, black-legged cockroaches, Japanese cockroaches, German cockroaches), coniferous mites (for example, prickly tick) , Flies (for example, houseflies, nymphae, butterflies, drosophila, chironomids), flyfish, phylums, hymenoptera insects (for example, ants such as the crocodile and fire ant, bees such as the giant hornet) Arthropods (for example, Paramecium, Funabushi, Dangamushi), Hemiptera insects (for example, bed bugs), polypods of arthropods (for example, centipedes, gejis, millipedes), arachnid arthropods Animals (e
- insects to which the pest control agent of the present invention is applied are lepidopterous insects, hemiptera pests, thrips pests, diptera pests, Coleoptera pests, animal parasitic fleas , Mites, dog filamentous worms (e.g. diamondback moth, scallops, cotton aphids, peach aphids, scallops, leafhoppers, white-spotted plant, leafhoppers, red-spotted winged turtles, red-winged beetles, tickling moths, tickling, And at least one insect species selected from the group consisting of dog filamentous insects), more preferably hemipods, Coleoptera, ticks, particularly preferably planthoppers and leafhoppers.
- dog filamentous worms e.g. diamondback moth, scallops, cotton aphids, peach aphids, scallops, leafhoppers, white-spotted plant, leafhoppers, red-spotted winged turtles, red-winged beetles, tickling
- the pest control agents provided by the present invention include, for example, agricultural and horticultural insecticides, animal endoparasite control agents, animal ectoparasite control agents, sanitary pest control agents, unpleasant pest control agents, grain storage and storage Food pest control agents, house pest control agents and the like can be mentioned, and preferred are agricultural and horticultural insecticides, animal endoparasite control agents, and animal ectoparasite control agents.
- the pest control agent of the present invention can be prepared by using a carrier corresponding to the method of use in addition to the compound represented by the chemical formula (I).
- the pest control agent of the present invention is an agricultural pest control agent
- it is usually mixed with an appropriate solid carrier, liquid carrier, gaseous carrier, surfactant, dispersing agent or other formulation auxiliary agent to prepare an emulsion or liquid.
- an appropriate solid carrier liquid carrier, gaseous carrier, surfactant, dispersing agent or other formulation auxiliary agent to prepare an emulsion or liquid.
- Suspensions wettable powders, flowables, powders, granules, tablets, oils, aerosols, smokes and the like.
- solid carrier examples include talc, bennite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.
- liquid carrier examples include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methylnaphthalene.
- alcohols such as methanol, n-hexanol and ethylene glycol
- ketones such as acetone, methyl ethyl ketone and cyclohexanone
- aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methylnaphthalene.
- Aromatic hydrocarbons such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean oil , Vegetable oils such as cottonseed oil, dimethyl sulfoxide, water and the like.
- gaseous carrier examples include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.
- Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, A lignin sulfonate can be used.
- an adjuvant for improving the properties of the preparation for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like can be used.
- the above carriers, surfactants, dispersants, and adjuvants can be used alone or in combination as necessary.
- the content of the active ingredient in the preparation is not particularly limited, but is usually 1 to 75% by weight for emulsions, 0.3 to 25% by weight for powders, 1 to 90% by weight for wettable powders, and 0.5 to 10 for granules. % By weight.
- the compound represented by the chemical formula (I), a preparation containing these, and a mixture of these with other pest control agents are harmful insects, plants, plant propagation materials (eg, seeds, plant foliage) Part, root, germinated plant, and young plant), soil, nutrient solution in hydroponic culture, solid medium in hydroponic culture, and rooms that need to prevent the invasion of pests it can.
- Applied plants include genetically modified crops. These applications can be made before and after pest infestation.
- the compound represented by the chemical formula (Ie), a preparation containing these, and a mixture of them with other pest control agents, effective amounts, plant seeds, roots, tubers, bulbs, rhizomes, germinated Pests can be controlled by applying to an object selected from the group consisting of plants, seedlings, soil, nutrient solution in hydroponic culture, and solid medium in hydroponic culture, and osmotically transferred into the plant.
- suitable examples of application methods are not particularly limited as long as they do not impede osmotic transfer, but immersion methods, powder coating methods, smearing methods , Spraying method, pellet method, coating method and the like.
- application methods include, for example, a dipping method, a powder coating method, a smearing method, a spraying method, a pellet method, a film method, and a fumigation method.
- the dipping method is a method in which seeds are immersed in a liquid drug solution.
- the powder coating method includes a dry powder coating method in which a powdered drug is attached to dry seeds, and a seed lightly soaked in water. There is a wet powder coating method to attach the drug in the shape.
- a smearing method in which a suspended drug is applied to the seed surface in a mixer and a spraying method in which the suspension is sprayed onto the seed surface.
- the immersion time and temperature are appropriately determined by those skilled in the art according to the application target, the type and amount of the drug, and the like. And although it does not specifically limit as penetration transfer time, For example, it is 1 hour or more. Further, the temperature in the permeation transfer is, for example, 5 to 45 ° C.
- a preparation containing these compounds of the present invention and a granule of a mixture of them with other pesticides may be applied in or on the soil.
- Preferred soil application methods are spraying, strips, grooves, and planting hole application methods.
- the spraying treatment includes surface treatment over the entire area to be treated and subsequent mechanical introduction into the soil.
- the effective amount of the compound of formula (I) or a salt thereof or the compound of formula (Ie) or a salt thereof is the same as that of the compound of formula (1) or formula (Ie) in the subsequent osmotic transfer step.
- An amount sufficient to penetrate into the plant is preferable.
- the effective amount can be appropriately determined in consideration of the nature of the compound, the type and amount of the object to be applied, the length of the subsequent osmotic transfer step, temperature, etc.
- the formula (I) The amount of the compound or salt thereof or the compound of formula (Ie) or salt thereof is preferably 1 g to 10 kg, more preferably 10 g to 1 kg per 10 kg of seed.
- the amount of the compound of formula (I) or a salt thereof or the compound of formula (Ie) or a salt thereof is preferably 0.1 g to 10 kg, more preferably 1 g 1kg.
- the amount of the compound of formula (I) or a salt thereof or the compound of formula (Ie) or a salt thereof is preferably 0.1 to 10 kg, more preferably 1 g per 10 ares of cultivated land. It is desirable to process ⁇ 1kg.
- the pest control agent of the present invention is an animal parasitic pest control agent
- it is a liquid, emulsion, liquefied drop, spray, foam preparation, tablet, granule, fine granule, powder, capsule, tablet, It is provided as a chewable agent, injection agent, suppository, cream agent, shampoo agent, rinse agent, resin agent, smoke agent, poison bait, etc., but it is particularly preferable that it is provided as a liquid agent or a liquefied drop agent.
- the liquid preparation can further contain formulation emulsifiers such as ordinary emulsifiers, dispersants, spreading agents, wetting agents, suspending agents, preservatives, propellants, etc.
- a forming agent can also be blended.
- Surfactants for emulsification, dispersion, spreading, etc. include, for example, soaps, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene alkyl allyl ethers, polyoxyethylene fatty acid esters, higher alcohols, alkylaryls A sulfonate or the like can be used.
- the dispersant include casein, gelatin, polysaccharides, lignin derivatives, saccharides, and synthetic water-soluble polymers.
- Examples of spreading / wetting agents include glycerin and polyethylene glycol.
- Examples of the suspending agent include casein, gelatin, hydroxypropyl cellulose, and gum arabic.
- Examples of the stabilizing agent include phenolic antioxidants (BHT, BHA, etc.) and amine antioxidants (diphenylamine, etc.). ) And organic sulfur-based antioxidants.
- Examples of the preservative include methyl paraoxybenzoate, ethyl paraoxybenzoate, propyl paraoxybenzoate, and butyl paraoxybenzoate.
- the above carriers, surfactants, dispersants, and adjuvants can be used alone or in combination as required. Furthermore, you may contain a fragrance
- the content of the active ingredient in the pesticidal composition of the present invention is usually 1 to 75% by weight in a liquid preparation.
- Examples of the carrier used for preparing the cream include non-volatile hydrocarbons (such as liquid paraffin), lanolin-added oils and fats, higher fatty acids, fatty acid esters, animal and vegetable oils, silicone oils, and water. Furthermore, emulsifiers, moisturizers, antioxidants, fragrances, borax, and ultraviolet absorbers can be used alone or in combination as required. Examples of the emulsifier include fatty acid sorbitan, polyoxyethylene alkyl ether, and fatty acid polyoxyethylene. The content of the active ingredient in the pest control agent of the present invention is usually 0.5 to 70% by weight for creams.
- the active ingredient in the composition of the present invention is appropriately subdivided and mixed with a diluent or a carrier such as starch, lactose, talc, and a disintegrant such as magnesium stearate. And / or a binder can be added and used as a tablet if necessary.
- Injections must be prepared as sterile solutions.
- An injection may contain, for example, sufficient salt or glucose to make the solution isotonic with blood.
- Carriers that can be used to prepare injectables include glycerides, esters such as benzyl benzoate, isopropyl myristate and fatty acid derivatives of propylene glycol, organic solvents such as N-methylpyrrolidone, glycerol formal.
- the content of the active ingredient in the pest control agent of the present invention is usually 0.01 to 10% by weight for injections.
- the carrier for preparing the resin agent examples include vinyl chloride polymers and polyurethane. If necessary, plasticizers such as phthalates, adipic esters, and stearic acid can be added to these substrates. After kneading the active ingredient in the substrate, it can be molded by injection molding, extrusion molding, press molding or the like. Furthermore, it can be made into an animal ear tag or an animal insect repellent collar through appropriate steps such as molding, cutting and cutting.
- Carriers for poisonous baits include dietary substances and attractants (flours such as wheat flour and corn flour, starches such as corn starch and potato starch, sugars such as granulated sugar, maltose and honey, foods such as glycerin, onion flavor and milk flavor. And animal powders such as flavors, rice cake powders, and fish meals, and various pheromones).
- the content of the active ingredient of the pest control agent of the present invention is usually 0.0001 to 90% by weight for poisonous baits.
- the pest control agent of the present invention can be controlled by administering it to the body of an applied animal orally or by injection, or by administering to the whole or part of the body surface of the applied animal. Moreover, pests can also be controlled by covering the places where pests are expected to invade, parasitize and move with the pest control agent of the present invention.
- the pest control agent of the present invention may be used as it is, but depending on the case, it can be diluted with water, a liquid carrier, a commercially available shampoo, rinse, bait, a breeding house underlay or the like.
- the pest control agent according to the present invention can be used by mixing with other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like.
- Drugs that can be used in combination include those listed in the Pesticide Manual (13th edition, The British Crop Protection Council issued) and Shibuya Index (SHIBUYA INDEX 13th edition, 2008, issued by SHIBUYA INDEX RESEARCH GROUP). It is done.
- Organophosphate compounds such as pyraclofos, chlorpyrifos-methyl, diazinon, fosthiazate, imiciafos, mesomyl, thiodicarb, aldicarb ( Like aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran, benfuracarb Carbamate compounds, cartap, nereistoxin derivatives such as thiocyclam, organochlorine compounds such as dicofol, tetradifon, permethrin, tefluthrin, cypermethrin pyreth
- other compounds include buprofezin, hexythiazox, amitraz, chlordimeform, pyridaben, fenpyroxymate, pyrimidifen, tebufenrad, tebufenrad, tebufenrad, tebufenrad ), Fluacrypyrim, acequinocyl, cyflumetofen, flubendizmide, ethiprole, fipronil, etoxazole, imidaclopric, imidacloprid, imidacloprid, imidaclopridum thiamethoxam, acetamiprid, nitenpyram, thiacloprid, dinotefuran, pymetro Gin (pymetrozine), bifenazate (spirodiclofen), spiromesifen (spiromesifen), flonicamid (flonicamid), chlorfenapyr (chlorfen
- the pest control agent of the present invention can be used in combination with or in combination with microbial pesticides such as BT agents and entomopathogenic virus agents.
- fungicides used in combination or in combination include strobilurins such as azoxystrobin, kresoxym-methyl, trifloxystrobin, metinominostrobin, oryastrotrobin.
- strobilurins such as azoxystrobin, kresoxym-methyl, trifloxystrobin, metinominostrobin, oryastrotrobin.
- Compounds, mepanipyrim, pyrimethanil, anilinopyrimidine compounds such as cyprodinil, triadimefon, bitertanol, triflumizole, metconconazole, metoconazole Propiconazole, penconazole, flusilazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz, simecazole azole compounds such as onazole), quinoxaline compounds such as quinometh
- Ar represents an optionally substituted phenyl group or an optionally substituted 5- to 6-membered heterocycle
- R2 is a C1-6 alkylcarbonyl group in which the alkyl part may be substituted with a halogen atom, a C1-6 alkyloxycarbonyl group in which the alkyl part may be substituted with a halogen atom, and the alkyl part is substituted with a halogen atom.
- An optionally substituted C1-6 alkylsulfonyl group CONR6R7 (wherein R6 and R7 are independently of each other a hydrogen atom, a C1-6 alkyl group optionally substituted by halogen), an alkyl moiety is substituted by a halogen atom C1-6 O, O′-alkylphosphoryl group, cyano group, formyl group or nitro group, which may be R3 is a C1-8 alkylene group optionally substituted by a halogen atom, a C2-8 alkenylene group optionally substituted by a halogen atom, a C2-8 alkynylene group optionally substituted by a halogen atom, substituted
- R2 does not represent a C1-6 alkyloxycarbonyl group in which the alkyl moiety may be substituted with a halogen atom.
- a halide, anhydride, ester or the like of R2 [R2 has the same meaning as defined in the above chemical formula (I)] can be added in the presence or absence of a base. It can be obtained by reaction.
- R2 halides, anhydrides, and esters include carboxylic acid halides, carboalkyloxyhalides, sulfonyl halides, O, O'-alkylphosphoryl halides, carboxylic anhydrides, dialkyl dicarbonates, carboxylic acid esters, and carbonates.
- R2 halides, anhydrides, and esters include carboxylic acid halides, carboalkyloxyhalides, sulfonyl halides, O, O'-alkylphosphoryl halides, carboxylic anhydrides, dialkyl dicarbonates, carboxylic acid esters, and carbonates.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be performed using no solvent or a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform, chlorobenzene, Halogen hydrocarbons such as dichlorobenzene and solvents such as water can be used alone or in combination, but dimethylformamide, acetonitrile,
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- R2 in the chemical formula (Ia) is a C1-6 alkylcarbonyl group in which the alkyl moiety may be substituted with a halogen atom
- the compound represented by the chemical formula (II) may be converted to R2′-COOH [where R2 'Can also be obtained by reacting a carboxylic acid represented by a C1-6 alkyl group optionally substituted with a halogen atom in the presence of a dehydrating condensing agent.
- carbodiimide compounds such as dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride can be used.
- the reaction is preferably performed using a solvent.
- amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, ethers such as diethyl ether and tetrahydrofuran, ethyl acetate, butyl acetate
- Esters such as, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogens such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene Hydrocarbons can be used alone or in combination of two or more, but dichloromethane, chloroform, etc. are preferably used.
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- R2 in the above chemical formula (Ia) is a cyano group
- a known cyanating reagent can be reacted with the compound represented by formula (II) in the presence or absence of a base.
- cyanating reagent bromocyanide, iodocyanide, 1-cyanoimidazole, 1-cyanobenzotriazole, substituted or unsubstituted benzenesulfonylcyanide and the like can be used.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal acetates such as sodium acetate, and tertiary amines such as triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal acetates such as sodium acetate
- tertiary amines such as triethylamine.
- Substituted or unsubstituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , Aliphatic hydrocarbons such as heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and solvents such as water can be used alone or in combination.
- reaction can usually be carried out at 0 to 100 ° C., and it is preferable to slowly raise the temperature to about 20 to 50 ° C. by adding a cyanating reagent at 0 ° C.
- the compound represented by the chemical formula (II) can be synthesized from the compound represented by the following chemical formula (IIIa) or (IIIb).
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine Tertiary amines such as pyridine, unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , One or a combination of two or more solvents such as aliphatic hydrocarbons such as heptane and octane and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene. Kill, but dimethylformamide, acet
- the reaction can usually be carried out at 0 to 200 ° C. It is preferable to add a reagent at 0 ° C., slowly raise the temperature to 20 to 50 ° C., and raise the temperature to a temperature higher than that depending on the progress of the reaction.
- the addition amount of the compound represented by (IIIa) with respect to the compound represented by (IVa) is preferably 1 mol or less with respect to 1 mol of the compound represented by (IVa).
- X represents a halogen atom or OTs, OMs, etc.
- the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine Triethylamine.
- Tertiary amines such as pyridine, pyridines having unsubstituted or substituted groups such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , Aliphatic hydrocarbons such as heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and solvents such as water can be used alone or in combination. But it is, dimethylformamide, amide
- the reaction can be usually carried out at 0 ° C. to 200 ° C., and a reagent is added at 0 ° C., the temperature is slowly raised to 20-50 ° C., and the temperature is preferably raised to a higher temperature depending on the progress of the reaction.
- the amount of the compound represented by (IVb) to the compound represented by (IIIb) is preferably 1 mol or less with respect to 1 mol of the compound represented by (IIIb).
- the compound represented by (II) above forms an imine by adding a compound represented by the following chemical formula (IVc) to the compound represented by (IIIb) in the presence or absence of an acid. Thereafter, it can be obtained by carrying out a reduction reaction.
- R3 ′ and R3 ′′ may be the same or different and each represents a hydrogen atom or a C1-7 alkyl group, and R3 ′ and R3 ′′ may combine to form a ring. However, R3 ′ and R3 ′′ do not represent hydrogen atoms at the same time, and the sum of the number of carbon atoms of R3 ′ and R3 ′′ is smaller than 7.
- R4 has the same meaning as defined in chemical formula (I) above]
- a solvent is preferably used.
- the solvent lower alcohols such as methanol and ethanol, acetonitrile, dichloromethane, dichloroethane and the like can be used, but methanol, ethanol and the like are preferably used.
- an acid for example, hydrochloric acid, substituted, unsubstituted benzenesulfonic acid, acetic acid and the like can be used.
- the reduction reaction can be performed using a hydride reducing reagent such as sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride.
- a hydride reducing reagent such as sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride.
- the reduction reaction can also be performed by a catalytic hydrogenation reaction using a metal catalyst.
- a metal catalyst palladium, platinum, rhodium, nickel, iron or the like can be used.
- the reaction can usually be performed at 20 to 100 ° C.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- Non-substituted or substituted pyridines such as tertiary amines such as pyridine and 4-dimethylaminopyridine can be used, but alkali metal hydrides such as sodium hydride are preferably used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , Aliphatic hydrocarbons such as heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and solvents such as water can be used alone or in combination. But it is, dimethylformamide, amide
- the compound represented by (Va) is a compound represented by (IIIb), a halide, anhydride, ester, or the like of R2 [R2 has the same meaning as defined in the above chemical formula (I)] It can be obtained by reacting in the presence or absence.
- halides, anhydrides and esters of R2 include carboxylic acid halides, carboalkyloxy halides, sulfonyl halides, O, O′-alkylphosphoryl halides, carboxylic anhydrides, dialkyl dicarbonates, carboxylic acid esters, carbonate esters, cyanoesters.
- a halide or the like can be used.
- the reaction preferably uses a solvent, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate , Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform and chlorobenzene
- amides such as dimethylformamide and dimethylacetamide
- nitriles such as acetonitrile
- sulfoxides such as dimethyl sulfoxide
- ethers such as dieth
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- Tertiary amines such as pyridine, unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the compound represented by (Va) is a compound represented by (IIIa), a compound represented by R2-NH 2 [R2 has the same meaning as defined in the above chemical formula (I)], It can also be obtained by reacting in the presence or absence of a base.
- the reaction preferably uses a solvent, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate , Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform and chlorobenzene
- solvents such as halogen hydrocarbons such as dichlorobenzene and water can be used, and acetonitrile or the like is preferably used.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- Tertiary amines such as pyridine, unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- non-substituted or substituted pyridines such as tertiary amines such as pyridine and 4-dimethylaminopyridine can be used
- alkali metal hydrides such as sodium hydride are preferably used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , Aliphatic hydrocarbons such as heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and solvents such as water can be used alone or in combination. But it is, dimethylformamide, amide
- the compound represented by (Vb) is a compound represented by (IVa), a halide, anhydride, ester, or the like of R2 [R2 has the same meaning as defined in the above chemical formula (I)] It can be obtained by reacting in the presence or absence.
- halides, anhydrides and esters of R2 include carboxylic acid halides, carboalkyloxy halides, sulfonic acid halides, O, O′-alkylphosphoryl halides, carboxylic acid anhydrides, dialkyloxydicarbonates, carboxylic acid esters, carbonyls. Acid esters, cyanohalides and the like can be used.
- the reaction preferably uses a solvent, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate , Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform and chlorobenzene
- amides such as dimethylformamide and dimethylacetamide
- nitriles such as acetonitrile
- sulfoxides such as dimethyl sulfoxide
- ethers such as dieth
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- Tertiary amines such as pyridine, unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the compound represented by (Vb) is represented by X-R3R4 [R3, R4 has the same meaning as defined in the above chemical formula (I), X represents a halogen atom], R2-NH 2 [R2 is A compound represented by the same meaning as defined in the above chemical formula (I)] can also be obtained by reacting in the presence or absence of a base.
- the reaction preferably uses a solvent, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate , Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform and chlorobenzene , Halogen hydrocarbons such as dichlorobenzene, solvents such as water can be used alone or in combination of two or more, but acetonitrile or tetrahydrofuran can be used. It is preferable
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- Tertiary amines such as pyridine, unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the compound represented by the following chemical formula (Ib) is a compound represented by R 2 NH 2 [R 2 is the same as defined in the above chemical formula (I)], ArCH 2 X [X is a halogen atom Can be obtained by reacting in the presence or absence of a base.
- Ar and R2 have the same meaning as defined in chemical formula (I) above]
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine Triethylamine.
- Tertiary amines such as pyridine, pyridines having unsubstituted or substituted groups such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane Solvents such as aliphatic hydrocarbons such as heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene may be used alone or in combination. Kill, but it is preferable to use such as amide
- the reaction can usually be performed at 0 to 200 ° C., and it is preferable to add a reagent at 20 to 40 ° C. and perform the reaction at 60 to 80 ° C.
- R1 represents a C1-6 alkyl group and Ar, R2, R3, R4 have the same meaning as defined in the above chemical formula (I)]
- a halide, an anhydride, an ester, or the like of R2 is present in the presence or absence of a base. It can obtain by making it react.
- R2 halides, anhydrides, and esters include carboxylic acid halides, carboalkyloxyhalides, sulfonyl halides, O, O'-alkylphosphoryl halides, carboxylic anhydrides, dialkyl dicarbonates, carboxylic acid esters, and carbonates.
- carboxylic acid halides carboalkyloxyhalides, sulfonyl halides, O, O'-alkylphosphoryl halides, carboxylic anhydrides, dialkyl dicarbonates, carboxylic acid esters, and carbonates.
- acetyl chloride, ethyl chloroformate, methanesulfonyl chloride, diethyl chlorophosphate, trifluoroacetic anhydride, ethyl formate and the like are preferably used.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- Tertiary amines such as pyridine, unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , Aliphatic hydrocarbons such as heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and solvents such as water can be used alone or in combination. But it is, dimethylformamide, amide
- the reaction can usually be carried out at -80 to 100 ° C, but is preferably carried out in the range of 20 to 50 ° C.
- R2 of the compound represented by (Ic) is a C1-6 alkylcarbonyl group in which the alkyl moiety may be substituted with a halogen atom
- the compound represented by (VIa) is substituted with R2′-COOH
- R2 ′ can also be obtained by reacting a carboxylic acid represented by a C1-6 alkyl group optionally substituted with a halogen atom in the presence of a dehydrating condensing agent.
- carbodiimide compounds such as dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride can be used.
- the reaction is preferably performed using a solvent.
- amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, ethers such as diethyl ether and tetrahydrofuran, ethyl acetate, butyl acetate
- Esters such as, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogens such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene Hydrocarbons can be used alone or in combination of two or more, but dichloromethane, chloroform and the like are preferably used.
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- R2 of the compound represented by (Ic) is a cyano group
- the compound represented by (IVa) can be obtained by reacting a known cyanating reagent in the presence or absence of a base.
- cyanating reagent bromocyanide, iodocyanide, 1-cyanoimidazole, 1-cyanobenzotriazole, substituted or unsubstituted benzenesulfonylcyanide and the like can be used.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal acetates such as sodium acetate, and tertiary amines such as triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal acetates such as sodium acetate
- tertiary amines such as triethylamine.
- Substituted or unsubstituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , Aliphatic hydrocarbons such as heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and solvents such as water can be used alone or in combination. But it is, diethyl ether
- the reaction can usually be performed at 0 to 100 ° C., and it is preferable to add a cyanating reagent at 0 ° C. and slowly raise the temperature to about 20 to 50 ° C.
- the compound represented by (VIa) is a compound represented by the following chemical formula (VII):
- the reaction preferably uses a solvent, and the solvent is preferably a lower alcohol such as methanol or ethanol, dichloromethane, chloroform or the like, but acetonitrile or the like can also be used.
- the solvent is preferably a lower alcohol such as methanol or ethanol, dichloromethane, chloroform or the like, but acetonitrile or the like can also be used.
- an acid for example, hydrochloric acid, substituted, unsubstituted benzenesulfonic acid, acetic acid and the like can be used.
- the reduction reaction can be performed using a hydride reducing reagent such as sodium borohydride, sodium cyanoborohydride, or sodium triacetoxyborohydride.
- a hydride reducing reagent such as sodium borohydride, sodium cyanoborohydride, or sodium triacetoxyborohydride.
- the reduction reaction can also be performed by a catalytic hydrogenation reaction using a metal catalyst.
- a metal catalyst palladium, platinum, rhodium, nickel, iron or the like can be used.
- the reaction temperature can usually be in the range of 20 ° C to 100 ° C.
- Bases include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and copper carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, metal oxides such as copper oxide and magnesium oxide, Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as 4-dimethylaminopyridine can be used, but a strong base such as potassium t-butyrate is preferably used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, hexane , Aliphatic hydrocarbons such as heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and solvents such as water can be used alone or in combination. But it is, it is preferable to use
- the reaction can usually be carried out at -80 to 100 ° C, but is preferably carried out at 20 to 50 ° C.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, and triethylamine.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- triethylamine Tertiary amines such as pyridine, pyridines having unsubstituted or substituted groups such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be carried out without solvent or using a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, diethyl Ethers such as ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone
- solvents such as aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene Can be used in conjunction seen, it is preferable
- the reaction can usually be performed at 0 to 200 ° C., and it is preferable to add a reagent at 20 to 40 ° C. and perform the reaction at 60 to 80 ° C.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be performed using no solvent or a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform, chlorobenzene, Halogen hydrocarbons such as dichlorobenzene and solvents such as water can be used alone or in combination, but dimethylformamide, acetonitrile
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- the compound represented by the above reaction formula (IX) comprises a compound represented by the above (IXa) and a carboxylic acid represented by R4e-COOH [the definition of R4e- is the same as described above] And can be obtained by reacting in the presence or absence of a base.
- carbodiimide compounds such as dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride can be used.
- examples of the base include carbonates such as potassium carbonate and sodium carbonate, tertiary amines such as triethylamine, unsubstituted or substituted groups such as pyridine and 4-dimethylaminopyridine.
- the pyridine which has can be used.
- the reaction is preferably performed using a solvent.
- amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, ethers such as diethyl ether and tetrahydrofuran, ethyl acetate, butyl acetate
- Esters such as, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogens such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene Hydrocarbons can be used alone or in combination of two or more, but dichloromethane, chloroform, etc. are preferably used.
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- Tertiary amines such as triethylamine and unsubstituted or substituted pyridines
- pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be performed using no solvent or a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform, chlorobenzene, Halogen hydrocarbons such as dichlorobenzene and solvents such as water can be used alone or in combination, but dimethylformamide, acetonitrile
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- the compound represented by the above reaction formula (Ie) is obtained by dehydrating a compound represented by the above (IXb) or a salt thereof and a carboxylic acid represented by R4e-COOH [the definition of R4e is the same as described above]. It can also be obtained by reacting in the presence or absence of a base using a condensing agent.
- carbodiimide compounds such as dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride can be used.
- examples of the base include carbonates such as potassium carbonate and sodium carbonate, tertiary amines such as triethylamine, unsubstituted or substituted groups such as pyridine and 4-dimethylaminopyridine.
- the pyridine which has can be used.
- the reaction is preferably performed using a solvent.
- amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethylsulfoxide, ethers such as diethyl ether and tetrahydrofuran, ethyl acetate, butyl acetate
- Esters such as, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogens such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene Hydrocarbons can be used alone or in combination of two or more, but dichloromethane, chloroform, etc. are preferably used.
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- the compound represented by the above (IXb) is obtained by combining a compound represented by the above (IXa) with a compound represented by ArCH (R1) X [wherein the definitions of Ar, R1, and X are the same as those described above]. It can be obtained by reacting in the presence or absence.
- examples of the base include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- alkali metal hydrides such as sodium hydride
- carbonates such as potassium carbonate and sodium carbonate
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- Tertiary amines such as triethylamine and unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine can be used.
- the reaction can be performed using no solvent or a solvent that does not affect the reaction.
- a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform, chlorobenzene, Halogen hydrocarbons such as dichlorobenzene and solvents such as water can be used alone or in combination, but dimethylformamide, acetonitrile
- the reaction can usually be carried out at -80 to 100 ° C, preferably 20 to 50 ° C.
- Tables 6 to 9 show the spectrum data of the compounds obtained in Synthesis Examples 1 to 13 and compounds obtained by the same method.
- N-((6-chloropyridin-3-yl) methyl) ethane - 1,2-diamine 4.61 g (24.9 mmol) was synthesized by the method described in Comparative Example 4. This was dissolved in 40 ml of anhydrous acetonitrile, and 4.60 g (21.3 mmol) of dimethyl (2,2,2-trifluoroacetyl) carbonimide dithioate obtained by the above method was added, and the mixture was heated to reflux for 90 minutes. After completion of the reaction, the reaction solution was returned to room temperature and then the solvent was distilled off under reduced pressure. The precipitated solid was collected by filtration and washed with a small amount of acetonitrile to obtain the desired product.
- Formulation Example 1 [Granule] Compound 1 5% by weight Bentonite 40% by weight Talc 10% by weight 43% by weight of clay 2% by weight calcium lignin sulfonate The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.
- Formulation Example 2 [Granule] Compound 212 2% by weight Sun extract P-252 5% by weight Binder 1.5% by weight Granulation improver 0.5% by weight 91% by weight clay The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.
- Formulation Example 3 [wettable powder] Compound 3 30% by weight 50% by weight of clay 2% white carbon Diatomaceous earth 13% by weight Calcium lignin sulfonate 4% by weight Sodium lauryl sulfate 1% by weight The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.
- Formulation Example 4 [Granule wettable powder] Compound 212 30% by weight 60% clay Dextrin 5% by weight Alkyl maleic acid copolymer 4% by weight Sodium lauryl sulfate 1% by weight The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain a granular wettable powder.
- Formulation Example 6 Compound 1 15% by weight N, N-dimethylformamide 20% by weight Solvesso 150 (ExxonMobil Co., Ltd.) 55% by weight 10% by weight of polyoxyethylene alkyl aryl ether The above ingredients were uniformly mixed and dissolved to obtain an emulsion.
- Formulation Example 7 [powder] Compound 14 2% by weight 60% clay Talc 37% by weight Calcium stearate 1% by weight The said component was mixed uniformly and the powder agent was obtained.
- Formulation Example 8 [DL powder] Compound 1 2% by weight DL clay 94.5% by weight 2% white carbon Calcium stearate 1% by weight Light liquid paraffin 0.5% by weight The said component was mixed uniformly and the powder agent was obtained.
- Formulation Example 9 [Fine Granule F ] Compound 3 2% by weight Carrier 94% by weight 2% white carbon Hyzol SAS-296 2% by weight The said component was mixed uniformly and the powder agent was obtained.
- Formulation Example 10 (Liquid drops) Compound 1 10% by weight Benzyl alcohol 74.9% by weight 15% by weight propylene carbonate BHT 0.1 wt% The above components were uniformly stirred and dissolved to obtain a liquefied droplet.
- Formulation Example 12 [Granule] Compound 212 2% by weight Probenazole 24% by weight Binder 3.0% by weight Granulation improver 0.5% by weight Clay 70.5% by weight The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.
- Test Example 1-1 Leafhopper disc of 5.0 cm in diameter was cut out from cabbage grown in the potter control test pot pot, and a chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (added with 0.05% Tween 20) was prepared. Scattered. After air drying, the 2nd instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead) ⁇ x 100
- compound 9,10,49,196,211,81,82,89,92,104,107,108,109,110,111,112,114,128,131,140,141,144,145,146,152,165,167,170,171,172,176,179,180,181183,184,187,237,242,240,235,241,240 Showed insecticidal activity with a death rate of 80% or more.
- Test Example 1-2 Leafhopper of 5.0 cm in diameter was cut out from cabbage grown in the potter's beak prevention test pot, and a chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (added with 0.05% Tween 20) was prepared. Scattered. After air drying, the 2nd instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead) ⁇ x 100
- Test Example 2 Cut-out leaf disc of 5.0 cm in diameter from cabbage grown in a pot- spotted carp control pot and sprayed with a chemical solution of the present compound of a predetermined concentration prepared so as to be 50% acetone water (added with 0.05% Tween 20) . After air drying, the 3rd instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead) ⁇ x 100
- the compound 46,202,68,82,89,92,96,104,108,128,140,176,184,189,190,193,212,219,227,229,230,239 showed insecticidal activity with a mortality rate of 80% or more after treatment with 500 ppm of foliage.
- Test Example 3-1 Cotton Aphid Control Test A leaf disc having a diameter of 2.0 cm was cut out from a cucumber cultivated in a pot, and 50% acetone water (added with 0.05% Tween 20) was added thereto to prepare a chemical solution of the compound of the present invention at a predetermined concentration. Sprayed. After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead insects) ⁇ x 100
- the compound 1,2,3,6,7,8,9,10,12,14,15,18,20,21,22,25,27,29,30,31 by 500 ppm of foliage treatment 32,33,34,36,37,41,42,43,44,45,46,49,50,52,58,61,68,69,71,72,73,76,77,79,81, 82,83,85,88,89,92,96,100,101,102,103,104,119,122,131,132,135,139,165,167,170,179,182,183,184,186,189,192,193,194,196,199,200,202,208,210,211,212,219,221,222,223,225,243,80,239,234
- Test Example 3-2 Cotton aphid control test A leaf disk having a diameter of 2.0 cm was cut out from a cucumber grown in a pot, and 50% acetone water (added with 0.05% Tween 20) was added thereto to prepare a chemical solution of the compound of the present invention at a predetermined concentration. Sprayed. After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- Test Example 3-3 Cotton Aphid Control Test A leaf solution having a diameter of 2.0 cm was cut out from a cucumber cultivated in a pot, and a chemical solution of the compound of the present invention having a predetermined concentration was prepared so as to be 50% acetone water (added with 0.05% Tween 20). Sprayed. After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- Test Example 4 Peach Aphid Control Test A leaf disc having a diameter of 2.8 cm was cut out from cabbage grown in a pot, and four adult aphids were released. One day later, the adults were removed and the number of first instar larvae laid on the leaf discs was adjusted to 10. Thereafter, a chemical solution of the compound of the present invention having a predetermined concentration prepared so as to be 50% acetone water (added with 0.05% Tween 20) was sprayed on the leaf disk infested with the hatched larvae. After air drying, the petri dish was covered and left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- the compound 1,2,3,6,7,8,9,10,11,212 showed insecticidal activity with a mortality rate of 80% or more after 100 ppm foliage treatment.
- Test Example 5 A rice seedling grown in a pot plant control test pot plant was sprayed with a chemical solution of the compound of the present invention having a predetermined concentration prepared to be 50% acetone water (added with 0.05% Tween 20). After air drying, the 2nd instar larvae were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- the compounds 212, 213, 215, 216, 227, 229, and 230 showed an insecticidal activity with a mortality rate of 80% or more after the foliar treatment at 100 ppm.
- Test Example 6 Leafhopper plant control test The rice seedlings grown in pots were sprayed with a chemical solution of the compound of the present invention having a predetermined concentration prepared to be 50% acetone water (added with 0.05% Tween20). After air drying, the 2nd instar larvae were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). The insects were observed for life and death 6 days after the release, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- compounds 1,2,3,6,7,8 showed insecticidal activity with a mortality rate of 80% or more after treatment with 100 ppm of foliage.
- Test Example 7 A plant solution of a predetermined concentration of the compound of the present invention prepared to be 50% acetone water (added with 0.05% Tween 20) was sprayed onto a rice seedling cultivated in a white-spotted planthopper control test pot. After air drying, the 2nd instar larvae were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). Insects were observed for life and death 4 days after release, and the mortality was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- Compound 1 showed an insecticidal activity with a mortality rate of 80% or more after treatment with 100 ppm of foliage.
- Test Example 8 Rice seedlings grown in a pot leafhopper control test pot were sprayed with a chemical solution of the compound of the present invention having a predetermined concentration prepared to be 50% acetone water (added with 0.05% Tween20). After air drying, the 2nd instar larvae were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). Insects were observed for life and death 4 days after release, and the mortality was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- the compound 1,212 showed an insecticidal activity with a death rate of 80% or more after treatment with 100 ppm of foliage.
- Test Example 9 On-spot whitefly control test An adult on-spot whitefly was released in a pot-cultivated cucumber and allowed to lay eggs overnight. One day after the start of egg laying, the adults were removed and left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. Three days after the completion of egg laying, a leaf disk having a diameter of 2.0 cm was cut out from the cucumber, and after egg laying was confirmed, a chemical solution having a predetermined concentration prepared to be 50% acetone water (added with 0.05% Tween 20) was sprayed on the leaf disk. After spraying, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 14 days after spraying, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ (number of eggs laid-number of live insects) / number of eggs laid ⁇ x 100
- compound 212,229,230 showed a high insecticidal activity with a death rate of 80% or more by treatment with 100 ppm of foliage.
- the compound 213 showed a high insecticidal activity with a death rate of 80% or more by treatment with 20 ppm of foliage.
- Test Example 10-1 Citrus thrips control test A leaf disk having a diameter of 2.8 cm was cut out from a green bean grown in a pot, and 50% acetone water (added with 0.05% Tween 20) was added to the leaf disk. The chemical solution was sprayed. After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- Test Example 10-2 Citrus thrips control test A leaf disc having a diameter of 2.8 cm was cut out from a green bean grown in a pot, and 50% acetone water (added with 0.05% Tween 20) was added to the leaf disc. The chemical solution was sprayed. After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. Two continuous tests.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- the compound 2,3,6,7,8,9,10,90,91,104,128,137,186,193,212,213,216,238 showed high insecticidal activity with a mortality rate of 80% or more after 100 ppm foliage treatment.
- the compounds 132, 141, 144, 183, 184, 189, 190, 192, 193, 194, 212, 227, 229, 230, 231, 233, 236, 239, 242 and 243 showed insecticidal activity with a mortality rate of 80% or more after immersion in a chemical solution of 50 ppm.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- the compound 212 showed an insecticidal activity with a mortality rate of 80% or more after treatment with 50 ppm of foliage.
- Test Example 13 Rice Drosophila Control Test On the back of adults collected in the field, 1 ⁇ L (/ 1 head) of a drug solution of the compound of the present invention prepared to a predetermined concentration with acetone was locally applied with a microsyringe. After chemical treatment, adults were transferred to rice seedlings so that there were 5 per strain, and left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). After 48 hours of treatment, adult mortality was observed, and the mortality was calculated according to the following formula.
- Test Example 14 The back of an adult female reared in a housefly control test room was treated with 1 ⁇ L (one head) of a drug solution of the compound of the present invention prepared to a predetermined concentration with acetone. After the chemical treatment, adults were transferred to plastic cups so that there were 5 per cup, and left in a constant temperature room (25 hours-8 hours dark period) at 25 ° C. After 24 hours of treatment, the state of agony of adults was observed, and the rate of agony was calculated according to the following formula. The test was conducted by a two-run system.
- Rate of bitter worms ⁇ number of bitter worms / (number of surviving insects + number of bitter worms) ⁇ ⁇ 100
- Example 15 Japanese planthopper control test 48 hours after sowing, a seedling root of wheat was treated with a chemical solution of the compound of the present invention prepared to a concentration of 10% acetone water. After 72 hours of absorption of the drug from the root, 10 second larvae were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). Insects were observed for life and death 4 days after release, and the mortality was calculated according to the following formula. The test was carried out by two consecutive systems.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead insects) ⁇ x 100
- the compound 212,213,215,216,222,223,226,227,228,230,231,233,234,235,237,212,213,214,215,216,222,223,227,228,229,231,233,234,235,237,238,239,240,241 showed a high insecticidal activity of 80% or more at a treatment amount of 20 ⁇ g / plant.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead insects) ⁇ x 100
- the compound 212,227,229,231,233,237,238,239,242,243 showed a mortality rate of 80% or more at a treatment amount of 0.05 mg / seedling, and the compound 212 showed a high insecticidal activity with a mortality rate of 95% at a treatment amount of 0.005 mg / seedling.
- Test Example 17 White- seed planthopper control test Potted rice seedlings were subjected to soil irrigation treatment with a chemical solution of the compound of the present invention prepared to a concentration of 10% acetone water. Three days after the treatment, 10 white larvae second instar larvae were released. After that, it was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. The test was carried out by two consecutive systems.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead insects) ⁇ x 100
- the compound 212,227,229,231 showed high insecticidal activity with a death rate of 80% or more at a treatment amount of 0.05 mg / seedling.
- Test Example 18 Rice weevil control test Potted rice seedlings were subjected to soil irrigation treatment with a chemical solution prepared to be 10% acetone water. Two days after the treatment, 5 adult rice weevil were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. The test was conducted by a two-run system.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead insects) ⁇ x 100
- the compound 212 showed a high insecticidal activity with a death rate of 80% or more at a treatment amount of 0.1 mg / seedling.
- Test Example 19 Rice planthopper control test planted rice seedlings were subjected to soil irrigation treatment with a chemical solution of the compound of the present invention having a predetermined concentration prepared to be 10% acetone water. Three days after the treatment, 10 second-instar larvae of low drug sensitivity were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. The test was carried out by two consecutive systems.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead insects) ⁇ x 100
- test pests are insects that have been raised indoors for a long period of time (susceptible strains), (I) in 2007 in Kumamoto prefecture, and (II) in 2005 in Fukuoka prefecture, and then insects that have been raised in the room. (Field collection system) was used.
- Compound 212 showed a mortality rate of 100% when treated with 0.05 mg / seedling and a mortality rate of 90% or more when treated with 0.005 mg / seedling for all strains.
- imidacloprid was found to have a death rate (susceptible strain) of 100%, (I) 40%, and (II) 60% by treating 0.05 mg / plant.
- the compound 212 has a high insecticidal activity against imidacloprid low sensitivity brown planthopper.
- Test Example 20 A rice seedling grown in a pot plant control test pot was irrigated with a chemical solution of the compound of the present invention having a predetermined concentration prepared to be 10% acetone water. Three days after treatment, 10 second-instar larvae of low drug sensitivity were released. After that, it was left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after release, and the death rate was calculated according to the following formula. The test was carried out by two consecutive systems.
- Mortality rate (%) ⁇ number of dead insects / (number of living insects tens of dead insects) ⁇ x 100
- test pests used were insects (sustainable strains) that had been raised indoors for a long period of time, and insects that had been raised in Kumamoto Prefecture in 2006 and then raised indoors (field collection strains).
- Compound 212 showed a mortality rate of 100% when treated with 0.01 mg / seedling, and a mortality rate of 90% or more when treated with 0.005 mg / seedling for all strains.
- imidacloprid had a death rate (susceptible line) of 100% and (field collection line) of 50% when treated with 0.01 mg / plant.
- fipronil was treated with 0.01 mg / seedling and the death rate (susceptible strain) was 100% and (field collection strain) was 70%.
- Compound 212 has a high insecticidal activity against imidacloprid and fipronil-hypersensitive Himetobunkika.
- Test Example 21 In Vitro Metabolic Test Pest Management Science (2003), 59 (3), 347-352, and Journal of Pesticide Science (2004), 29 (2) using Compound 212 and Imidacloprid Housefly Crude Enzyme Extract As described in 110-116, imidacloprid undergoes oxidative metabolism and is known to be inactivated, and is also considered as one of the mechanisms for acquiring resistance. The following experiment was conducted in order to confirm the effect on pests that acquired such resistance.
- the reagent was mixed in the following ratio in a 1.5 mL tube and reacted at 25 ° C. for 40 hours. After the reaction, 1 mL of acetone was added and stirred, and the resulting precipitate was removed by centrifugation at 12000 rpm for 5 minutes. The acetone in the supernatant was distilled off and injected into LC / MS for analysis.
- the total area% of the metabolites was O.08 for compound number 212, but 2.55 for imidacloprid, and the amount of the metabolite of compound number 212 was small compared to imidacloprid. From the above results, it was shown that the compound 212 can be effectively controlled against a resistant pest that metabolically inactivates imidacloprid.
- Test Example 21 A 200 mL, 10 ppm, acetone solution of 30 ppm of a mite control compound was placed in a 4 mL glass vial. This was placed on a shaker and air-dried while rotating to form a dry film of the compound on the inner wall of the vial. After the vial was dried for 24 hours or more, 10 larvae of ticklet ticks were released and capped. The vial was placed in a constant temperature room at 25 ° C., 85% humidity and all dark conditions. Life and death were observed one day after release, and the death rate was calculated according to the following formula. The test was conducted by a two-run system.
- Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead) ⁇ ⁇ 100
- imidacloprid had a death rate of 4% at a treatment amount of 10 ppm.
- Test Example 22 Effect of controlling ticklet tick on the surface of the mouse A back surface hair of a mouse (ICR, male, 5 weeks old) was cut by about 2 cm in diameter, and a 15 mL polystyrene conical tube cut to a height of about 1.5 cm was instantly bonded. Adhesion was performed using an agent.
- Blood sucking inhibition rate (%) 100 ⁇ ⁇ number of blood sucking ticks / (number of living ticks tens of dead ticks) ⁇ ⁇ 100
- the following compound 212 showed a blood sucking inhibition rate of 91%.
- Test Example 23 Effect on canine filamentous worms The activity was evaluated based on the change in the motility of microfilariae of canine filamentous worms. After dissolving in RPMI1640 liquid medium so that the compound concentration was 3.13 ppm, about 20 mice were added to each of the microfilariae of canine worms and cultured at 37 ° C. Forty-eight hours after the start of culture, the motility of the dog filamentous microfilariae was observed, and the activity was evaluated according to the following evaluation criteria.
- Table 12 shows a summary of the insecticidal effects of Compound Nos. 212, 227, 229, 231, 237, 238, 239, 242, and 243, which are particularly preferable compounds in the present invention.
- Table 13 shows a comparison of the effects of the compound Nos. 212, 227, 229, 231, 237, 238, 239, 242, and 243, which are particularly preferred compounds of the present invention, on the low-sensitivity insect pests of the comparative examples.
- the amine derivative of the present invention has an excellent pesticidal effect against a large number of pests such as Japanese moth, Japanese scallop, cotton aphid, Japanese brown planthopper, brown planthopper, leafhopper, mite and other pests.
- a high effect can also be shown on insect species with low drug sensitivity.
- the treatment with soil or a cultivation carrier also shows an effect, and since the opportunity for the operator to be exposed to the drug can be reduced, it can be used safely in pest control. Therefore, the present invention can greatly contribute to the field of pest control.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
R1は、水素原子、またはC1~6アルキル基を示し
R2は、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルオキシカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基、CONR6R7、アルキル部分がハロゲン原子により置換されていてもよいC1~6 O,O’-アルキルホスホリル基、シアノ基、ホルミル基またはニトロ基を示し、
R3は、ハロゲン原子により置換されていてもよいC1~8アルキレン基、ハロゲン原子により置換されていてもよいC2~8アルケニレン基、ハロゲン原子により置換されていてもよいC2~8アルキニレン基、置換されていてもよいフェニレン基、または置換されていてもよい5~6員のヘテロ環二価基を示し、
R4は、水素原子、シアノ基、置換されていてもよいフェニル基、置換されていてもよい3~8員の環状アルキル基、置換されていてもよい3~8員のヘテロ環、ハロゲン原子、OR5、OCOR5、OCOOR5、COR5、COOR5、SR5、SOR5、SO2R5、N-CO-OR8、N-CO-SR8、N-CS-OR8、N-CS-SR8、N-O-CO-R8、O-CO-R8、O-CO-OR8、O-CO-SR8、O-CS-OR8、O-CS-SR8、S-CS-OR8、S-CS-SR8、S-CO-OR8、S-CO-SR8、S-CS-R8、またはNR9R10、O-CO-NR9R10、O-CS-NR9R10、S-CO-NR9R10、S-CS-NR9R10を示す
ここでR5はハロゲン原子により置換されていてもよいC1~6アルキル基、ハロゲン原子により置換されていてもよいアリール基、ハロゲン原子により置換されていてもよいアラルキル基を示す。
(2)化学式(I)中のArが6-クロロ-3-ピリジル基または5-クロロ-3-チアゾリル基である、(1)に記載の有害生物防除剤。
R1は、水素原子、またはC1~6アルキル基を示し
R2は、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルオキシカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基、CONR6R7、アルキル部分がハロゲン原子により置換されていてもよいC1~6 O,O’-アルキルホスホリル基、シアノ基、ホルミル基またはニトロ基を示し、
R3は、ハロゲン原子により置換されていてもよいC1~8アルキレン基、ハロゲン原子により置換されていてもよいC2~8アルケニレン基、ハロゲン原子により置換されていてもよいC2~8アルキニレン基、置換されていてもよいフェニレン基、または置換されていてもよい5~6員のヘテロ環二価基を示し、
R4は、水素原子、シアノ基、置換されていてもよいフェニル基、置換されていてもよい3~8員の環状アルキル基、置換されていてもよい3~8員のヘテロ環、ハロゲン原子、OR5、OCOR5、OCOOR5、COR5、COOR5、SR5、SOR5、SO2R5、N-CO-OR8、N-CO-SR8、N-CS-OR8、N-CS-SR8、N-O-CO-R8、O-CO-R8、O-CO-OR8、O-CO-SR8、O-CS-OR8、O-CS-SR8、S-CS-OR8、S-CS-SR8、S-CO-OR8、S-CO-SR8、S-CS-R8、またはNR9R10、O-CO-NR9R10、O-CS-NR9R10、S-CO-NR9R10、S-CS-NR9R10を示す
ここでR5はハロゲン原子により置換されていてもよいC1~6アルキル基、ハロゲン原子により置換されていてもよいアリール基、ハロゲン原子により置換されていてもよいアラルキル基を示す。
(13)化学式(I)中のArが6-クロロ-3-ピリジル基または5-クロロ-3-チアゾリル基である、(12)に記載のアミン誘導体またはその塩。
(16)化学式(Ie’)中のR4eが、ハロゲン原子により置換されたC1~6アルキル基である、(15)に記載のアミン誘導体またはその塩。
R9、R10が示す「ハロゲン原子により置換されていてもよいC1~6アルキル基」としては、具体的にはメチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、n-ペンチル基、2-トリフルオロエチル基、2-クロロエチル基が挙げられ、好ましくはメチル基、エチル基である。
Arは、4-ニトロフェニル基、4-シアノフェニル基、3,5-ジブロモフェニル基、2,4-ジブロモフェニル基、6-クロロ-3-ピリジル基、5-クロロ-3-チアゾリル基、6-クロロ-5-フルオロ-3-ピリジル基、6-ブロモ-3-ピリジル基、6-フルオロ-3-ピリジル基、5,6-ジクロロ-3-ピリジル基、または6-トリフルオロメチル-3-ピリジル基を示し、
R1は、水素原子、またはメチル基を示し、
R2は、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基、またはシアノ基を示し、
R3は、メチレン基、エチレン基、プロピレン基、または1-プロピニレン基を示し、
R4は、水素原子、シアノ基、SR5(R5は、ハロゲンにより置換されていてもよいC1~6アルキル基を示す)、S-CS-OR8、S-CS-SR8(R8は、ハロゲンにより置換されていてもよいC1~6アルキル基を示す)を示す。
R1は、水素原子を示し、
R2は、トリフルオロメチルスルホニル基を示し、
R3は、メチレン基、エチレン基、1-プロピニレン基を示し、
R4は、水素原子またはシアノ基を示す化合物、
(ii)Arは、6-クロロ-3-ピリジル基、5-クロロ-3-チアゾリル基、または6-トリフルオロメチル-3-ピリジル基を示し、
R1は、水素原子またはメチル基を示し、
R2は、シアノ基、またはトリフルオロメチルカルボニル基を示し、
R3は、エチレン基を示し、
R4は、水素原子、SR5(R5は、ハロゲンにより置換されていてもよいC1~6アルキル基を示す)、S-CS-OR8、S-CS-SR8(R8は、ハロゲンにより置換されていてもよいC1~6アルキル基を示す)を示す化合物、
(iii)式(Ie)で示される化合物
特に好ましい化合物の例は下記(i)から(iii)の化合物である。
R1は、水素原子を示し、
R2は、トリフルオロメチルスルホニル基を示し、
R3は、メチレン基、エチレン基、1-プロピニレン基を示し、
R4は、水素原子を示す化合物、
(ii)Arは、6-クロロ-3-ピリジル基、5-クロロ-3-チアゾリル基、または6-トリフルオロメチル-3-ピリジル基を示し、
R1は、水素原子またはメチル基を示し、
R2は、シアノ基、またはトリフルオロメチルカルボニル基を示し、
R3は、エチレン基を示し、
R4は、SR5(R5は、ハロゲンにより置換されていてもよいC1~6アルキル基を示す)、S-CS-OR8、S-CS-SR8(R8は、ハロゲンにより置換されていてもよいC1~6アルキル基を示す)を示す化合物、
(iii)式(Ie)で示される化合物
式(Ie)で示される化合物の好ましい態様は、
Arは、3-ピリジル基、6-クロロ-3-ピリジル基、5-クロロ-3-チアゾリル基、6-クロロ-5-フルオロ-3-ピリジル基、6-ブロモ-3-ピリジル基、6-フルオロ-3-ピリジル基、5,6-ジクロロ-3-ピリジル基、6-トリフルオロメチル-3-ピリジル基、2-クロロ-5-ピリミジル基を示し、
R1は、水素原子またはメチル基、エチル基を示し、
Yは、水素原子、ハロゲン原子、メチル基を示し、
R4eは、トリフルオロメチル基、トリクロロメチル基、ジクロロメチル基、ジフルオロメチル基、ジフルオロクロロメチル基、クロロメチル基、ペンタフルオロエチル基を示す化合物であり、
より好ましくは
Arは、6-クロロ-3-ピリジル基、6-フルオロ-3-ピリジル基、6-クロロ-5-フルオロ-3-ピリジル基、6-ブロモ-3-ピリジル基、2-クロロ-5-ピリミジル基を示し、
R1は、水素原子、またはメチル基を示し、
Yは、水素原子を示し
R4eは、トリフルオロメチル基、ジフルオロメチル基、ジフルオロクロロメチル基、クロロメチル基、ペンタフルオロエチル基を示す化合物である。
化合物番号212:N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、
化合物番号227:N-〔1-((6-クロロ-5-フルオロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、
化合物番号229:N-〔1-((6-フルオロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、
化合物番号231:N-〔1-((6-ブロモピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、
化合物番号237:N-〔1-(1-(6-クロロピリジン-3-イル)エチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、
化合物番号238:N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2-ジフルオロアセタミド、
化合物番号239:2-クロローN-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2-ジフルオロアセタミド
化合物番号242:N-〔1-((6-クロロピリジンー3-イル)メチル)ピリジンー2(1H)-イリデン〕-2,2,3,3,3-ペンタフルオロプロパナミド
化合物番号243:N-〔1-((2-クロロピリミジン-5-イル)メチル)ピリジンー2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド
である。
(a)粉末X線回折において、少なくとも下記回折角(2θ)に回折角ピークを有する。
回折角:8.6±0.2°、14.2±0.2°、17.5±0.2°、18.3±0.2°、19.7±0.2°、22.3±0.2°、30.9±0.2°、35.3±0.2°
(b)示差走査熱量分析(DSC)において、融点が155~158℃を示す。
これらの適用は、害虫の侵入の前および後に行うことができる。
(1)次の化学式(Ia)で表される化合物は、
R2は、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルオキシカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基、CONR6R7(ここでR6、R7は互いに独立して、水素原子、ハロゲンにより置換されていてもよいC1~6アルキル基)、アルキル部分がハロゲン原子により置換されていてもよいC1~6 O,O’-アルキルホスホリル基、シアノ基、ホルミル基またはニトロ基を示し、
R3は、ハロゲン原子により置換されていてもよいC1~8アルキレン基、ハロゲン原子により置換されていてもよいC2~8アルケニレン基、ハロゲン原子により置換されていてもよいC2~8アルキニレン基、置換されていてもよいフェニレン基、置換されていてもよい5~6員のヘテロ環二価基を示し、
R4は、水素原子、置換されていてもよいフェニル基、置換されていてもよい3~8員の炭素およびヘテロ環、ハロゲン原子、OR5、OCOR5、OCOOR5、COR5、COOR5、SR5、SOR5、SO2R5(ここでR5はハロゲンにより置換されていてもよいC1~C6アルキル基、アリール基、アラルキル基を示す)、N-CO-OR8、N-CO-SR8、N-CS-OR8、N-CS-SR8、N-O-CO-R8、O-CO-R8、O-CO-OR8、O-CO-SR8、O-CS-OR8、O-CS-SR8、S-CS-OR8、S-CS-SR8、S-CO-OR8、S-CO-SR8(ここでR8は、置換されていてもよいC1~6アルキル基を示し、置換基は、ハロゲン、C1~4アルキルオキシカルボニル基、C1~4アルキルカルボニル基、ハロゲンまたはハロゲンにより置換されていてもよいC1~4アルキル基に置換されていてもよいベンゾイル基、C1~4アルキルオキシ基、C1~4アルキルチオ基である)、NR9R10(ここでR9、R10は互いに独立して、水素原子、ハロゲンにより置換されていてもよいC1~6アルキル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニルオキシ基を示す)を示す。
次の化学式(II)で表される化合物に、R2[R2は上記化学式(I)で定義されている意味と同じ]のハロゲン化物、無水物、エステルなどを、塩基存在下あるいは非存在下で反応させて得ることができる。
R2のハロゲン化物、無水物、エステルとしては、カルボン酸ハライド、カルボアルキルオキシハライド、スルホニルハライド、O,O’-アルキルホスホリルハライド、無水カルボン酸、ジアルキルジカーボネート、カルボン酸エステル、炭酸エステルなどを用いることができるが、具体的には、アセチルクロリド、クロロギ酸エチル、メタンスルホニルクロリド、クロロリン酸ジエチル、無水トリフルオロ酢酸、ギ酸エチルなどを用いることが好ましい。
(IIIa)で表される化合物から合成する場合、(IIIa)で表される化合物に、次の化学式(IVa)で表される化合物を、塩基存在下または非存在下で反応させて得ることができる。
塩基存在下で反応を行う場合、塩基としては、例えば水素化ナトリウムなどのアルカリ金属水素化物、炭酸カリウムや炭酸ナトリウムなどの炭酸塩、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物、トリエチルアミンなどの第3級アミン類、ピリジン、4-ジメチルアミノピリジンなどの無置換または置換基を有するピリジン類などを用いることができる。
塩基存在下で反応を行う場合、塩基としては、例えば水素化ナトリウムなどのアルカリ金属水素化物、炭酸カリウムや炭酸ナトリウムなどの炭酸塩、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物、トリエチルアミンなどの第3級アミン類、ピリジン、4-ジメチルアミノピリジンなどの無置換または置換基を有するピリジン類を用いることができる。
反応は、溶媒を用いることが好ましく、溶媒はメタノール、エタノールなどの低級アルコール、アセトニトリル、ジクロロメタン、ジクロロエタンなどを用いることができるが、メタノール、エタノールなどを用いることが好ましい。
(Va)で表される化合物と、X-R3R4[R3R4は上記化学式(I)で定義されている意味と同じ、Xはハロゲン原子を表す]を、塩基存在下または非存在下で反応させて得ることができる。
(Vb)で表される化合物と、Ar-CH2-X[Arは上記化学式(I)で定義されている意味と同じ、Xはハロゲン原子またはOTs、OMs等を表す]で表される化合物を、塩基存在下または非存在下で反応させて得ることができる。
塩基存在下で反応を行う場合、塩基としては、例えば水素化ナトリウムなどのアルカリ金属水素化物、炭酸カリウムや炭酸ナトリウムなどの炭酸塩、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物、トリエチルアミンなどの第3級アミン類、ピリジン、4-ジメチルアミノピリジンなどの無置換または置換基を有するピリジン類を用いることができる。
次の化学式(VIa)で表される化合物に、R2[R2は上記化学式(I)で定義されている意味と同じ]の、ハロゲン化物、無水物、エステルなどを、塩基存在下あるいは非存在下で反応させて得ることができる。
R2のハロゲン化物、無水物、エステルとしては、カルボン酸ハライド、カルボアルキルオキシハライド、スルホニルハライド、O,O’-アルキルホスホリルハライド、無水カルボン酸、ジアルキルジカーボネート、カルボン酸エステル、炭酸エステルなどを用いることができるが、例えばアセチルクロリド、クロロギ酸エチル、メタンスルホニルクロリド、クロロリン酸ジエチル、無水トリフルオロ酢酸、ギ酸エチルなどを用いることが好ましい。
酸存在下、または非存在下で、H2N-R3R4[R3、R4は上記化学式(I)で定義されている意味と同じ]で表される化合物を加えてイミンを形成させたのち、還元反応を実施することによって得ることができる。
反応温度は、通常20℃から100℃の範囲で行うことができる。
文献(Journal of Medicinal Chemistry 1999, 42(12), 2227-2234)に記載の方法で合成できる次の化学式(VIII)で表される化合物に、塩基存在下、二硫化炭素、R8-Xで表される化合物[R8は上記化学式(I)で定義されている意味と同じ、Xはハロゲン原子を表す]を反応させることで得ることができる。
塩基としては、水素化ナトリウムなどのアルカリ金属水素化物、炭酸カリウムや炭酸銅などの炭酸塩、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物、酸化銅や酸化マグネシウムなどの金属酸化物、トリエチルアミンなどの第3級アミン類、ピリジン、4-ジメチルアミノピリジンなどの無置換または置換基を有するピリジン類を用いることができるが、カリウムt-ブチレートなどの強塩基を用いることが好ましい。
次の式中(IX)で表される化合物と、ArCH(R1)X[Ar、R1の定義は前述と同じ、XはハロゲンまたはOTs、OMs等を示す]で表される化合物とを、塩基存在下、または非存在下で反応させることで得ることができる。
塩基存在下で反応を行う場合、塩基としては、例えば水素化ナトリウムなどのアルカリ金属水素化物、炭酸カリウムや炭酸ナトリウムなどの炭酸塩、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物、トリエチルアミンなどの第3級アミン類、ピリジン、4-ジメチルアミノピリジンなどの無置換または置換基を有するピリジン類を用いることができる。
塩基存在下で反応を行う場合、塩基としては、例えば、水素化ナトリウムなどのアルカリ金属水素化物、炭酸カリウムや炭酸ナトリウムなどの炭酸塩、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物、トリエチルアミンなどの第3級アミン類、ピリジン、4-ジメチルアミノピリジンなどの無置換、または置換基を有するピリジン類を用いることができる。
塩基存在下で反応を行う場合、塩基としては、例えば、水素化ナトリウムなどのアルカリ金属水素化物、炭酸カリウムや炭酸ナトリウムなどの炭酸塩、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物、トリエチルアミンなどの第3級アミン類、ピリジン、4-ジメチルアミノピリジンなどの無置換、または置換基を有するピリジン類を用いることができる。
2-メチルチオ-エチルアミン3.0g(33mmol)を無水ジメチルホルムアミド25mlに溶かし、2-クロロ-5-クロロメチルピリジン5.3g(33mmol)、水素化ナトリウム(60%)1.6g(正味950mg,40mmol)の順に加え、70℃で90分攪拌した。反応液を0℃に冷却し、水約30mlを少量ずつ加えて反応を終了し、ジクロロメタン約50mlで2回抽出した。ジクロロメタン層を無水硫酸マグネシウムで乾燥後濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:1→酢酸エチル→ジクロロメタン:メタノール=1:19→ ジクロロメタン:メタノール= 1:10)で精製した。収量4.6g(収率64%)
ブロモシアン123mg(1.16mmol)に無水ジエチルエーテル4mlを加え、0℃に冷却した。これに、無水ジエチルエーテル3mlに溶解した2-クロロ-5-[N-(2-メチルチオエチル)]アミノメチルピリジン(参考例1)(250mg;1.16mmol)、酢酸ナトリウム95mg(1.16mmol)の順に加え、室温で一晩攪拌した。反応液に1%水酸化ナトリウム水溶液約10mlを加えて1時間攪拌し、ジエチルエーテル約20mlを加えて分液した。ジエチルエーテル層を水約10ml、1%塩酸.約10mlの順で洗浄後、無水硫酸マグネシウムで乾燥し、減圧濃縮した。収量209mg(収率75%).
2-クロロ-5-[N-(2-メチルチオ)エチル]アミノメチルピリジン(参考例1)132mg(0.61mmol)に、ギ酸エチル10mlを加え、3時間還流した。反応液を室温に戻したのち、溶媒を減圧留去し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=7:3→1:1)で精製して目的物を得た。収量159mg(収率81%)。
無水トリフロオロ酢酸(140mg;0.67mmol)を5mlの無水ジクロロメタンに溶かした溶液を、US2009306041に記載の方法で合成したエチル-(2-クロロ-5-ピリジルメチル)アミン(120mg;070mmol)とトリエチルアミン(101mg;1mmol)を5mlの無水ジクロロメタンに溶かした溶液に、氷冷しながら滴下した。滴下後室温で一晩攪拌した後、反応液を氷冷した1%水酸化ナトリウム水溶液、水、1%塩酸、つづいて水の順序で洗浄し無水硫酸マグネシウムで乾燥した。溶媒を減圧留去することにより目的物が得られた。収量107mg(収率78%)。
2-クロロ-5-アミノエチルピリジン50mg(0.26mmol)にアセトン2ml、メタノール1mlを加え、酢酸ナトリウム43mg(0.52mmol)を加えて、室温で4時間攪拌した。続いて水素化ホウ素ナトリウム30mg(0.78mmol)を加え、室温で1時間攪拌した。反応液をろ過後濃縮し、酢酸エチルと水を加えて分液した。有機層を無水硫酸マグネシウムで乾燥後濃縮し、分取用TLCプレートで精製し、2-クロロ-5-[N-(2-イソプロピルアミノメチル)]ピリジンを得た。収量17mg(収率36%)
得られた2-クロロ-5-[N-(2-イソプロピルアミノメチル)]ピリジン57mgを用いて、合成例1に記載の方法で目的物が得られた。収量54mg(収率47%)。
2-クロロ-5-アミノエチルピリジン1.50g(10.6mmol)を無水ジメチルホルムアミド10mlに溶かし、水素化ナトリウム(60%)486mg(正味292mg,12.7mmol),プロパルギルブロミド1.25g(10.6mmol)の順に加え、70℃で3時間半攪拌した。反応液を室温に戻し、水をゆっくり加えて反応を停止し、酢酸エチルで抽出した。酢酸エチル層を無水硫酸マグネシウムで乾燥後濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:1)で精製して2-クロロ-5-[N-(2-プロパルギル)]アミノメチルピリジンを得た。収量892mg(収率47%)
得られた2-クロロ-5-[N-(2-プロパルギル)]アミノメチルピリジン60mgを用いて、合成例1に記載の方法で目的物が得られた。収量20mg(収率30%)。
6-クロロ-3-クロロメチルピリジン(648mg,4mmol),50%アンモニウムシアニド水溶液(100mg),炭酸カリウム(590mg,5mmol)をアセトニトリル(20ml)に懸濁し、40時間加熱還流した。熱時濾過し、濾液を濃縮し、残渣をエーテルと水で洗った。粘稠な混合物を少量のメタノールから結晶化することにより、目的物を得た。収量28mg
1H-NMR(CDCl3,δ,ppm):4.17(4H,s),7.40(2H,d),7.68(2H,dd),8.31(2H,d)
IR:2207(CN)
MS:m/z=293(M+H)
合成例6と同様の方法で、4-クロロベンジルクロリド1.61gより標記化合物を得た。収量450mg(収率15%)。
1H-NMR(CDCl3,δ,ppm):4.10(2H,s),7.23(2H,d),7.36(2H,d)
MS:m/z=291(M+H)
6-クロロ-3-アセチルピリジン(1.03g,0.3mmol)と30%エチルアミンメタノール溶液(1.0ml)を8mlのクロロホルムに混ぜ、還流した。8時間後に30%エチルアミンメタノール溶液を1ml追加し、さらに12時間同温度で攪拌を続けた。クロロホルムを留去し、残渣を10mlのメタノール溶かし、氷冷した。水素化ホウ素ナトリウム(1g)を少しづつ加え、一晩攪拌した。メタノールを留去し、残渣をアセトニトリルで抽出した。抽出液を減圧濃縮した。アセトニトリル抽出と減圧濃縮をさらに2回繰り返した後、残渣をクロロホルムに溶かし、1% NaOHaqで洗浄し、クロロホルム相を固体KOHで乾燥した。クロロホルムを減圧留去し、N-[1-(6-クロロ-3-ピリジル)エチル]-N-エチルアミンの粗生成物(純度薬80%)が790mg得られた。
得られたN-[1-(6-クロロ-3-ピリジル)エチル]-N-エチルアミンの粗生成物100mgを用いて、合成例1に記載の方法で目的物が得られた。収量55mg(収率60%)
1H-NMR(CDCl3,δ,ppm):1.25(3H,t),1.66(3H,d),2.91(2H,m),4.14(1H,q),7.37(1H,d),7.73(1H,dd),8.30(1H,d)
IR:2211(CN):2206(CN)
文献(Journal of Medicinal Chemistry 1999, 42(12), 2227)に記載の方法で合成した(6-クロロ-3-ピリジルメチル)-2-イミノ-1,3-チアゾリジン(228mg,1mmol)を15mlのテトラヒドロフランに溶かした溶液に、カリウムt-ブチレート(112mg,1mmol)を加え、30分間室温で攪拌した後、二硫化炭素(228mg,3mmol)を少しずつ加えてからさらに1時間攪拌を続けた。ヨウ化メチル(142mg,1mmol)を滴下し、2時間攪拌した。不溶固体を、セライトを通して濾去し、濾液を減圧で濃縮した。粘稠な残渣から、酢酸エチル/ヘキサン(1:1,容量比)を展開溶媒に用いたシリカゲルカラムクロマトグラフィーにより、黄色油状の目的物を単離した。収量130mg(41%)
1H-NMR(CDCl3,δ,ppm):2.76(3H,s),3.31(2H,t),3.63(2H,t),4.28(2H,s),7.38(1H,d),7.73(1H,dd),8.35(1H,d)
IR:2211(CN)
合成例5に記載の方法で得られた2-クロロ-5-[N-(2-プロピニル)]アミノメチルピリジン104mg(0.58mmol)を無水ジクロロメタン10mlに溶解し、無水トリフルオロスルホン酸191μl(1.16mmol,326mg)を加えて室温で2時間攪拌した。反応終了後、反応液にジクロロメタンを加えて薄め、1%水酸化ナトリウム水溶液、1%塩酸水溶液の順で洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=2:8)で精製して目的物を得た。収量55mg(収率30%)
比較例の方法で合成したN-[(6-クロロピリジン-3-イル)メチル]シアナミド30mg(0.18mmol)を無水DMF3mlに溶解し、水素化ナトリウム(60%)10mg(正味6mg,0.26mmol)を加えて室温で20分攪拌した。続いて(クロロメチル)シクロプロパン52μg(0.57mmol)、ヨウ化カリウム5mgの順に加えて、室温で20時間攪拌した。反応終了後、反応液に少量の水を加えて反応を停止し、1%塩酸と酢酸エチルで分液した。有機層を1%塩酸で洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮し、分取用TLCプレート(0.5mmプレート1枚、ヘキサン:酢酸エチル=1:1で展開)で精製して目的物を得た。収量18mg(収率45%)
1、2-ビス(トシルオキシ)エタン8.86g(24.0mmol)を無水DMF100mlに溶解し、氷冷下で比較例の方法で合成したN-[(6-クロロピリジン-3-イル)メチル]シアナミド2.00g(12.0mmol)、NaH(60%)500mg(正味300mg,13.2mmol)、KI44mgの順に加えて、室温で80分攪拌した。反応終了後、0℃でメタノールを少しずつ加え、続いて水を加えて反応を停止した。これに酢酸エチルと1%塩酸を加えて分液を行い、有機層を1%塩酸で洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=2:8→6:4)で精製した。目的物を含むフラクションを集めて濃縮したところ、DMFが残っていたため、少量の酢酸エチルを加えて、1%塩酸で2回洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮することによってDMFを除き、2-[N-(6-クロロ-3-ピリジルメチル)シアナミド]エチル 4-メチルベンゼンスルホネート(化合物84)を得た。収量1.43g(収率33%)。
ベンジルエチルアミン55mg(0.41mmol)を無水THF5mlに溶解し、カリウムt-ブチレート46mg(0.41mmol)を加えて室温で20分攪拌した。続いて二硫化炭素49μg(62mg,0.41mmol)、合成例12の方法で合成した2-[N-(6-クロロ-3-ピリジルメチル)シアナミド]エチル 4-メチルベンゼンスルホネート(化合物84)50mg(0.14mmol)を無水THF3mlに溶かしたもの、ヨウ化カリウム5mgの順に加え、40℃で1時間攪拌した。反応終了後、少量の水を加えて反応を停止し、セライトを用いて反応液をろ過し、ろ液を濃縮した。シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=7:3)で精製して目的物を得た。収量41mg(収率72%)。
A:合成例1~5、10と同様の方法
B:合成例6、7と同様の方法
C:合成例8と同様の方法
D:合成例9と同様の方法
E:合成例11と同様の方法
F:合成例12、13と同様の方法
(1)2-アミノピリジン25g(270mmol)を無水ジクロロメタン200mlに溶解し、トリエチルアミン41ml(30g,300mmol)を加えて0℃に冷却した。ここに無水トリフルオロ酢酸38ml(57g,270mmol)を15分間かけて滴下し、室温で2時間攪拌した。反応終了後、反応液を約100mlの氷水に注ぎ込み、10分間攪拌した。分液ロートに移して分液を行い、有機層を150mlの水で2回、150mlの1%HCL水溶液で2回洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮して2,2,2-トリフルオローN-(ピリジン-2(1H)-イリデン)アセタミド36g(収率71%)を得た。
1H-NMR(CDCl3,δ,ppm):7.20(1H,ddd),7.83(1H,td),8.20(1H,d),8.35(1H,d),10.07(1H,brs)
13C-NMR(CDCl3,δ,ppm):115.3,115.5(q),121.6,139.1,147.9,149.5,155.3(q)
MS:m/z=191(M+H)
(2)2-クロロー5-クロロメチルピリジン20g(126mmol)を無水アセトニトリル200mlに溶解し、前述の方法で得られた2,2,2-トリフルオローN-(ピリジン-2(1H)-イリデン)アセタミド24g(126mmol)、炭酸カリウム21g(151mmol)を加えて、6時間加熱還流したのち、室温で10時間攪拌した。反応終了後、反応液をろ過し、ろ液を減圧濃縮した。これにジエチルエーテルを加えて結晶化し、得られた結晶をろ集し、ジエチルエーテルと水でよく洗浄した。得られた結晶を60℃で1時間減圧乾燥し、目的物を得た。収量26g(収率66%)。
1H-NMR(CDCl3,δ,ppm):5.57(2H,s),6.92(1H,td),7.31(1H,d),7.80(1H,td),7.87(1H,dd),7.99(1H,dd),8.48(2H,m)
13C-NMR(CDCl3,δ,ppm):53.8,115.5,117.2(q),122.1,124.7,130.0,139.2,140.0,142.5,149.7,151.8,158.9,163.5(q)
MS:m/z=316(M+H)
(3)粉末X線結晶解析
粉末X線回折においては、以下の条件で測定した。
装置名:RINT-2200(株式会社リガク)
X線:Cu-Kα(40kV、20mA)
走査範囲:4~40° サンプリング幅:0.02° 走査速度:1°/分
結果は、以下の通りである(図1)。
回折角(2θ)8.7°、14.2°、17.5°、18.3°、19.8°、22.4°、30.9°、35.3°
(4)示差走査熱量分析(DSC)
示差走査熱量分析においては、以下の条件で測定した。
装置名:DSC-60
試料セル:アルミニウム
温度範囲:50℃~250℃(昇温:10℃/分)
結果を、図2に示した。
化合物212(700mg)にヘキサン約25ml、酢酸エチル約25mlを加えて、湯浴で65℃に加熱して完全に溶解させた。これをゆっくり室温に戻して一晩放置した。析出した結晶をろ集し、少量のヘキサン:酢酸エチル=95:5の溶液で結晶を洗浄した。これをデシケーターに入れて2時間減圧下で乾燥させて、白色結晶349mgを得た。
回折角(2θ)8.5°、14.0°、17.3°、18.1°、19.6°、22.2°、30.8°、35.2°
示差走査熱量分析の結果は、図4に示した。
化合物212(1.0g)に2-プロパノール28mlを加え、湯浴で65℃に加熱して完全に溶解させた。これをゆっくり室温に戻して一晩放置した。析出した結晶をろ集し、少量の2-プロパノールで洗浄後、デシケーターに入れて2時間減圧下で乾燥させて、白色結晶695mgを得た。
化合物212(700mg)にトルエン約30mlを加え、湯浴で65℃に加熱して完全に溶解させた。これをゆっくり室温に戻して一晩放置した。析出した結晶をろ集し、少量のトルエンで洗浄後、デジケーターに入れて2時間減圧下で乾燥させて、白色結晶440mgを得た。
回折角(2θ)8.6°、14.2°、17.5°、18.3°、19.7°、22.3°、30.9°、35.3°
示差走査熱量分析の結果は、図7に示した。
化合物212(50mg)にメタノール約2ml、水約2mlを加え、湯浴で65℃に加熱して溶解させた。これを室温に戻して一晩放置した。析出した結晶をろ集して白色結晶16mgを得た。
2-アミノピリジン1.0g(10.6mmol)を酢酸エチル10mlに溶解し、トリエチルアミン1.78ml(1.2eq)を加えて、氷冷下、無水トリフルオロ酢酸1.62ml(1.1eq)を添加した。その後室温で2時間攪拌後、酢酸エチル10mlと水10mlを加えて攪拌後分液した。酢酸エチル層をさらに水10mlで二回洗浄後、無水硫酸マグネシウムで乾燥し、減圧濃縮して、2,2,2-トリフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド 1.56g(77.2%)を得た。
2-アミノピリジン0.94g(10mmol)をTHF 20mLに溶解した。これにトリフルオロ酢酸エチルエステル2.84g(20mmol)及びジメチルアミノピリジン1.22g(10mmol)を加え、22時間還流した。THFを留去後、シリカゲルカラム(展開溶媒:ヘキサン/酢酸エチル 4/1)で精製し、2,2,2-トリフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド0.26g(収率13.7%)を得た。
2-クロロー5-クロロメチルピリジン3.00g(18.6mmol)を無水DMF20mlに溶解し、2-アミノピリジン1.75g(18.6mmol)を加えて80℃で8時間、室温で5時間攪拌した。反応終了後、DMFを減圧留去し、アセトニトリルを加えたところ固体が析出したので、ろ集し、アセトニトリルでよく洗浄後乾燥して1-〔(6-クロロピリジン-3-イル)メチル〕ピリジン-2(1H)-イミン塩酸塩2.07g(収率44%)を得た。
1H-NMR(DMSO-d6,δ,ppm):5.65(2H,s),6.96(1H,t),7.23(1H,m),7.57(1H,d),7.80(1H,m),7.91(1H,m),8.28(1H,m),8.49(1H,d),9.13(2H,brs)
前述の方法で得られた1-〔(6-クロロピリジン-3-イル)メチル〕ピリジン-2(1H)-イミン塩酸塩50mg(0.20mmol)を無水ジクロロメタン5mlに溶解し、氷冷下でDMAP122mg(1.00mmol)、無水トリフルオロ酢酸50mg(0.24mmol)の順に加えて、室温で1時間攪拌した。反応終了後、反応液をジクロロメタンで薄め、1%塩酸で洗浄後、無水硫酸マグネシウムで乾燥した。ジクロロメタンを減圧留去することで目的物を得た。収量42mg(収率67%)。NMRは前述の方法のものと一致した。
合成例14の別法に記載の方法で得られた1-〔(6-クロロピリジン-3-イル)メチル〕ピリジン-2(1H)-イミン塩酸塩200mg(0.78mmol)、DMAP238mg(1.95mmol)、EDC-HCl224mg(1.17mmol)を無水ジクロロメタン10mlに溶解し、ジブロモ酢酸101μl(202mg,1.17mmol)を加えて室温で一晩攪拌した。反応終了後、反応液をジクロロメタンで薄め、水で1回、1%HCl水溶液で2回洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮して目的物を得た。収量50mg(収率15%)
1H-NMR(CDCl3,δ,ppm):5.56(2H,s),5.99(1H,s),6.78(1H,td),7.33(1H,d),7.69(1H,td),7.76(1H,dd),7.93(1H,dd),8.39(1H,d),8.50(1H,d)
13C-NMR(CDCl3,δ,ppm):44.6,53.1,113.7,121.9,124.8,130.1,138.2,139.7,141.2,149.5,152.0,159.4,172.2
2-クロロ-3-フルオロ-5-メチルピリジン4.00g(27.6mmol)を四塩化炭素80mlに溶かし、N-ブロモスクシンイミド7.37g(41.4mmol)、過酸化ベンゾイル20mgを加えて一晩加熱還流した。反応終了後、反応液を室温に戻して減圧濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=19:1)で精製して5-(ブロモメチル)ー2-クロロー3-フルオロピリジン3.06g(収率51%)を得た。
1H-NMR(CDCl3,δ,ppm):4.45(2H,s),7.54(1H,dd),8.23(1H,s)
上記の方法で得た5-(ブロモメチル)-2-クロロ-3-フルオロピリジン50mg(0.22mmol)を無水アセトニトリル5mlに溶かし、合成例14の(1)に記載の方法で得られた2,2,2-トリフルオローN-(ピリジンー2(1H)-イリデン)アセタミド42mg(0.22mmol)、炭酸カリウム36mg(0.26mmol)の順に加えて7時間加熱還流した。反応終了後、反応液を室温に戻して不溶物をろ過し、ろ液を減圧濃縮した。これにジエチルエーテルを加えたところ固体が析出したので、ろ集し、ジエチルエーテルで洗浄後デシケーターで減圧乾燥して目的物を得た。収量29mg(収率40%)。
1H-NMR(CDCl3,δ,ppm):5.54(2H,s),6.89(1H,td),7.76(1H,dd),7.80(1H,td),7.85(1H,d),8.29(1H,d),8.57(1H,d)
MS:m/z=334(M+H)
2-フルオロ-5-メチルピリジン500mg(4.50mmol)を四塩化炭素50mlに溶解し、N-ブロモスクシンイミド1.20g(6.76mmol)、過酸化ベンゾイル20mgを加えて2.5時間加熱還流した。反応終了後、反応液を室温に戻して溶媒を減圧留去し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=19:1)で精製して5-ブロモメチル-2-フルオロピリジン300mg(収率35%)を得た。
1H-NMR(CDCl3,δ,ppm):5.56(2H,s),6.89(1H,td),6.94(1H,d),7.79(1H,td),7.87(1H,d),8.03(1H,m),8.31(1H,s),8.54(1H,d)
MS:m/z=300(M+H)
2-ブロモ-5-メチルピリジン500mg(2.92mmol)を四塩化炭素15mlに溶解し、N-ブロモスクシンイミド623mg(3.50mmol)、過酸化ベンゾイル10mgを加えて19時間加熱還流した。反応終了後、反応液を室温に戻して減圧濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン;酢酸エチル=19:1)で精製して2-ブロモ-5-ブロモメチルピリジン143mg(収率20%)を得た。
1H-NMR(CDCl3,δ,ppm):4.42(2H,s),7.47(1H,d),7.59(1H,dd),8.38(1H,d)
上記の方法で得た2-ブロモ-5-ブロモメチルピリジン70mg(0.28mmol)を無水アセトニトリル10mlに溶かし、合成例14の(1)に記載の方法で合成した2,2,2-トリフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド54mg(0.28mmol)、炭酸カリウム46mg(0.34mmol)の順に加えて、6時間加熱還流した。反応終了後、反応液を室温に戻して不溶物をろ過し、ろ液を減圧濃縮した。これにジエチルエーテルを加えたところ固体が析出したので、ろ集し、ジエチルエーテルで洗浄後デシケーターで減圧乾燥して目的物を得た。収量81mg(収率82%)。
1H-NMR(CDCl3,δ,ppm):5.52(2H,s),6.88(1H,t),7.48(1H,d),7.78(2H,m),7.84(1H,d),8.44(1H,d),8.53(1H,d)
MS:m/z=360(M+H)
合成例14の別法に記載の方法で得られた1-〔(6-クロロピリジン-3-イル)メチル〕ピリジン-2(1H)-イミン塩酸塩70mg(0.27mmol)を無水ジクロロメタン4mlに溶解し、DMAP82mg(0.67mmol)、クロロ酢酸25mg(0.27mmol)、EDC-HCl 62mg(0.32mmol)の順に加えて、室温で一晩攪拌した。反応終了後、ジクロロメタンを加えて薄め、水、1% HClaq.で洗浄し、無水硫酸マグネシウムで乾燥後、減圧濃縮して目的物を得た。収量4mg(収率5%)。
1H-NMR(CDCl3,δ,ppm):4.17(2H,s),5.46(2H,s),6.64(1H,td),7.31(1H,d),7.60(1H,td),7.64(1H,dd),7.80(1H,dd),8.32(1H,d),8.45(1H,d)
MS:m/z=296(M+H)
合成例14の(1)に記載の方法で得られた2,2,2-トリフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド44mg(0.23mmol)を無水アセトニトリル8mlに溶解し、Biosci. Biotechnol. Biochem., 67(5), 980-988, 2003に記載の方法で合成した1-(6-クロロピリジン-3-イル)エチル 4-メチルベンゼンスルホネート72mg(0.23mmol)、炭酸カリウム38mgを加えて、100分加熱還流した。反応終了後、反応液を室温に戻して不溶物をろ過して取り除き、ろ液を減圧濃縮した。シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=3:1)で精製して目的物を得た。収量24mg(収率32%)。
1H-NMR(CDCl3,δ,ppm):1.89(3H,d),6.89(1H,td),7.08(1H,q),7.32(1H,d),7.66(1H,dd),7.76(2H,m),8.44(1H,d),8.50(1H,d)
13C-NMR(CDCl3,δ,ppm):19.2,55.1,115.1,117.4(q),122.0,124,8,133.7,135.2,138.4,141.4,148.6,151.9,159.1,163.9(q)
MS:m/z=330(M+H)
2-アミノピリジン400mg(4.26mmol)を無水ジクロロメタン10mlに溶解し、ジフルオロ酢酸322μl(490mg、5.11mmol)、EDC-HCl 982mg(5.10mmol)、DMAP 622mg(5.11mmol)を加えて、室温で61時間攪拌した。反応終了後、反応液をジクロロメタンで薄め、水で1回、1%HClaq.で2回洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮して2,2-ジフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド 102mg(収率14%)を得た。
1H-NMR(CDCl3,δ,ppm):6.03(1H,t),7.15(1H,m),7.78(1H,td),8.20(1H,d),8.34(1H,dd),8.72(1H,brs)
上記の方法で得られた2,2-ジフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド100mg(0.58mmol)を無水アセトニトリル10mlに溶解し、2-クロロ-5-クロロメチルピリジン94mg(0.58mmol)を無水アセトニトリル5mlに溶解して加え、続いて炭酸カリウム84mg(0.63mmol)を加えて140分加熱還流した。反応終了後、反応液を室温に戻し、不溶物をろ過して取り除いて減圧濃縮した。これにエーテルを加えると固体が析出したので、ろ集し、よく乾燥して目的物を得た。収量63mg(収率37%)。
1H-NMR(CDCl3,δ,ppm):5.52(2H,s),5.90(1H,t),6.79(1H,td),7.33(1H,d),7.71(1H,m),7.77(1H,dd),7.85(1H,dd),8.45(1H,d),8.50(1H,d)
13C-NMR(DMSO-d6,δ,ppm):53.0,111.0(t),115.2,120.7,124.7,131.7,140.6,141.6,143.2,150.4,150.9,158.3,169.4(t)
MS:m/z=298(M+H)
2-アミノピリジン200mg(2.13mmol)をジクロロメタン5mlに溶解し、EDC-HCl 491mg(2.55mmol)、DMAP 311mg(2.55mmol)、クロロジフルオロ酢酸187μl(2.23mmol、290mg)の順に加えて一晩攪拌した。反応終了後、反応液をジクロロメタンで薄め、水、1%塩酸で洗浄後、無水硫酸マグネシウムで乾燥して2-クロロ-2,2-ジフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド105mg(収率24%)を得た。
1H-NMR(CDCl3,δ,ppm):7.19(1H,dd),7.82(1H,m),8.18(1H,d),8.36(1H,d),9.35(1H,brs)
上記の方法で合成した2-クロロ-2,2-ジフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド68mg(0.33mmol)に、無水アセトニトリル6mlに溶解した2-クロロ-5-クロロメチルピリジン53mg(0.33mmol)を加え、続いて炭酸カリウム50mg(0.36mmol)を加えて1時間加熱還流した。反応終了後、反応液を室温に戻してから減圧濃縮した。これに字エチルエーテルを加えたところ固体が析出したので、ろ集し、乾燥することで目的物を得た。収量49mg(収率45%)。
1H-NMR(CDCl3,δ,ppm):5.56(2H,s),6.92(1H,t),7.33(1H,d),7.82(1H,m),7.91(1H,dd),8.02(1H,d),8.45(1H,d),8.48(1H,d)
13C-NMR(CDCl3,δ,ppm):53.8,115.2,120.1(t),122.1,124.8,139.0,140.0,142.3,150.0,151.9,159.1,159.1,165.8(t)
MS:m/z=332(M+H)
合成例14の別法に記載の方法で得られた1-〔(6-クロロピリジン-3-イル)メチル〕ピリジン-2(1H)-イミン塩酸塩70mg(0.27mmol)を無水ジクロロメタン4mlに溶解し、トリエチルアミン94μl(0.68mmol、68mg)、トリクロロアセチルクロリド33μg(0.27mmol、49mg)の順に加えて室温で1時間攪拌した。反応終了後、水を加えて反応停止し、ジクロロメタンと水で分液した。有機層を水で1回、1%塩酸で2回洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮した。これにジエチルエーテルを加えたところ、固体が析出したので、ろ集、乾燥して目的物を得た。収量61mg(収率62%)。
1H-NMR(CDCl3,δ,ppm):5.59(2H,s),6.86(1H,t),7.32(1H,d),7.78(1H,td),7.91(2H,m),8.43(1H,d),8.50(1H,d)
MS:m/z=364(M+H)
2-アミノピリジン300mg(3.19mmol)を無水ジクロロメタン15mlに溶解し、EDC-HCl 919mg(4.78mmol)、DMAP 583mg(4.78mmol)、ペンタフルオロプロピオン酸397μl(628mg、3.83mmol)の順に加えて室温で一晩攪拌した。反応終了後、反応液をジクロロメタンで薄め、水で1回、1%塩酸で2回洗浄後、無水硫酸マグネシウムで乾燥、減圧濃縮して2,2,3,3,3-ペンタフルオロ-N-(ピリジン-2(1H)-イリデン)プロパナミド85mg(収率11%)を得た。
1H-NMR(CDCl3,δ,ppm):5.56(2H,s),6.90(1H,td),7.32(1H,d),7.79(2H,m),7.84(1H,d),8.43(1H,d),8.56(1H,d)
MS:m/z=366(M+H)
2-クロロ-5-メチルピリミジン1.04g(8.13mmol)を四塩化炭素30mlに溶かし、N-ブロモスクシンイミド1.73g(9.75mmol)、過酸化ベンゾイル20mgを加えて、6時間加熱還流した。反応終了後、反応液を室温に戻して減圧濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=3:1)で精製して5-ブロモメチル-2-クロロピリジン641mg(収率38%)を得た。
1H-NMR(CDCl3,δ,ppm):4.42(2H,s),8.66(2H,s)
上記の方法で得た5-ブロモメチル-2-クロロピリジン104mg(0.50mmol)を無水アセトニトリル6mlに溶解し、合成例14の(1)に記載の方法で得られた2,2,2-トリフルオロ-N-(ピリジン-2(1H)-イリデン)アセタミド96mg(0.50mmol)、炭酸カリウム76mg(0.55mmol)を加えて1時間加熱還流した。反応終了後、反応液を室温に戻して不溶物をろ過して取り除き、ろ液を減圧濃縮した。これにジエチルエーテルを加えたところ固体が析出したので、ろ集し、ジエチルエーテルで洗浄後デシケーターに入れて減圧乾燥して目的物を得た。収量92mg(収率58%)。
1H-NMR(CDCl3,δ,ppm):5.54(2H,s),6.98(1H,m),7.87(1H,m),8.18(1H,m),8.48(1H,m),8.83(2H,m)
13C-NMR(CDCl3,δ,ppm):60.0,115.6,117.1(q),122.1,127.5,139.2,142.9,158.8,160.3(2C),161.4,163.8(q)
MS:m/z=317(M+H)
合成例14~25と同様の方法で得られた化合物のスペクトルデータを表10から11に示す。
ブロモシアン220mg(2.09mmol)を無水クロロホルム10mlに溶解し、0℃に冷却した。これに、2-クロロ-5-アミノメチルピリジン500mg(3.49mmol)を無水クロロホルム10mlに溶解させたものを滴下し、0℃で1時間攪拌した。反応液をろ過し、水を加えて分液後、クロロホルム層を無水硫酸マグネシウムで乾燥し、減圧濃縮した。これをシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:1)で精製して標題化合物122mg(収率35%)を得た。
1H-NMR(CDCl3,δ,ppm):4.21(2H,s),5.74(1H,brs),7.36(1H,d),7.71(1H,dd),8.30(1H,d)
13C-NMR(CDCl3,δ,ppm):46.5,116.1,124.8,131.5,138.9,148.9,151.4
MS:m/z=166(M-H)
1N-NMR(CDCl3,δ,ppm):5.28(2H,s),6.55(1H,m),7.33(2H,m),7.56(2H,m),7.75(1H,dd),8.40(1H,d)
1N-NMR(CDCl3,δ,ppm):2.21(3H,s),5.35(2H,s),6.46(1H,m),7.32(1H,d),7.48(2H,m),7.75(1H,d),8.10(1H,dd),8.45(1H,dd)
MS:m/z=262(M+H)
1N-NMR(CDCl3,δ,ppm):2.56(3H,s),2.58(2H,s),6.25(1H,s)
また、2-クロロー5-クロロメチルピリジン2.0g(12.4mmol)にエチレンジアミン20mlを加えて、一晩攪拌した。反応終了後、減圧濃縮し、アセトニトリルを加えて不溶物をろ過して取り除いた。これを減圧濃縮してN-((6-クロロピリジン-3-イル)メチル)エタンー1,2-ジアミン2.45g(収率:100%)を得た。
1N-NMR(CDCl3,δ,ppm):3.49(2H,t),3.78(2H,t),4.40(2H,s),5.13(1H,s),7.37(1H,d),7.56(1H,dd),8.31(1H,d),9.34(1H,brs)
m/z=306(M+H)
1N-NMR(CDCl3,δ,ppm):3.35(2H,m),4.02(2H,m),5.61(1H,s),10.40(1H,brs)
上記の方法で得た1,1,1-トリフルオロ-3-(チアゾリジン-2-イリデン)プロパン-2-オン65mg(0.33mmol)に、無水アセトニトリル8mlに溶解した2-クロロ-5-クロロメチルピリジン80mg(0.50mmol)、炭酸カリウム69mg(0.50mmol)を加え、2時間加熱還流した。反応終了後、反応液を室温に戻して、不溶物をろ過して取り除いた後、減圧濃縮した。シリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=1:1→1:3)で精製して目的物を得た。収量53mg(収率50%)
1N-NMR(CDCl3,δ,ppm):3.20(2H,t),3.73(2H,t),4.61(2H,s),5.80(1H,s),7.36(1H,d),7.53(1H,dd),8.31(1H,d)
MS:m/z=323(M+H)
1N-NMR(CD3OD,δ,ppm):3.87(4H,m),4.51(2H,s),7.50(1H,d),7.82(1H,dd),8.35(1H,d)
MS:m/z=402(M+H)
比較例4に記載の方法で、N-((6-クロロピリジン-3-イル)メチル)エタン-1,2-ジアミン4.61g(24.9mmol)を合成した。これを無水アセトニトリル40mlに溶解し、上記の方法で得たジメチル(2,2,2-トリフルオロアセチル)カルボニミドジチオエート4.60g(21.3mmol)を加え、90分間加熱還流した。反応終了後、反応液を室温に戻してから溶媒を減圧留去し、析出した固体をろ集し、少量のアセトニトリルで洗浄することで目的物を得た。収量2.17g(収率33%)。
1N-NMR(CDCl3,δ,ppm):3.50(2H,m),3.76(2H,m),4.60(2H,s),7.34(1H,d)7.70(1H,dd)8.33(1H,d)
融点;168-170℃
1N-NMR(CDCl3,δ,ppm):3.27(2H,m),3.73(2H,m),4.86(2H,s),7.36(1H,d)7.72(1H,dd)8.36(1H,d)
融点:96℃
製剤例1〔粒剤〕
化合物1 5重量%
ベントナイト 40重量%
タルク 10重量%
クレー 43重量%
リグニンスルホン酸カルシウム 2重量%
上記成分を均一に粉砕混合し、水を加えてよく練合した後、造粒乾燥して粒剤を得た。
化合物212 2重量%
サンエキスP―252 5重量%
結合剤 1.5重量%
造粒性改良剤 0.5重量%
クレー 91重量%
上記成分を均一に粉砕混合し、水を加えてよく練合した後、造粒乾燥して粒剤を得た。
化合物3 30重量%
クレー 50重量%
ホワイトカーボン 2重量%
ケイソウ土 13重量%
リグニンスルホン酸カルシウム 4重量%
ラウリル硫酸ナトリウム 1重量%
上記成分を均一に混合し、粉砕して水和剤を得た。
化合物212 30重量%
クレー 60重量%
デキストリン 5重量%
アルキルマレイン酸共重合物 4重量%
ラウリル硫酸ナトリウム 1重量%
上記成分を均一に粉砕混合し、水を加えてよく練合した後、造粒乾燥して顆粒水和剤を得た。
化合物8 25重量%
POEポリスチリルフェニルエーテル硫酸塩 5重量%
プロピレングリコール 6重量%
ベントナイト 1重量%
キサンタンガム1%水溶液 3重量%
PRONAL EX-300(東邦化学工業株式会社)0.05重量%
ADDAC 827(ケイ・アイ化成株式会社) 0.02重量%
水 加えて100重量%
上記配合からキサンタンガム1%水溶液と適当量の水を除いた全量を予備混合した後、湿式粉砕機にて粉砕した。その後、キサンタンガム1%水溶液と残りの水を加え100重量%としてフロアブル剤を得た。
化合物1 15重量%
N,N-ジメチルホルムアミド 20重量%
ソルベッソ150(エクソンモービル有限会社) 55重量%
ポリオキシエチレンアルキルアリールエーテル 10重量%
上記成分を均一に混合、溶解して乳剤を得た。
化合物14 2重量%
クレー 60重量%
タルク 37重量%
ステアリン酸カルシウム 1重量%
上記成分を均一に混合して粉剤を得た。
化合物1 2重量%
DLクレー 94.5重量%
ホワイトカーボン 2重量%
ステアリン酸カルシウム 1重量%
軽質流動パラフィン 0.5重量%
上記成分を均一に混合して粉剤を得た。
化合物3 2重量%
キャリヤー 94重量%
ホワイトカーボン 2重量%
ハイゾールSAS-296 2重量%
上記成分を均一に混合して粉剤を得た。
化合物1 10重量%
ベンジルアルコール 74.9重量%
プロピレンカーボネート 15重量%
BHT 0.1重量%
上記成分を均一に攪拌、溶解して液化滴剤を得た。
化合物212 48重量%
エタノール 52重量%
上記成分を均一に混合して液化滴剤を得た。
化合物212 2重量%
プロベナゾール
24重量%
結合剤 3.0重量%
造粒性改良剤 0.5重量%
クレー 70.5重量%
上記成分を均一に粉砕混合し、水を加えてよく練合した後、造粒乾燥して粒剤を得た。
<茎葉散布処理試験>
試験例1-1 コナガ防除試験
ポット栽培のキャベツから直径5.0cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに2令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
が死虫率80%以上の殺虫活性を示した。
ポット栽培のキャベツから直径5.0cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに2令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
が死虫率80%以上の殺虫活性を示した。
ポット栽培のキャベツから直径5.0cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに3令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のキュウリから直径2.0cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに1令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のキュウリから直径2.0cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに1令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のキュウリから直径2.0cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに1令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のキャベツから直径2.8cmのリーフディスクを切り抜き、これにアブラムシ成虫を4頭放飼した。その1日後、成虫を取り除いて、リーフディスクに産下された1令幼虫の数を10頭に調整した。その後、この孵化幼虫の寄生するリーフディスクに、50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、シャーレに蓋をして、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のイネ苗に、50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を茎葉散布処理した。風乾後、これに2令幼虫を放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のイネ苗に、50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を茎葉散布処理した。風乾後、これに2令幼虫を放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼6日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のイネ苗に、50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を茎葉散布処理した。風乾後、これに2令幼虫を放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼4日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のイネ苗に、50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を茎葉散布処理した。風乾後、これに2令幼虫を放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼4日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のキュウリにオンシツコナジラミ成虫を放飼し、1晩産卵させた。産卵開始1日後、成虫を除去し、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。産卵終了3日後に、キュウリより直径2.0cmのリーフディスクを切り抜き、産卵を確認した後、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の薬液を散布した。散布後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。散布14日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のインゲンから直径2.8cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに1令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
ポット栽培のインゲンから直径2.8cmのリーフディスクを切り抜き、これに50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これに1令幼虫を放飼した。その後、これを25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。2連制試験。
50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液に、播種4日後のコムギ苗茎葉部を30秒間浸漬した。風乾後、これをガラス筒に入れて、さらに、同じガラス筒中にアカヒゲホソミドリカスミカメ2令幼虫2頭を放飼した。放虫後、筒に蓋をして25℃の恒温室(16時間明期-8時間暗期)にて放置した。試験中コムギに給水するため、ガラス筒下からコムギに水を吸わせた。処理3日後に幼虫の生死を観察し、次式に従って死虫率を算出した。
死虫率(%)={死亡虫数/(生存虫数十死亡虫数)}×100
野外において採集したリンゴ幼果に、50%アセトン水(0.05%Tween20加用)となるように調製した所定濃度の本発明化合物の薬液を散布した。風乾後、これをプラスチックカップに入れ、さらに、チャバネアオカメムシ成虫2頭を放飼した。放虫後、25℃の恒温室(16時間明期-8時間暗期)にて放置した。放飼6日後に成虫の生死を観察し、次式に従って死虫率を算出した。
野外採集した成虫の背面に、アセトンにて所定濃度に調製した本発明化合物の薬剤液1μL(/1頭)をマイクロシリンジにより局所施用処理した。薬剤処理後、1株当たり5頭となるように、成虫をイネ苗へ移して、25℃の恒温室(16時間明期-8時間暗期)に放置した。処理48時間後に、成虫の生死を観察し、次式に従って死虫率を算出した。
室内にて飼育している雌成虫の背面に、アセトンにて所定濃度に調製した本発明化合物の薬剤液を1μL(/1頭)処理した。薬剤処理後、カップ当たり5頭となるように、成虫をプラスチックカップへ移して、25℃の恒温室(16時間明期-8時間暗期)に放置した。処理24時間後に、成虫の苦悶状況を観察し、次式に従って苦悶虫率を算出した。試験は、2連制により行った。
試験例15 ヒメトビウンカ防除試験
播種48時間後のコムギ苗根部を、10%アセトン水となるように調製した所定濃度の本発明化合物の薬液を処理した。72時間根部より薬剤を吸収させた後、これにヒメトビウンカ2令幼虫を10頭ずつ放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼4日後に虫の生死を観察し、次式に従って死虫率を算出した。試験は2連制により行った。
試験例16 ヒメトビウンカ防除試験
ポット栽培のイネ苗に、10%アセトン水となるように調製した所定濃度の本発明化合物の薬液を土壌潅注処理した。処理3日後、これにヒメトビウンカ2令幼虫を10頭ずつ放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。試験は2連制により行った。
ポット栽培のイネ苗に、10%アセトン水となるように調製した所定濃度の本発明化合物の薬液を土壌潅注処理した。処理3日後、これにセジロウンカ2令幼虫を10頭ずつ放飼した。その後、25℃の恒温室(16時間明期一8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。試験は2連制により行った。
ポット栽培のイネ苗に、10%アセトン水となるように調製した薬液を土壌潅注処理した。処理2日後、これにイネミズゾウムシ成虫を5頭ずつ放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。試験は2連制により行った。
試験例19 トビイロウンカ防除試験
ポット栽培のイネ苗に、10%アセトン水となるように調製した所定濃度の本発明化合物の薬液を土壌潅注処理した。処理3日後、これに薬剤低感受性トビイロウンカ2令幼虫を10頭ずつ放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。試験は2連制により行った。
ポット栽培のイネ苗に、10%アセトン水となるように調製した所定濃度の本発明化合物の薬液を土壌潅注処理した。処理3日後、これに薬剤低感受性ヒメトビウンカ2令幼虫を10頭ずつ放飼した。その後、25℃の恒温室(16時間明期-8時間暗期)に放置した。放飼3日後に虫の生死を観察し、次式に従って死虫率を算出した。試験は2連制により行った。
Pest Management Science(2003),59(3),347-352、およびJournal of Pesticide Science(2004),29(2),110-116に記載されているように、イミダクロプリドは酸化的な代謝を受け、不活化されることが知られており、抵抗性獲得の機構のひとつとしても考えられている。このような抵抗性を獲得した害虫に対する効果を確認するために以下の実験を行った。
化合物のDMSO溶液:5uL
グルコース6リン酸溶液:5uL
NADP+溶液:5uL
グルコース6リン酸デヒドロゲナーゼ溶液:5uL
リン酸カリウム緩衝液(pH7.4, 1mM EDTA含有):180uL
カラム:カプセルパックC18MG
移動相組成:
0~3分:85%水、5%アセトニトリル、10%ギ酸水溶液(0.1v/v%)
3~30分:85→25%水、5→65%アセトニトリル、10%ギ酸水溶液(0.1v/v%)
30.1~36分:90%アセトニトリル、10%ギ酸水溶液(0.1v/v%)
カラム温度:40℃ 流速:0.35mL/分 注入量:100uL
UV波長:化合物212:325nm
:イミダクロプリド:300nm
試験例21 フタトゲチマダニ防除試験
化合物の200ppm、10ppmのアセトン溶液30μLを、4mL容ガラスバイアルに入れた。これをシェーカーに載せて、回転させながら風乾してバイアル内壁に化合物のドライフィルムを形成させた。24時間以上、バイアルを乾燥させた後、これにフタトゲチマダニ幼ダニ10頭を放飼して、蓋をした。バイアルは、25℃、湿度85%、全暗条件の恒温室に静置した。放飼1日後に生死を観察し、次式に従って死虫率を算出した。試験は、2連制により行った。
マウス(ICR、雄、5週令)の背面体毛を直径約2cm刈り、そこに高さ約1.5cmに切取った15mLポリスチレンコニカルチューブを、瞬間接着剤を用いて接着した。
犬糸状虫のミクロフィラリアの運動性の変化により活性を評価した。化合物濃度が3.13ppmとなるようRPMI1640液体培地にて溶解後、犬糸状虫のミクロフィラリアを1培養液あたり、約20匹ずつ入れ、37℃で培養した。培養開始後48時間に、犬糸状虫ミクロフィラリアの運動性を観察し、以下の評価基準により活性を評価した。
B:ほとんどの虫体に何らかの影響または1/3以上の虫体が死亡
C:影響なし~1/3未満の虫体が死亡
Claims (24)
- 下記化学式(I)で示される化合物およびその塩を少なくとも1種以上含んでなる有害生物防除剤。
R1は、水素原子、またはC1~6アルキル基を示し
R2は、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルオキシカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基、CONR6R7、アルキル部分がハロゲン原子により置換されていてもよいC1~6 O,O’-アルキルホスホリル基、シアノ基、ホルミル基またはニトロ基を示し、
R3は、ハロゲン原子により置換されていてもよいC1~8アルキレン基、ハロゲン原子により置換されていてもよいC2~8アルケニレン基、ハロゲン原子により置換されていてもよいC2~8アルキニレン基、置換されていてもよいフェニレン基、または置換されていてもよい5~6員のヘテロ環二価基を示し、
R4は、水素原子、シアノ基、置換されていてもよいフェニル基、置換されていてもよい3~8員の環状アルキル基および置換されていてもよい3~8員のヘテロ環、ハロゲン原子、OR5、OCOR5、OCOOR5、COR5、COOR5、SR5、SOR5、SO2R5、N-CO-OR8、N-CO-SR8、N-CS-OR8、N-CS-SR8、N-O-CO-R8、O-CO-R8、O-CO-OR8、O-CO-SR8、O-CS-OR8、O-CS-SR8、S-CS-OR8、S-CS-SR8、S-CO-OR8、S-CO-SR8、S-CS-R8、またはNR9R10、O-CO-NR9R10、O-CS-NR9R10、S-CO-NR9R10、S-CS-NR9R10を示す
ここでR5はハロゲン原子により置換されていてもよいC1~6アルキル基、ハロゲン原子により置換されていてもよいアリール基、ハロゲン原子により置換されていてもよいアラルキル基を示す。
R6、R7は互いに独立して、水素原子、ハロゲン原子により置換されていてもよいC1~6アルキル基を示す。
R8は、置換されていてもよいC1~6アルキル基を示し、置換されていてもよい置換基は、ハロゲン原子、C1~4アルキルオキシカルボニル基、C1~4アルキルカルボニル基、ハロゲン原子またはハロゲン原子により置換されていてもよいC1~4アルキル基に置換されていてもよいベンゾイル基、C1~4アルキルオキシ基、C1~4アルキルチオ基を示す。
R9、R10は互いに独立して、水素原子、ホルミル基、ハロゲン原子により置換されていてもよいC1~6アルキル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニルオキシ基、置換されていてもよいフェニル基(置換されていてもよい置換基としては、ハロゲン原子またはハロゲン原子に置換されていてもよいC1-4アルキル基、ハロゲン原子に置換されていてもよいC1-4アルキルオキシ基)、置換されていてもよいベンジル基(置換されていてもよい置換基としては、ハロゲンまたはハロゲンに置換されていてもよいC1-4アルキル基、ハロゲンに置換されていてもよいC1-4アルキルオキシ基)を示すか、R9、R10が環を形成して1つ以上の窒素原子を含む3-10員のヘテロシクロアルキル基を示すか、またはN、R9、R10が環を形成して1つ以上の窒素原子を含む5-6員の芳香族ヘテロ環を示す。
また、N、R2、R3、R4が一緒になって式(E)で示される基を示してもよい。
ただし、Arが2,6-ジクロロ-4-ピリジル基を示すとき、R2はアルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルオキシカルボニル基を示さない] - 化学式(I)中のArが、6-クロロ-3-ピリジル基または5-クロロ-3-チアゾリル基である、請求項1に記載の有害生物防除剤。
- 化学式(I)中のR2が、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基またはシアノ基である、請求項1または2に記載の有害生物防除剤。
- 化学式(Ie)中のR4eが、ハロゲン原子により置換されたC1~6アルキル基である、請求項4に記載の有害生物防除剤。
- 化学式(Ie)中のYが、水素原子またはハロゲン原子である、請求項4に記載の有害生物防除剤。
- 化学式(Ie)中のR4eが、ハロゲン原子により置換されたC1~6アルキル基であり、Yが、水素原子またはハロゲン原子である、請求項4に記載の有害生物防除剤。
- 化学式(Ie)で示される化合物が、N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-クロロ-5-フルオロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-フルオロピリジンー3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-ブロモピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-(1-(6-クロロピリジン-3-イル)エチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2-ジフルオロアセタミド、2-クロロ-N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2-ジフルオロアセタミド、N-〔1-((2-クロロピリミジン-5-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミドおよびN-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,3,3,3-ペンタフルオロプロパナミドからなる群より選択される化合物である、請求項4に記載の有害生物防除剤。
- 鱗翅目害虫、半翅目害虫、アザミウマ目害虫、双翅目害虫、鞘翅目害虫、動物寄生性のノミ類やダニ類、犬糸状虫からなる群より選択される少なくとも1つの虫種に対して防除活性を有する、請求項1から8のいずれかに記載の有害生物防除剤。
- 有害生物が、農園芸上の害虫または動物寄生性害虫である、請求項1から9のいずれかに記載の有害生物防除剤。
- 有害生物が、薬剤抵抗性の有害生物である、請求項1から9のいずれかに記載の有害生物防除剤。
- 下記化学式(I)で示されるアミン誘導体またはその塩。
R1は、水素原子、またはC1~6アルキル基を示し
R2は、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルオキシカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基、CONR6R7、アルキル部分がハロゲン原子により置換されていてもよいC1~6 O,O’-アルキルホスホリル基、シアノ基、ホルミル基またはニトロ基を示し、
R3は、ハロゲン原子により置換されていてもよいC1~8アルキレン基、ハロゲン原子により置換されていてもよいC2~8アルケニレン基、ハロゲン原子により置換されていてもよいC2~8アルキニレン基、置換されていてもよいフェニレン基、または置換されていてもよい5~6員のヘテロ環二価基を示し、
R4は、水素原子、シアノ基、置換されていてもよいフェニル基、置換されていてもよい3~8員の環状アルキル基、置換されていてもよい3~8員のヘテロ環、ハロゲン原子、OR5、OCOR5、OCOOR5、COR5、COOR5、SR5、SOR5、SO2R5、N-CO-OR8、N-CO-SR8、N-CS-OR8、N-CS-SR8、N-O-CO-R8、O-CO-R8、O-CO-OR8、O-CO-SR8、O-CS-OR8、O-CS-SR8、S-CS-OR8、S-CS-SR8、S-CO-OR8、S-CO-SR8、S-CS-R8、またはNR9R10、O-CO-NR9R10、O-CS-NR9R10、S-CO-NR9R10、S-CS-NR9R10を示す。
ここでR5はハロゲン原子により置換されていてもよいC1~6アルキル基、ハロゲン原子により置換されていてもよいアリール基、ハロゲン原子により置換されていてもよいアラルキル基を示す。
R6、R7は互いに独立して、水素原子、ハロゲン原子により置換されていてもよいC1~6アルキル基を示す。
R8は、置換されていてもよいC1~6アルキル基を示し、置換されていてもよい置換基は、ハロゲン原子、C1~4アルキルオキシカルボニル基、C1~4アルキルカルボニル基、ハロゲン原子またはハロゲン原子により置換されていてもよいC1~4アルキル基に置換されていてもよいベンゾイル基、C1~4アルキルオキシ基、C1~4アルキルチオ基を示す。
R9、R10は互いに独立して、水素原子、ホルミル基、ハロゲン原子により置換されていてもよいC1~6アルキル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニルオキシ基、置換されていてもよいフェニル基(置換されていてもよい置換基としては、ハロゲン原子またはハロゲン原子に置換されていてもよいC1-4アルキル基、ハロゲン原子に置換されていてもよいC1-4アルキルオキシ基)、置換されていてもよいベンジル基(置換されていてもよい置換基としては、ハロゲンまたはハロゲンに置換されていてもよいC1-4アルキル基、ハロゲンに置換されていてもよいC1-4アルキルオキシ基)を示すか、R9、R10が環を形成して1つ以上の窒素原子を含む3-10員のヘテロシクロアルキル基を示すか、またはN、R9、R10が環を形成して1つ以上の窒素原子を含む5-6員の芳香族ヘテロ環を示す。
また、Arが置換されていてもよいピリジル基、置換されていてもよいピリミジル基を示すとき、N、R2、R3、R4が一緒になって式(E)で示される基を示してもよい。
ただし、Arが2,6-ジクロロ-4-ピリジル基を示すとき、R2はアルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルオキシカルボニル基を示さず、Arが6-クロロ-3-ピリジル基を示すとき、R1が水素原子かつYが5-メチル基かつR4eがトリフルオロメチル基を示さない] - 化学式(I)中のArが6-クロロ-3-ピリジル基または5-クロロ-3-チアゾリル基である、請求項12に記載のアミン誘導体またはその塩。
- 化学式(I)中のR2が、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルカルボニル基、アルキル部分がハロゲン原子により置換されていてもよいC1~6アルキルスルホニル基またはシアノ基である、請求項12または13に記載のアミン誘導体またはその塩。
- 化学式(I)で示される化合物が下記化学式(Ie’)で示される化合物である、請求項12に記載のアミン誘導体またはその塩。
ただし、Ar’が6-クロロ-3-ピリジル基を示すとき、R1が水素原子かつYが5-メチル基かつR4eがトリフルオロメチル基を示さない] - 化学式(Ie’)中のR4eが、ハロゲン原子により置換されたC1~6アルキル基である、請求項15に記載のアミン誘導体またはその塩。
- 化学式(Ie’)中のYが、水素原子またはハロゲン原子である、請求項15に記載のアミン誘導体またはその塩。
- 化学式(Ie’)中のR4eが、ハロゲン原子により置換されたC1~6アルキル基であり、Yが、水素原子またはハロゲン原子である、請求項15に記載のアミン誘導体またはその塩。
- 上記式(Ie’)で示される化合物が、N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-クロロ-5-フルオロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-フルオロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-ブロモピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-(1-(6-クロロピリジン-3-イル)エチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミド、N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2-ジフルオロアセタミド、2-クロロ-N-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2-ジフルオロアセタミド、N-〔1-((2-クロロピリミジン-5-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,2-トリフルオロアセタミドおよびN-〔1-((6-クロロピリジン-3-イル)メチル)ピリジン-2(1H)-イリデン〕-2,2,3,3,3-ペンタフルオロプロパナミドからなる群より選択される化合物である、請求項15に記載のアミン誘導体またはその塩。
- 鱗翅目害虫、半翅目害虫、アザミウマ目害虫、双翅目害虫、鞘翅目害虫、動物寄生性のノミ類やダニ類、犬糸状虫からなる群より選択される少なくとも1つの虫種に対して防除活性を有する、請求項12から19のいずれかに記載のアミン誘導体またはその塩。
- 請求項1から9のいずれかに記載の有害生物防除剤、または請求項12から20のいずれかに記載のアミン誘導体もしくはその塩を用いる、有害生物を防除する方法。
- 請求項1から9のいずれかに記載の有害生物防除剤、または請求項12から20のいずれかに記載のアミン誘導体もしくはその塩を、植物の種子、根、塊茎、球根、根茎、土壌、養液栽培における養液、養液栽培における固形培地、または植物を生育させる担体に処理して化合物を植物内に浸透移行させることを含んでなる、農園芸上の害虫の防除方法。
有害生物を防除する方法。 - 有害生物が、農園芸上の害虫または動物寄生性害虫である、請求項21に記載の方法。
- 有害生物が、薬剤抵抗性の有害生物である、請求項21に記載の方法。
Priority Applications (57)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GEAP201113043A GEP201706728B (en) | 2010-08-31 | 2011-08-26 | Noxious organism control agent |
CR20190244A CR20190244A (es) | 2010-08-31 | 2011-08-26 | Agentes control de plaga |
AU2011297160A AU2011297160B2 (en) | 2010-08-31 | 2011-08-26 | Noxious organism control agent |
SG2013011887A SG187883A1 (en) | 2010-08-31 | 2011-08-26 | Pest control agent |
CN201180023561.8A CN102892290B (zh) | 2010-08-31 | 2011-08-26 | 有害生物防除剂 |
JP2012501048A JPWO2012029672A1 (ja) | 2010-08-31 | 2011-08-26 | 有害生物防除剤 |
CA2808144A CA2808144C (en) | 2010-08-31 | 2011-08-26 | Amine derivatives as pest control agents |
BR112013004818A BR112013004818B8 (pt) | 2010-08-31 | 2011-08-26 | Derivados de amina, agente de controle de peste e método para controlar pestes agrícolas e horticulturais |
CU20130026A CU24170B1 (es) | 2010-08-31 | 2011-08-26 | Derivados de amina y sus sales para el control de plagas |
MX2013002233A MX363956B (es) | 2010-08-31 | 2011-08-26 | Agente de control de plagas. |
KR1020137012387A KR101442445B1 (ko) | 2010-08-31 | 2011-08-26 | 유해 생물 방제제 |
US13/814,753 US8957214B2 (en) | 2010-08-31 | 2011-08-26 | Pest control agent |
CR20200540A CR20200540A (es) | 2010-08-31 | 2011-08-26 | DERIVADOS DE AMINA PARA EL CONTROL DE PLAGAS (Divisional 2019-0244) |
PL15175471T PL2984930T3 (pl) | 2010-08-31 | 2011-08-26 | Środek do zwalczania szkodników |
EP15175471.0A EP2984930B1 (en) | 2010-08-31 | 2011-08-26 | Pest control agent |
EA201390320A EA022848B1 (ru) | 2010-08-31 | 2011-08-26 | Средство борьбы с вредителями |
UAA201303921A UA109149C2 (xx) | 2010-08-31 | 2011-08-26 | Засіб боротьби зі шкідниками |
EP11821689.4A EP2628389A4 (en) | 2010-08-31 | 2011-08-26 | AGENT FOR COMBATING HARMFUL ORGANISMS |
MA35778A MA34551B1 (fr) | 2010-08-31 | 2011-08-26 | Agent de lutte contre des organismes nuisibles |
AP2013006782A AP3539A (en) | 2010-08-31 | 2011-08-26 | Pest control agent |
NZ607939A NZ607939A (en) | 2010-08-31 | 2011-08-26 | Noxious organism control agent |
KR1020137008197A KR20130132775A (ko) | 2010-08-31 | 2011-08-26 | 유해 생물 방제제 |
BR112014004268A BR112014004268A8 (pt) | 2011-08-26 | 2012-08-24 | método para a produção de agente de controle de praga |
ARP120103150A AR087683A1 (es) | 2011-08-26 | 2012-08-24 | N-[1-((6-cloropiridin-3-il)metil)piridin-2-(1h)-ilideno]-2,2,2-trifluoroacetamida, metodo para su preparacion y un intermediario para su sintesis |
KR1020147002461A KR20140054004A (ko) | 2011-08-26 | 2012-08-24 | 유해 생물 방제제의 제조방법 |
CA3024817A CA3024817A1 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest control agent |
PCT/JP2012/071399 WO2013031671A1 (ja) | 2011-08-26 | 2012-08-24 | 有害生物防除剤の製造法 |
TW101130855A TWI554501B (zh) | 2011-08-26 | 2012-08-24 | Manufacture of pest control agents |
EP17200356.8A EP3318554B1 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest control agent |
CA2844916A CA2844916A1 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest control agent |
NZ623022A NZ623022B2 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest controlling agent |
HUE17200356A HUE056549T2 (hu) | 2011-08-26 | 2012-08-24 | Eljárás kártevõirtószer elõállítására |
MX2014000588A MX351639B (es) | 2011-08-26 | 2012-08-24 | Metodo para producir un agente para el control de plagas. |
AP2014007518A AP3749A (en) | 2011-08-26 | 2012-08-24 | Method for producing pest controlling agent |
CN201280041558.3A CN103781764B (zh) | 2011-08-26 | 2012-08-24 | 有害生物防除剂的制造法 |
PL17200356T PL3318554T3 (pl) | 2011-08-26 | 2012-08-24 | Sposób wytwarzania środka do zwalczania szkodników |
JP2013531274A JP6092778B2 (ja) | 2011-08-26 | 2012-08-24 | 有害生物防除剤の製造法 |
US14/238,299 US9357776B2 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest control agent |
NZ709742A NZ709742B2 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest controlling agent |
PL12828367T PL2749555T3 (pl) | 2011-08-26 | 2012-08-24 | Sposób wytwarzania środka do zwalczania szkodników |
BR122019001978A BR122019001978A8 (pt) | 2011-08-26 | 2012-08-24 | Método para a produção de agente de controle de praga |
AU2012302922A AU2012302922A1 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest controlling agent |
EP12828367.8A EP2749555B1 (en) | 2011-08-26 | 2012-08-24 | Method for producing pest controlling agent |
CN201610472854.9A CN106117132B (zh) | 2011-08-26 | 2012-08-24 | 有害生物防除剂的制造法 |
HUE12828367A HUE041416T2 (hu) | 2011-08-26 | 2012-08-24 | Eljárás rovarkártevõ ellenes szer elõállítására |
IL224592A IL224592A (en) | 2010-08-31 | 2013-02-06 | Causes pest control |
US13/761,306 US9073866B2 (en) | 2010-08-31 | 2013-02-07 | Pest control agent |
ZA2013/01156A ZA201301156B (en) | 2010-08-31 | 2013-02-13 | Pest control agent |
ZA2014/00602A ZA201400602B (en) | 2011-08-26 | 2014-01-24 | Method for producing pest control agent |
IL230737A IL230737A0 (en) | 2011-08-26 | 2014-01-30 | A method for producing a pesticide |
MA36841A MA35447B1 (fr) | 2011-08-26 | 2014-03-20 | Procédé de production d'un agent de lutte contre les ravageurs |
IL232581A IL232581A0 (en) | 2010-08-31 | 2014-05-13 | causes pest control |
US14/573,344 US9328068B2 (en) | 2010-08-31 | 2014-12-17 | N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of animal parasitic pests and agricultural/horticultural pests |
US15/080,971 US9717242B2 (en) | 2010-08-31 | 2016-03-25 | N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of agricultural/horticultural pests |
US15/141,960 US9883673B2 (en) | 2011-08-26 | 2016-04-29 | Method for producing pest control agent |
JP2017022407A JP6335348B2 (ja) | 2011-08-26 | 2017-02-09 | 有害生物防除剤の製造法 |
US15/634,284 US10085449B2 (en) | 2010-08-31 | 2017-06-27 | N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2- trifluoroacetamide for control of agricultural/horticultural pests |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010194584 | 2010-08-31 | ||
JP2010-194584 | 2010-08-31 |
Related Child Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/814,753 A-371-Of-International US8957214B2 (en) | 2010-08-31 | 2011-08-26 | Pest control agent |
US13/761,306 Division US9073866B2 (en) | 2010-08-31 | 2013-02-07 | Pest control agent |
US14/573,344 Division US9328068B2 (en) | 2010-08-31 | 2014-12-17 | N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of animal parasitic pests and agricultural/horticultural pests |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012029672A1 true WO2012029672A1 (ja) | 2012-03-08 |
Family
ID=45772762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2011/069352 WO2012029672A1 (ja) | 2010-08-31 | 2011-08-26 | 有害生物防除剤 |
Country Status (34)
Country | Link |
---|---|
US (5) | US8957214B2 (ja) |
EP (5) | EP2789237A1 (ja) |
JP (2) | JPWO2012029672A1 (ja) |
KR (2) | KR20130132775A (ja) |
CN (3) | CN103960242B (ja) |
AP (1) | AP3539A (ja) |
AU (1) | AU2011297160B2 (ja) |
BR (1) | BR112013004818B8 (ja) |
CA (1) | CA2808144C (ja) |
CL (2) | CL2013000570A1 (ja) |
CO (1) | CO6680699A2 (ja) |
CR (2) | CR20190244A (ja) |
CU (1) | CU24170B1 (ja) |
DO (1) | DOP2013000046A (ja) |
EA (1) | EA022848B1 (ja) |
EC (1) | ECSP13012527A (ja) |
ES (2) | ES2563461T3 (ja) |
GE (1) | GEP201706728B (ja) |
HK (1) | HK1188595A1 (ja) |
HU (2) | HUE040676T2 (ja) |
IL (2) | IL224592A (ja) |
MA (1) | MA34551B1 (ja) |
MX (1) | MX363956B (ja) |
MY (1) | MY163072A (ja) |
NI (1) | NI201300025A (ja) |
NZ (4) | NZ722021A (ja) |
PE (1) | PE20131380A1 (ja) |
PL (2) | PL2984930T3 (ja) |
SG (1) | SG187883A1 (ja) |
TR (1) | TR201816134T4 (ja) |
TW (2) | TWI538620B (ja) |
UA (1) | UA109149C2 (ja) |
WO (1) | WO2012029672A1 (ja) |
ZA (1) | ZA201301156B (ja) |
Cited By (316)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2633756A1 (en) * | 2012-02-29 | 2013-09-04 | Meiji Seika Pharma Co., Ltd. | Pest control composition including novel iminopyridine derivate |
EP2634174A3 (en) * | 2012-02-29 | 2013-09-11 | Meiji Seika Pharma Co., Ltd. | Nitrogen-containing hetercyclic derivate having 2-imino group and pest control agent including the same |
WO2013144223A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyrimidinylidene compounds and derivatives for combating animal pests |
WO2013144213A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyridinylidene compounds and derivatives for combating animal pests |
WO2013174645A1 (en) | 2012-05-24 | 2013-11-28 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2013186089A2 (en) | 2012-06-14 | 2013-12-19 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests |
WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
WO2014053404A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2014053405A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
WO2014053403A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling insecticide resistant insects |
WO2014053395A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Use of n-thio-anthranilamide compounds on cultivated plants |
WO2014053406A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling ryanodine-modulator insecticide resistant insects |
WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
WO2014079752A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079772A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079841A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079804A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079813A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079814A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079764A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079770A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
WO2014079766A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079774A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079773A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014090700A1 (en) | 2012-12-14 | 2014-06-19 | Basf Se | Malononitrile compounds for controlling animal pests |
WO2014102244A1 (en) | 2012-12-27 | 2014-07-03 | Basf Se | 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests |
US20140213791A1 (en) * | 2011-08-26 | 2014-07-31 | Meiji Seika Pharma Co., Ltd. | Method for producing pest control agent |
WO2014128136A1 (en) | 2013-02-20 | 2014-08-28 | Basf Se | Anthranilamide compounds and their use as pesticides |
WO2014170300A1 (en) | 2013-04-19 | 2014-10-23 | Basf Se | N-substituted acyl-imino-pyridine compounds and derivatives for combating animal pests |
WO2014192717A1 (ja) * | 2013-05-27 | 2014-12-04 | Meiji Seikaファルマ株式会社 | ミツバチ寄生性害虫に対する防除剤及びそれらを使用したミツバチ寄生性害虫の防除方法 |
WO2014202751A1 (en) | 2013-06-21 | 2014-12-24 | Basf Se | Methods for controlling pests in soybean |
WO2015007682A1 (en) | 2013-07-15 | 2015-01-22 | Basf Se | Pesticide compounds |
WO2015040116A1 (en) | 2013-09-19 | 2015-03-26 | Basf Se | N-acylimino heterocyclic compounds |
WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
WO2015055757A1 (en) | 2013-10-18 | 2015-04-23 | Basf Se | Use of pesticidal active carboxamide derivative in soil and seed application and treatment methods |
WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
WO2015059088A1 (de) | 2013-10-23 | 2015-04-30 | Bayer Cropscience Ag | Substituierte chinoxalin-derivate als schädlingsbekämpfungsmittel |
WO2015091649A1 (en) | 2013-12-18 | 2015-06-25 | Basf Se | N-substituted imino heterocyclic compounds |
WO2015091645A1 (en) | 2013-12-18 | 2015-06-25 | Basf Se | Azole compounds carrying an imine-derived substituent |
WO2015101622A1 (de) | 2014-01-03 | 2015-07-09 | Bayer Cropscience Ag | Neue pyrazolyl-heteroarylamide als schädlingsbekämpfungsmittel |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
WO2015107133A1 (de) | 2014-01-20 | 2015-07-23 | Bayer Cropscience Ag | Chinolinderivate als insektizide und akarizide |
WO2015150300A1 (de) | 2014-04-02 | 2015-10-08 | Bayer Cropscience Ag | N-(1-(hetero)aryl-1h-pyrazol-4-yl)-(hetero)arylamid-derivate und ihre verwendung als schädlingsbekämpfungsmittel |
WO2015169776A1 (en) | 2014-05-08 | 2015-11-12 | Bayer Cropscience Ag | Pyrazolopyridine sulfonamides as nematicides |
WO2015185531A1 (de) | 2014-06-05 | 2015-12-10 | Bayer Cropscience Aktiengesellschaft | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
WO2016001129A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Verbesserte insektizide zusammensetzungen |
WO2016001119A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2016008830A1 (de) | 2014-07-15 | 2016-01-21 | Bayer Cropscience Aktiengesellschaft | Aryl-triazolyl-pyridine als schädlingsbekämpfungsmittel |
WO2016055096A1 (en) | 2014-10-07 | 2016-04-14 | Bayer Cropscience Ag | Method for treating rice seed |
WO2016071499A1 (en) | 2014-11-06 | 2016-05-12 | Basf Se | 3-pyridyl heterobicyclic compound for controlling invertebrate pests |
WO2016091857A1 (de) | 2014-12-11 | 2016-06-16 | Bayer Cropscience Aktiengesellschaft | Fünfgliedrige c-n-verknüpfte arylsulfid- und arylsulfoxid-derivate als schädlingsbekämpfungsmittel |
WO2016124557A1 (de) | 2015-02-05 | 2016-08-11 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2016124563A1 (de) | 2015-02-05 | 2016-08-11 | Bayer Cropscience Aktiengesellschsaft | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlings-bekämpfungsmittel |
WO2016128298A1 (de) | 2015-02-09 | 2016-08-18 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-thioimidazolyl-carboxamide als schädlingsbekämpfungsmittel |
WO2016128261A2 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
US9422280B2 (en) | 2012-03-29 | 2016-08-23 | Basf Se | N-substituted hetero-bicyclic compounds and derivatives for combating animal pests II |
WO2016142394A1 (de) | 2015-03-10 | 2016-09-15 | Bayer Animal Health Gmbh | Pyrazolyl-derivate als schädlingsbekämpfungsmittel |
WO2016162371A1 (en) | 2015-04-07 | 2016-10-13 | Basf Agrochemical Products B.V. | Use of an insecticidal carboxamide compound against pests on cultivated plants |
WO2016162318A1 (de) | 2015-04-08 | 2016-10-13 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel und deren zwischenprodukte |
EP3081085A1 (en) | 2015-04-14 | 2016-10-19 | Bayer CropScience AG | Method for improving earliness in cotton |
WO2016174049A1 (en) | 2015-04-30 | 2016-11-03 | Bayer Animal Health Gmbh | Anti-parasitic combinations including halogen-substituted compounds |
WO2016180802A1 (de) | 2015-05-13 | 2016-11-17 | Bayer Cropscience Aktiengesellschaft | Insektizide arylpyrrolidine, verfahren zu ihrer herstellung und ihre verwendung als wirkstoffe zur bekämpfung tierischer schädlinge |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
WO2017005717A1 (en) | 2015-07-06 | 2017-01-12 | Bayer Cropscience Aktiengesellschaft | Heterocyclic compounds as pesticides |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
JPWO2015137216A1 (ja) * | 2014-03-10 | 2017-04-06 | Meiji Seikaファルマ株式会社 | 2−アシルイミノピリジン誘導体の製造法 |
WO2017072039A1 (de) | 2015-10-26 | 2017-05-04 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017093163A1 (en) | 2015-11-30 | 2017-06-08 | Basf Se | Mixtures of cis-jasmone and bacillus amyloliquefaciens |
WO2017093214A1 (de) | 2015-12-03 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Mesolonische halogenierte 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olat derivate und verwandte verbindungen als insektizide |
WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017137339A1 (de) | 2016-02-11 | 2017-08-17 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-oxyimidazolyl-carboxamide als schädlingsbekämpfungsmittel |
WO2017137338A1 (de) | 2016-02-11 | 2017-08-17 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-(het)aryl-imidazolyl-carboxyamide als schädlingsbekämpfungsmittel |
EP3210468A1 (de) | 2016-02-26 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen |
WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017153217A1 (en) | 2016-03-09 | 2017-09-14 | Basf Se | Spirocyclic derivatives |
WO2017153218A1 (en) | 2016-03-11 | 2017-09-14 | Basf Se | Method for controlling pests of plants |
WO2017157735A1 (de) | 2016-03-15 | 2017-09-21 | Bayer Cropscience Aktiengesellschaft | Substituierte sulfonylamide zur bekämpfung tierischer schädlinge |
WO2017157885A1 (de) | 2016-03-16 | 2017-09-21 | Bayer Cropscience Aktiengesellschaft | N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel |
US9776967B2 (en) | 2013-10-14 | 2017-10-03 | Bayer Animal Health Gmbh | Carboxamide derivatives as pesticidal compounds |
WO2017167832A1 (en) | 2016-04-01 | 2017-10-05 | Basf Se | Bicyclic compounds |
WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
WO2017178416A1 (en) | 2016-04-15 | 2017-10-19 | Bayer Animal Health Gmbh | Pyrazolopyrimidine derivatives |
WO2017186536A1 (de) | 2016-04-25 | 2017-11-02 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-alkylimidazolyl-carboxamide als schädlingsbekämpfungsmittel |
EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
EP3245865A1 (en) | 2016-05-17 | 2017-11-22 | Bayer CropScience Aktiengesellschaft | Method for increasing yield in brassicaceae |
WO2017198452A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in soybean |
WO2017198455A2 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in beta spp. plants |
WO2017198454A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in cotton |
WO2017198449A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in brassicaceae |
WO2017198450A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in maize |
WO2017198588A1 (en) | 2016-05-18 | 2017-11-23 | Basf Se | Capsules comprising benzylpropargylethers for use as nitrification inhibitors |
WO2017198453A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in potato, tomato or alfalfa |
WO2017198451A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in small grain cereals such as wheat and rice |
WO2018011111A1 (de) | 2016-07-12 | 2018-01-18 | Bayer Cropscience Aktiengesellschaft | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
WO2018013381A1 (en) | 2016-07-11 | 2018-01-18 | Covestro Llc, Et Al. | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
WO2018013382A1 (en) | 2016-07-11 | 2018-01-18 | Covestro Llc, Et Al | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
WO2018013380A1 (en) | 2016-07-11 | 2018-01-18 | Covestro Llc, Et Al. | Methods for treating seeds with an aqueous compostion and seeds treated therewith |
WO2018015289A1 (de) | 2016-07-19 | 2018-01-25 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018019937A1 (en) | 2016-07-29 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Formulation comprising a beneficial p. bilaii strain and talc for use in seed treatment |
WO2018019711A1 (en) | 2016-07-29 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Substituted halogen(thio)acyl compounds |
WO2018029102A1 (de) | 2016-08-10 | 2018-02-15 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-heterocyclyl-imidazolyl-carboxamide als schädlingsbekämpfungsmittel |
EP3284739A1 (de) | 2017-07-19 | 2018-02-21 | Bayer CropScience Aktiengesellschaft | Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel |
WO2018033455A1 (de) | 2016-08-15 | 2018-02-22 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018050825A1 (de) | 2016-09-19 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Pyrazolo[1,5-a]pyridin- derivative und ihre verwendung als schädlingsbekämpfungsmittel |
WO2018052115A1 (ja) | 2016-09-16 | 2018-03-22 | Meiji Seikaファルマ株式会社 | 有害生物防除剤の最適化製造法 |
EP3305786A2 (de) | 2018-01-22 | 2018-04-11 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
WO2018065292A1 (de) | 2016-10-06 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlings-bekämpfungsmittel |
WO2018069841A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
WO2018069842A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
WO2018083288A1 (de) | 2016-11-07 | 2018-05-11 | Bayer Aktiengesellschaft | Substituierte sulfonylamide zur bekämpfung tierischer schädlinge |
WO2018087036A1 (en) | 2016-11-11 | 2018-05-17 | Bayer Animal Health Gmbh | New anthelmintic quinoline-3-carboxamide derivatives |
WO2018095953A1 (de) | 2016-11-23 | 2018-05-31 | Bayer Cropscience Aktiengesellschaft | 2-[3-(alkylsulfonyl)-2h-indazol-2-yl]-3h-imidazo[4,5-b]pyridin-derivate und ähnliche verbindungen als schädlingsbekämpfungsmittel |
WO2018104500A1 (en) | 2016-12-09 | 2018-06-14 | Bayer Cropscience Aktiengesellschaft | Plant health effect of purpureocillium lilacinum |
WO2018108791A1 (en) | 2016-12-16 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Thiadiazole derivatives as pesticides |
WO2018108671A1 (en) | 2016-12-16 | 2018-06-21 | Basf Se | Pesticidal compounds |
WO2018108730A1 (de) | 2016-12-16 | 2018-06-21 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
WO2018116073A1 (en) | 2016-12-21 | 2018-06-28 | Pi Industries Ltd. | 1, 2, 3-thiadiazole compounds and their use as crop protecting agent |
WO2018116072A1 (en) | 2016-12-20 | 2018-06-28 | Pi Industries Ltd. | Heterocyclic compounds |
WO2018130443A1 (de) | 2017-01-10 | 2018-07-19 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018130437A1 (de) | 2017-01-10 | 2018-07-19 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018139560A1 (ja) | 2017-01-26 | 2018-08-02 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018141954A1 (de) | 2017-02-06 | 2018-08-09 | Bayer Aktiengesellschaft | Aryl- oder heteroaryl-substituierte imidazopyridinderivate und deren anwendung als schädlingsbekämpfungsmittel |
KR20180098631A (ko) | 2015-12-29 | 2018-09-04 | 메이지 세이카 파루마 가부시키가이샤 | 이미노피리딘 유도체를 함유하는 유해 생물 방제용 조성물 |
EP3369320A1 (de) | 2017-03-02 | 2018-09-05 | Bayer CropScience Aktiengesellschaft | Wirkstoff zur bekämpfung von wanzen |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
WO2018169045A1 (ja) | 2017-03-17 | 2018-09-20 | Meiji Seikaファルマ株式会社 | 中気門亜目ダニ類の防除剤 |
WO2018177970A1 (en) | 2017-03-31 | 2018-10-04 | Basf Se | Process for preparing chiral 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium compounds |
WO2018177995A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Trizyklische carboxamide zur bekämpfung von anthropoden |
WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
WO2018177781A1 (en) | 2017-03-28 | 2018-10-04 | Basf Se | Pesticidal compounds |
WO2018190352A1 (ja) | 2017-04-11 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018189077A1 (de) | 2017-04-12 | 2018-10-18 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
WO2018190350A1 (ja) | 2017-04-10 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018190351A1 (ja) | 2017-04-10 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018192872A1 (de) | 2017-04-21 | 2018-10-25 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
WO2018193385A1 (en) | 2017-04-20 | 2018-10-25 | Pi Industries Ltd. | Novel phenylamine compounds |
WO2018197692A1 (en) | 2017-04-27 | 2018-11-01 | Bayer Aktiengesellschaft | Heteroarylphenylaminoquinolines and analogues |
WO2018197466A1 (en) | 2017-04-26 | 2018-11-01 | Basf Se | Substituted succinimide derivatives as pesticides |
WO2018197401A1 (en) | 2017-04-27 | 2018-11-01 | Bayer Animal Health Gmbh | New bicyclic pyrazole derivatives |
WO2018197257A1 (de) | 2017-04-24 | 2018-11-01 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018202715A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylbenzylbenzimidazoles and analogues |
WO2018202706A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylheteroaryloxyquinolines and analogues |
WO2018202712A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylmethylphenoxyquinolines and analogues |
WO2018202524A1 (de) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | 2-{[2-(phenyloxymethyl)pyridin-5-yl]oxy}-ethanamin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel z.b. für den pflanzenschutz |
WO2018202501A1 (de) | 2017-05-02 | 2018-11-08 | Bayer Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018202525A1 (en) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | Phenoxyethanamine derivatives for controlling pests |
WO2018202494A1 (de) | 2017-05-02 | 2018-11-08 | Bayer Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018206479A1 (en) | 2017-05-10 | 2018-11-15 | Basf Se | Bicyclic pesticidal compounds |
US10149477B2 (en) | 2014-10-06 | 2018-12-11 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
WO2018225829A1 (ja) | 2017-06-08 | 2018-12-13 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
WO2018229202A1 (en) | 2017-06-16 | 2018-12-20 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2018234202A1 (en) | 2017-06-19 | 2018-12-27 | Basf Se | SUBSTITUTED PYRIMIDINIUM COMPOUNDS AND DERIVATIVES FOR CONTROLLING HARMFUL ANIMALS |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | SUBSTITUTED CYCLOPROPYL DERIVATIVES |
WO2019002132A1 (en) | 2017-06-30 | 2019-01-03 | Bayer Animal Health Gmbh | NEW AZAQUINOLINE DERIVATIVES |
WO2019007891A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007888A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007887A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2019025341A1 (en) | 2017-08-04 | 2019-02-07 | Bayer Animal Health Gmbh | QUINOLINE DERIVATIVES FOR THE TREATMENT OF INFECTIONS BY HELMINTHES |
WO2019035881A1 (en) | 2017-08-17 | 2019-02-21 | Bayer Cropscience Lp | DISPERSIBLE COMPOSITIONS IN LIQUID FERTILIZER AND ASSOCIATED METHODS |
WO2019038195A1 (de) | 2017-08-22 | 2019-02-28 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
WO2019059412A1 (en) | 2017-09-20 | 2019-03-28 | Mitsui Chemicals Agro, Inc. | AGENT FOR EXTENDED CONTROL OF ECTOPARASITES FOR ANIMAL |
WO2019068572A1 (de) | 2017-10-04 | 2019-04-11 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019072906A1 (en) | 2017-10-13 | 2019-04-18 | Basf Se | IMIDAZOLIDINE PYRIMIDINIUM COMPOUNDS FOR CONTROL OF HARMFUL ANIMALS |
EP3473100A1 (en) | 2017-10-18 | 2019-04-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
EP3473103A1 (de) | 2017-10-17 | 2019-04-24 | Bayer AG | Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon |
WO2019076754A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
WO2019076751A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
WO2019076750A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDE PROPERTIES7ACARICIDES |
WO2019076752A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS AYNT INSECTICIDE / ACARICIDE PROPERTIES |
WO2019076749A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
WO2019092086A1 (en) | 2017-11-13 | 2019-05-16 | Bayer Aktiengesellschaft | Tetrazolylpropyl derivatives and their use as fungicides |
WO2019105875A1 (en) | 2017-11-28 | 2019-06-06 | Bayer Aktiengesellschaft | Heterocyclic compounds as pesticides |
WO2019123196A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Fluoralkenyl compounds, process for preparation and use thereof |
WO2019121159A1 (en) | 2017-12-21 | 2019-06-27 | Basf Se | Pesticidal compounds |
WO2019122319A1 (en) | 2017-12-21 | 2019-06-27 | Bayer Aktiengesellschaft | Trisubstitutedsilylmethylheteroaryloxyquinolines and analogues |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
WO2019145140A1 (en) | 2018-01-09 | 2019-08-01 | Basf Se | Silylethynyl hetaryl compounds as nitrification inhibitors |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
WO2019155066A1 (en) | 2018-02-12 | 2019-08-15 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
WO2019162228A1 (en) | 2018-02-21 | 2019-08-29 | Bayer Aktiengesellschaft | 1-(5-substituted imidazol-1-yl)but-3-en derivatives and their use as fungicides |
WO2019162174A1 (de) | 2018-02-21 | 2019-08-29 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019166561A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of alkoxypyrazoles as nitrification inhibitors |
WO2019166560A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of n-functionalized alkoxy pyrazole compounds as nitrification inhibitors |
WO2019166558A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
WO2019175046A1 (de) | 2018-03-12 | 2019-09-19 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
WO2019197615A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften |
WO2019197371A1 (en) | 2018-04-10 | 2019-10-17 | Bayer Aktiengesellschaft | Oxadiazoline derivatives |
WO2019197623A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
WO2019202077A1 (en) | 2018-04-20 | 2019-10-24 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
WO2019201921A1 (de) | 2018-04-20 | 2019-10-24 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019201835A1 (en) | 2018-04-17 | 2019-10-24 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
WO2019215182A1 (en) | 2018-05-09 | 2019-11-14 | Bayer Animal Health Gmbh | New quinoline derivatives |
WO2019219529A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Mixtures comprising benzpyrimoxan and oxazosulfyl and uses and methods of applying them |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2019224143A1 (de) | 2018-05-24 | 2019-11-28 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
WO2020005678A1 (en) | 2018-06-25 | 2020-01-02 | Bayer Cropscience Lp | Seed treatment method |
WO2020002189A1 (de) | 2018-06-27 | 2020-01-02 | Bayer Aktiengesellschaft | Wirkstoffkombinationen |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
WO2020007905A1 (en) | 2018-07-05 | 2020-01-09 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
WO2020021082A1 (en) | 2018-07-27 | 2020-01-30 | Bayer Aktiengesellschaft | Controlled release formulations for agrochemicals |
WO2020020777A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
WO2020020816A1 (en) | 2018-07-26 | 2020-01-30 | Bayer Aktiengesellschaft | Novel triazole derivatives |
WO2020020765A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of a substituted thiazolidine compound as nitrification inhibitor |
WO2020022412A1 (ja) | 2018-07-25 | 2020-01-30 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2020020813A1 (en) | 2018-07-25 | 2020-01-30 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
WO2020025650A1 (en) | 2018-07-31 | 2020-02-06 | Bayer Aktiengesellschaft | Controlled release formulations with lignin for agrochemicals |
US10556844B2 (en) | 2015-02-06 | 2020-02-11 | Basf Se | Pyrazole compounds as nitrification inhibitors |
WO2020035826A1 (en) | 2018-08-17 | 2020-02-20 | Pi Industries Ltd. | 1,2-dithiolone compounds and use thereof |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
EP3620052A1 (en) | 2018-12-12 | 2020-03-11 | Bayer Aktiengesellschaft | Use of phenoxypyridinyl-substituted (1h-1,2,4-triazol-1-yl)alcohols for controlling fungicidal diseases in maize |
WO2020053282A1 (de) | 2018-09-13 | 2020-03-19 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2020057939A1 (en) | 2018-09-17 | 2020-03-26 | Bayer Aktiengesellschaft | Use of the fungicide isoflucypram for controlling claviceps purpurea and reducing sclerotia in cereals |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
WO2020064492A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof |
WO2020067404A1 (ja) | 2018-09-27 | 2020-04-02 | Meiji Seikaファルマ株式会社 | 水性懸濁状農薬組成物 |
WO2020070050A1 (en) | 2018-10-01 | 2020-04-09 | Bayer Aktiengesellschaft | Fungicidal 5-substituted imidazol-1-yl carbinol derivatives |
WO2020079232A1 (en) | 2018-10-20 | 2020-04-23 | Bayer Aktiengesellschaft | Oxetanylphenoxyquinolines and analogues |
WO2020079173A1 (en) | 2018-10-18 | 2020-04-23 | Bayer Aktiengesellschaft | Pyridylphenylaminoquinolines and analogues |
WO2020079167A1 (en) | 2018-10-18 | 2020-04-23 | Bayer Aktiengesellschaft | Heteroarylaminoquinolines and analogues |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
EP3643711A1 (en) | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
WO2020109391A1 (en) | 2018-11-28 | 2020-06-04 | Bayer Aktiengesellschaft | Pyridazine (thio)amides as fungicidal compounds |
WO2020109039A1 (en) | 2018-11-28 | 2020-06-04 | Basf Se | Pesticidal compounds |
EP3669652A1 (en) | 2018-12-21 | 2020-06-24 | Bayer AG | Active compound combination |
WO2020126591A1 (en) | 2018-12-18 | 2020-06-25 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
WO2020127780A1 (en) | 2018-12-20 | 2020-06-25 | Bayer Aktiengesellschaft | Heterocyclyl pyridazine as fungicidal compounds |
WO2020126980A1 (en) | 2018-12-18 | 2020-06-25 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2020127974A1 (en) | 2018-12-21 | 2020-06-25 | Bayer Aktiengesellschaft | 1,3,4-oxadiazoles and their derivatives as new antifungal agents |
EP3679793A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679791A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679790A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679789A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679792A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2020178307A1 (en) | 2019-03-05 | 2020-09-10 | Bayer Aktiengesellschaft | Active compound combination |
WO2020178067A1 (en) | 2019-03-01 | 2020-09-10 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
WO2020182929A1 (en) | 2019-03-13 | 2020-09-17 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
WO2020187656A1 (en) | 2019-03-15 | 2020-09-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2020231751A1 (en) | 2019-05-10 | 2020-11-19 | Bayer Cropscience Lp | Active compound combinations |
WO2020239517A1 (en) | 2019-05-29 | 2020-12-03 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2020254488A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and use thereof as fungicides |
WO2020254486A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2020254489A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Benzylphenyl hydroxyisoxazolines and analogues as new antifungal agents |
WO2020254490A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Phenoxyphenyl hydroxyisoxazolines and analogues as new antifungal agents |
WO2020254494A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
WO2020254492A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2020254487A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2020254493A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Thienylhydroxyisoxazolines and derivatives thereof |
WO2021001331A1 (en) | 2019-07-03 | 2021-01-07 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides and derivatives thereof as microbicides |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2021018839A1 (en) | 2019-07-30 | 2021-02-04 | Bayer Animal Health Gmbh | Isoquinoline derivatives and their use for the treatment of parasitic infections |
WO2021048188A1 (de) | 2019-09-11 | 2021-03-18 | Bayer Aktiengesellschaft | Hochwirksame formulierungen auf basis von 2-[(2;4-dichlorphenyl)-m ethyl|-4,4'-dimethyl- 3-isoxazolidinone sowie vorauflaufherbiziden |
WO2021122986A1 (en) | 2019-12-20 | 2021-06-24 | Bayer Aktiengesellschaft | Thienyloxazolones and analogues |
WO2021123051A1 (en) | 2019-12-20 | 2021-06-24 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides, thiophene carboxylic acids and derivatives thereof |
US11053175B2 (en) | 2015-05-12 | 2021-07-06 | Basf Se | Thioether compounds as nitrification inhibitors |
US11142514B2 (en) | 2015-10-02 | 2021-10-12 | Basf Se | Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents |
WO2021204930A1 (en) | 2020-04-09 | 2021-10-14 | Bayer Animal Health Gmbh | Substituted condensed azines as anthelmintic compounds |
EP3896065A1 (de) | 2015-08-07 | 2021-10-20 | Bayer CropScience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2021209366A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209368A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209364A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209365A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209490A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Cyclaminephenylaminoquinolines as fungicides |
WO2021209363A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021224220A1 (en) | 2020-05-06 | 2021-11-11 | Bayer Aktiengesellschaft | Pyridine (thio)amides as fungicidal compounds |
WO2021228734A1 (en) | 2020-05-12 | 2021-11-18 | Bayer Aktiengesellschaft | Triazine and pyrimidine (thio)amides as fungicidal compounds |
WO2021233861A1 (en) | 2020-05-19 | 2021-11-25 | Bayer Aktiengesellschaft | Azabicyclic(thio)amides as fungicidal compounds |
EP3915371A1 (en) | 2020-11-04 | 2021-12-01 | Bayer AG | Active compound combinations and fungicide compositions comprising those |
EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
WO2021245087A1 (en) | 2020-06-04 | 2021-12-09 | Bayer Aktiengesellschaft | Heterocyclyl pyrimidines and triazines as novel fungicides |
WO2021249995A1 (en) | 2020-06-10 | 2021-12-16 | Bayer Aktiengesellschaft | Azabicyclyl-substituted heterocycles as fungicides |
WO2021255089A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines and 1,3,4-oxadiazole pyridines as fungicides |
WO2021255091A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazoles and their derivatives as fungicides |
WO2021255071A1 (en) | 2020-06-18 | 2021-12-23 | Bayer Aktiengesellschaft | 3-(pyridazin-4-yl)-5,6-dihydro-4h-1,2,4-oxadiazine derivatives as fungicides for crop protection |
WO2021255170A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines as fungicides |
WO2021255169A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines as fungicides |
WO2022058327A1 (en) | 2020-09-15 | 2022-03-24 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
KR20220047968A (ko) | 2019-06-21 | 2022-04-19 | 메이지 세이카 파루마 가부시키가이샤 | 플루피리민을 포함하는 벼 해충 방제용 고형 제제 |
WO2022129196A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | Heterobicycle substituted 1,2,4-oxadiazoles as fungicides |
WO2022129190A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | (hetero)aryl substituted 1,2,4-oxadiazoles as fungicides |
WO2022129188A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | 1,2,4-oxadiazol-3-yl pyrimidines as fungicides |
WO2022162129A1 (en) | 2021-01-28 | 2022-08-04 | Rhodia Operations | Method for treating rice seed with improved retention of agrochemical, micronutrient and colorant |
WO2022167488A1 (en) | 2021-02-02 | 2022-08-11 | Basf Se | Synergistic action of dcd and alkoxypyrazoles as nitrification inhibitors |
WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022243521A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of ethynylpyridine compounds as nitrification inhibitors |
WO2022243523A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of an n-functionalized alkoxy pyrazole compound as nitrification inhibitor |
WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022268810A1 (en) | 2021-06-21 | 2022-12-29 | Basf Se | Metal-organic frameworks with pyrazole-based building blocks |
WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
EP4148052A1 (en) | 2021-09-09 | 2023-03-15 | Bayer Animal Health GmbH | New quinoline derivatives |
WO2023078915A1 (en) | 2021-11-03 | 2023-05-11 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether (thio)amides as fungicidal compounds |
WO2023092050A1 (en) | 2021-11-20 | 2023-05-25 | Bayer Cropscience Lp | Beneficial combinations with recombinant bacillus cells expressing a serine protease |
WO2023099445A1 (en) | 2021-11-30 | 2023-06-08 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether oxadiazines as fungicidal compounds |
WO2023110656A1 (en) | 2021-12-15 | 2023-06-22 | Bayer Aktiengesellschaft | Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis |
WO2023203066A1 (en) | 2022-04-21 | 2023-10-26 | Basf Se | Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers |
WO2023205602A1 (en) | 2022-04-18 | 2023-10-26 | Basf Corporation | High-load agricultural formulations and methods of making same |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
TWI843864B (zh) | 2019-06-21 | 2024-06-01 | 日商三井化學植保股份有限公司 | 含有氟吡嘧(flupyrimin)之水稻害蟲防除用固形製劑 |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MX363956B (es) * | 2010-08-31 | 2019-04-09 | Meiji Seika Pharma Co Ltd Star | Agente de control de plagas. |
WO2015028630A1 (en) * | 2013-08-30 | 2015-03-05 | Basf Se | N-substituted pyridylidene compounds and derivatives for combating animal pests |
EP3046916A1 (en) * | 2013-09-19 | 2016-07-27 | Basf Se | N-acrylimino heterocyclic compounds |
WO2015055505A1 (de) * | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff zur bekämpfung von stinkwanzen |
CN106414426A (zh) | 2013-11-22 | 2017-02-15 | 巴斯夫欧洲公司 | N-酰基亚氨基杂环化合物 |
US20180179177A1 (en) * | 2014-03-27 | 2018-06-28 | Basf Se | N-acylimino heterocyclic compounds for controlling invertebrate pests |
WO2016001122A1 (de) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Methoden zur verbesserung des pflanzenwachstums |
WO2016001121A1 (en) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Method for improved utilization of the production potential of transgenic plants |
WO2016001120A1 (de) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2016001125A1 (en) * | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Active compound combinations and methods to protect the propagation material of plants |
TW201613866A (en) * | 2014-07-07 | 2016-04-16 | Bayer Cropscience Ag | Process for preparing fluorinated iminopyridine compounds |
JPWO2017104692A1 (ja) * | 2015-12-15 | 2018-09-27 | Meiji Seikaファルマ株式会社 | シロアリ防除剤 |
EP3689877A4 (en) | 2017-11-03 | 2020-08-19 | South China Agricultural University | MERGED TRICYCLIC COMPOUND CONTAINING NITROGEN AND ITS USE AS AN AGROFORESTRY INSECTICIDE |
CN108503559B (zh) * | 2018-04-23 | 2021-10-01 | 上海诗丹德生物技术有限公司 | 辣椒碱卤代衍生物的合成及其应用 |
AR117291A1 (es) | 2018-12-14 | 2021-07-28 | Syngenta Crop Protection Ag | Compuestos heterocíclicos de cianamida con actividad pesticida |
WO2020169526A1 (en) | 2019-02-18 | 2020-08-27 | Syngenta Crop Protection Ag | Pesticidally-active cyanamide heterocyclic compounds |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0259738A2 (de) | 1986-09-10 | 1988-03-16 | Nihon Tokushu Noyaku Seizo K.K. | Heterocyclische Verbindungen |
EP0268915A2 (de) | 1986-11-21 | 1988-06-01 | Bayer Ag | Trifluormethylcarbonyl-Derivate |
EP0432600A2 (de) | 1989-12-14 | 1991-06-19 | Bayer Ag | 2-Iminopyridin-Derivate |
JPH0578323A (ja) | 1991-03-11 | 1993-03-30 | Nippon Soda Co Ltd | 新規なヘテロ環化合物、その製造方法及び殺虫剤 |
WO2002050035A2 (de) | 2000-12-20 | 2002-06-27 | Bayer Cropscience Ag | Insektizde und fungizide (2,6-dichlor-4-pyridyl)-methylcarbamate als pflanzenschutzmittel |
JP2002520384A (ja) * | 1998-07-16 | 2002-07-09 | アベンテイス・アグリカルチヤー・リミテツド | アリールビニルエーテル誘導体およびそれらの除草剤としての使用 |
JP2003026661A (ja) | 2001-06-27 | 2003-01-29 | Sinon Corp | 複素環化合物 |
JP2005225860A (ja) * | 2003-11-11 | 2005-08-25 | Ishihara Sangyo Kaisha Ltd | ビフェニル誘導体又はその塩、それらを有効成分として含有する有害生物防除剤 |
WO2007105814A1 (ja) * | 2006-03-10 | 2007-09-20 | Nissan Chemical Industries, Ltd. | 置換イソキサゾリン化合物及び有害生物防除剤 |
US20090306041A1 (en) | 2008-02-05 | 2009-12-10 | Roche Palo Alto Llc | Inhibitors of Bruton's tyrosine kinase |
JP2010138082A (ja) * | 2008-12-09 | 2010-06-24 | Nippon Soda Co Ltd | 環状アミン化合物またはその塩、並びに有害生物防除剤 |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1285390A (en) * | 1969-12-23 | 1972-08-16 | Pharmacia Ab | Improvements in the n-alkylation of acylated amino compounds |
US3867447A (en) * | 1972-08-25 | 1975-02-18 | Du Pont | Hydroxyguanidine O-carbamates |
AU5950573A (en) | 1972-08-25 | 1975-02-27 | Du Pont | Mono- and disubstituted hydroxyguanidines |
US4203988A (en) * | 1975-11-12 | 1980-05-20 | Merck & Co., Inc. | Pyridinyl ureas and pharmaceutical use |
US4206141A (en) * | 1978-12-15 | 1980-06-03 | Stauffer Chemical Company | Process for preparation of di-substituted cyanamides using quaternary salt catalysis |
JPS63227552A (ja) * | 1987-03-13 | 1988-09-21 | Shionogi & Co Ltd | 2−フルオロエチル誘導体、その製造法およびそれを有効成分とする有害生物防除剤 |
JP2859301B2 (ja) * | 1989-07-08 | 1999-02-17 | 武田薬品工業株式会社 | 農園芸用殺虫組成物 |
HU207047B (en) * | 1989-11-07 | 1993-03-01 | Richter Gedeon Vegyeszet | Process for producing new pyridine derivatives and pharmaceutical copositions comprising same |
US5559108A (en) * | 1994-09-02 | 1996-09-24 | Bristol-Myers Squibb Company | Cephalosporin derivatives |
US5804686A (en) * | 1996-01-19 | 1998-09-08 | Neurogen Corporation | fused pyrrolecarboxamides; a new class of GABA brain receptor ligands |
DK0976737T3 (da) | 1997-04-07 | 2009-07-20 | Nihon Nohyaku Co Ltd | Pyrazolderivater, fremgangsmåder til fremstilling deraf, intermediater og skadedyrsbekæmpelsesmidler indholdende disse som aktiv ingrediens |
JP3190859B2 (ja) | 1997-07-29 | 2001-07-23 | 松下電器産業株式会社 | Cdma無線送信装置及びcdma無線受信装置 |
AR046698A1 (es) | 2003-11-11 | 2005-12-21 | Ishihara Sangyo Kaisha | Derivado bifenilo o su sal, y pesticida que lo contienen como un ingrediente activo |
DE102004018953A1 (de) | 2004-04-20 | 2005-11-17 | Bayer Cropscience Gmbh | 4-Halogenalkylpyridin-3-sulfonsäureamide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
DE102004041529A1 (de) | 2004-08-27 | 2006-03-02 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Ketoenolen |
US8604055B2 (en) * | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
WO2006138147A1 (en) * | 2005-06-13 | 2006-12-28 | Bayer Cropscience Ag | Pesticidal 5-di-(substituted)aminopyrazole derivatives |
EP2030971B1 (en) | 2006-06-20 | 2011-10-12 | Ishihara Sangyo Kaisha, Ltd. | Pest control agent containing novel pyridyl-methanamine derivative or salt thereof |
JP5078323B2 (ja) | 2006-11-20 | 2012-11-21 | 株式会社カプコン | ゲーム装置、そのゲーム装置を実現するためのプログラム及び記録媒体 |
JP4985025B2 (ja) | 2007-03-28 | 2012-07-25 | 凸版印刷株式会社 | マイクロニードルチップ集合体、マイクロニードルチップ、医療器具、マイクロニードルチップ集合体製造方法およびマイクロニードルチップ製造方法 |
JP2008260691A (ja) * | 2007-04-10 | 2008-10-30 | Bayer Cropscience Ag | 殺虫性アリールイソオキサゾリン誘導体 |
JP2008266230A (ja) * | 2007-04-23 | 2008-11-06 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
JPWO2009038064A1 (ja) * | 2007-09-19 | 2011-01-06 | 株式会社医薬分子設計研究所 | I型11βヒドロキシステロイド脱水素酵素阻害活性を有する複素環誘導体 |
JP2011514315A (ja) * | 2008-02-07 | 2011-05-06 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺虫性アリールピロリン類 |
MX363956B (es) * | 2010-08-31 | 2019-04-09 | Meiji Seika Pharma Co Ltd Star | Agente de control de plagas. |
AU2012302922A1 (en) * | 2011-08-26 | 2014-04-17 | Meiji Seika Pharma Co., Ltd. | Method for producing pest controlling agent |
AU2013226812B2 (en) * | 2012-02-29 | 2016-10-27 | Mitsui Chemicals Crop & Life Solutions, Inc. | Pest control composition including novel iminopyridine derivative |
-
2011
- 2011-08-26 MX MX2013002233A patent/MX363956B/es active IP Right Grant
- 2011-08-26 CA CA2808144A patent/CA2808144C/en active Active
- 2011-08-26 CN CN201410153185.XA patent/CN103960242B/zh active Active
- 2011-08-26 HU HUE15175471A patent/HUE040676T2/hu unknown
- 2011-08-26 NZ NZ722021A patent/NZ722021A/en unknown
- 2011-08-26 EP EP20140168966 patent/EP2789237A1/en not_active Withdrawn
- 2011-08-26 EA EA201390320A patent/EA022848B1/ru unknown
- 2011-08-26 KR KR1020137008197A patent/KR20130132775A/ko not_active Application Discontinuation
- 2011-08-26 AU AU2011297160A patent/AU2011297160B2/en active Active
- 2011-08-26 EP EP15175467.8A patent/EP2959775A1/en not_active Withdrawn
- 2011-08-26 CU CU20130026A patent/CU24170B1/es active IP Right Grant
- 2011-08-26 AP AP2013006782A patent/AP3539A/xx active
- 2011-08-26 CN CN201180023561.8A patent/CN102892290B/zh not_active Expired - Fee Related
- 2011-08-26 PL PL15175471T patent/PL2984930T3/pl unknown
- 2011-08-26 TR TR2018/16134T patent/TR201816134T4/tr unknown
- 2011-08-26 KR KR1020137012387A patent/KR101442445B1/ko active IP Right Grant
- 2011-08-26 BR BR112013004818A patent/BR112013004818B8/pt active IP Right Grant
- 2011-08-26 CR CR20190244A patent/CR20190244A/es unknown
- 2011-08-26 SG SG2013011887A patent/SG187883A1/en unknown
- 2011-08-26 NZ NZ703964A patent/NZ703964A/en unknown
- 2011-08-26 GE GEAP201113043A patent/GEP201706728B/en unknown
- 2011-08-26 EP EP15175471.0A patent/EP2984930B1/en active Active
- 2011-08-26 UA UAA201303921A patent/UA109149C2/uk unknown
- 2011-08-26 HU HUE13157997A patent/HUE026428T2/en unknown
- 2011-08-26 JP JP2012501048A patent/JPWO2012029672A1/ja not_active Ceased
- 2011-08-26 WO PCT/JP2011/069352 patent/WO2012029672A1/ja active Application Filing
- 2011-08-26 NZ NZ703862A patent/NZ703862A/en unknown
- 2011-08-26 PE PE2013000357A patent/PE20131380A1/es active IP Right Grant
- 2011-08-26 ES ES13157997.1T patent/ES2563461T3/es active Active
- 2011-08-26 MA MA35778A patent/MA34551B1/fr unknown
- 2011-08-26 ES ES15175471.0T patent/ES2693089T3/es active Active
- 2011-08-26 MY MYPI2013700309A patent/MY163072A/en unknown
- 2011-08-26 CN CN201310150071.5A patent/CN103254125B/zh active Active
- 2011-08-26 EP EP11821689.4A patent/EP2628389A4/en not_active Withdrawn
- 2011-08-26 NZ NZ607939A patent/NZ607939A/en unknown
- 2011-08-26 US US13/814,753 patent/US8957214B2/en active Active
- 2011-08-26 PL PL13157997T patent/PL2631235T3/pl unknown
- 2011-08-26 CR CR20200540A patent/CR20200540A/es unknown
- 2011-08-26 EP EP13157997.1A patent/EP2631235B1/en active Active
- 2011-08-30 TW TW100131116A patent/TWI538620B/zh active
- 2011-08-30 TW TW104142934A patent/TWI554210B/zh active
-
2012
- 2012-02-29 JP JP2012042723A patent/JP4993641B2/ja active Active
-
2013
- 2013-02-06 IL IL224592A patent/IL224592A/en active IP Right Grant
- 2013-02-07 US US13/761,306 patent/US9073866B2/en not_active Expired - Fee Related
- 2013-02-13 ZA ZA2013/01156A patent/ZA201301156B/en unknown
- 2013-02-22 DO DO2013000046A patent/DOP2013000046A/es unknown
- 2013-02-26 NI NI201300025A patent/NI201300025A/es unknown
- 2013-02-27 CL CL2013000570A patent/CL2013000570A1/es unknown
- 2013-03-06 CO CO13045134A patent/CO6680699A2/es unknown
- 2013-03-27 EC ECSP13012527 patent/ECSP13012527A/es unknown
- 2013-11-08 HK HK14101510.3A patent/HK1188595A1/zh unknown
-
2014
- 2014-05-13 IL IL232581A patent/IL232581A0/en unknown
- 2014-12-17 US US14/573,344 patent/US9328068B2/en active Active
-
2016
- 2016-03-25 US US15/080,971 patent/US9717242B2/en active Active
- 2016-10-12 CL CL2016002590A patent/CL2016002590A1/es unknown
-
2017
- 2017-06-27 US US15/634,284 patent/US10085449B2/en active Active
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0259738A2 (de) | 1986-09-10 | 1988-03-16 | Nihon Tokushu Noyaku Seizo K.K. | Heterocyclische Verbindungen |
EP0268915A2 (de) | 1986-11-21 | 1988-06-01 | Bayer Ag | Trifluormethylcarbonyl-Derivate |
EP0432600A2 (de) | 1989-12-14 | 1991-06-19 | Bayer Ag | 2-Iminopyridin-Derivate |
JPH03190859A (ja) * | 1989-12-14 | 1991-08-20 | Bayer Ag | 2―イミノピリジン誘導体、その製法及び該誘導体からなる除草剤 |
JPH0578323A (ja) | 1991-03-11 | 1993-03-30 | Nippon Soda Co Ltd | 新規なヘテロ環化合物、その製造方法及び殺虫剤 |
JP2002520384A (ja) * | 1998-07-16 | 2002-07-09 | アベンテイス・アグリカルチヤー・リミテツド | アリールビニルエーテル誘導体およびそれらの除草剤としての使用 |
WO2002050035A2 (de) | 2000-12-20 | 2002-06-27 | Bayer Cropscience Ag | Insektizde und fungizide (2,6-dichlor-4-pyridyl)-methylcarbamate als pflanzenschutzmittel |
JP2004524287A (ja) * | 2000-12-20 | 2004-08-12 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ジクロロピリジルメチルアミド類 |
JP2003026661A (ja) | 2001-06-27 | 2003-01-29 | Sinon Corp | 複素環化合物 |
JP2005225860A (ja) * | 2003-11-11 | 2005-08-25 | Ishihara Sangyo Kaisha Ltd | ビフェニル誘導体又はその塩、それらを有効成分として含有する有害生物防除剤 |
WO2007105814A1 (ja) * | 2006-03-10 | 2007-09-20 | Nissan Chemical Industries, Ltd. | 置換イソキサゾリン化合物及び有害生物防除剤 |
US20090306041A1 (en) | 2008-02-05 | 2009-12-10 | Roche Palo Alto Llc | Inhibitors of Bruton's tyrosine kinase |
JP2010138082A (ja) * | 2008-12-09 | 2010-06-24 | Nippon Soda Co Ltd | 環状アミン化合物またはその塩、並びに有害生物防除剤 |
Non-Patent Citations (12)
Title |
---|
BIOSCI. BIOTECHNOL. BIOCHEM., vol. 67, no. 5, 2003, pages 980 - 988 |
CHEMISCHE BERICHTE, vol. 88, 1955, pages 1103 - 8 |
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 58, no. 4, 2010, pages 2419 |
JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, no. 12, 1999, pages 2227 |
JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, no. 12, 1999, pages 2227 - 2234 |
JOURNAL OF PESTICIDE SCIENCE, vol. 29, no. 2, 2004, pages 110 - 116 |
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B: BIOLOGY, vol. 98, no. 1, 2010, pages 57 |
PEST MANAGEMENT SCIENCE, vol. 59, no. 3, 2003, pages 347 - 352 |
PEST MANAGEMENT SCIENCE, vol. 61, no. 8, 2005, pages 742 |
PEST MANAGEMENT SCIENCE, vol. 64, no. 11, 2008, pages 1115 - 1121 |
See also references of EP2628389A4 |
SHIBUYA INDEX, vol. 14TH ED., 2009, pages 208 * |
Cited By (376)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2749555A4 (en) * | 2011-08-26 | 2015-05-06 | Meiji Seika Pharma Co Ltd | METHOD FOR PRODUCING A PESTICIDIZING AGENT |
EP3318554A1 (en) * | 2011-08-26 | 2018-05-09 | Meiji Seika Pharma Co., Ltd. | Method for producing pest control agent |
US9883673B2 (en) | 2011-08-26 | 2018-02-06 | Meiji Seika Pharma Co., Ltd. | Method for producing pest control agent |
US20140213791A1 (en) * | 2011-08-26 | 2014-07-31 | Meiji Seika Pharma Co., Ltd. | Method for producing pest control agent |
US9357776B2 (en) * | 2011-08-26 | 2016-06-07 | Meiji Seika Pharma Co., Ltd. | Method for producing pest control agent |
JP2015509908A (ja) * | 2012-02-29 | 2015-04-02 | Meiji Seikaファルマ株式会社 | 新規イミノピリジン誘導体を含む有害生物防除用組成物 |
EP2634174A3 (en) * | 2012-02-29 | 2013-09-11 | Meiji Seika Pharma Co., Ltd. | Nitrogen-containing hetercyclic derivate having 2-imino group and pest control agent including the same |
WO2013129688A1 (en) * | 2012-02-29 | 2013-09-06 | Meiji Seika Pharma Co., Ltd. | Pest control composition including novel iminopyridine derivative |
CN104125774A (zh) * | 2012-02-29 | 2014-10-29 | 明治制果药业株式会社 | 包括新型亚氨基吡啶衍生物的有害物防治组合物 |
EP2633756A1 (en) * | 2012-02-29 | 2013-09-04 | Meiji Seika Pharma Co., Ltd. | Pest control composition including novel iminopyridine derivate |
US11771086B2 (en) | 2012-02-29 | 2023-10-03 | Mmag Co., Ltd. | Pest control composition including novel iminopyridine derivative |
JP2015511577A (ja) * | 2012-02-29 | 2015-04-20 | Meiji Seikaファルマ株式会社 | 2−イミノ基を有する含窒素ヘテロ環誘導体及びそれを含んでなる有害生物防除剤 |
US9301525B2 (en) | 2012-02-29 | 2016-04-05 | Meui Seika Pharma Co., Ltd. | Pest control composition including novel iminopyridine derivative |
US10736319B2 (en) | 2012-02-29 | 2020-08-11 | Meiji Seika Pharma Co., Ltd. | Pest control composition including novel iminopyridine derivative |
EA026369B1 (ru) * | 2012-02-29 | 2017-03-31 | Мейдзи Сейка Фарма Ко., Лтд. | Композиция для борьбы с вредителями, включающая новое производное иминопиридина |
US10349655B2 (en) | 2012-02-29 | 2019-07-16 | Meiji Seika Pharma Co., Ltd. | Pest control composition including novel iminopyridine derivative |
US9422280B2 (en) | 2012-03-29 | 2016-08-23 | Basf Se | N-substituted hetero-bicyclic compounds and derivatives for combating animal pests II |
WO2013144213A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyridinylidene compounds and derivatives for combating animal pests |
WO2013144223A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyrimidinylidene compounds and derivatives for combating animal pests |
CN104202981B (zh) * | 2012-03-30 | 2018-01-30 | 巴斯夫欧洲公司 | 防治动物害虫的n‑取代的吡啶亚基化合物和衍生物 |
JP2015512907A (ja) * | 2012-03-30 | 2015-04-30 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 有害動物を駆除するためのn−置換ピリジニリデン化合物および誘導体 |
CN104202981A (zh) * | 2012-03-30 | 2014-12-10 | 巴斯夫欧洲公司 | 防治动物害虫的n-取代的吡啶亚基化合物和衍生物 |
US9334238B2 (en) | 2012-03-30 | 2016-05-10 | Basf Se | N-substituted pyridinylidenes for combating animal pests |
WO2013174645A1 (en) | 2012-05-24 | 2013-11-28 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2013186089A2 (en) | 2012-06-14 | 2013-12-19 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests |
WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
WO2014053395A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Use of n-thio-anthranilamide compounds on cultivated plants |
WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
WO2014053404A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2014053405A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
WO2014053403A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling insecticide resistant insects |
WO2014053406A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling ryanodine-modulator insecticide resistant insects |
WO2014079766A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079774A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079764A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079814A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079770A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079804A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079841A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079772A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079773A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
WO2014079813A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079752A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
US10117430B2 (en) | 2012-12-14 | 2018-11-06 | Basf Se | Malononitrile compounds for controlling animal pests |
WO2014090700A1 (en) | 2012-12-14 | 2014-06-19 | Basf Se | Malononitrile compounds for controlling animal pests |
WO2014102244A1 (en) | 2012-12-27 | 2014-07-03 | Basf Se | 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests |
WO2014128136A1 (en) | 2013-02-20 | 2014-08-28 | Basf Se | Anthranilamide compounds and their use as pesticides |
WO2014170300A1 (en) | 2013-04-19 | 2014-10-23 | Basf Se | N-substituted acyl-imino-pyridine compounds and derivatives for combating animal pests |
JP5704737B1 (ja) * | 2013-05-27 | 2015-04-22 | Meiji Seikaファルマ株式会社 | ミツバチ寄生性害虫に対する防除剤及びそれらを使用したミツバチ寄生性害虫の防除方法 |
EA029532B1 (ru) * | 2013-05-27 | 2018-04-30 | Мейдзи Сейка Фарма Ко., Лтд. | Средства для борьбы с вредителями-паразитами медоносных пчел и способ борьбы с вредителями-паразитами медоносных пчел с их использованием |
US9066517B2 (en) | 2013-05-27 | 2015-06-30 | Meiji Seika Pharma Co., Ltd. | Pest control agents for honeybee parasitic pests, and pest control method for honeybee parasitic pests using the pest control agents |
WO2014192717A1 (ja) * | 2013-05-27 | 2014-12-04 | Meiji Seikaファルマ株式会社 | ミツバチ寄生性害虫に対する防除剤及びそれらを使用したミツバチ寄生性害虫の防除方法 |
AU2014271925B2 (en) * | 2013-05-27 | 2017-11-23 | Meiji Seika Pharma Co., Ltd. | Control agents for honeybee parasites and control method for honeybee parasites using same |
WO2014202751A1 (en) | 2013-06-21 | 2014-12-24 | Basf Se | Methods for controlling pests in soybean |
WO2015007682A1 (en) | 2013-07-15 | 2015-01-22 | Basf Se | Pesticide compounds |
WO2015040116A1 (en) | 2013-09-19 | 2015-03-26 | Basf Se | N-acylimino heterocyclic compounds |
US10206397B2 (en) | 2013-09-19 | 2019-02-19 | Basf Se | N-acylimino heterocyclic compounds |
US10757938B2 (en) | 2013-09-19 | 2020-09-01 | Basf Se | N-acylimino Heterocyclic Compounds |
WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
US9776967B2 (en) | 2013-10-14 | 2017-10-03 | Bayer Animal Health Gmbh | Carboxamide derivatives as pesticidal compounds |
WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
WO2015055757A1 (en) | 2013-10-18 | 2015-04-23 | Basf Se | Use of pesticidal active carboxamide derivative in soil and seed application and treatment methods |
EP3456201A1 (en) | 2013-10-18 | 2019-03-20 | BASF Agrochemical Products B.V. | Use of pesticidal active carboxamide derivative in soil and seed application and treatment meth-ods |
WO2015059088A1 (de) | 2013-10-23 | 2015-04-30 | Bayer Cropscience Ag | Substituierte chinoxalin-derivate als schädlingsbekämpfungsmittel |
WO2015091649A1 (en) | 2013-12-18 | 2015-06-25 | Basf Se | N-substituted imino heterocyclic compounds |
WO2015091645A1 (en) | 2013-12-18 | 2015-06-25 | Basf Se | Azole compounds carrying an imine-derived substituent |
WO2015101622A1 (de) | 2014-01-03 | 2015-07-09 | Bayer Cropscience Ag | Neue pyrazolyl-heteroarylamide als schädlingsbekämpfungsmittel |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
WO2015107133A1 (de) | 2014-01-20 | 2015-07-23 | Bayer Cropscience Ag | Chinolinderivate als insektizide und akarizide |
JPWO2015137216A1 (ja) * | 2014-03-10 | 2017-04-06 | Meiji Seikaファルマ株式会社 | 2−アシルイミノピリジン誘導体の製造法 |
US9975851B2 (en) | 2014-03-10 | 2018-05-22 | Meiji Seika Pharma Co., Ltd. | Method for producing 2-acyliminopyridine derivative |
WO2015150300A1 (de) | 2014-04-02 | 2015-10-08 | Bayer Cropscience Ag | N-(1-(hetero)aryl-1h-pyrazol-4-yl)-(hetero)arylamid-derivate und ihre verwendung als schädlingsbekämpfungsmittel |
WO2015169776A1 (en) | 2014-05-08 | 2015-11-12 | Bayer Cropscience Ag | Pyrazolopyridine sulfonamides as nematicides |
WO2015185531A1 (de) | 2014-06-05 | 2015-12-10 | Bayer Cropscience Aktiengesellschaft | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
WO2016001129A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Verbesserte insektizide zusammensetzungen |
WO2016001119A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2016008830A1 (de) | 2014-07-15 | 2016-01-21 | Bayer Cropscience Aktiengesellschaft | Aryl-triazolyl-pyridine als schädlingsbekämpfungsmittel |
US10149477B2 (en) | 2014-10-06 | 2018-12-11 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
WO2016055096A1 (en) | 2014-10-07 | 2016-04-14 | Bayer Cropscience Ag | Method for treating rice seed |
WO2016071499A1 (en) | 2014-11-06 | 2016-05-12 | Basf Se | 3-pyridyl heterobicyclic compound for controlling invertebrate pests |
WO2016091857A1 (de) | 2014-12-11 | 2016-06-16 | Bayer Cropscience Aktiengesellschaft | Fünfgliedrige c-n-verknüpfte arylsulfid- und arylsulfoxid-derivate als schädlingsbekämpfungsmittel |
WO2016124557A1 (de) | 2015-02-05 | 2016-08-11 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2016124563A1 (de) | 2015-02-05 | 2016-08-11 | Bayer Cropscience Aktiengesellschsaft | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlings-bekämpfungsmittel |
US10556844B2 (en) | 2015-02-06 | 2020-02-11 | Basf Se | Pyrazole compounds as nitrification inhibitors |
WO2016128298A1 (de) | 2015-02-09 | 2016-08-18 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-thioimidazolyl-carboxamide als schädlingsbekämpfungsmittel |
US10701937B2 (en) | 2015-02-11 | 2020-07-07 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
WO2016128261A2 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
WO2016142394A1 (de) | 2015-03-10 | 2016-09-15 | Bayer Animal Health Gmbh | Pyrazolyl-derivate als schädlingsbekämpfungsmittel |
WO2016162371A1 (en) | 2015-04-07 | 2016-10-13 | Basf Agrochemical Products B.V. | Use of an insecticidal carboxamide compound against pests on cultivated plants |
WO2016162318A1 (de) | 2015-04-08 | 2016-10-13 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel und deren zwischenprodukte |
EP3081085A1 (en) | 2015-04-14 | 2016-10-19 | Bayer CropScience AG | Method for improving earliness in cotton |
WO2016174049A1 (en) | 2015-04-30 | 2016-11-03 | Bayer Animal Health Gmbh | Anti-parasitic combinations including halogen-substituted compounds |
US11053175B2 (en) | 2015-05-12 | 2021-07-06 | Basf Se | Thioether compounds as nitrification inhibitors |
WO2016180802A1 (de) | 2015-05-13 | 2016-11-17 | Bayer Cropscience Aktiengesellschaft | Insektizide arylpyrrolidine, verfahren zu ihrer herstellung und ihre verwendung als wirkstoffe zur bekämpfung tierischer schädlinge |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
WO2017005717A1 (en) | 2015-07-06 | 2017-01-12 | Bayer Cropscience Aktiengesellschaft | Heterocyclic compounds as pesticides |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
EP3896066A2 (de) | 2015-08-07 | 2021-10-20 | Bayer CropScience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
EP3896065A1 (de) | 2015-08-07 | 2021-10-20 | Bayer CropScience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
US11142514B2 (en) | 2015-10-02 | 2021-10-12 | Basf Se | Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents |
WO2017072039A1 (de) | 2015-10-26 | 2017-05-04 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017093163A1 (en) | 2015-11-30 | 2017-06-08 | Basf Se | Mixtures of cis-jasmone and bacillus amyloliquefaciens |
WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017093214A1 (de) | 2015-12-03 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Mesolonische halogenierte 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olat derivate und verwandte verbindungen als insektizide |
KR20180098631A (ko) | 2015-12-29 | 2018-09-04 | 메이지 세이카 파루마 가부시키가이샤 | 이미노피리딘 유도체를 함유하는 유해 생물 방제용 조성물 |
WO2017137338A1 (de) | 2016-02-11 | 2017-08-17 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-(het)aryl-imidazolyl-carboxyamide als schädlingsbekämpfungsmittel |
WO2017137339A1 (de) | 2016-02-11 | 2017-08-17 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-oxyimidazolyl-carboxamide als schädlingsbekämpfungsmittel |
WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
EP3210468A1 (de) | 2016-02-26 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen |
WO2017144497A1 (de) | 2016-02-26 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen |
WO2017153217A1 (en) | 2016-03-09 | 2017-09-14 | Basf Se | Spirocyclic derivatives |
WO2017153218A1 (en) | 2016-03-11 | 2017-09-14 | Basf Se | Method for controlling pests of plants |
WO2017157735A1 (de) | 2016-03-15 | 2017-09-21 | Bayer Cropscience Aktiengesellschaft | Substituierte sulfonylamide zur bekämpfung tierischer schädlinge |
WO2017157885A1 (de) | 2016-03-16 | 2017-09-21 | Bayer Cropscience Aktiengesellschaft | N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel |
WO2017167832A1 (en) | 2016-04-01 | 2017-10-05 | Basf Se | Bicyclic compounds |
WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
WO2017178416A1 (en) | 2016-04-15 | 2017-10-19 | Bayer Animal Health Gmbh | Pyrazolopyrimidine derivatives |
WO2017186536A1 (de) | 2016-04-25 | 2017-11-02 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-alkylimidazolyl-carboxamide als schädlingsbekämpfungsmittel |
EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017198449A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in brassicaceae |
WO2017198450A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in maize |
WO2017198453A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in potato, tomato or alfalfa |
WO2017198452A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in soybean |
WO2017198455A2 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in beta spp. plants |
EP3245865A1 (en) | 2016-05-17 | 2017-11-22 | Bayer CropScience Aktiengesellschaft | Method for increasing yield in brassicaceae |
WO2017198454A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in cotton |
WO2017198451A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in small grain cereals such as wheat and rice |
WO2017198588A1 (en) | 2016-05-18 | 2017-11-23 | Basf Se | Capsules comprising benzylpropargylethers for use as nitrification inhibitors |
WO2018013382A1 (en) | 2016-07-11 | 2018-01-18 | Covestro Llc, Et Al | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
WO2018013381A1 (en) | 2016-07-11 | 2018-01-18 | Covestro Llc, Et Al. | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
WO2018013380A1 (en) | 2016-07-11 | 2018-01-18 | Covestro Llc, Et Al. | Methods for treating seeds with an aqueous compostion and seeds treated therewith |
WO2018011111A1 (de) | 2016-07-12 | 2018-01-18 | Bayer Cropscience Aktiengesellschaft | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
WO2018015289A1 (de) | 2016-07-19 | 2018-01-25 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018019711A1 (en) | 2016-07-29 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Substituted halogen(thio)acyl compounds |
WO2018019937A1 (en) | 2016-07-29 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Formulation comprising a beneficial p. bilaii strain and talc for use in seed treatment |
WO2018029102A1 (de) | 2016-08-10 | 2018-02-15 | Bayer Cropscience Aktiengesellschaft | Substituierte 2-heterocyclyl-imidazolyl-carboxamide als schädlingsbekämpfungsmittel |
WO2018033455A1 (de) | 2016-08-15 | 2018-02-22 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
EP4089075A1 (en) | 2016-09-16 | 2022-11-16 | MMAG Co., Ltd. | Optimized production method for pest control agent |
WO2018052115A1 (ja) | 2016-09-16 | 2018-03-22 | Meiji Seikaファルマ株式会社 | 有害生物防除剤の最適化製造法 |
KR20190051952A (ko) | 2016-09-16 | 2019-05-15 | 메이지 세이카 파루마 가부시키가이샤 | 유해 생물 방제제의 최적화된 제조방법 |
JPWO2018052115A1 (ja) * | 2016-09-16 | 2019-06-27 | Meiji Seikaファルマ株式会社 | 有害生物防除剤の最適化製造法 |
WO2018050825A1 (de) | 2016-09-19 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Pyrazolo[1,5-a]pyridin- derivative und ihre verwendung als schädlingsbekämpfungsmittel |
WO2018065292A1 (de) | 2016-10-06 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte bicyclische heterocyclen-derivate als schädlings-bekämpfungsmittel |
WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
US11155517B2 (en) | 2016-10-14 | 2021-10-26 | Pi Industries Ltd. | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
WO2018069842A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
WO2018069841A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
WO2018083288A1 (de) | 2016-11-07 | 2018-05-11 | Bayer Aktiengesellschaft | Substituierte sulfonylamide zur bekämpfung tierischer schädlinge |
WO2018087036A1 (en) | 2016-11-11 | 2018-05-17 | Bayer Animal Health Gmbh | New anthelmintic quinoline-3-carboxamide derivatives |
US11505545B2 (en) | 2016-11-11 | 2022-11-22 | Bayer Animal Health Gmbh | Anthelmintic quinoline-3-carboxamide derivatives |
US10889573B2 (en) | 2016-11-11 | 2021-01-12 | Bayer Animal Health Gmbh | Anthelmintic quinoline-3-carboxamide derivatives |
WO2018095953A1 (de) | 2016-11-23 | 2018-05-31 | Bayer Cropscience Aktiengesellschaft | 2-[3-(alkylsulfonyl)-2h-indazol-2-yl]-3h-imidazo[4,5-b]pyridin-derivate und ähnliche verbindungen als schädlingsbekämpfungsmittel |
WO2018104500A1 (en) | 2016-12-09 | 2018-06-14 | Bayer Cropscience Aktiengesellschaft | Plant health effect of purpureocillium lilacinum |
WO2018108730A1 (de) | 2016-12-16 | 2018-06-21 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
WO2018108671A1 (en) | 2016-12-16 | 2018-06-21 | Basf Se | Pesticidal compounds |
WO2018108791A1 (en) | 2016-12-16 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Thiadiazole derivatives as pesticides |
WO2018116072A1 (en) | 2016-12-20 | 2018-06-28 | Pi Industries Ltd. | Heterocyclic compounds |
WO2018116073A1 (en) | 2016-12-21 | 2018-06-28 | Pi Industries Ltd. | 1, 2, 3-thiadiazole compounds and their use as crop protecting agent |
WO2018130437A1 (de) | 2017-01-10 | 2018-07-19 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018130443A1 (de) | 2017-01-10 | 2018-07-19 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018139560A1 (ja) | 2017-01-26 | 2018-08-02 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018141954A1 (de) | 2017-02-06 | 2018-08-09 | Bayer Aktiengesellschaft | Aryl- oder heteroaryl-substituierte imidazopyridinderivate und deren anwendung als schädlingsbekämpfungsmittel |
EP3369320A1 (de) | 2017-03-02 | 2018-09-05 | Bayer CropScience Aktiengesellschaft | Wirkstoff zur bekämpfung von wanzen |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
WO2018169045A1 (ja) | 2017-03-17 | 2018-09-20 | Meiji Seikaファルマ株式会社 | 中気門亜目ダニ類の防除剤 |
WO2018177781A1 (en) | 2017-03-28 | 2018-10-04 | Basf Se | Pesticidal compounds |
US11825838B2 (en) | 2017-03-31 | 2023-11-28 | Bayer Cropscience Aktiengesellschaft | Tricyclic carboxamides for controlling arthropods |
EP3978504A1 (en) | 2017-03-31 | 2022-04-06 | Basf Se | Chiral 2,3-dihydrothiazolo[3,2-a]pyrimidine derivatives for combating animal pests |
WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
WO2018177995A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Trizyklische carboxamide zur bekämpfung von anthropoden |
WO2018177970A1 (en) | 2017-03-31 | 2018-10-04 | Basf Se | Process for preparing chiral 2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium compounds |
WO2018190351A1 (ja) | 2017-04-10 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018190350A1 (ja) | 2017-04-10 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018190352A1 (ja) | 2017-04-11 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018189077A1 (de) | 2017-04-12 | 2018-10-18 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
US11524934B2 (en) | 2017-04-20 | 2022-12-13 | Pi Industries Ltd | Phenylamine compounds |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
WO2018193385A1 (en) | 2017-04-20 | 2018-10-25 | Pi Industries Ltd. | Novel phenylamine compounds |
WO2018192872A1 (de) | 2017-04-21 | 2018-10-25 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
WO2018197257A1 (de) | 2017-04-24 | 2018-11-01 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018197466A1 (en) | 2017-04-26 | 2018-11-01 | Basf Se | Substituted succinimide derivatives as pesticides |
US11130768B2 (en) | 2017-04-27 | 2021-09-28 | Bayer Animal Health Gmbh | Bicyclic pyrazole derivatives |
WO2018197692A1 (en) | 2017-04-27 | 2018-11-01 | Bayer Aktiengesellschaft | Heteroarylphenylaminoquinolines and analogues |
WO2018197401A1 (en) | 2017-04-27 | 2018-11-01 | Bayer Animal Health Gmbh | New bicyclic pyrazole derivatives |
WO2018202494A1 (de) | 2017-05-02 | 2018-11-08 | Bayer Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018202501A1 (de) | 2017-05-02 | 2018-11-08 | Bayer Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2018202712A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylmethylphenoxyquinolines and analogues |
WO2018202706A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylheteroaryloxyquinolines and analogues |
WO2018202715A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylbenzylbenzimidazoles and analogues |
US11827616B2 (en) | 2017-05-04 | 2023-11-28 | Discovery Purchaser Corporation | Heterocyclic compounds as pesticides |
WO2018202525A1 (en) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | Phenoxyethanamine derivatives for controlling pests |
WO2018202524A1 (de) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | 2-{[2-(phenyloxymethyl)pyridin-5-yl]oxy}-ethanamin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel z.b. für den pflanzenschutz |
WO2018206479A1 (en) | 2017-05-10 | 2018-11-15 | Basf Se | Bicyclic pesticidal compounds |
EP3400801A1 (en) | 2017-05-10 | 2018-11-14 | Bayer CropScience Aktiengesellschaft | Plant health effect of purpureocillium lilacinum |
WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
WO2018225829A1 (ja) | 2017-06-08 | 2018-12-13 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2018229202A1 (en) | 2017-06-16 | 2018-12-20 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2018234202A1 (en) | 2017-06-19 | 2018-12-27 | Basf Se | SUBSTITUTED PYRIMIDINIUM COMPOUNDS AND DERIVATIVES FOR CONTROLLING HARMFUL ANIMALS |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | SUBSTITUTED CYCLOPROPYL DERIVATIVES |
WO2019002132A1 (en) | 2017-06-30 | 2019-01-03 | Bayer Animal Health Gmbh | NEW AZAQUINOLINE DERIVATIVES |
WO2019007887A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
WO2019007888A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007891A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
EP3284739A1 (de) | 2017-07-19 | 2018-02-21 | Bayer CropScience Aktiengesellschaft | Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel |
WO2019025341A1 (en) | 2017-08-04 | 2019-02-07 | Bayer Animal Health Gmbh | QUINOLINE DERIVATIVES FOR THE TREATMENT OF INFECTIONS BY HELMINTHES |
WO2019035881A1 (en) | 2017-08-17 | 2019-02-21 | Bayer Cropscience Lp | DISPERSIBLE COMPOSITIONS IN LIQUID FERTILIZER AND ASSOCIATED METHODS |
WO2019038195A1 (de) | 2017-08-22 | 2019-02-28 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019043183A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING PESTS OF RICE IN RICE |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
WO2019059412A1 (en) | 2017-09-20 | 2019-03-28 | Mitsui Chemicals Agro, Inc. | AGENT FOR EXTENDED CONTROL OF ECTOPARASITES FOR ANIMAL |
WO2019068572A1 (de) | 2017-10-04 | 2019-04-11 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019072906A1 (en) | 2017-10-13 | 2019-04-18 | Basf Se | IMIDAZOLIDINE PYRIMIDINIUM COMPOUNDS FOR CONTROL OF HARMFUL ANIMALS |
WO2019076744A1 (de) | 2017-10-17 | 2019-04-25 | Bayer Aktiengesellschaft | Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinone |
EP3473103A1 (de) | 2017-10-17 | 2019-04-24 | Bayer AG | Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon |
WO2019076752A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS AYNT INSECTICIDE / ACARICIDE PROPERTIES |
WO2019076750A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDE PROPERTIES7ACARICIDES |
WO2019076751A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
WO2019076749A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
WO2019076754A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
EP3473100A1 (en) | 2017-10-18 | 2019-04-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2019092086A1 (en) | 2017-11-13 | 2019-05-16 | Bayer Aktiengesellschaft | Tetrazolylpropyl derivatives and their use as fungicides |
WO2019105875A1 (en) | 2017-11-28 | 2019-06-06 | Bayer Aktiengesellschaft | Heterocyclic compounds as pesticides |
WO2019123196A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Fluoralkenyl compounds, process for preparation and use thereof |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
WO2019121159A1 (en) | 2017-12-21 | 2019-06-27 | Basf Se | Pesticidal compounds |
WO2019122319A1 (en) | 2017-12-21 | 2019-06-27 | Bayer Aktiengesellschaft | Trisubstitutedsilylmethylheteroaryloxyquinolines and analogues |
WO2019145140A1 (en) | 2018-01-09 | 2019-08-01 | Basf Se | Silylethynyl hetaryl compounds as nitrification inhibitors |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
EP3305786A2 (de) | 2018-01-22 | 2018-04-11 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
WO2019155066A1 (en) | 2018-02-12 | 2019-08-15 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
WO2019162174A1 (de) | 2018-02-21 | 2019-08-29 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019162228A1 (en) | 2018-02-21 | 2019-08-29 | Bayer Aktiengesellschaft | 1-(5-substituted imidazol-1-yl)but-3-en derivatives and their use as fungicides |
WO2019166561A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of alkoxypyrazoles as nitrification inhibitors |
WO2019166558A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
WO2019166560A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of n-functionalized alkoxy pyrazole compounds as nitrification inhibitors |
WO2019175045A1 (de) | 2018-03-12 | 2019-09-19 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019175046A1 (de) | 2018-03-12 | 2019-09-19 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
WO2019197371A1 (en) | 2018-04-10 | 2019-10-17 | Bayer Aktiengesellschaft | Oxadiazoline derivatives |
WO2019197615A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften |
WO2019197623A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
WO2019201835A1 (en) | 2018-04-17 | 2019-10-24 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
EP4039682A1 (en) | 2018-04-17 | 2022-08-10 | Bayer Aktiengesellschaft | Novel heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
WO2019202077A1 (en) | 2018-04-20 | 2019-10-24 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
WO2019201921A1 (de) | 2018-04-20 | 2019-10-24 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2019215182A1 (en) | 2018-05-09 | 2019-11-14 | Bayer Animal Health Gmbh | New quinoline derivatives |
WO2019219529A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Mixtures comprising benzpyrimoxan and oxazosulfyl and uses and methods of applying them |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2019224143A1 (de) | 2018-05-24 | 2019-11-28 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
WO2020005678A1 (en) | 2018-06-25 | 2020-01-02 | Bayer Cropscience Lp | Seed treatment method |
WO2020002189A1 (de) | 2018-06-27 | 2020-01-02 | Bayer Aktiengesellschaft | Wirkstoffkombinationen |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
WO2020007902A1 (en) | 2018-07-05 | 2020-01-09 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
WO2020007905A1 (en) | 2018-07-05 | 2020-01-09 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
US11952359B2 (en) | 2018-07-05 | 2024-04-09 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
US11884643B2 (en) | 2018-07-05 | 2024-01-30 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
WO2020007904A1 (en) | 2018-07-05 | 2020-01-09 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
WO2020020777A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
WO2020020765A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of a substituted thiazolidine compound as nitrification inhibitor |
WO2020022412A1 (ja) | 2018-07-25 | 2020-01-30 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
WO2020020813A1 (en) | 2018-07-25 | 2020-01-30 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
WO2020020816A1 (en) | 2018-07-26 | 2020-01-30 | Bayer Aktiengesellschaft | Novel triazole derivatives |
WO2020021082A1 (en) | 2018-07-27 | 2020-01-30 | Bayer Aktiengesellschaft | Controlled release formulations for agrochemicals |
WO2020025650A1 (en) | 2018-07-31 | 2020-02-06 | Bayer Aktiengesellschaft | Controlled release formulations with lignin for agrochemicals |
WO2020035826A1 (en) | 2018-08-17 | 2020-02-20 | Pi Industries Ltd. | 1,2-dithiolone compounds and use thereof |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
WO2020053282A1 (de) | 2018-09-13 | 2020-03-19 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2020057939A1 (en) | 2018-09-17 | 2020-03-26 | Bayer Aktiengesellschaft | Use of the fungicide isoflucypram for controlling claviceps purpurea and reducing sclerotia in cereals |
JP7301062B2 (ja) | 2018-09-27 | 2023-06-30 | 三井化学クロップ&ライフソリューション株式会社 | 水性懸濁状農薬組成物 |
JPWO2020067404A1 (ja) * | 2018-09-27 | 2021-09-16 | Meiji Seikaファルマ株式会社 | 水性懸濁状農薬組成物 |
US12063931B2 (en) | 2018-09-27 | 2024-08-20 | Mitsui Chemicals Crop & Life Solutions, Inc. | Aqueous suspension-form pesticidal composition |
KR20210066835A (ko) | 2018-09-27 | 2021-06-07 | 메이지 세이카 파루마 가부시키가이샤 | 수성 현탁상 농약 조성물 |
KR102702570B1 (ko) | 2018-09-27 | 2024-09-04 | 미츠이 가가쿠 크롭 앤 라이프 솔루션 가부시키가이샤 | 수성 현탁상 농약 조성물 |
WO2020067404A1 (ja) | 2018-09-27 | 2020-04-02 | Meiji Seikaファルマ株式会社 | 水性懸濁状農薬組成物 |
WO2020064408A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
WO2020064480A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
WO2020064492A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof |
WO2020070050A1 (en) | 2018-10-01 | 2020-04-09 | Bayer Aktiengesellschaft | Fungicidal 5-substituted imidazol-1-yl carbinol derivatives |
WO2020079173A1 (en) | 2018-10-18 | 2020-04-23 | Bayer Aktiengesellschaft | Pyridylphenylaminoquinolines and analogues |
WO2020079167A1 (en) | 2018-10-18 | 2020-04-23 | Bayer Aktiengesellschaft | Heteroarylaminoquinolines and analogues |
WO2020079232A1 (en) | 2018-10-20 | 2020-04-23 | Bayer Aktiengesellschaft | Oxetanylphenoxyquinolines and analogues |
WO2020083971A2 (en) | 2018-10-24 | 2020-04-30 | Bayer Animal Health Gmbh | New anthelmintic compounds |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
EP3643711A1 (en) | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
WO2020083733A1 (en) | 2018-10-24 | 2020-04-30 | Basf Se | Pesticidal compounds |
WO2020109039A1 (en) | 2018-11-28 | 2020-06-04 | Basf Se | Pesticidal compounds |
WO2020109391A1 (en) | 2018-11-28 | 2020-06-04 | Bayer Aktiengesellschaft | Pyridazine (thio)amides as fungicidal compounds |
EP3620052A1 (en) | 2018-12-12 | 2020-03-11 | Bayer Aktiengesellschaft | Use of phenoxypyridinyl-substituted (1h-1,2,4-triazol-1-yl)alcohols for controlling fungicidal diseases in maize |
WO2020126591A1 (en) | 2018-12-18 | 2020-06-25 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
WO2020126980A1 (en) | 2018-12-18 | 2020-06-25 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2020127780A1 (en) | 2018-12-20 | 2020-06-25 | Bayer Aktiengesellschaft | Heterocyclyl pyridazine as fungicidal compounds |
EP3669652A1 (en) | 2018-12-21 | 2020-06-24 | Bayer AG | Active compound combination |
WO2020127974A1 (en) | 2018-12-21 | 2020-06-25 | Bayer Aktiengesellschaft | 1,3,4-oxadiazoles and their derivatives as new antifungal agents |
EP3679793A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679789A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679791A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679790A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3679792A1 (en) | 2019-01-08 | 2020-07-15 | Bayer AG | Active compound combinations |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2020178067A1 (en) | 2019-03-01 | 2020-09-10 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2020178307A1 (en) | 2019-03-05 | 2020-09-10 | Bayer Aktiengesellschaft | Active compound combination |
WO2020182929A1 (en) | 2019-03-13 | 2020-09-17 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
WO2020187656A1 (en) | 2019-03-15 | 2020-09-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
WO2020231751A1 (en) | 2019-05-10 | 2020-11-19 | Bayer Cropscience Lp | Active compound combinations |
WO2020239517A1 (en) | 2019-05-29 | 2020-12-03 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2020254494A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
WO2020254486A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
KR20220047968A (ko) | 2019-06-21 | 2022-04-19 | 메이지 세이카 파루마 가부시키가이샤 | 플루피리민을 포함하는 벼 해충 방제용 고형 제제 |
TWI843864B (zh) | 2019-06-21 | 2024-06-01 | 日商三井化學植保股份有限公司 | 含有氟吡嘧(flupyrimin)之水稻害蟲防除用固形製劑 |
WO2020254488A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and use thereof as fungicides |
WO2020254490A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Phenoxyphenyl hydroxyisoxazolines and analogues as new antifungal agents |
WO2020254492A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2020254489A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Benzylphenyl hydroxyisoxazolines and analogues as new antifungal agents |
WO2020254493A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Thienylhydroxyisoxazolines and derivatives thereof |
WO2020254487A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2021001331A1 (en) | 2019-07-03 | 2021-01-07 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides and derivatives thereof as microbicides |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
WO2021013561A1 (en) | 2019-07-19 | 2021-01-28 | Basf Se | Pesticidal pyrazole and triazole derivatives |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
WO2021018839A1 (en) | 2019-07-30 | 2021-02-04 | Bayer Animal Health Gmbh | Isoquinoline derivatives and their use for the treatment of parasitic infections |
WO2021048188A1 (de) | 2019-09-11 | 2021-03-18 | Bayer Aktiengesellschaft | Hochwirksame formulierungen auf basis von 2-[(2;4-dichlorphenyl)-m ethyl|-4,4'-dimethyl- 3-isoxazolidinone sowie vorauflaufherbiziden |
WO2021122986A1 (en) | 2019-12-20 | 2021-06-24 | Bayer Aktiengesellschaft | Thienyloxazolones and analogues |
WO2021123051A1 (en) | 2019-12-20 | 2021-06-24 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides, thiophene carboxylic acids and derivatives thereof |
EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
WO2021204930A1 (en) | 2020-04-09 | 2021-10-14 | Bayer Animal Health Gmbh | Substituted condensed azines as anthelmintic compounds |
WO2021209365A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209368A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209364A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209490A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Cyclaminephenylaminoquinolines as fungicides |
WO2021209363A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021209366A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
WO2021224220A1 (en) | 2020-05-06 | 2021-11-11 | Bayer Aktiengesellschaft | Pyridine (thio)amides as fungicidal compounds |
WO2021228734A1 (en) | 2020-05-12 | 2021-11-18 | Bayer Aktiengesellschaft | Triazine and pyrimidine (thio)amides as fungicidal compounds |
WO2021233861A1 (en) | 2020-05-19 | 2021-11-25 | Bayer Aktiengesellschaft | Azabicyclic(thio)amides as fungicidal compounds |
WO2021245087A1 (en) | 2020-06-04 | 2021-12-09 | Bayer Aktiengesellschaft | Heterocyclyl pyrimidines and triazines as novel fungicides |
WO2021249995A1 (en) | 2020-06-10 | 2021-12-16 | Bayer Aktiengesellschaft | Azabicyclyl-substituted heterocycles as fungicides |
WO2021255071A1 (en) | 2020-06-18 | 2021-12-23 | Bayer Aktiengesellschaft | 3-(pyridazin-4-yl)-5,6-dihydro-4h-1,2,4-oxadiazine derivatives as fungicides for crop protection |
WO2021255089A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines and 1,3,4-oxadiazole pyridines as fungicides |
WO2021255169A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines as fungicides |
WO2021255091A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazoles and their derivatives as fungicides |
WO2021255170A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines as fungicides |
WO2022058327A1 (en) | 2020-09-15 | 2022-03-24 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
EP3915371A1 (en) | 2020-11-04 | 2021-12-01 | Bayer AG | Active compound combinations and fungicide compositions comprising those |
EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
WO2022129188A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | 1,2,4-oxadiazol-3-yl pyrimidines as fungicides |
WO2022129196A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | Heterobicycle substituted 1,2,4-oxadiazoles as fungicides |
WO2022129190A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | (hetero)aryl substituted 1,2,4-oxadiazoles as fungicides |
WO2022162129A1 (en) | 2021-01-28 | 2022-08-04 | Rhodia Operations | Method for treating rice seed with improved retention of agrochemical, micronutrient and colorant |
WO2022167488A1 (en) | 2021-02-02 | 2022-08-11 | Basf Se | Synergistic action of dcd and alkoxypyrazoles as nitrification inhibitors |
WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022243523A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of an n-functionalized alkoxy pyrazole compound as nitrification inhibitor |
WO2022243521A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of ethynylpyridine compounds as nitrification inhibitors |
WO2022268810A1 (en) | 2021-06-21 | 2022-12-29 | Basf Se | Metal-organic frameworks with pyrazole-based building blocks |
WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023036821A1 (en) | 2021-09-09 | 2023-03-16 | Bayer Animal Health Gmbh | New quinoline derivatives |
EP4148052A1 (en) | 2021-09-09 | 2023-03-15 | Bayer Animal Health GmbH | New quinoline derivatives |
WO2023078915A1 (en) | 2021-11-03 | 2023-05-11 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether (thio)amides as fungicidal compounds |
WO2023092050A1 (en) | 2021-11-20 | 2023-05-25 | Bayer Cropscience Lp | Beneficial combinations with recombinant bacillus cells expressing a serine protease |
WO2023099445A1 (en) | 2021-11-30 | 2023-06-08 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether oxadiazines as fungicidal compounds |
WO2023110656A1 (en) | 2021-12-15 | 2023-06-22 | Bayer Aktiengesellschaft | Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis |
WO2023205602A1 (en) | 2022-04-18 | 2023-10-26 | Basf Corporation | High-load agricultural formulations and methods of making same |
WO2023203066A1 (en) | 2022-04-21 | 2023-10-26 | Basf Se | Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4993641B2 (ja) | 有害生物防除剤 | |
JP6236396B2 (ja) | 2−イミノ基を有する含窒素ヘテロ環誘導体及びそれを含んでなる有害生物防除剤 | |
WO2013187480A1 (ja) | 新規環状デプシペプチド誘導体およびそれを含んでなる有害生物防除剤 | |
JP2012077078A (ja) | 新規トリアゾロン誘導体およびそれを有効成分として含有する有害生物防除剤 | |
OA16334A (en) | Noxious organism control agent | |
AU2014250649A1 (en) | Noxious organism control agent |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201180023561.8 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012501048 Country of ref document: JP |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11821689 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 4123/KOLNP/2012 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12013500237 Country of ref document: PH |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13814753 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2808144 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: MX/A/2013/002233 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2013000570 Country of ref document: CL Ref document number: CR2013-000089 Country of ref document: CR |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REEP | Request for entry into the european phase |
Ref document number: 2011821689 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 000357-2013 Country of ref document: PE Ref document number: 2011821689 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13045134 Country of ref document: CO Ref document number: 14238759 Country of ref document: CO |
|
ENP | Entry into the national phase |
Ref document number: 2011297160 Country of ref document: AU Date of ref document: 20110826 Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20137008197 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13043 Country of ref document: GE Ref document number: A201303921 Country of ref document: UA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 201390320 Country of ref document: EA |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112013004818 Country of ref document: BR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 232581 Country of ref document: IL |
|
ENP | Entry into the national phase |
Ref document number: 112013004818 Country of ref document: BR Kind code of ref document: A2 Effective date: 20130228 |