JPWO2009130900A1 - Oxime derivatives, intermediate compounds and plant disease control agents - Google Patents
Oxime derivatives, intermediate compounds and plant disease control agents Download PDFInfo
- Publication number
- JPWO2009130900A1 JPWO2009130900A1 JP2010509080A JP2010509080A JPWO2009130900A1 JP WO2009130900 A1 JPWO2009130900 A1 JP WO2009130900A1 JP 2010509080 A JP2010509080 A JP 2010509080A JP 2010509080 A JP2010509080 A JP 2010509080A JP WO2009130900 A1 JPWO2009130900 A1 JP WO2009130900A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- unsubstituted
- substituted
- formula
- represented
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 51
- 201000010099 disease Diseases 0.000 title claims abstract description 50
- 150000002923 oximes Chemical class 0.000 title claims abstract description 48
- 150000001875 compounds Chemical class 0.000 title claims description 135
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 21
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- -1 azole oxime Chemical class 0.000 description 180
- 238000006243 chemical reaction Methods 0.000 description 84
- 239000002904 solvent Substances 0.000 description 58
- 238000004519 manufacturing process Methods 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 239000012442 inert solvent Substances 0.000 description 11
- 241000221785 Erysiphales Species 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000123650 Botrytis cinerea Species 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000233679 Peronosporaceae Species 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 241000233622 Phytophthora infestans Species 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- 240000003768 Solanum lycopersicum Species 0.000 description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000642 acaricide Substances 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 4
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 244000045561 useful plants Species 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 3
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 3
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 3
- 125000006023 1-pentenyl group Chemical group 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 3
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 3
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 3
- 125000006024 2-pentenyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 3
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000006042 4-hexenyl group Chemical group 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- HEHFKZSTTDBTLE-RGEXLXHISA-N 6-[[(z)-[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-amine Chemical compound CN1N=NN=C1\C(C=1C=CC=CC=1)=N/OCC1=CC=CC(N)=N1 HEHFKZSTTDBTLE-RGEXLXHISA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001480061 Blumeria graminis Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 241001281803 Plasmopara viticola Species 0.000 description 3
- 206010039509 Scab Diseases 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229930182692 Strobilurin Natural products 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012351 deprotecting agent Substances 0.000 description 3
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000006606 n-butoxy group Chemical group 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- FVVWZVFLUXFCJJ-UHFFFAOYSA-N (6-anilinopyridin-2-yl)methanol Chemical compound OCc1cccc(Nc2ccccc2)n1 FVVWZVFLUXFCJJ-UHFFFAOYSA-N 0.000 description 2
- 125000006039 1-hexenyl group Chemical group 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 2
- AVTZQAFEAUPCKL-UHFFFAOYSA-N 2,2-difluoro-2-(4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C(F)(F)C(O)=O)C=C1 AVTZQAFEAUPCKL-UHFFFAOYSA-N 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 125000006043 5-hexenyl group Chemical group 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241001444083 Aphanomyces Species 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000005730 Azoxystrobin Substances 0.000 description 2
- BWHFFUDMAGVSIO-UHFFFAOYSA-N CC1=NC(=NC(=C1)C)C1=NC(=CC=C1N)CO Chemical compound CC1=NC(=NC(=C1)C)C1=NC(=CC=C1N)CO BWHFFUDMAGVSIO-UHFFFAOYSA-N 0.000 description 2
- VJIOPMFAABGXNA-FLIBITNWSA-N CN1N=NN=C1\C(=N/O)C1=CC=CC=C1 Chemical compound CN1N=NN=C1\C(=N/O)C1=CC=CC=C1 VJIOPMFAABGXNA-FLIBITNWSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- DIOCJPHJXVJSNQ-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)NC1=NC(=CC=C1)CCl Chemical compound Cl.C1(=CC=CC=C1)NC1=NC(=CC=C1)CCl DIOCJPHJXVJSNQ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000005807 Metalaxyl Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000233654 Oomycetes Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241000918585 Pythium aphanidermatum Species 0.000 description 2
- 241000576755 Sclerotia Species 0.000 description 2
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 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 2
- 244000052616 bacterial pathogen Species 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 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
- 235000013312 flour Nutrition 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- SEEGHKWOBVVBTQ-NFMPGMCNSA-N gibberellin A7 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 SEEGHKWOBVVBTQ-NFMPGMCNSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 2
- 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 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-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
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-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
- 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
- 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
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- 125000004725 1,1-dimethylbutylthio group Chemical group CC(CCC)(S*)C 0.000 description 1
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- 125000004726 1,2-dimethylbutylthio group Chemical group CC(C(CC)C)S* 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- 125000004727 1,3-dimethylbutylthio group Chemical group CC(CC(C)C)S* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- ZZVVDIVWGXTDRQ-UHFFFAOYSA-N 1-[(4-tert-butylphenyl)methylsulfanyl]-1-butylsulfanyl-n-pyridin-3-ylmethanimine Chemical compound C=1C=CN=CC=1N=C(SCCCC)SCC1=CC=C(C(C)(C)C)C=C1 ZZVVDIVWGXTDRQ-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
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 description 1
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
- 125000004731 1-ethylbutylthio group Chemical group C(C)C(CCC)S* 0.000 description 1
- 125000004717 1-ethylpropylthio group Chemical group C(C)C(CC)S* 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000004721 1-methylpentylthio group Chemical group CC(CCCC)S* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- MGDCBOKBTJIJBT-UHFFFAOYSA-N 2,2-difluoro-1,3-dimethylimidazolidine Chemical compound CN1CCN(C)C1(F)F MGDCBOKBTJIJBT-UHFFFAOYSA-N 0.000 description 1
- 125000004728 2,2-dimethylbutylthio group Chemical group CC(CS*)(CC)C 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- 125000004565 2,3-dihydrobenzofuran-4-yl group Chemical group O1CCC2=C1C=CC=C2* 0.000 description 1
- NFTOEHBFQROATQ-UHFFFAOYSA-N 2,3-dihydrofuran-5-carboxylic acid Chemical compound OC(=O)C1=CCCO1 NFTOEHBFQROATQ-UHFFFAOYSA-N 0.000 description 1
- 125000004729 2,3-dimethylbutylthio group Chemical group CC(CS*)C(C)C 0.000 description 1
- OZGSEIVTQLXWRO-UHFFFAOYSA-N 2,4,6-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=C(Cl)C=C1Cl OZGSEIVTQLXWRO-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-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
- 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
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 description 1
- CZWJCQXZZJHHRH-YCRXJPFRSA-N 2-[(1r,2r,3s,4r,5r,6s)-3-(diaminomethylideneamino)-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O CZWJCQXZZJHHRH-YCRXJPFRSA-N 0.000 description 1
- SSUQLEQBRSRBRM-UHFFFAOYSA-N 2-acetyloxy-2-(4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C(OC(C)=O)C(O)=O)C=C1 SSUQLEQBRSRBRM-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 1
- 125000004722 2-methylpentylthio group Chemical group CC(CS*)CCC 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004730 3,3-dimethylbutylthio group Chemical group CC(CCS*)(C)C 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004723 3-methylpentylthio group Chemical group CC(CCS*)CC 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 1
- 125000004724 4-methylpentylthio group Chemical group CC(CCCS*)C 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
- 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 1
- YHBIGBYIUMCLJS-UHFFFAOYSA-N 5-fluoro-1,3-benzothiazol-2-amine Chemical compound FC1=CC=C2SC(N)=NC2=C1 YHBIGBYIUMCLJS-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- FFISWZPYNKWIRR-UHFFFAOYSA-N 5-oxidophenazin-5-ium Chemical compound C1=CC=C2[N+]([O-])=C(C=CC=C3)C3=NC2=C1 FFISWZPYNKWIRR-UHFFFAOYSA-N 0.000 description 1
- 239000005660 Abamectin 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
- 241000743339 Agrostis Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000352690 Alternaria kikuchiana Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- MQVRGDZCYDEQML-UHFFFAOYSA-N Astragalin Natural products C1=CC(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 MQVRGDZCYDEQML-UHFFFAOYSA-N 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000190150 Bipolaris sorokiniana Species 0.000 description 1
- 241000499339 Botrytis allii Species 0.000 description 1
- SJUYFHILHFZJIO-UHFFFAOYSA-N BrC1=NC(=CC=C1C)O[Si](C)(C)C(C)(C)C Chemical compound BrC1=NC(=CC=C1C)O[Si](C)(C)C(C)(C)C SJUYFHILHFZJIO-UHFFFAOYSA-N 0.000 description 1
- 241000219193 Brassicaceae Species 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- JTTHVZOEOLZATQ-UHFFFAOYSA-N C(C)(=O)OC(C(=O)NC(ON=CC1=CC=CC=C1)C1=CC=CC=N1)C1=CC=C(C=C1)OC Chemical compound C(C)(=O)OC(C(=O)NC(ON=CC1=CC=CC=C1)C1=CC=CC=N1)C1=CC=C(C=C1)OC JTTHVZOEOLZATQ-UHFFFAOYSA-N 0.000 description 1
- APVBVHCCVCIDQS-SWKFRHMKSA-N C(C)(=O)OC(C(=O)NC(O\N=C(\C1=CC=CC=C1)/C1=NN=NN1C)C1=CC=CC=N1)C1=CC=C(C=C1)OC Chemical compound C(C)(=O)OC(C(=O)NC(O\N=C(\C1=CC=CC=C1)/C1=NN=NN1C)C1=CC=CC=N1)C1=CC=C(C=C1)OC APVBVHCCVCIDQS-SWKFRHMKSA-N 0.000 description 1
- HPDCFUSITWYUEB-PHLNKCJMSA-N C(C=CC1=CC=CC=C1)(=O)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C Chemical compound C(C=CC1=CC=CC=C1)(=O)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C HPDCFUSITWYUEB-PHLNKCJMSA-N 0.000 description 1
- BZNKKQYLGDEUFU-QQTULTPQSA-N C1(=CC=CC=C1)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C Chemical compound C1(=CC=CC=C1)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C BZNKKQYLGDEUFU-QQTULTPQSA-N 0.000 description 1
- XBSLGRRDWNXHLD-NFFVHWSESA-N C1OC=2C=C(C=CC2O1)CC(=O)NC=1C(=NC=CC1)C1=C(C=CC=C1)/C(/C1=NN=NN1C)=N/OC Chemical compound C1OC=2C=C(C=CC2O1)CC(=O)NC=1C(=NC=CC1)C1=C(C=CC=C1)/C(/C1=NN=NN1C)=N/OC XBSLGRRDWNXHLD-NFFVHWSESA-N 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- ALAAWQMGVNHBCF-DIBXZPPDSA-N CC1=NC(=NC(=C1)C)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C Chemical compound CC1=NC(=NC(=C1)C)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C ALAAWQMGVNHBCF-DIBXZPPDSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- 241001658057 Cercospora kikuchii Species 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- AIZIPWIPXPTTKM-UHFFFAOYSA-N ClCC1=C(C=CC2=C1OCO2)CC(=O)NC2=NC=CC=C2 Chemical compound ClCC1=C(C=CC2=C1OCO2)CC(=O)NC2=NC=CC=C2 AIZIPWIPXPTTKM-UHFFFAOYSA-N 0.000 description 1
- 241000395107 Cladosporium cucumerinum Species 0.000 description 1
- 241000228437 Cochliobolus Species 0.000 description 1
- 241001133184 Colletotrichum agaves Species 0.000 description 1
- 241000152100 Colletotrichum horii Species 0.000 description 1
- 241000609458 Corynespora Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- URDNHJIVMYZFRT-UHFFFAOYSA-N Diclobutrazol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)CC1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 239000005762 Dimoxystrobin Substances 0.000 description 1
- 241001523339 Discula theae-sinensis Species 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- 241000125117 Elsinoe Species 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- 241000510928 Erysiphe necator Species 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
- XERWDHVWVLYZSS-ANYBSYGZSA-N FC(C(=O)NC(O\N=C(\C1=CC=CC=C1)/C1=NN=NN1C)C1=CC=CC=N1)C1=CC=C(C=C1)OC Chemical compound FC(C(=O)NC(O\N=C(\C1=CC=CC=C1)/C1=NN=NN1C)C1=CC=CC=N1)C1=CC=C(C=C1)OC XERWDHVWVLYZSS-ANYBSYGZSA-N 0.000 description 1
- 239000005772 Famoxadone Substances 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
- 239000005898 Fenoxycarb Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005782 Fluopicolide Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- LXMQMMSGERCRSU-UHFFFAOYSA-N Fluotrimazole Chemical compound FC(F)(F)C1=CC=CC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)N2N=CN=C2)=C1 LXMQMMSGERCRSU-UHFFFAOYSA-N 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005790 Fosetyl Substances 0.000 description 1
- 241000221778 Fusarium fujikuroi Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 229930191978 Gibberellin Natural products 0.000 description 1
- RSQSQJNRHICNNH-UHFFFAOYSA-N Gibberellin A4 Natural products OC(=O)C1C2(CC3=C)CC3CCC2C2(OC3=O)C1C3(C)C(O)CC2 RSQSQJNRHICNNH-UHFFFAOYSA-N 0.000 description 1
- HHDWSDSMWJQURA-UHFFFAOYSA-N Gibberellin A51 Natural products C12CCC(C3)C(=C)CC23C(C(O)=O)C2C3(C)C(=O)OC21CC(O)C3 HHDWSDSMWJQURA-UHFFFAOYSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 241001555627 Melonis Species 0.000 description 1
- 239000005805 Mepanipyrim Substances 0.000 description 1
- 239000005956 Metaldehyde Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000005918 Milbemectin Substances 0.000 description 1
- 241001518729 Monilinia Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 description 1
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
- ZWPAPYMTEGCURN-UHFFFAOYSA-N N1=C(C=CC=C1)NC1=NC(=CC=C1)CCl Chemical compound N1=C(C=CC=C1)NC1=NC(=CC=C1)CCl ZWPAPYMTEGCURN-UHFFFAOYSA-N 0.000 description 1
- DILNVQAMAFSMQI-PLRJNAJWSA-N N1=C(C=CC=C1)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C Chemical compound N1=C(C=CC=C1)NC1=NC(=CC=C1)CO\N=C(\C1=CC=CC=C1)/C1=NN=NN1C DILNVQAMAFSMQI-PLRJNAJWSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241001329956 Nothopassalora personata Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- JAYZFNIOOYPIAH-UHFFFAOYSA-N Oxydeprofos Chemical compound CCS(=O)CC(C)SP(=O)(OC)OC JAYZFNIOOYPIAH-UHFFFAOYSA-N 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 241000315044 Passalora arachidicola Species 0.000 description 1
- 241000222291 Passalora fulva Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 241001507673 Penicillium digitatum Species 0.000 description 1
- 241000122123 Penicillium italicum Species 0.000 description 1
- 235000002233 Penicillium roqueforti Nutrition 0.000 description 1
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
- 241001670203 Peronospora manshurica Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241001609671 Phyllactinia kakicola Species 0.000 description 1
- 241000948155 Phytophthora sojae Species 0.000 description 1
- 239000005923 Pirimicarb Substances 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241001503436 Plasmodiophora brassicae Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241000896242 Podosphaera Species 0.000 description 1
- 241001337898 Podosphaera aphanis Species 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- YPWHZCPMOQGCDQ-UHFFFAOYSA-N Populnin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=CC(O)=CC=3)OC2=C1 YPWHZCPMOQGCDQ-UHFFFAOYSA-N 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- MKIMSXGUTQTKJU-UHFFFAOYSA-N Propamocarb hydrochloride Chemical compound [Cl-].CCCOC(=O)NCCC[NH+](C)C MKIMSXGUTQTKJU-UHFFFAOYSA-N 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000301598 Pseudocercospora kaki Species 0.000 description 1
- 241000682843 Pseudocercosporella Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241000202873 Pythium iwayamai Species 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 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
- PNAAEIYEUKNTMO-UHFFFAOYSA-N S-Seven Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C(Cl)C=C1Cl PNAAEIYEUKNTMO-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 101000984731 Salvia officinalis (+)-bornyl diphosphate synthase, chloroplastic Proteins 0.000 description 1
- 241001300361 Sclerotinia borealis Species 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- JSCQSBGXKRTPHZ-WMSPMLHYSA-N Strobilurin A Natural products COC=C(/C(=C/C=C/c1ccccc1)/C)C(=O)OC JSCQSBGXKRTPHZ-WMSPMLHYSA-N 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- NHTFLYKPEGXOAN-UHFFFAOYSA-N Trichlamide Chemical compound CCCCOC(C(Cl)(Cl)Cl)NC(=O)C1=CC=CC=C1O NHTFLYKPEGXOAN-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 239000005942 Triflumuron Substances 0.000 description 1
- ZKEKDTIKFVCKMW-UHFFFAOYSA-N Trifolin Natural products OCC1OC(Oc2cc(O)ccc2C3=CC(=O)c4c(O)cc(O)cc4O3)C(O)C(O)C1O ZKEKDTIKFVCKMW-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000007070 Ustilago nuda Species 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241001669638 Venturia nashicola Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000005870 Ziram Substances 0.000 description 1
- BZMIHNKNQJJVRO-LVZFUZTISA-N [(e)-c-(3-chloro-2,6-dimethoxyphenyl)-n-ethoxycarbonimidoyl] benzoate Chemical compound COC=1C=CC(Cl)=C(OC)C=1C(=N/OCC)\OC(=O)C1=CC=CC=C1 BZMIHNKNQJJVRO-LVZFUZTISA-N 0.000 description 1
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 1
- QSGNQELHULIMSJ-POHAHGRESA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] dimethyl phosphate Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl QSGNQELHULIMSJ-POHAHGRESA-N 0.000 description 1
- GNKTYDVQMKUXLA-UHFFFAOYSA-N [6-(pyridin-2-ylamino)pyridin-2-yl]methanol Chemical compound OCc1cccc(Nc2ccccn2)n1 GNKTYDVQMKUXLA-UHFFFAOYSA-N 0.000 description 1
- FKAGSWXLDPZJCL-UHFFFAOYSA-J [Ti](Cl)(Cl)(Cl)Cl.B(I)(I)I Chemical compound [Ti](Cl)(Cl)(Cl)Cl.B(I)(I)I FKAGSWXLDPZJCL-UHFFFAOYSA-J 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 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
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 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 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 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
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 description 1
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 1
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical class C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-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
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- CXNPLSGKWMLZPZ-UHFFFAOYSA-N blasticidin-S Natural products O1C(C(O)=O)C(NC(=O)CC(N)CCN(C)C(N)=N)C=CC1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-UHFFFAOYSA-N 0.000 description 1
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 1
- FOANIXZHAMJWOI-UHFFFAOYSA-N bromopropylate Chemical compound C=1C=C(Br)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Br)C=C1 FOANIXZHAMJWOI-UHFFFAOYSA-N 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
- 239000001273 butane Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 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
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- RXDMAYSSBPYBFW-PKFCDNJMSA-N carpropamide Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(=O)[C@@]1(CC)[C@H](C)C1(Cl)Cl RXDMAYSSBPYBFW-PKFCDNJMSA-N 0.000 description 1
- 239000000969 carrier Substances 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
- 239000007810 chemical reaction solvent Substances 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
- 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
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 229960001591 cyfluthrin Drugs 0.000 description 1
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-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
- 229960005424 cypermethrin Drugs 0.000 description 1
- 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 1
- 229960002483 decamethrin Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 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
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004986 diarylamino group Chemical group 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
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 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
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- 229960001162 dihydrostreptomycin sulfate Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- INWPVWWXVOWZDU-UHFFFAOYSA-N dimethyl 2,2,2-trichloroethyl phosphate Chemical group COP(=O)(OC)OCC(Cl)(Cl)Cl INWPVWWXVOWZDU-UHFFFAOYSA-N 0.000 description 1
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 1
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- 230000000967 entomopathogenic effect Effects 0.000 description 1
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- HEZNVIYQEUHLNI-UHFFFAOYSA-N ethiofencarb Chemical compound CCSCC1=CC=CC=C1OC(=O)NC HEZNVIYQEUHLNI-UHFFFAOYSA-N 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- FSFFJEWAYWRLFT-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CC=C(OC)C=C1 FSFFJEWAYWRLFT-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000005290 ethynyloxy group Chemical group C(#C)O* 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
- 208000030533 eye disease 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
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-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
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- 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 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
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 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 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
- VUERQRKTYBIULR-UHFFFAOYSA-N fosetyl Chemical compound CCOP(O)=O VUERQRKTYBIULR-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- RSQSQJNRHICNNH-NFMPGMCNSA-N gibberellin A4 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@@]2(OC3=O)[C@H]1[C@@]3(C)[C@@H](O)CC2 RSQSQJNRHICNNH-NFMPGMCNSA-N 0.000 description 1
- SEEGHKWOBVVBTQ-UHFFFAOYSA-N gibberellin GA7 Natural products OC(=O)C1C2(CC3=C)CC3CCC2C2(C=CC3O)C1C3(C)C(=O)O2 SEEGHKWOBVVBTQ-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000004249 isobenzofuran-1-yl group Chemical group [H]C1=C2C([H])=C([H])C([H])=C([H])C2=C(*)O1 0.000 description 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 description 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
- JPUKWEQWGBDDQB-DTGCRPNFSA-N kaempferol 3-O-beta-D-galactoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O JPUKWEQWGBDDQB-DTGCRPNFSA-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
- 239000003350 kerosene Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting 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
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- BSDQITJYKQHXQR-UHFFFAOYSA-N methyl prop-2-eneperoxoate Chemical compound COOC(=O)C=C BSDQITJYKQHXQR-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- JSCQSBGXKRTPHZ-SYKZHUKTSA-N mucidin Chemical compound CO\C=C(\C(=O)OC)/C(/C)=C\C=C\C1=CC=CC=C1 JSCQSBGXKRTPHZ-SYKZHUKTSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000004676 n-butylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- 229960000321 oxolinic acid Drugs 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 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
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 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
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 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
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 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 compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-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
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 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 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 description 1
- 125000004553 quinoxalin-5-yl group Chemical group N1=CC=NC2=C(C=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 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
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-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
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—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
-
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本発明は、式(1)(式中、R1はC1〜6アルキル基等、qは0〜5のいずれかの整数、R2及びR21は水素原子等、Aはヘテロアリール基、Dはヘテロアリール基を表す。)で表されるオキシム誘導体及びその塩、並びにこれらの少なくとも一種を有効成分として含有する植物病害防除剤を提供する。The present invention is represented by formula (1) (wherein R1 is a C1-6 alkyl group, q is an integer of 0-5, R2 and R21 are hydrogen atoms, A is a heteroaryl group, D is heteroaryl. A plant disease control agent comprising the oxime derivative represented by the following formula:
Description
本発明は、新規なオキシム誘導体及びその塩、中間体化合物、並びにこのオキシム誘導体及びその塩を有効成分として含有する植物病害防除剤に関する。
本願は、2008年4月24日に、日本国に出願された特願2008−113377号、2008年4月24日に、日本国に出願された特願2008−114384号、2008年4月24日に、日本国に出願された特願2008−114390号及び2008年9月29日に、日本国に出願された特願2008−251604号に基づき優先権を主張し、その内容をここに援用する。The present invention relates to a novel oxime derivative and a salt thereof, an intermediate compound, and a plant disease control agent containing the oxime derivative and a salt thereof as an active ingredient.
This application is based on Japanese Patent Application No. 2008-113377 filed in Japan on April 24, 2008, Japanese Patent Application No. 2008-114384 filed in Japan on April 24, 2008, April 24, 2008. Claiming priority based on Japanese Patent Application No. 2008-114390 filed in Japan and Japanese Patent Application No. 2008-251604 filed in Japan on September 29, 2008, the contents of which are incorporated herein by reference. To do.
農園芸作物の栽培に当り、作物の病害に対して、多数の防除薬剤が使用されているが、その防除効力が不十分であったり、薬剤耐性の病原菌の出現によりその使用が制限されたり、また、植物体に薬害や汚染を生じたり、あるいは人畜魚類などに対する毒性が強かったりすることから、必ずしも満足すべき防除薬剤とは言い難いものが少なくない。従って、かかる欠点の少ない安全に使用できる植物病害防除剤の開発が要望されている。 In the cultivation of agricultural and horticultural crops, many control agents are used against crop diseases, but their control efficacy is insufficient, their use is limited by the emergence of drug-resistant pathogens, In addition, since there are phytotoxicity and pollution in plants, and toxicity to human and livestock fish is strong, there are many things that are not necessarily satisfactory control agents. Therefore, there is a demand for the development of a plant disease control agent that can be safely used with few such drawbacks.
本発明に関連して、特許文献1及び2には、本発明のオキシム誘導体と類似の構造を有するアゾールオキシム誘導体が植物病害防除剤として有用であることが報告されている。
しかし、これらの文献には、本発明のオキシム誘導体は記載されていない。In relation to the present invention, Patent Documents 1 and 2 report that an azole oxime derivative having a structure similar to that of the oxime derivative of the present invention is useful as a plant disease control agent.
However, these documents do not describe the oxime derivatives of the present invention.
本発明は、かかる従来技術の実情に鑑みてなされたものであり、有用植物に対する薬害が少なく、且つ、植物病害に対する防除効果に優れた、オキシム誘導体及びその塩(以下、オキシム誘導体等と称することがある。)、このオキシム誘導体等を製造する際の中間体として用いられる中間体化合物、並びにこのオキシム誘導体等の少なくとも一種を有効成分として含有する植物病害防除剤を提供することを課題とする。 The present invention has been made in view of the state of the prior art, and has an oxime derivative and a salt thereof (hereinafter referred to as an oxime derivative or the like) that have little phytotoxicity on useful plants and have excellent control effects on plant diseases. It is an object of the present invention to provide an intermediate compound used as an intermediate in producing the oxime derivative and the like, and a plant disease control agent containing at least one of the oxime derivative and the like as an active ingredient.
本発明者らは、上記課題を解決すべく、多くのオキシム誘導体を合成し、それらの生理活性を鋭意検討した。その結果、下記式(1)で表されるオキシム誘導体が、低薬量で優れた植物病害の防除効果を示し、かつ、有用植物に対する薬害の心配がないことを見いだし、本発明を完成するに至った。
かくして、本発明は、In order to solve the above-mentioned problems, the present inventors have synthesized many oxime derivatives and intensively studied their physiological activities. As a result, it has been found that the oxime derivative represented by the following formula (1) exhibits an excellent plant disease control effect at a low dose, and that there is no fear of phytotoxicity on useful plants, thereby completing the present invention. It came.
Thus, the present invention
(1)式(1)
R2及びR21は、夫々独立して、水素原子、ハロゲン原子、又は無置換若しくは置換基を有するC1〜6アルキル基を表す。
Aは、式(2)又は(3)
で表されるヘテロアリール基を表す。
Dは、式(4)又は式(5)で表されるヘテロアリール基を表す。
Zは、下記式(6)
Q11は、単結合または直鎖C1〜3アルキレン基を表す。
Q1は、置換基を有するC6〜10アリール基、又は無置換若しくは置換基を有するヘテロアリール基を表す。)、
下記式(7)
n2は1〜3のいずれかの整数を表し、n2が2以上の場合、R4同士及びR41同士は同一又は異なっていてもよい。但しR4及びR41の全てが水素原子となることはない。
Jは酸素原子又は硫黄原子を表す。)で表される2価基を表す。
Q2は、無置換若しくは置換基を有するC6〜10アリール基、又は無置換若しくは置換基を有するヘテロアリール基を表す。)、
下記式(8)
下記式(9)
Q4は、C4〜6シクロアルキル基、無置換若しくは置換基を有するC6〜10アリール基、又は無置換若しくは置換基を有するヘテロアリール基を表す。)で表されるいずれかの基を表す。]}で示されることを特徴とするオキシム誘導体及びその塩である。(1) Formula (1)
R 2 and R 21 each independently represent a hydrogen atom, a halogen atom, or an unsubstituted or substituted C 1-6 alkyl group.
A is the formula (2) or (3)
The heteroaryl group represented by these is represented.
D represents the heteroaryl group represented by Formula (4) or Formula (5).
Z represents the following formula (6)
Q 11 represents a single bond or a linear C1-3 alkylene group.
Q 1 represents a C6-10 aryl group having a substituent or an unsubstituted or substituted heteroaryl group. ),
Following formula (7)
n2 represents any integer of 1 to 3, and when n2 is 2 or more, R 4 and R 41 may be the same or different. However, not all of R 4 and R 41 are hydrogen atoms.
J represents an oxygen atom or a sulfur atom. Represents a divalent group represented by:
Q 2 represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group. ),
Following formula (8)
Following formula (9)
Q 4 represents a C4-6 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group. ) Represents any group represented. ]}, And an oxime derivative and a salt thereof.
さらに、本発明は、
(2)前記(1)に記載のオキシム誘導体及びその塩の少なくとも一種を有効成分として含有することを特徴とする植物病害防除剤である。
さらに、本発明は、
(3)式(10)
で表される化合物である。Furthermore, the present invention provides
(2) A plant disease control agent comprising at least one of the oxime derivative and the salt thereof according to (1) as an active ingredient.
Furthermore, the present invention provides
(3) Formula (10)
It is a compound represented by these.
本発明のオキシム誘導体及びその塩は、ごく低薬量で極めて優れた植物病害に対する防除効果を示し、かつ、有用植物に対する薬害の心配がない。
また、本発明の植物病害防除剤は、本発明のオキシム誘導体等を有効成分として含有するものであるため、植物病害に対する優れた防除効果を有する。
また、本発明の化合物は、本発明のオキシム誘導体等を製造する際の中間体として用いられる中間体化合物を提供する。The oxime derivative and the salt thereof of the present invention exhibit an extremely excellent control effect against plant diseases at a very low dose, and there is no fear of phytotoxicity against useful plants.
Moreover, since the plant disease control agent of this invention contains the oxime derivative etc. of this invention as an active ingredient, it has the outstanding control effect with respect to a plant disease.
Moreover, the compound of this invention provides the intermediate compound used as an intermediate body at the time of manufacturing the oxime derivative etc. of this invention.
以下、本発明を、1)式(1)で表されるオキシム誘導体及びその塩;2)式(10)で表される化合物;3)本発明のオキシム誘導体等の適用病害;4)植物病害防除剤;に項分けして詳細に説明する。 Hereinafter, the present invention is classified into 1) an oxime derivative represented by the formula (1) and a salt thereof; 2) a compound represented by the formula (10); 3) an applicable disease such as an oxime derivative of the present invention; 4) a plant disease. This will be explained in detail by dividing into control agents.
1)式(1)で表されるオキシム誘導体及びその塩
本発明は、前記式(1)で表されるオキシム誘導体及びその塩である。なお、本発明の誘導体及びその塩には、水和物、各種溶媒和物や結晶多形等も含まれる。
1−1)置換基1) Oxime derivative represented by formula (1) and salt thereof The present invention is an oxime derivative represented by formula (1) and a salt thereof. The derivatives and salts thereof of the present invention also include hydrates, various solvates and crystal polymorphs.
1-1) Substituent
(置換基R1)
前記式(1)中、R1は、無置換若しくは置換基を有するC1〜6アルキル基、無置換若しくは置換基を有するC1〜6アルコキシ基、ハロゲン原子、ニトロ基、シアノ基、無置換若しくは置換基を有するアリール基、又は無置換若しくは置換基を有するC1〜6アルキルスルホニル基を表す。(Substituent R 1 )
In the formula (1), R 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, a halogen atom, a nitro group, a cyano group, unsubstituted or substituted. Represents an aryl group having a group, or an unsubstituted or substituted C1-6 alkylsulfonyl group.
R1の、「無置換若しくは置換基を有するC1〜6アルキル基」の「C1〜6アルキル基」としては、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、s−ブチル基、i−ブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基等が挙げられる。
前記C1〜6アルキル基の置換基としては、化学的に許容されるものであれば特に限定されないが、フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;メトキシ基、エトキシ基、n−プロポキシ基、i−プロポキシ基、n−ブトキシ基、s−ブトキシ基、i−ブトキシ基、t−ブトキシ基等のC1〜6アルコキシ基;フェニル基、4−メチルフェニル基、2−クロロフェニル基等の無置換若しくは置換基を有するフェニル基;ニトロ基;シアノ基;アミノ基、メチルアミノ基、ジメチルアミノ基、アセチルアミノ基、ベンゾイルアミノ基等の無置換若しくは置換基を有するアミノ基;ホルミル基、アセチル基、ベンゾイル基等のアシル基;メトキシカルボニル基等のアルコキシカルボニル基;メチルチオ基等のアルキルチオ基;等が挙げられる。As the “C 1-6 alkyl group” of the “unsubstituted or substituted C 1-6 alkyl group” of R 1 , a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, Examples include s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group and the like.
The substituent of the C1-6 alkyl group is not particularly limited as long as it is chemically acceptable, but halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; methoxy group, ethoxy group, n -C 1-6 alkoxy groups such as propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; phenyl group, 4-methylphenyl group, 2-chlorophenyl group, etc. An unsubstituted or substituted phenyl group; a nitro group; a cyano group; an amino group, a methylamino group, a dimethylamino group, an acetylamino group, an amino group having an unsubstituted group such as a benzoylamino group; a formyl group; Acyl groups such as acetyl group and benzoyl group; alkoxycarbonyl groups such as methoxycarbonyl group; alkylthio groups such as methylthio group Etc. The.
R1の、「無置換若しくは置換基を有するC1〜6アルコキシ基」の「C1〜6アルコキシ基」としては、メトキシ基、エトキシ基、n−プロポキシ基、i−プロポキシ基、n−ブトキシ基、s−ブトキシ基、i−ブトキシ基、t−ブトキシ基等が挙げられる。
前記C1〜6アルコキシ基の置換基としては、化学的に許容されるものであれば特に限定されないが、前記R1のC1〜6アルキル基の置換基として例示したものと同様のものが挙げられる。
R1のハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられる。As the “C1-6 alkoxy group” of the “unsubstituted or substituted C1-6 alkoxy group” of R 1 , a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, Examples thereof include s-butoxy group, i-butoxy group, t-butoxy group and the like.
Examples of the substituent of the C1~6 alkoxy group, as long as it is chemically acceptable but not particularly limited, and examples thereof include the same ones as exemplified as the substituents of C1~6 alkyl group of said R 1 .
Examples of the halogen atom for R 1 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
R1の、「無置換若しくは置換基を有するアリール基」の「アリール基」は、単環又は多環のアリール基を意味する。ここで、多環アリール基の場合は、完全不飽和に加え、部分飽和の基も包含する。例えばフェニル基、ナフチル基、アズレニル基、インデニル基、インダニル基、テトラリニル基等が挙げられる。これらのうち、好ましくは、C6〜10アリール基である。さらに具体的には、フェニル基、1−ナフチル基、2−ナフチル基等が挙げられる。
前記アリール基の置換基としては、化学的に許容されるものであれば特に限定されないが、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、s−ブチル基、i−ブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基等のC1〜6アルキル基;ビニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−メチル−2−プロペニル基、2−メチル−2−プロペニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、1−メチル−2−ブテニル基、2−メチル−2−ブテニル基、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、4−ヘキセニル基、5−ヘキセニル基等のC2〜6アルケニル基;エチニル基、1−プロピニル基、2−プロピニル基、1−ブチニル基、2−ブチニル基、3−ブチニル基、1−メチル−2−プロピニル基、2−メチル−3−ブチニル基、1−ペンチニル基、2−ペンチニル基、3−ペンチニル基、4−ペンチニル基、1−メチル−2−ブチニル基、2−メチル−3−ペンチニル基、1−ヘキシニル基、1,1−ジメチル−2−ブチニル基等のC2〜6アルキニル基;メトキシ基、エトキシ基、n−プロポキシ基、i−プロポキシ基、n−ブトキシ基、s−ブトキシ基、i−ブトキシ基、t−ブトキシ基等のC1〜6アルコキシ基;ニトロ基;シアノ基;アミノ基、メチルアミノ基、ジメチルアミノ基、アセチルアミノ基、ベンゾイルアミノ基等の無置換若しくは置換基を有するアミノ基;フェニル基、p−トリフルオロメチルフェニル基、p−メトキシフェニル基等の無置換若しくは置換基を有するアリール基;2−ピリジル基、3−ピリジル基、4−ピリジル基、5−(2−クロロ)ピリジル基、6−(2−アミノ)ピリジル基等の無置換若しくは置換基を有するヘテロアリール基;メトキシカルボニル基、エトキシカルボニル基、n−ブトキシカルボニル基、t−ブトキシカルボニル基等のアルコキシカルボニル基;ホルミル基、アセチル基、ベンゾイル基、ピバロイル基等のアシル基;カルボキシル基;等が挙げられる。The “aryl group” of the “unsubstituted or substituted aryl group” of R 1 means a monocyclic or polycyclic aryl group. Here, in the case of a polycyclic aryl group, a partially saturated group is included in addition to the fully unsaturated group. Examples thereof include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group. Of these, a C6-10 aryl group is preferable. More specifically, a phenyl group, 1-naphthyl group, 2-naphthyl group and the like can be mentioned.
The substituent of the aryl group is not particularly limited as long as it is chemically acceptable, and examples thereof include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl group, ethyl group, n- C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; vinyl group, 1- Propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, -C2-6 alkenyl group such as hexenyl group; ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2- Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, C2-6 alkynyl group such as 1,1-dimethyl-2-butynyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t -C1-6 alkoxy group such as butoxy group; nitro group; cyano group; amino group, methylamino group, dimethylamino group, acetylamino group, benzoylamino group, etc. An amino group having a substituent; an aryl group having an unsubstituted or substituted group such as a phenyl group, a p-trifluoromethylphenyl group, and a p-methoxyphenyl group; a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, An unsubstituted or substituted heteroaryl group such as 5- (2-chloro) pyridyl group, 6- (2-amino) pyridyl group; methoxycarbonyl group, ethoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl An alkoxycarbonyl group such as a group; an acyl group such as a formyl group, an acetyl group, a benzoyl group and a pivaloyl group; a carboxyl group;
R1の、「無置換若しくは置換基を有するC1〜6アルキルスルホニル基」の「C1〜6アルキルスルホニル基としては、メチルスルホニル基、エチルスルホニル基、n−プロピルスルホニル基、n−ブチルスルホニル基、t−ブチルスルホニル基、n−ヘキシルスルホニル基等が挙げられる。
前記アルキルスルホニル基の置換基としては、化学的に許容されるものであれば特に限定されず、前記R1のアルキル基の置換基と同様のものが挙げられる。As the “C 1-6 alkylsulfonyl group” of the “unsubstituted or substituted C 1-6 alkylsulfonyl group” of R 1 , a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an n-butylsulfonyl group, Examples thereof include a t-butylsulfonyl group and an n-hexylsulfonyl group.
The substituent for the alkylsulfonyl group is not particularly limited as long as it is chemically acceptable, and examples thereof include the same substituents for the alkyl group for R 1 .
qは0〜5のいずれかの整数を表し、0又は1であるのが好ましい。
qが2以上のとき、複数のR1は同一でも相異なっていてもよい。
(置換基R2、R21)q represents an integer of 0 to 5, and is preferably 0 or 1.
When q is 2 or more, the plurality of R 1 may be the same or different.
(Substituents R 2 and R 21 )
前記式(1)中、R2及びR21は、夫々独立して、水素原子、ハロゲン原子、又は無置換若しくは置換基を有するC1〜6アルキル基を表す。
R2及びR21の、ハロゲン原子及び無置換若しくは置換基を有するC1〜6アルキル基としては、前記R1の、ハロゲン原子及びアルキル基として例示したのと同様の基が挙げられる。
(置換基A)In the formula (1), R 2 and R 21 each independently represent a hydrogen atom, a halogen atom, or an unsubstituted or substituted C 1-6 alkyl group.
Examples of the halogen atom and unsubstituted or substituted C1-6 alkyl group of R 2 and R 21 include the same groups as those exemplified as the halogen atom and alkyl group of R 1 .
(Substituent A)
前記式(1)中、Aは、前記式(2)又は(3)で示されるヘテロアリール基を表す。
前記式(2)及び(3)中、B1、B2はそれぞれ独立して、CH又は窒素原子を表す。ただし、B1、B2が同時にCHになることはない。In the formula (1), A represents a heteroaryl group represented by the formula (2) or (3).
In the formulas (2) and (3), B 1 and B 2 each independently represent CH or a nitrogen atom. However, B 1 and B 2 are not simultaneously CH.
前記式(2)及び(3)中、Yはアルキル基を表し、炭素数1〜6のアルキル基が好ましい。
Yのアルキル基の具体例としては、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、s−ブチル基、i−ブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基等が挙げられる。In said formula (2) and (3), Y represents an alkyl group and a C1-C6 alkyl group is preferable.
Specific examples of the alkyl group of Y include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, and n-pentyl group. , N-hexyl group and the like.
前記Aの好ましい具体例としては、下記のものが挙げられる。
なかでも、Aとしては、下記のものがより好ましい。
前記式(1)中、Dは、前記式(4)または式(5)で表されるヘテロアリール基を表す。
前記式(4)中、R3は、ハロゲン原子、無置換若しくは置換基を有するC1〜6アルキル基、無置換若しくは置換基を有するC1〜6アルキルチオ基、無置換若しくは置換基を有するC1〜6アルコキシ基、または無置換若しくは置換基を有するアミノ基を表す。
q1は0〜3のいずれかの整数を表す。
前記式(5)中、R31は、水素原子、ハロゲン原子、無置換若しくは置換基を有するC1〜6アルキル基、無置換若しくは置換基を有するC1〜6アルキルチオ基、無置換若しくは置換基を有するC1〜6アルコキシ基、又は無置換若しくは置換基を有するアミノ基を表す。In the formula (1), D represents a heteroaryl group represented by the formula (4) or the formula (5).
In the formula (4), R 3 is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6. An alkoxy group or an amino group which is unsubstituted or has a substituent is represented.
q1 represents any integer of 0 to 3.
In the formula (5), R 31 has a hydrogen atom, a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted group. A C1-6 alkoxy group or an amino group which is unsubstituted or has a substituent is represented.
R3、R31の、「ハロゲン原子」、「無置換若しくは置換基を有するC1〜6アルキル基」及び「無置換若しくは置換基を有するC1〜6アルコキシ基」は、前記R1の、「ハロゲン原子」、「無置換若しくは置換基を有するC1〜6アルキル基」及び「無置換若しくは置換基を有するC1〜6アルコキシ基」として例示したのと同様の基が挙げられる。The “halogen atom”, “unsubstituted or substituted C1-6 alkyl group” and “unsubstituted or substituted C1-6 alkoxy group” of R 3 and R 31 are the same as the “halogen” of R 1. Examples thereof include the same groups as those exemplified as “atom”, “unsubstituted or substituted C1-6 alkyl group” and “unsubstituted or substituted C1-6 alkoxy group”.
R3、R31の「無置換若しくは置換基を有するC1〜6アルキルチオ基」の「アルキルチオ基」の具体例としては、メチルチオ基、エチルチオ基、n−プロピルチオ基、イソプロピルチオ基、n−ブチルチオ基、イソブチルチオ基、sec−ブチルチオ基、tert−ブチルチオ基等が挙げられる。
前記C1〜6アルキルチオ基の置換基としては、化学的に許容される限り特に制限されず、R1のアルキル基の置換基として挙げられたのと同様の基が挙げられる。
R3、R31の、「無置換若しくは置換基を有するアミノ基」としては、アミノ基;メチルアミノ基、エチルアミノ基等のモノアルキルアミノ基、好ましくはモノC1〜6アルキルアミノ基;ジメチルアミノ基、ジエチルアミノ基等のジアルキルアミノ基、好ましくはジC1〜6アルキルアミノ基;フェニルアミノ基、4−メチルフェニルアミノ基等のモノアリールアミノ基、好ましくはモノC6〜10アリールアミノ基;ジ1−ナフチルアミノ基等のジアリールアミノ基、好ましくはジC6〜10アリールアミノ基;アセチルアミノ基、ベンゾイルアミノ基等のアシルアミノ基、好ましくはC1〜6アシルアミノ基等が挙げられる。
前記式(4)及び(5)中、Zは前記式(6)、式(7)、式(8)及び式(9)で表されるいずれかの基を表す。
前記式(6)中、R5は、水素原子、無置換若しくは置換基を有するC1〜6アルキル基、又は無置換若しくは置換基を有するC1〜7アシル基を表す。
R5の「無置換若しくは置換基を有するC1〜6アルキル基」の「C1〜6アルキル基」は、前記R1のアルキル基として例示したのと同様の基が挙げられる。
R5の「無置換若しくは置換基を有するC1〜7アシル基」の「C1−7アシル基」は、水素原子、アルキル基、アリール基、又はへテロアリール基がカルボニル基と結合した基であり、具体的には、ホルミル基;アセチル基、プロピオニル基、n−プロピルカルボニル基、i−プロピルカルボニル基、n−ブチルカルボニル基、i−ブチルカルボニル基等のアルキルカルボニル基;ベンゾイル基等のアリールカルボニル基;2−ピリジルカルボニル基、チエニルカルボニル基等のヘテロアリールカルボニル基;が挙げられる。
前記C1〜7アシル基の置換基は、前記R1のアルキル基の置換基として挙げられたのと同じ基が挙げられる。
前記式(6)中、Q11は、単結合または直鎖C1〜3アルキレン基を表す。
前記式(6)中、Q1は、置換基を有するC6〜10アリール基、または無置換若しくは置換基を有するヘテロアリール基を表す。
Q1の「置換基を有するC6〜10アリール基」としては、前記R1の置換基を有するC6〜10アリール基として例示したのと同様の基が挙げられる。
Q1の「無置換若しくは置換基を有するヘテロアリール基」の「ヘテロアリール基」は、環を構成する原子として炭素原子以外に、窒素原子、酸素原子及び硫黄原子から選ばれる1〜4個の複素原子を含む5〜10員の芳香族環を意味し、例えば、2−フリル基、3−フリル基、2−チエニル基、3−チエニル基、ピロール−1−イル基、オキサゾール−2−イル基、1−メチルピラゾール−3−イル基、イソオキサゾール−3−イル基、チアゾール−2−イル基、ピロ−ル−2−イル基、ピリジン−2−イル基、ピリジン−3−イル基、ピリジン−4−イル基、ピラジン−2−イル基、ピラジン−3−イル基、ピリミジン−2−イル基、ピリミジン−4−イル基、ピリダジン−3−イル基、ピリダジン−4−イル基、1,3−ベンゾジオキソール−4−イル基、1,3−ベンゾジオキソール−5−イル基、1,4−ベンゾジオキサン−5−イル基、1,4−ベンゾジオキサン−6−イル基、3,4−ジヒドロ−2H−1,5−ベンゾジオキセピン−6−イル基、3,4−ジヒドロ−2H−1,5−ベンゾジオキセピン−7−イル基、2,3−ジヒドロベンゾフラン−4−イル基、2,3−ジヒドロベンゾフラン−5−イル基、2,3−ジヒドロベンゾフラン−6−イル基、2,3−ジヒドロベンゾフラン−7−イル基、ベンゾフラン−2−イル基、ベンゾフラン−3−イル基、ベンゾチオフェン−2−イル基、ベンゾチオフェン−3−イル基、キノキサリン−2−イル基、キノキサリン−5−イル基、インドール−1−イル基、インドール−2−イル基、イソインドール−1−イル基、イソインドール−2−イル基、イソベンゾフラン−1−イル基、イソベンゾフラン−4−イル基、クロメン−2−イル基、クロメン−3−イル基、イミダゾール−1−イル基、イミダゾール−2−イル基、イミダゾール−4−イル基、ピラゾール−1−イル基、ピラゾール−3−イル基、チアゾール−2−イル基、チアゾール−4−イル基、オキサゾール−2−イル基、オキサゾール−4−イル基、イソオキサゾール−3−イル基、イソオキサゾール−4−イル基、ピロリジン−2−イル基、ピロリジン−3−イル基、ベンゾイミダゾール−1−イル基、ベンゾイミダゾール−2−イル基、ベンゾチアゾール−2−イル基、ベンゾチアゾール−4−イル基、ベンゾオキサゾール−2−イル基、ベンゾオキサゾール−4−イル基、キノリン−2−イル基、キノリン−3−イル基、イソキノリン−1−イル基、イソキノリン−3−イル基、1,3,4−オキサジアゾール−2−イル基、1,2,3−トリアゾール−2−イル基、1,2,4−トリアゾール−3−イル基1,3,4−チアジアゾール−2−イル基、1,2,3−トリアゾール−1−イル基、1,2,3−トリアゾール−4−イル基、テトラゾール−1−イル基、テトラゾール−2−イル基、インドリン−4−イル基、インドリン−5−イル基、モルホリン−4−イル基、ピペラジン−2−イル基、ピペリジンー2−イル基、1,2,3,4−テトラヒドロキノリン−5−イル基、1,2,3,4−テトラヒドロキノリン−6−イル基、1,2,3,4−テトラヒドロイソキノリン−5−イル基、1,2,3,4−テトラヒドロイソキノリン−6−イル基等が挙げられる。これらのうち、5〜10員へテロアリール基が好ましい。
前記Q1の、へテロアリール基の置換基としては、前記R1のアリール基の置換基として例示したのと同様の基が挙げられる。Specific examples of the “alkylthio group” of the “unsubstituted or substituted C1-6 alkylthio group” of R 3 and R 31 include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, and an n-butylthio group. , Isobutylthio group, sec-butylthio group, tert-butylthio group and the like.
The substituent for the C1-6 alkylthio group is not particularly limited as long as it is chemically acceptable, and examples thereof include the same groups as those exemplified as the substituent for the alkyl group of R 1 .
The “unsubstituted or substituted amino group” of R 3 and R 31 is an amino group; a monoalkylamino group such as a methylamino group or an ethylamino group, preferably a monoC1-6 alkylamino group; dimethylamino Group, dialkylamino group such as diethylamino group, preferably diC1-6 alkylamino group; monoarylamino group such as phenylamino group, 4-methylphenylamino group, preferably monoC6-10 arylamino group; Examples thereof include a diarylamino group such as a naphthylamino group, preferably a diC6-10 arylamino group; an acylamino group such as an acetylamino group and a benzoylamino group, preferably a C1-6 acylamino group.
In the formulas (4) and (5), Z represents any group represented by the formula (6), the formula (7), the formula (8), or the formula (9).
In the formula (6), R 5 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, or an unsubstituted or substituted C1-7 acyl group.
Examples of the “C1-6 alkyl group” of the “unsubstituted or substituted C1-6 alkyl group” of R 5 include the same groups as those exemplified as the alkyl group of R 1 .
“C1-7 acyl group” of “unsubstituted or substituted C1-7 acyl group” of R 5 is a group in which a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group is bonded to a carbonyl group, Specifically, formyl group; acetyl group, propionyl group, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group and other alkylcarbonyl groups; benzoyl group and other arylcarbonyl groups A heteroarylcarbonyl group such as a 2-pyridylcarbonyl group and a thienylcarbonyl group;
Substituents of the C1~7 acyl group include the same groups as those mentioned as substituents for the alkyl group of said R 1.
In the formula (6), Q 11 represents a single bond or a linear C1~3 alkylene group.
In the formula (6), Q 1 represents a heteroaryl group having C6~10 aryl group or an unsubstituted or substituted group, has a substituent.
Examples of the “C6-10 aryl group having a substituent” for Q 1 include the same groups as those exemplified as the C6-10 aryl group having a substituent for R 1 .
The “heteroaryl group” of the “unsubstituted or substituted heteroaryl group” of Q 1 is 1 to 4 atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom as an atom constituting the ring Means a 5- to 10-membered aromatic ring containing a heteroatom, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-1-yl, oxazol-2-yl Group, 1-methylpyrazol-3-yl group, isoxazol-3-yl group, thiazol-2-yl group, pyrrol-2-yl group, pyridin-2-yl group, pyridin-3-yl group, Pyridin-4-yl group, pyrazin-2-yl group, pyrazin-3-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyridazin-3-yl group, pyridazin-4-yl group, 1 , 3-Benzodioxy Sole-4-yl group, 1,3-benzodioxol-5-yl group, 1,4-benzodioxan-5-yl group, 1,4-benzodioxan-6-yl group, 3,4-dihydro -2H-1,5-benzodioxepin-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin-7-yl group, 2,3-dihydrobenzofuran-4-yl group 2,3-dihydrobenzofuran-5-yl group, 2,3-dihydrobenzofuran-6-yl group, 2,3-dihydrobenzofuran-7-yl group, benzofuran-2-yl group, benzofuran-3-yl group Benzothiophen-2-yl group, benzothiophen-3-yl group, quinoxalin-2-yl group, quinoxalin-5-yl group, indol-1-yl group, indol-2-yl group, isoindole-1- I Group, isoindol-2-yl group, isobenzofuran-1-yl group, isobenzofuran-4-yl group, chromen-2-yl group, chromen-3-yl group, imidazol-1-yl group, imidazole-2 -Yl group, imidazol-4-yl group, pyrazol-1-yl group, pyrazol-3-yl group, thiazol-2-yl group, thiazol-4-yl group, oxazol-2-yl group, oxazole-4- Yl group, isoxazol-3-yl group, isoxazol-4-yl group, pyrrolidin-2-yl group, pyrrolidin-3-yl group, benzimidazol-1-yl group, benzimidazol-2-yl group, benzo Thiazol-2-yl group, benzothiazol-4-yl group, benzoxazol-2-yl group, benzoxazol-4-yl group, quinoli 2-yl group, quinolin-3-yl group, isoquinolin-1-yl group, isoquinolin-3-yl group, 1,3,4-oxadiazol-2-yl group, 1,2,3-triazole- 2-yl group, 1,2,4-triazol-3-yl group 1,3,4-thiadiazol-2-yl group, 1,2,3-triazol-1-yl group, 1,2,3-triazole -4-yl group, tetrazol-1-yl group, tetrazol-2-yl group, indoline-4-yl group, indoline-5-yl group, morpholin-4-yl group, piperazin-2-yl group, piperidin-2 -Yl group, 1,2,3,4-tetrahydroquinolin-5-yl group, 1,2,3,4-tetrahydroquinolin-6-yl group, 1,2,3,4-tetrahydroisoquinolin-5-yl Group 1,2,3,4-teto And lahydroisoquinolin-6-yl group. Of these, 5-10 membered heteroaryl groups are preferred.
Examples of the substituent for the heteroaryl group of Q 1 include the same groups as those exemplified as the substituent for the aryl group of R 1 .
前記式(7)中、Q2は、無置換若しくは置換基を有するC6〜10アリール基、または無置換若しくは置換基を有するヘテロアリール基を表す。
前記Q2の、「無置換若しくは置換基を有するC6〜10アリール基」としては、前記R1の「無置換若しくは置換基を有するC6〜10アリール基」として挙げられたのと同様の基が挙げられる。
前記Q2の、「無置換若しくは置換基を有するヘテロアリール基」としては、前記Q1の「無置換若しくは置換基を有するヘテロアリール基」として例示したのと同様の基が挙げられる。In the formula (7), Q 2 represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group.
As the “unsubstituted or substituted C6-10 aryl group” of Q 2 , the same groups as those mentioned as the “unsubstituted or substituted C6-10 aryl group” of R 1 are mentioned. Can be mentioned.
Examples of the “unsubstituted or substituted heteroaryl group” of Q 2 include the same groups as those exemplified as the “unsubstituted or substituted heteroaryl group” of Q 1 .
前記式(7)中、Q21は前記式(7’)又は(7’’)で表される。
前記式(7’)中、R4及びR41は、夫々独立して、水素原子、ハロゲン原子、ヒドロキシ基、シアノ基、無置換若しくは置換基を有するC1〜6アルキル基、無置換若しくは置換基を有するC2〜6アルケニル基、無置換若しくは置換基を有するC2〜8アルキニル基、無置換若しくは置換基を有するC1〜6アルコキシ基、無置換若しくは置換基を有するC3〜8シクロアルキル基、無置換若しくは置換基を有するC3〜8シクロアルコキシ基、無置換若しくは置換基を有するC2〜6アルケニルオキシ基、無置換若しくは置換基を有するC2〜6アルキニルオキシ基、無置換若しくは置換基を有するC1〜6アルキルチオ基、無置換若しくは置換基を有するC1〜7アシルオキシ基を表す。In the formula (7), Q 21 is represented by the formula (7 ′) or (7 ″).
In the formula (7 ′), R 4 and R 41 each independently represent a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted group. A C2-6 alkenyl group having an unsubstituted or substituted C2-8 alkynyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted Or a substituted C3-8 cycloalkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted C2-6 alkynyloxy group, an unsubstituted or substituted C1-6 An alkylthio group, an unsubstituted or substituted C1-7 acyloxy group is represented.
前記式(7’)中、R4及びR41の、「ハロゲン原子」、「C1〜6アルキル基」、「C1〜6アルコキシ基」としては、R1のハロゲン原子、C1〜6アルキル基、C1〜6アルコキシ基として挙げられたのと同じものが挙げられる。
R4及びR41の、「無置換若しくは置換基を有するC2〜6アルケニル基」の「C2〜6アルケニル基」としては、ビニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−メチル−2−プロペニル基、2−メチル−2−プロペニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、1−メチル−2−ブテニル基、2−メチル−2−ブテニル基、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、4−ヘキセニル基、5−ヘキセニル基等が挙げられる。In the above formula (7 ′), as the “halogen atom”, “C1-6 alkyl group”, and “C1-6 alkoxy group” of R 4 and R 41 , a halogen atom of R 1 , a C1-6 alkyl group, The same thing as mentioned as a C1-6 alkoxy group is mentioned.
Examples of the “C2-6 alkenyl group” of the “unsubstituted or substituted C2-6 alkenyl group” of R 4 and R 41 include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1- Examples include methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.
R4及びR41の、「無置換若しくは置換基を有するC2〜8アルキニル基」の「C2〜8アルキニル基」としては、エチニル基、1−プロピニル基、2−プロピニル基、1−ブチニル基、2−ブチニル基、3−ブチニル基、1−メチル−2−プロピニル基、2−メチル−3−ブチニル基、1−ペンチニル基、2−ペンチニル基、3−ペンチニル基、4−ペンチニル基、1−メチル−2−ブチニル基、2−メチル−3−ペンチニル基、1−ヘキシニル基、1,1−ジメチル−2−ブチニル基等のアルキニル基等が挙げられる。As the “C2-8 alkynyl group” of the “unsubstituted or substituted C2-8 alkynyl group” of R 4 and R 41 , an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1- Examples thereof include alkynyl groups such as methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group and 1,1-dimethyl-2-butynyl group.
R4及びR41の「無置換若しくは置換基を有するC3〜8シクロアルキル基」は、環状構造を有するアルキル基を意味し、例えば、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロへキシル基、シクロヘプチル基、シクロオクチル基等が挙げられる。
R4及びR41の、「無置換若しくは置換基を有するC3〜8シクロアルコキシ基」の「C3〜8シクロアルコキシ基」は、環状構造を有するアルコキシ基を意味し、例えば、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロへプチルオキシ基、シクロオクチルオキシ基、シクロプロピルメチルオキシ基、シクロへキシルメチルオキシ基等が挙げられる。The “unsubstituted or substituted C3-8 cycloalkyl group” of R 4 and R 41 means an alkyl group having a cyclic structure, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, A cycloheptyl group, a cyclooctyl group, etc. are mentioned.
The “C3-8 cycloalkoxy group” of the “unsubstituted or substituted C3-8 cycloalkoxy group” of R 4 and R 41 means an alkoxy group having a cyclic structure, such as a cyclopropyloxy group, A cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, a cyclopropylmethyloxy group, a cyclohexylmethyloxy group and the like can be mentioned.
R4及びR41の、「無置換若しくは置換基を有するC2〜6アルケニルオキシ基」としては、エテニルオキシ基、プロパ−1−エン−1−イルオキシ基、プロパ−2−エン−1−イルオキシ基、プロパ−1−エン−2−イルオキシ基、ブタ−1−エン−1−イルオキシ基、ブタ−2−エン−1−イルオキシ基、ブタ−3−エン−1−イルオキシ基、ブタ−1−エン−2−イルオキシ基、ブタ−3−エン−2−イルオキシ基、ペンタ−1−エン−1−イルオキシ基、ペンタ−4−エン−1−イルオキシ基、ペンタ−1−エン−2−イルオキシ基、ペンタ−4−エン−2−イルオキシ基、3−メチル−ブタ−1−エン−1−イルオキシ基、ヘキサ−1−エン−1−イルオキシ基、ヘキサ−5−エン−1−イルオキシ基等が挙げられる。Examples of the “unsubstituted or substituted C2-6 alkenyloxy group” for R 4 and R 41 include an ethenyloxy group, a prop-1-en-1-yloxy group, a prop-2-en-1-yloxy group, Prop-1-en-2-yloxy group, but-1-en-1-yloxy group, but-2-en-1-yloxy group, but-3-en-1-yloxy group, but-1-ene- 2-yloxy group, but-3-en-2-yloxy group, penta-1-en-1-yloxy group, penta-4-en-1-yloxy group, penta-1-en-2-yloxy group, penta -4-en-2-yloxy group, 3-methyl-but-1-en-1-yloxy group, hexa-1-en-1-yloxy group, hexa-5-en-1-yloxy group and the like. .
R4及びR41の、「無置換若しくは置換基を有するC2〜6アルキニルオキシ基」の「C2〜6アルキニルオキシ基」としては、エチニルオキシ基、プロパ−1−イン−1−イルオキシ基、ブタ−1−イン−1−イルオキシ基、ペンタ−1−イン−1−イルオキシ基、ヘキサ−1−イン−1−イルオキシ基等が挙げられる。
R4及びR41の、「無置換若しくは置換基を有するC1〜6アルキルチオ基」の「C1〜6アルキルチオ基」としては、R3のアルキルチオ基として挙げたもののほか、1−エチルプロピルチオ基、n−ヘキシルチオ基、イソヘキシルチオ基、4−メチルペンチルチオ基、3−メチルペンチルチオ基、2−メチルペンチルチオ基、1−メチルペンチルチオ基、3,3−ジメチルブチルチオ基、2,2−ジメチルブチルチオ基、1,1−ジメチルブチルチオ基、1,2−ジメチルブチルチオ基、1,3−ジメチルブチルチオ基、2,3−ジメチルブチルチオ基、1−エチルブチルチオ基、2−エチルブチルチオ基等が挙げられる。
R4及びR41の、「無置換若しくは置換基を有するC1〜7アシルオキシ基」の「C1〜7アシルオキシ基」としては、ホルミルオキシ基;アセチルオキシ基;プロピオニルオキシ基;ベンゾイルオキシ基、シクロヘキシルカルボニルオキシ基等が挙げられる。
R4及びR41の、「無置換若しくは置換基を有するアミノ基」は、前記R3のアミノ基として挙げられたのと同じ基が挙げられる。Examples of the “C2-6 alkynyloxy group” of the “unsubstituted or substituted C2-6 alkynyloxy group” of R 4 and R 41 include an ethynyloxy group, a prop-1-in-1-yloxy group, butane Examples include a -1-in-1-yloxy group, a penta-1-in-1-yloxy group, and a hexa-1-in-1-yloxy group.
As the “C1-6 alkylthio group” of the “unsubstituted or substituted C1-6 alkylthio group” of R 4 and R 41 , in addition to those mentioned as the alkylthio group of R 3 , a 1-ethylpropylthio group, n-hexylthio group, isohexylthio group, 4-methylpentylthio group, 3-methylpentylthio group, 2-methylpentylthio group, 1-methylpentylthio group, 3,3-dimethylbutylthio group, 2,2 -Dimethylbutylthio group, 1,1-dimethylbutylthio group, 1,2-dimethylbutylthio group, 1,3-dimethylbutylthio group, 2,3-dimethylbutylthio group, 1-ethylbutylthio group, 2 -An ethyl butylthio group etc. are mentioned.
The “C1-7 acyloxy group” of the “unsubstituted or substituted C1-7 acyloxy group” of R 4 and R 41 includes formyloxy group; acetyloxy group; propionyloxy group; benzoyloxy group, cyclohexylcarbonyl An oxy group etc. are mentioned.
Examples of the “unsubstituted or substituted amino group” of R 4 and R 41 include the same groups as those mentioned as the amino group of R 3 .
上記C2〜6アルケニル基、C2〜8アルキニル基、C3〜8シクロアルキル基、C3〜8シクロアルコキシ基、C2〜6アルケニルオキシ基、C2〜6アルキニルオキシ基、C1〜6アルキルチオ基、C1〜7のアシルオキシ基の置換基としては、化学的に許容されるものであれば特に限定されないが、フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;メチル基、エチル基、n−プロピル基、i−プロピル基等のC1〜6アルキル基;ビニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−メチル−2−プロペニル基、2−メチル−2−プロペニル基、1−ペンテニル基、2−ペンテニル基、4−ヘキセニル基、5−ヘキセニル基等のC2−6アルケニル基;エチニル基、1−プロピニル基、2−プロピニル基、1−ブチニル基、2−ブチニル基、3−ブチニル基、1−メチル−2−プロピニル基、2−メチル−3−ブチニル基、1−ペンチニル基、2−ペンチニル基、1−ヘキシニル基、1,1−ジメチル−2−ブチニル基等のC2〜6アルキニル基;メトキシ基、エトキシ基、n−プロポキシ基等のC1〜6アルコキシ基;ニトロ基;シアノ基;アミノ基、メチルアミノ基、ジメチルアミノ基等の無置換若しくは置換基を有するアミノ基;フェニル基、p−トリフルオロメチルフェニル基、p−メトキシフェニル基等の無置換若しくは置換基を有するアリール基;2−ピリジル基、3−ピリジル基、4−ピリジル基、5−(2−クロロ)ピリジル基、6−(2−アミノ)ピリジル基等の無置換若しくは置換基を有するヘテロアリール基;メトキシカルボニル基、エトキシカルボニル基、n−ブトキシカルボニル基、t−ブトキシカルボニル基等のアルコキシカルボニル基;アセチル基、ピバロイル基等のアシル基;カルボキシル基;等が挙げられる。
前記式(7’)中、n2は1〜3のいずれかの整数を表し、n2が2以上の場合、R4同士及びR41同士は同一でも異なっていてもよい。但しR4及びR41の全てが水素原子となることはない。C2-6 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C3-8 cycloalkoxy group, C2-6 alkenyloxy group, C2-6 alkynyloxy group, C1-6 alkylthio group, C1-7 The substituent of the acyloxy group is not particularly limited as long as it is chemically acceptable, but halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group A C1-6 alkyl group such as i-propyl group; vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, C2-6 alkenyl groups such as 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 4-hexenyl group and 5-hexenyl group; ethynyl 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2 -C2-6 alkynyl group such as pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group; C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group; nitro group; cyano group Amino groups, methylamino groups, dimethylamino groups, etc., unsubstituted or substituted amino groups; phenyl groups, p-trifluoromethylphenyl groups, p-methoxyphenyl groups, etc., unsubstituted or substituted aryl groups Unsubstituted or substituted 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 5- (2-chloro) pyridyl group, 6- (2-amino) pyridyl group; Heteroaryl groups having a group; an acetyl group, an acyl group such as pivaloyl group; a methoxycarbonyl group, an ethoxycarbonyl group, n- butoxycarbonyl group, an alkoxycarbonyl group such as a t- butoxycarbonyl group carboxy group; and the like.
In formula (7 ′), n2 represents any integer of 1 to 3, and when n2 is 2 or more, R 4 and R 41 may be the same or different. However, not all of R 4 and R 41 are hydrogen atoms.
前記式(7’’)中、Jは、酸素原子又は硫黄原子である。
前記式(8)中、Q3は、無置換若しくは置換基を有するC6〜10アリール基、または無置換若しくは置換基を有するヘテロアリール基を表す。波線は結合様式によってE体及びZ体の何れの幾何学異性体を形成してもよいことを示す。
前記Q3の、「無置換若しくは置換基を有するC6〜10アリール基」としては、前記R1の「無置換若しくは置換基を有するC6〜10アリール基」として挙げられたのと同様の基が挙げられる。
前記Q3の、「無置換若しくは置換基を有するヘテロアリール基」としては、前記Q1の「無置換若しくは置換基を有するヘテロアリール基」として例示したのと同様の基が挙げられる。In said formula (7 ''), J is an oxygen atom or a sulfur atom.
In the formula (8), Q 3 represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group. The wavy line indicates that any geometric isomer of E-form and Z-form may be formed depending on the bonding mode.
As the “unsubstituted or substituted C6-10 aryl group” of Q 3 , the same groups as those mentioned as the “unsubstituted or substituted C6-10 aryl group” of R 1 are mentioned. Can be mentioned.
Examples of the “unsubstituted or substituted heteroaryl group” of Q 3 include the same groups as those exemplified as the “unsubstituted or substituted heteroaryl group” of Q 1 .
前記式(9)中、R5は、前記式(6)のR5と同じである。
前記式(9)中、Q4は、C4〜6シクロアルキル基、無置換若しくは置換基を有するC6〜10アリール基、又は無置換若しくは置換基を有するヘテロアリール基を表す。
前記Q4の、「無置換若しくは置換基を有するアリール基」としては、前記R1の「無置換若しくは置換基を有するC6〜10アリール基」として挙げられたのと同様の基が挙げられる。
前記Q4の、「無置換若しくは置換基を有するヘテロアリール基」としては、前記Q1の「無置換若しくは置換基を有するヘテロアリール基」として例示したのと同じ基が挙げられる。
Q4の、「C4〜6シクロアルキル基」としては、シクロブチル基、シクロペンチル基、シクロヘキシル基などが挙げられる。In the formula (9), R 5 is the same as R 5 in the formula (6).
In the formula (9), Q 4 represents a C4-6 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group.
Examples of the “unsubstituted or substituted aryl group” of Q 4 include the same groups as those exemplified as the “unsubstituted or substituted C 6-10 aryl group” of R 1 .
Examples of the “unsubstituted or substituted heteroaryl group” of Q 4 include the same groups as those exemplified as the “unsubstituted or substituted heteroaryl group” of Q 1 .
Examples of the “C4-6 cycloalkyl group” of Q 4 include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
1−2)式(1)で表されるオキシム誘導体の例示 1-2) Examples of oxime derivatives represented by formula (1)
次に、式(1)で表されるオキシム誘導体を、具体的に第1−a表〜第4−e表に示す。
表中、記号は以下の意味を表す。
Me:メチル基、Et:エチル基、Pr:プロピル基、Bu:ブチル基、
Pent:ペンチル、Hex:ヘキシルn:ノルマル、i:イソ、
t:ターシャリー、c:シクロ、Ph:フェニル、Py:ピリジル、
Ac:アセチル、3,4−OCH2O:3,4−ジオキソメチレン、
*1:オキシム部分の立体異性体の種類(Z体とE体)、
*3:化合物が塩酸塩であることを示す、
Z:炭素−窒素二重結合に基づく2種類の幾何異性体のうちのZ異性体、
E:炭素−窒素二重結合に基づく2種類の幾何異性体のうちのE異性体、
また、[ ]は、融点(℃)を示す。
In the table, symbols represent the following meanings.
Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group,
Pent: pentyl, Hex: hexyl n: normal, i: iso,
t: tertiary, c: cyclo, Ph: phenyl, Py: pyridyl,
Ac: Acetyl, 3,4-OCH 2 O: 3,4-Dioxomethylene,
* 1: Types of stereoisomers of the oxime moiety (Z and E forms)
* 3: Indicates that the compound is hydrochloride.
Z: Z isomer of two kinds of geometric isomers based on a carbon-nitrogen double bond,
E: E isomer of two geometric isomers based on a carbon-nitrogen double bond,
[] Indicates a melting point (° C.).
(Zが式(6)で表されるオキシム誘導体等の製造方法)
前記式(1)においてDが前記式(4)又は(5)で表され、前記式(4)及び(5)においてZが前記式(6)で表されるオキシム誘導体は、例えば、WO03/016303号パンフレットに記載された方法により製造することができる。(Method for producing oxime derivative or the like in which Z is represented by formula (6))
In formula (1), D is represented by formula (4) or (5), and in formulas (4) and (5), Z is represented by formula (6). For example, WO03 / It can be produced by the method described in 016303 pamphlet.
(式中、A、Q1、Q11、R1、R5、R2、R21、R3、q及びq1は前記と同じ意味を表し、Lはハロゲン原子等の脱離基を表す。)
すなわち、式(11)で示されるオキシム体と式(12)で示される化合物とを、塩基の存在下に反応させることにより、本発明のオキシム誘導体等の一種である、式(13)で示される化合物を得ることができる。このようにして得られるオキシム誘導体等は、第1−a表〜第1−n表に示されている。(In the formula, A, Q 1 , Q 11 , R 1 , R 5 , R 2 , R 21 , R 3 , q and q 1 represent the same meaning as described above, and L represents a leaving group such as a halogen atom. )
That is, by reacting the oxime compound represented by the formula (11) and the compound represented by the formula (12) in the presence of a base, the oxime derivative represented by the formula (13) is a kind of the oxime derivative of the present invention. Can be obtained. The oxime derivatives and the like thus obtained are shown in Tables 1-a to 1-n.
式(11)で表される化合物と式(12)で表される化合物とのこの反応に用いる塩基としては、水酸化ナトリウム、水素化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の無機塩基;トリエチルアミン、4−(ジメチルアミノ)ピリジン、ピリジン、1,8−ジアザビシクロ[5.4.0]ウンデセン−7、1,5−ジアザビシクロ[4.3.0]ノネン−5等の有機塩基;等を使用することができる。これらの塩基は一種単独で、あるいは二種以上を組み合わせて用いることができる。
塩基の使用量は、特に限定されないが、式(11)で表される化合物に対し、通常0.01〜100倍モル、好ましくは0.1〜5倍モルである。Examples of the base used for this reaction between the compound represented by the formula (11) and the compound represented by the formula (12) include inorganic bases such as sodium hydroxide, sodium hydride, potassium hydroxide, sodium carbonate, and potassium carbonate. Organic bases such as triethylamine, 4- (dimethylamino) pyridine, pyridine, 1,8-diazabicyclo [5.4.0] undecene-7, 1,5-diazabicyclo [4.3.0] nonene-5, etc. Can be used. These bases can be used alone or in combination of two or more.
Although the usage-amount of a base is not specifically limited, It is 0.01-100 times mole normally with respect to the compound represented by Formula (11), Preferably it is 0.1-5 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されない。例えば、ペンタン、ヘキサン、ヘプタン、ベンゼン、トルエン、キシレン等の炭化水素系溶媒;ジクロロメタン、クロロホルム、四塩化炭化水素等のハロゲン系溶媒;アセトニトリル、プロピオンニトリル等のニトリル系溶媒;ジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル系溶媒;N,N−ジメチルホルムアミド、N,N−ジメチルアセタミド、N−メチルピロリドン等のアミド系溶媒;ジメチルスルホキシド等のスルホキシド系溶媒;水;及びこれらの混合溶媒;等が挙げられる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, hydrocarbon solvents such as pentane, hexane, heptane, benzene, toluene and xylene; halogen solvents such as dichloromethane, chloroform and tetrachloride hydrocarbon; nitrile solvents such as acetonitrile and propiononitrile; diethyl ether, dioxane and tetrahydrofuran Ether solvents such as N; N-dimethylformamide, N, N-dimethylacetamide, amide solvents such as N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; water; and mixed solvents thereof; Can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
(Zが式(7)で表されるオキシム誘導体等の製造方法) (Method for producing oxime derivative or the like in which Z is represented by formula (7))
[骨格の製造方法1]
前記式(1)においてDが前記式(4)又は(5)で表され、前記式(4)及び(5)においてZが前記式(7)で表されるオキシム誘導体等は、下記に示すように、塩基存在下、式(11)で表される化合物に式(14)で表される化合物を反応させることにより目的の化合物(15)を得ることができる。さらに、式(15)で表される化合物にR5を脱離させるための試薬を作用させることにより目的の化合物(16)を得ることができる。また、R5が水素原子の場合、特にそのような操作を行わず、(11)と(14)より直接(16)を得ることができる。このようにして得られるオキシム誘導体等は、第2−a表〜第2−f表に示す。
In formula (1), D is represented by formula (4) or (5), and in formulas (4) and (5), Z is represented by formula (7). Thus, the target compound (15) can be obtained by reacting the compound represented by the formula (11) with the compound represented by the formula (14) in the presence of a base. Furthermore, the target compound (16) can be obtained by allowing a reagent for eliminating R 5 to act on the compound represented by the formula (15). When R 5 is a hydrogen atom, (16) can be obtained directly from (11) and (14) without performing such an operation. The oxime derivatives and the like thus obtained are shown in Tables 2-a to 2-f.
(式中、A、Q2、Q21、R1、R3、R2、R21、R3、q及びq1は前記と同様の意味を表し、Lはハロゲン等の脱離基を表す。ここで、R5は水素原子以外を表す。)(In the formula, A, Q 2 , Q 21 , R 1 , R 3 , R 2 , R 21 , R 3 , q and q 1 represent the same meaning as described above, and L represents a leaving group such as halogen. Here, R 5 represents other than a hydrogen atom.)
式(11)で表される化合物と式(14)で表される化合物との反応に用いる塩基としては、式(11)で表される化合物と式(12)で表される化合物との反応に用いる塩基と同じものを用いることができる。
塩基の使用量は、式(11)で表される化合物に対し、通常0.01〜20倍モル、好ましくは0.1〜5倍モルである。As a base used for reaction of the compound represented by Formula (11) and the compound represented by Formula (14), reaction of the compound represented by Formula (11) and the compound represented by Formula (12) The same base as used in the above can be used.
The usage-amount of a base is 0.01-20 times mole normally with respect to the compound represented by Formula (11), Preferably it is 0.1-5 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。 The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C. Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
式(15)で表される化合物から式(16)で表される化合物を得る反応に用いる酸としては、塩化水素、塩酸、硫酸、硝酸、リン酸等の無機酸;酢酸、トリフルオロ酢酸、p−トルエンスルホン酸等の有機酸;等が挙げられる。
酸の使用量は、特に限定されないが、式(15)で表される化合物に対し、通常0.01〜100倍モル、好ましくは0.1〜10倍モルである。Examples of the acid used for the reaction for obtaining the compound represented by the formula (16) from the compound represented by the formula (15) include inorganic acids such as hydrogen chloride, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid; acetic acid, trifluoroacetic acid, and organic acids such as p-toluenesulfonic acid.
Although the usage-amount of an acid is not specifically limited, It is 0.01-100 times mole normally with respect to the compound represented by Formula (15), Preferably it is 0.1-10 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
[骨格の製造方法2]
前記式(1)においてDが前記式(4)又は(5)で表され、前記式(4)及び(5)においてZが前記式(7)で表される化合物は、下記に示す反応によっても得ることができる。
すなわち、式(17)で表されるカルボン酸と、式(18)で表されるアミン化合物を、混合酸無水物法もしくは縮合剤の存在下に脱水縮合することで、式(16)で表される化合物を得ることができる。
In the formula (1), D is represented by the formula (4) or (5), and in the formulas (4) and (5), Z is represented by the formula (7). Can also be obtained.
That is, the carboxylic acid represented by the formula (17) and the amine compound represented by the formula (18) are subjected to dehydration condensation in the presence of a mixed acid anhydride method or a condensing agent, thereby being represented by the formula (16). Can be obtained.
(式中、A、Q2、Q21、R1、R2、R21、R3、q及びq1は前記と同様の意味を表す。)(In the formula, A, Q 2 , Q 21 , R 1 , R 2 , R 21 , R 3 , q and q 1 represent the same meaning as described above.)
上記反応で混合酸無水物法に用いる酸クロライドとしては、ピバル酸クロライド、2,4,6−トリクロロ安息香酸クロライド、等が挙げられる。塩基としては、水酸化ナトリウム、水素化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の無機塩基;トリエチルアミン、4−(ジメチルアミノ)ピリジン、ピリジン等の有機塩基;等が挙げられる。また、縮合剤としては、N,N−ジシクロヘキシルカルボジイミド、1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド塩酸塩、ベンゾトリアゾール−1−イルオキシ−トリスジメチルアミノホスホニウム塩、4−(4,6−ジメトキシ−1,3,5−トリアジン−2−イル)−4−メチルモルホリニウムクロライド、ヨウ化2−クロロ−1−メチルピリジニウム塩等が挙げられる。これらは一種単独で、あるいは二種以上を組み合わせて用いることができる。
塩基の使用量は、特に限定されないが、式(18)で表される化合物に対し、通常0.01〜20倍モル、好ましくは0.1〜5倍モルである。Examples of the acid chloride used in the mixed acid anhydride method in the above reaction include pivalic acid chloride and 2,4,6-trichlorobenzoic acid chloride. Examples of the base include inorganic bases such as sodium hydroxide, sodium hydride, potassium hydroxide, sodium carbonate, and potassium carbonate; organic bases such as triethylamine, 4- (dimethylamino) pyridine, and pyridine. As the condensing agent, N, N-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, benzotriazol-1-yloxy-trisdimethylaminophosphonium salt, 4- (4,6 -Dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride, 2-chloro-1-methylpyridinium iodide salt and the like. These can be used individually by 1 type or in combination of 2 or more types.
Although the usage-amount of a base is not specifically limited, It is 0.01-20 times mole normally with respect to the compound represented by Formula (18), Preferably it is 0.1-5 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されないが、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
[骨格の製造方法3]
前記式(1)においてDが前記式(4)又は(5)で表され、前記式(4)及び(5)においてZが前記式(7)で表され、式(7)においてQ21が式(7’’)で表される化合物は、下記に示すように酸ハライドとアミンの縮合アミド化反応によって得ることができる。[Frame Manufacturing Method 3]
In Formula (1), D is represented by Formula (4) or (5), in Formulas (4) and (5), Z is represented by Formula (7), and in Formula (7), Q 21 is The compound represented by the formula (7 ″) can be obtained by a condensation amidation reaction of an acid halide and an amine as shown below.
(式中、A、Q2、R1、R2、R21、R3、q及びq1は前記と同様の意味を表す。)(In the formula, A, Q 2 , R 1 , R 2 , R 21 , R 3 , q and q 1 represent the same meaning as described above.)
この反応の反応時間、反応温度、反応溶媒は、前記[骨格の製造方法1]と同様の条件を適用できる。 For the reaction time, reaction temperature, and reaction solvent of this reaction, the same conditions as in [Method for producing skeleton 1] can be applied.
[R4、R41がハロゲン原子である化合物の製造方法]
また、式(7)中のQ21が式(7’’)で表され、式(7’’)のJが酸素原子である化合物を、フッ素化剤を用いてハロゲン化し、式(7)中のQ21が式(7’)で表され、式(7’)中のR4、R41がハロゲン原子である化合物を得ることができる。
この反応に用いるハロゲン化剤としては、フッ化水素、フッ化水素ピリジン、三フッ化N,N−ジエチルアミノ硫黄、三フッ化ビス(2−メトキシエチル)アミノ硫黄、2,2−ジフルオロ−1,3−ジメチルイミダゾリジン等が挙げられる。これらは一種単独で、あるいは二種以上を組み合わせて用いることができる。[Method for producing compound wherein R 4 and R 41 are halogen atoms]
In addition, a compound in which Q 21 in formula (7) is represented by formula (7 ″) and J in formula (7 ″) is an oxygen atom is halogenated using a fluorinating agent to form formula (7) A compound in which Q 21 is represented by the formula (7 ′) and R 4 and R 41 in the formula (7 ′) are halogen atoms can be obtained.
Examples of halogenating agents used in this reaction include hydrogen fluoride, hydrogen fluoride pyridine, N, N-diethylaminosulfur trifluoride, bis (2-methoxyethyl) aminosulfur trifluoride, 2,2-difluoro-1, 3-dimethylimidazolidine etc. are mentioned. These can be used individually by 1 type or in combination of 2 or more types.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。 The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
(Zが式(8)で表されるオキシム誘導体等の製造方法) (Method for producing oxime derivative or the like in which Z is represented by formula (8))
[骨格の製造方法1]
前記式(1)においてDが式(4)または(5)で表され、前記式(4)及び(5)においてZが前記式(8)で表される化合物は、下記に示すように、塩基存在下、式(11)で表される化合物に式(21)で表される化合物を反応させることにより目的の式(22)で表される化合物を得ることができる。さらに、式(22)で表される化合物にR5を脱離させるための試薬を作用させることにより目的の化合物(23)を得ることができる。また、R5が水素原子の場合、特にそのような操作を行わず、式(11)で表される化合物と式(21)で表される化合物を反応させることにより、直接式(23)で表される化合物を得ることができる。このようにして得られる化合物は、第3−a表〜第3−e表に示される。[Method 1 for producing skeleton]
In the above formula (1), D is represented by formula (4) or (5), and in the above formulas (4) and (5), Z is represented by the above formula (8). The target compound represented by the formula (22) can be obtained by reacting the compound represented by the formula (11) with the compound represented by the formula (21) in the presence of a base. Furthermore, the target compound (23) can be obtained by allowing a reagent for removing R 5 to act on the compound represented by the formula (22). When R 5 is a hydrogen atom, the compound represented by the formula (11) and the compound represented by the formula (21) are allowed to react directly with each other without performing such an operation. The compounds represented can be obtained. The compounds thus obtained are shown in Tables 3-a to 3-e.
(式中、A、Q3、R1、R2、R21、R3、q及びq1は前記と同様の意味を表し、Lはハロゲン等の脱離基を表す。R5は水素原子以外を表す。)(In the formula, A, Q 3 , R 1 , R 2 , R 21 , R 3 , q and q 1 represent the same meaning as described above, L represents a leaving group such as halogen, etc. R 5 is other than a hydrogen atom. Represents.)
式(11)で表される化合物と式(21)で表される化合物との反応に用いる塩基としては、式(11)で表される化合物と式(12)で表される化合物との反応に用いる塩基と同じものを用いることができる。
塩基の使用量は、式(11)で表される化合物に対し、通常0.01〜20倍モル、好ましくは0.1〜5倍モルである。As a base used for reaction of the compound represented by Formula (11) and the compound represented by Formula (21), reaction of the compound represented by Formula (11) and the compound represented by Formula (12) The same base as used in the above can be used.
The usage-amount of a base is 0.01-20 times mole normally with respect to the compound represented by Formula (11), Preferably it is 0.1-5 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。 The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C. Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
式(22)で表される化合物から式(23)で表される化合物を得る反応に用いる酸としては、塩化水素、塩酸、硫酸、硝酸、リン酸等の無機酸;酢酸、トリフルオロ酢酸、p−トルエンスルホン酸等の有機酸;等が挙げられる。
酸の使用量は、特に限定されないが、式(22)で表される化合物に対し、通常0.01〜100倍モル、好ましくは0.1〜10倍モルである。Examples of the acid used in the reaction for obtaining the compound represented by the formula (23) from the compound represented by the formula (22) include inorganic acids such as hydrogen chloride, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid; acetic acid, trifluoroacetic acid, and organic acids such as p-toluenesulfonic acid.
Although the usage-amount of an acid is not specifically limited, It is 0.01-100 times mole normally with respect to the compound represented by Formula (22), Preferably it is 0.1-10 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。This reaction can be performed in the presence or absence of a solvent. The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
[骨格の製造方法2]
また、前記式(1)においてDが式(4)又は(5)で表され、前記式(4)及び(5)においてZが前記式(8)で表される化合物は、下記に示す反応によっても得ることができる。
すなわち、式(24)で表すカルボン酸と、式(25)で表されるアミン化合物を、混合酸無水物法もしくは縮合剤の存在下に脱水縮合することで式(23)で表される化合物を得ることができる。
In the formula (1), D is represented by the formula (4) or (5), and in the formulas (4) and (5), Z is represented by the formula (8). Can also be obtained.
That is, the compound represented by the formula (23) by dehydrating and condensing the carboxylic acid represented by the formula (24) and the amine compound represented by the formula (25) in the presence of a mixed acid anhydride method or a condensing agent. Can be obtained.
(式中、A、Q3、R1、R2、R21、R3、q及びq1は前記と同様の意味を表す。)(In the formula, A, Q 3 , R 1 , R 2 , R 21 , R 3 , q and q1 represent the same meaning as described above.)
上記反応で混合酸無水物法に用いる酸クロライドとしては、前記式(17)で表されるカルボン酸と式(18)で表されるアミン化合物との反応に用いる酸クロライドと同じものを用いることができる。
塩基の使用量は、式(25)で表される化合物に対し、通常0.01〜20倍モル、好ましくは0.1〜5倍モルである。As the acid chloride used in the mixed acid anhydride method in the above reaction, the same acid chloride used for the reaction between the carboxylic acid represented by the formula (17) and the amine compound represented by the formula (18) should be used. Can do.
The usage-amount of a base is 0.01-20 times mole normally with respect to the compound represented by Formula (25), Preferably it is 0.1-5 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から24時間の範囲である。 The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 24 hours.
(Zが式(9)で表される化合物の製造方法) (Method for producing a compound in which Z is represented by the formula (9))
[骨格の製造方法1]
前記式(1)においてDが式(4)又は(5)で表され、前記式(4)及び(5)においてZが前記式(9)で表される化合物は、下記に示すように、塩基存在下、式(11)で表される化合物と式(26)で表される化合物とを反応させることにより、目的の式(27)で表される化合物を得ることができる。さらに、式(27)で表される化合物にR5を脱離させる試薬を作用させることにより、目的の式(28)で表される化合物を得ることができる。また、R5が水素原子の場合、特にそのような操作を行わず、式(11)で表される化合物と式(26)で表される化合物とを反応させることにより、直接式(28)を得ることができる。このようにして得られるオキシム誘導体等は、第4−a表〜第4−e表に示される。
In the formula (1), D is represented by the formula (4) or (5), and in the formulas (4) and (5), Z is represented by the formula (9). By reacting the compound represented by the formula (11) and the compound represented by the formula (26) in the presence of a base, the target compound represented by the formula (27) can be obtained. Furthermore, the compound represented by the target formula (28) can be obtained by allowing a reagent for eliminating R 5 to act on the compound represented by the formula (27). Further, when R 5 is a hydrogen atom, the compound represented by the formula (11) and the compound represented by the formula (26) are reacted directly without performing such an operation, so that the direct formula (28) Can be obtained. The oxime derivatives and the like thus obtained are shown in Tables 4-a to 4-e.
(式中、A、Q4、R1、R2、R21、R3、q及びq1は前記と同様の意味を表す。ここで、R5は水素原子以外の基を表す)(In the formula, A, Q 4 , R 1 , R 2 , R 21 , R 3 , q and q1 represent the same meaning as described above. Here, R 5 represents a group other than a hydrogen atom.)
式(11)で表される化合物と式(26)で表される化合物との反応に用いる塩基としては、式(11)で表される化合物と式(12)で表される化合物との反応に用いる塩基と同じものを用いることができる。
塩基の使用量は、式(11)で表される化合物に対し、通常0.01〜20倍モル、好ましくは0.1〜5倍モルである。As a base used for reaction of the compound represented by Formula (11) and the compound represented by Formula (26), reaction of the compound represented by Formula (11) and the compound represented by Formula (12) The same base as used in the above can be used.
The usage-amount of a base is 0.01-20 times mole normally with respect to the compound represented by Formula (11), Preferably it is 0.1-5 times mole.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から150時間の範囲である。The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 150 hours.
本発明の、前記式(1)で表されるオキシム誘導体の塩は、常法に従い、前記式(1)で表されるオキシム誘導体に酸を作用させることにより製造することができる。 The salt of the oxime derivative represented by the formula (1) of the present invention can be produced by allowing an acid to act on the oxime derivative represented by the formula (1) according to a conventional method.
また、上記した、いずれの反応においても、反応終了後においては、通常の後処理操作を行うことにより、目的とする化合物を単離することができる。
また、生成物の精製が必要であれば、蒸留、再結晶又はカラムクロマトグラフィー等の公知慣用の精製手段を採用することができる。
2)式(10)で表される化合物In any of the above-described reactions, the target compound can be isolated by carrying out a normal post-treatment operation after the completion of the reaction.
In addition, if purification of the product is necessary, known and commonly used purification means such as distillation, recrystallization or column chromatography can be employed.
2) Compound represented by formula (10)
本発明の、式(10)で表される化合物は、Zが式(9)で表されるオキシム誘導体を製造する際の中間体として用いられる。
2−1)置換基
式(10)中、R3、R5、Q4、q1、R2及びR21は、式(1)中のR3、R5、Q4、q1、R2及びR21と同様の意味を表す。The compound represented by the formula (10) of the present invention is used as an intermediate when producing an oxime derivative in which Z is represented by the formula (9).
2-1) Substituent In the formula (10), R 3 , R 5 , Q 4 , q 1, R 2 and R 21 are R 3 , R 5 , Q 4 , q 1, R 2 and The same meaning as R 21 is represented.
式(10)中、Bは、ハロゲン原子又はOR6で表される基を表す。R6は、水素原子又はヒドロキシ基の保護基を表し、保護基としては例えば、アルキル基、アリール基、アルコキシアルキル基、アシル基、シリル基、又はカルバモイル基である。
前記保護基のアルキル基、アリール基としては具体的には前記R1のアルキル基、アリール基と同様のものが挙げられる。
前記保護基のアルコキシアルキル基としては、例えばC1〜6アルコキシC1〜6アルキル基が挙げられ、具体的には例えば、メトキシメチル基、エトキシエチル基、イソプロポキシメチル基、t−ブトキシメチル基、t−ブトキシエチル基等が挙げられる。In formula (10), B represents a halogen atom or a group represented by OR 6 . R 6 represents a protecting group for a hydrogen atom or a hydroxy group, and examples of the protecting group include an alkyl group, an aryl group, an alkoxyalkyl group, an acyl group, a silyl group, and a carbamoyl group.
Specific examples of the alkyl group and aryl group of the protecting group include the same alkyl groups and aryl groups as those described above for R 1 .
Examples of the alkoxyalkyl group of the protecting group include C1-6 alkoxy C1-6 alkyl groups, and specific examples thereof include methoxymethyl group, ethoxyethyl group, isopropoxymethyl group, t-butoxymethyl group, t -Butoxyethyl group etc. are mentioned.
前記保護基のアシル基としては、前記R5のアシル基と同様のものが挙げられる。
前記保護基のシリル基としては、トリメチルシリル基、エチルジメチルシリル基、メチルジエチルシリル基、トリエチルシリル基、イソプロピルジメチルシリル基、メチルジイソプロピルシリル基、トリイソプロピルシリル基、t−ブチルジメチルシリル基、メチルジ−t−ブチルシリル基、トリ−t−ブチルシリル基、フェニルジメチルシリル基、メチルジフェニルシリル基、トリフェニルシリル基等が挙げられる。
前記保護基のカルバモイル基としては、カルバモイル、メチルカルバモイル、ジエチルカルバモイル、フェニルカルバモイル基等が挙げられる。Examples of the acyl group of the protecting group include the same acyl groups as those described above for R 5 .
Examples of the silyl group of the protective group include trimethylsilyl group, ethyldimethylsilyl group, methyldiethylsilyl group, triethylsilyl group, isopropyldimethylsilyl group, methyldiisopropylsilyl group, triisopropylsilyl group, t-butyldimethylsilyl group, methyldi- Examples thereof include a t-butylsilyl group, a tri-t-butylsilyl group, a phenyldimethylsilyl group, a methyldiphenylsilyl group, and a triphenylsilyl group.
Examples of the carbamoyl group of the protecting group include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl group and the like.
前記式(10)中、Bのハロゲン原子としては、R1のハロゲン原子と同様のものが挙げられる。
但し、BがOR6であって、かつ、R2、R21、R5及びR6が全て水素原子の場合、Q4は、フェニル基、又は4−クロロフェニル基ではない。In the formula (10), examples of the halogen atom for B include the same as the halogen atom for R 1 .
However, when B is OR 6 and R 2 , R 21 , R 5 and R 6 are all hydrogen atoms, Q 4 is not a phenyl group or a 4-chlorophenyl group.
2−2)式(10)で表される化合物の例示
次に、第5−a表に、本発明の、式(10)で表される化合物を例示する。
本発明の、前記式(10)で表される化合物は、例えば、下記に示す方法により製造することができる。
即ち、不活性ガス雰囲気下、保護されたヒドロキシル基を有するハロゲン置換ピリジン(式(29))とアミン化合物(式(30))を、塩基、配位子及び触媒を用いて反応させるか、または、必要に応じて塩基存在下に式(29)で表されるピリジン化合物と式(30)で表されるアミン化合物を用いた芳香族求核置換反応により、式(31)で表されるアミノ置換ピリジン化合物を得ることができる。続いて、脱保護剤を加え、ヒドロキシ基を脱保護する。この反応によって、ヒドロキシル基を有するアミノ置換ピリジン化合物(式(32))を得ることができる。
That is, a halogen-substituted pyridine having a protected hydroxyl group (formula (29)) and an amine compound (formula (30)) are reacted with each other using a base, a ligand and a catalyst in an inert gas atmosphere, or The amino acid represented by the formula (31) is optionally subjected to an aromatic nucleophilic substitution reaction using a pyridine compound represented by the formula (29) and an amine compound represented by the formula (30) in the presence of a base. Substituted pyridine compounds can be obtained. Subsequently, a deprotecting agent is added to deprotect the hydroxy group. By this reaction, an amino-substituted pyridine compound having a hydroxyl group (formula (32)) can be obtained.
(式中、R2、R21、R3、R5、R6、Q4及びq1は前記と同様の意味を表し、Lはハロゲン原子等の脱離基を表す。)(In the formula, R 2 , R 21 , R 3 , R 5 , R 6 , Q 4 and q 1 represent the same meaning as described above, and L represents a leaving group such as a halogen atom.)
前記アミン化合物としては、前記式(9)中のQ4の「C4〜6シクロアルキル基」、「無置換若しくは置換基を有するアリール基」又は「無置換若しくは置換基を有するヘテロアリール基」の例示として挙げた基を有するアミンを用いることができ、例えばアニリン、トルイジン、(4,6−ジメチルピリミジル)アミン、2−ピリジルアミン等を用いることができる。
当該反応に用いる触媒としては、パラジウム、銅等の有機金属触媒が挙げられる。配位子としてはrac−BINAP、Xantphos、dppf、エチレンジアミン、1,2−ジアミノシクロヘキサン等の二座配位子、及び、Verkade配位子、トリフェニルホスフィン等の単座配位子が挙げられる。塩基としては、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、トリエチルアミン、ピリジン、N,N−ジメチルアミノピリジン、リン酸カリウム、炭酸カリウム、ナトリウム−t−ブトキシド、カリウム−t−ブトキシド等を用いることができる。Examples of the amine compound include the “C4-6 cycloalkyl group”, “unsubstituted or substituted aryl group” or “unsubstituted or substituted heteroaryl group” of Q 4 in the formula (9). Amines having the groups listed as examples can be used, and for example, aniline, toluidine, (4,6-dimethylpyrimidyl) amine, 2-pyridylamine and the like can be used.
Examples of the catalyst used for the reaction include organometallic catalysts such as palladium and copper. Examples of the ligand include bidentate ligands such as rac-BINAP, Xantphos, dppf, ethylenediamine, and 1,2-diaminocyclohexane, and monodentate ligands such as Verkade ligand and triphenylphosphine. Examples of the base include sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, triethylamine, pyridine, N, N-dimethylaminopyridine, potassium phosphate, potassium carbonate, sodium-t-butoxide, Potassium-t-butoxide or the like can be used.
前記脱保護剤としては、公知の脱保護剤が使用でき、例えば、TBAF(テトラブチルアンモニウムフルオリド)や酸などが挙げられる。 As the deprotecting agent, known deprotecting agents can be used, and examples thereof include TBAF (tetrabutylammonium fluoride) and acid.
上記2工程の反応は、溶媒存在下あるいは無溶媒で行うことができるが、溶媒存在下で行うのが好ましい。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されず、例えば、前記式(11)で表される化合物と式(12)で表される化合物との反応に用いられる溶媒と同じものが挙げられる。The reaction in the above two steps can be performed in the presence of a solvent or without a solvent, but is preferably performed in the presence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction. For example, the solvent used for the reaction between the compound represented by the formula (11) and the compound represented by the formula (12) The same can be mentioned.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+120℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から150時間の範囲である。The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 120 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 150 hours.
続いて、以上の反応で得たヒドロキシ基を有するピリジン化合物のヒドロキシ基をさらに脱離基に変換する。脱離基としては具体的には、ハロゲン原子、p−トルエンスルホニルオキシ基、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基等を例示でき、特にハロゲン原子が好ましい。ハロゲン原子に変換する方法として、必要に応じて塩基存在下にハロゲン化剤を反応させる方法がある。
ハロゲン化には公知の方法を用いることができ、ハロゲン化剤としては例えば、塩化チオニル、臭化チオニル、三塩化リン、五塩化リン、オキシ塩化リン、三ヨウ化リンが、三塩化ホウ素、三臭化ホウ素、三ヨウ化ホウ素四塩化チタン、四臭化チタン、四ヨウ化チタン等が挙げられる。Subsequently, the hydroxy group of the pyridine compound having a hydroxy group obtained by the above reaction is further converted into a leaving group. Specific examples of the leaving group include a halogen atom, a p-toluenesulfonyloxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, and the like, and a halogen atom is particularly preferable. As a method of converting to a halogen atom, there is a method of reacting a halogenating agent in the presence of a base, if necessary.
Known methods can be used for halogenation. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, phosphorus triiodide, boron trichloride, Examples thereof include boron bromide, boron triiodide titanium tetrachloride, titanium tetrabromide, titanium tetraiodide and the like.
この反応の反応温度は、通常、−70℃〜+200℃、好ましくは−20℃〜+100℃の範囲である。
反応時間は反応規模等にもよるが、通常、30分から100時間の範囲である。The reaction temperature for this reaction is usually in the range of -70 ° C to + 200 ° C, preferably -20 ° C to + 100 ° C.
Although the reaction time depends on the reaction scale and the like, it is usually in the range of 30 minutes to 100 hours.
この反応は、溶媒存在下あるいは無溶媒で行うことができる。
用いる溶媒としては、本反応に不活性な溶媒であれば特に限定されないが、例えば、ベンゼン、クロロホルム、四塩化炭素、ジクロロメタン等が挙げられる。
3)本発明のテトラゾイルオキシム化合物の適用対象
前記式(1)で表されるオキシム誘導体及びその塩(以下、「本発明化合物」という。)は、広範囲の種類の糸状菌、例えば、卵菌類(Oomycetes)、子のう(嚢)菌類(Ascomycetes)、不完全菌類(Deuteromycetes)、担子菌類(Basidiomycetes)に属する菌に対し優れた殺菌力を有する。従って、本発明化合物を有効成分とする組成物は、花卉、芝、牧草を含む農園芸作物の栽培に際し発生する種々の病害の防除に、種子処理、茎葉散布、土壌施用又は水面施用等により使用することができる。This reaction can be performed in the presence or absence of a solvent.
The solvent to be used is not particularly limited as long as it is an inert solvent for this reaction, and examples thereof include benzene, chloroform, carbon tetrachloride, and dichloromethane.
3) Application target of the tetrazoyl oxime compound of the present invention The oxime derivative represented by the formula (1) and a salt thereof (hereinafter referred to as “the compound of the present invention”) are a wide variety of filamentous fungi such as oomycetes. It has excellent bactericidal activity against bacteria belonging to (Omycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes. Therefore, the composition containing the compound of the present invention as an active ingredient is used by seed treatment, foliage application, soil application or water surface application, etc. can do.
本発明化合物は、例えば、
テンサイ 褐斑病(Cercospora beticola)
黒根病(Aphanomyces cochlloides)
ラッカセイ 褐斑病(Mycosphaerella arachidis)
黒渋病(Mycosphaerella berkeleyi)
キュウリ うどんこ病(Sphaerotheca fuliginea)
つる枯病(Mycosphaerella melonis)
菌核病(Sclerotinia sclerotiorum)
灰色かび病(Botrytis cinerea)
黒星病(Cladosporium cucumerinum)
べと病(Pseudoperonospora cubensis)
トマト 灰色かび病(Botrytis cinerea)
葉かび病(Cladosporium fulvum)
綿腐病(Phythium aphanidermatum)
疫病(Phytophthora infestans)
ナス 灰色かび病(Botrytis cinerea)
黒枯病(Corynespora melongenae)
うどんこ病(Erysiphe cichoracearum)
ホウレンソウ 苗立枯病(Pythium ultimum)
イチゴ 灰色かび病(Botrytis cinerea)
うどんこ病(Sphaerotheca aphanis)
タマネギ 灰色腐敗病(Botrytis allii)
灰色かび病(Botrytis cinerea)
インゲン 菌核病(Sclerotinia sclerotiorum)
灰色かび病(Botrytis cinerea)
リンゴ うどんこ病(Podosphaera leucotricha)
黒星病(Venturia inaequalis)
モニリア病(Monilinia mali)
カキ うどんこ病(Phyllactinia kakicola)
炭そ病(Gloeosporium kaki)
角斑落葉病(Cercospora kaki)The compound of the present invention includes, for example,
Sugar beet brown spot (Cercospora beticola)
Black root disease (Aphanomyces cochlloides)
Peanut brown spot (Mycosphaerella arachidis)
Black astringent disease (Mycosphaerella berkeleyi)
Cucumber powdery mildew (Sphaerotheca furiginea)
Vine Blight (Mycosphaella melonis)
Sclerotinia sclerotiorum
Gray mold disease (Botrytis cinerea)
Black star disease (Cladosporium cucumerinum)
Downy mildew (Pseudoperonospora cubensis)
Tomato gray mold (Botrytis cinerea)
Leaf mold (Cladosporium fulvum)
Cotton rot (Physium aphanidermatum)
Phytophthora infestans
Eggplant gray mold (Botrytis cinerea)
Black blight (Corynespora melogenae)
Powdery mildew (Erysiphe cichoracerarum)
Spinach seedling blight (Pythium ultimum)
Strawberry Gray mold disease (Botrytis cinerea)
Powdery mildew (Sphaerotheca aphanis)
Onion gray rot (Botrytis allii)
Gray mold disease (Botrytis cinerea)
Kidney bean sclerotia
Gray mold disease (Botrytis cinerea)
Apple powdery mildew (Podosphaera leukotricha)
Venturia inaequalis
Moniria disease
Oyster powdery mildew (Phyllactinia kakicola)
Anthracnose (Gloeosporium kaki)
Spotted leaf disease (Cercospora kaki)
モモ・オウトウ 灰星病(Monilinia fructicola)
ブドウ 灰色かび病(Botrytis cinerea)
うどんこ病(Uncinula necator)
晩腐病(Glomerella cingulata)
べと病(Plasmopara viticola)
ナシ 黒星病(Venturia nashicola)
赤星病(Gymnosporangium asiaticum)
黒斑病(Alternaria kikuchiana)
チャ 輪斑病(Pestalotia theae)
炭そ病(Colletotrichum theae−sinensis)カンキツ そうか病(Elsinoe fawcetti)
青かび病(Penicillium italicum)
緑かび病(Penicillium digitatum)
灰色かび病(Botrytis cinerea)
オオムギ うどんこ病(Erysiphe graminis f.sp.horde
i)
裸黒穂病(Ustilago nuda)
コムギ 赤かび病(Gibberella zeae)
赤さび病(Puccinia recondita)
斑点病(Cochliobolus sativus)
ふ枯病(Leptosphaeria nodorum)
眼紋病(Pseudocercosporella herpotrichoides)
褐色雪腐病(Pythium iwayamai)
うどんこ病(Erysiphe graminis f.sp.tritic
i)
紅色雪腐病(Micronectriella nivalis)Peach out ash scab (Monilinia fracticola)
Grapes Gray mold (Botrytis cinerea)
Powdery mildew (Uncinula necator)
Late rot (Glomerella cingulata)
Downy mildew (Plasmopara viticola)
Pear black scab (Venturia nashicola)
Red Star Disease (Gymnosporium asiaticum)
Black spot disease (Alternaria kikuchiana)
Cha ring spot disease (Pestaloti theae)
Colletotrichum theae-sinensis citrus scab (Elsinoe fawceti)
Blue mold disease (Penicillium italicum)
Green mold (Penicillium digitatum)
Gray mold disease (Botrytis cinerea)
Barley powdery mildew (Erysiphe graminis f.sp.
i)
Nasty Black Blight (Ustilago nuda)
Wheat Red mold disease (Gibberella zeae)
Red rust (Puccinia recondita)
Spot disease (Cochliobolus sativus)
Blight disease (Leptosphaeria nodorum)
Eye disease (Pseudocercosporella herpotriochoides)
Brown snow rot (Pythium iwayamai)
Powdery mildew (Erysiphe graminis f. Sp. Tritic
i)
Scarlet Snow Rot (Microlectriella nivalis)
イネ いもち病(Pyricularia oryzae)
紋枯病(Rhizoctonia solani)
馬鹿苗病(Gibberella fujikuroi)
ごま葉枯病(Cochliobolus niyabeanus)
苗立枯病(Pythium graminicolum)
ダイズ 紫斑病(Cercospora kikuchii)
べと病(Peronospora Manshurica)
茎疫病(Phytophthora sojae)
ジャガイモ 疫病(Phytophthora infestans)
アブラナ科植物根こぶ病(Plasmodiophora brassicae)
タバコ 菌核病(Sclerotinia sclerotiorum)
うどんこ病(Erysiphe cichoracearum)
チューリップ 灰色かび病(Botrytis cinerea)
ベントグラス 雪腐大粒菌核病(Sclerotinia borealis)
赤焼病(Pythium aphanidermatum)
オーチャードグラス うどんこ病(Erysiphe graminis)
等の防除に使用することができる。Rice blast disease (Pyricularia oryzae)
Rhizoctonia solani
Idiot Seedling (Gibberella fujikuroi)
Sesame leaf blight (Cochliobolus niyabeanus)
Seedling blight (Pythium gramicolium)
Soybean Purpura (Cercospora kikuchii)
Downy mildew (Peronospora Manshurica)
Phytophthora sojae
Phytophthora infestans
Brassicaceae plant clubroot (Plasmodiophora brassicae)
Tobacco sclerotia (Sclerotinia sclerotiorum)
Powdery mildew (Erysiphe cichoracerarum)
Tulip Gray mold disease (Botrytis cinerea)
Bentgrass (Sclerotinia borealis)
Red fire disease (Pythium aphanidermatum)
Orchardgrass powdery mildew (Erysiphe graminis)
It can be used for the control of etc.
また、近年種々の病原菌において、フェニルアマイド系殺菌剤やストロビルリン系殺菌剤等に対する耐性が発達し、それらの薬剤の効力不足を生じており、耐性菌にも有効な薬剤が望まれている。本発明のオキシム誘導体等は、それら薬剤に対し感受性の病原菌のみならず、耐性菌にも優れた殺菌効果を有する薬剤である。 In recent years, various pathogenic bacteria have developed resistance to phenylamide fungicides, strobilurin fungicides and the like, resulting in insufficient efficacy of these drugs, and drugs effective against resistant bacteria are desired. The oxime derivatives and the like of the present invention are drugs having an excellent bactericidal effect not only on pathogenic bacteria sensitive to these drugs but also resistant bacteria.
例えば、メタラキシルに耐性を示すジャガイモ・トマトの疫病(Phytophthora infestans)、キュウリべと病(Pseudoperonospora cubensis)、ブドウべと病(Plasmopara viticola)に対しても感受性菌と同様に本発明化合物は有効である。 For example, the compounds of the present invention are also effective against potato tomato disease resistant to metalaxyl (Phytophthora infestans), cucumber downy mildew (Pseudoperonospora cubensis) and grape downy mildew (Plasmopara viticocola). .
さらに、ストロビルリン系殺菌剤(例えば、クレソキシムメチル、アゾキシストロビン、ストロピルリン−A、メトミノストロピン、トリフロキシストロピン、ジモキシストロピン、オリサストロピン等)に耐性を示すキュウリべと病(Pseudoperonospora cubensis)、ブドウべと病(Plasmopara viticola)に対しても感受性菌と同様に本発明化合物は有効である。
適用がより好ましい病害としては、ブドウべと病菌(Plasmopara viticola)、ウリ類のべと病菌(Pseudoperonospora cubensis)、バレイショやトマトの疫病菌(Phytophthora infestans)
、芝のピシウム菌(Pythium aphanidermatum他)、テンサイ黒根病菌(Aphanomyces cochlloides)等を代表とする卵菌類が引き起こす多種の病害が挙げられる。Further, cucumber downy mildew (Pseudoperonospora cubensis) resistant to strobilurin-based fungicides (eg, cresoxime methyl, azoxystrobin, stropirulin-A, metminostropin, trifloxystropin, dimoxystropin, orisatropin, etc.) ), The compound of the present invention is also effective against grape downy mildew (Plasmopara viticola) as well as susceptible bacteria.
More preferable diseases that can be applied include Plasmopara viticola, cucumber downy mildew (Pseudoperonospora cubensis), potato and tomato fungus (Phytophthora infestans)
And various diseases caused by oomycetes such as Pythium aphanidermatum, sugar beet root fungus (Aphanomyces cochlloides), and the like.
本発明化合物は、水棲生物が船底、魚網等の水中接触物に付着するのを防止するための防汚剤として使用することもできる。
また本発明化合物の中間体化合物の中には殺菌活性を示すものもある。
さらにまた、本発明化合物を塗料や繊維等に混入させることで、壁や浴槽、あるいは靴や衣服の防菌、防黴剤として使用することもできる。The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contact objects such as ship bottoms and fish nets.
Some intermediate compounds of the compounds of the present invention exhibit bactericidal activity.
Furthermore, the compound of the present invention can be used as an antibacterial or antifungal agent for walls, bathtubs, shoes or clothes by mixing the compound of the present invention into paints or fibers.
4)植物病害防除剤
本発明は、本発明化合物の少なくとも一種を有効成分として含有する植物病害防除剤である。4) Plant disease control agent This invention is a plant disease control agent which contains at least 1 type of this invention compound as an active ingredient.
本発明の植物病害防除剤は、他成分を加えず本発明化合物のみからなるものであってもよいし、一般の農薬のとり得る形態、即ち、水和剤、粒剤、粉剤、乳剤、水溶剤、懸濁剤、フロアブル等の形態となっていてもよい。 The plant disease control agent of the present invention may be composed only of the compound of the present invention without adding other components, and forms that can be taken by general agricultural chemicals, that is, wettable powder, granule, powder, emulsion, water It may be in the form of a solvent, suspending agent, flowable or the like.
植物病害防除剤中に添加することのできる添加剤及び担体としては、固型剤を目的とするものとして、大豆粉、小麦粉等の植物性粉末、珪藻土、燐灰石、石こう、タルク、ベントナイト、パイロフィライト、クレイ等の鉱物性微粉末、安息香酸ソーダ、尿素、芒硝等の有機及び無機化合物が挙げられる。 Additives and carriers that can be added to plant disease control agents include solid powders, vegetable powders such as soybean flour and wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyll Examples thereof include mineral fine powders such as light and clay, and organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate.
また、液体の剤型を目的とするものとして、ケロシン、キシレン及びソルベントナフサ等の石油留分、シクロヘキサン、シクロヘキサノン、ジメチルホルムアミド、ジメチルスルホキシド、アルコール、アセトン、トリクロルエチレン、メチルイソブチルケトン、鉱物油、植物油、水等の溶剤が挙げられる。 Also intended for liquid dosage forms are petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil And solvents such as water.
さらに、これらの製剤において均一かつ安定な形態をとるために、必要に応じて界面活性剤を用いることもできる。 Furthermore, in order to take a uniform and stable form in these preparations, a surfactant can be used as necessary.
用いる界面活性剤としては、例えば、ポリオキシエチレンが付加したアルキルフェニルエーテル、ポリオキシエチレンが付加したアルキルエーテル、ポリオキシエチレンが付加した高級脂肪酸エステル、ポリオキシエチレンが付加したソルビタン高級脂肪酸エステル、ポリオキシエチレンが付加したトリスチリルフェニルエーテル等の非イオン性界面活性剤、ポリオキシエチレンが付加したアルキルフェニルエーテルの硫酸エステル塩、アルキルベンゼンスルホン酸塩、高級アルコールの硫酸エステル塩、アルキルナフタレンスルホン酸塩、ポリカルボン酸塩、リグニンスルホン酸塩、アルキルナフタレンスルホン酸塩のホルムアルデヒド縮合物、イソブチレン−無水マレイン酸の共重合体等が挙げられる。 Examples of the surfactant to be used include alkyl phenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, polyoxyethylene Nonionic surfactants such as tristyryl phenyl ether added with oxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfate ester salt of higher alcohol, alkyl naphthalene sulfonate, Examples thereof include polycarboxylates, lignin sulfonates, alkyl naphthalene sulfonate formaldehyde condensates, and isobutylene-maleic anhydride copolymers.
製剤中の有効成分量は、特に限定されないが、通常、組成物(製剤)全体に対して、好ましくは0.5〜95重量%であり、より好ましくは2〜70重量%である。
本発明の植物病害防除剤が水和剤、乳剤、フロアブル剤である場合には、これらを、水で所定の濃度に希釈して懸濁液あるいは乳濁液として用いることができる。また、粉剤・粒剤である場合には、そのまま植物に散布する方法で用いることができる。The amount of the active ingredient in the preparation is not particularly limited, but is usually preferably 0.5 to 95% by weight, more preferably 2 to 70% by weight, based on the entire composition (preparation).
When the plant disease control agent of the present invention is a wettable powder, an emulsion, or a flowable agent, these can be diluted with water to a predetermined concentration and used as a suspension or an emulsion. Moreover, when it is a powder agent and a granule, it can be used by the method of spraying to a plant as it is.
本発明化合物、又は本発明の植物病害防除剤は単独でも十分有効であることは言うまでもないが、各種の殺菌剤や殺虫・殺ダニ剤又は共力剤の1種又は2種以上と混合して使用することも出来る。 Needless to say, the compound of the present invention or the plant disease control agent of the present invention is sufficiently effective alone, but it is mixed with one or more of various fungicides, insecticides / miticides or synergists. Can also be used.
本発明化合物、又は本発明の植物病害防除剤と混合して使用出来る、殺菌剤、殺虫剤、殺ダニ剤、植物生長調節剤の代表例を以下に示す。 Representative examples of fungicides, insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention or the plant disease control agent of the present invention are shown below.
殺菌剤:
銅剤;塩基性塩化銅、塩基性硫酸銅等。硫黄剤;チウラム、ジネブ、マンネブ、マンコゼブ、ジラム、プロピネブ、ポリカーバメート等。
ポリハロアルキルチオ剤;キャプタン、フォルペット、ジクロルフルアニド等。
有機塩素剤;クロロタロニル、フサライド等。
有機リン剤;IBP、EDDP、トリクロホスメチル、ピラゾホス、ホセチル等。
ベンズイミダゾール剤;チオファネートメチル、ベノミル、カルベンダジム、チアベンダゾール等。
ジカルボキシイミド剤;イプロジオン、プロシミドン、ビンクロゾリン、フルオルイミド等。
カルボキシアミド剤;オキシカルボキシン、メプロニル、フルトラニル、テクロフタラム、トリクラミド、ペンシクロン等。
アシルアラニン剤;メタラキシル、オキサジキシル、フララキシル等。
メトキシアクリレート剤;クレソキシムメチル、アゾキシストロビン、メトミノストロビン等。Fungicide:
Copper agent; basic copper chloride, basic copper sulfate and the like. Sulfur agent; thiuram, dineb, manneb, mancozeb, ziram, propineb, polycarbamate, etc.
Polyhaloalkylthio agents; captan, phorpet, dichlorofluanide, etc.
Organochlorine agents; chlorothalonil, fusalide, etc.
Organophosphorus agent; IBP, EDDP, triclofosmethyl, pyrazophos, fosetyl and the like.
Benzimidazole agents; thiophanate methyl, benomyl, carbendazim, thiabendazole and the like.
Dicarboximide agents; iprodione, procymidone, vinclozolin, fluorimide, etc.
Carboxamide agents; oxycarboxin, mepronil, flutolanil, teclophthalam, trichlamide, pencyclon and the like.
Acylalanine agents; metalaxyl, oxadixyl, furaxyl and the like.
Methoxy acrylate agent; Cresoxime methyl, azoxystrobin, metminostrobin, etc.
アニリノピリミジン剤;アンドプリン、メパニピリム、ピリメタニル、ジプロジニル等。SBI剤;トリアジメホン、トリアジメノール、ビテルタノール、ミクロブタニル、ヘキサコナゾール、プロピコナゾール、トリフルミゾール、プロクロラズ、ペフラゾエート、フェナリモール、ピリフェノックス、トリホリン、フルシラゾール、エタコナゾール、ジクロブトラゾール、フルオトリマゾール、フルトリアフェン、ペンコナゾール、ジニコナゾール、イマザリル、トリデモルフ、フェンプロピモルフ、ブチオベート、エポキシコナゾール、、メトコナゾール等。
抗生物質剤;ポリオキシン、ブラストサイジンS、カスガマイシン、バリダマイシン、硫酸ジヒドロストレプトマイシン等。Anilinopyrimidine agents; and purine, mepanipyrim, pyrimethanil, diprodinil and the like. SBI agents; triadimephone, triadimenol, vitertanol, microbutanyl, hexaconazole, propiconazole, triflumizole, prochloraz, pefazoate, phenalimol, pyrifenox, trifolin, flusilazole, etaconazole, diclobutrazole, fluotrimazole, Flutriaphen, penconazole, diniconazole, imazalyl, tridemorph, fenpropimorph, butiobate, epoxiconazole, metconazole and the like.
Antibiotic agents; polyoxins, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, etc.
ストロビルリン系剤;ストロビルリン−A、メトミノストロビン、クレソキシム−メチル、トリフロキシストロビン、ジモキシストロビン、オリサストロビン等。
その他;プロパモカルブ塩酸塩、キントゼン、ヒドロキシイソオキサゾール、メタスルホカルブ、アニラジン、イソプロチオラン、プロベナゾール、キノメチオナート、ジチアノン、ジノカブ、ジクロメジン、フェルムゾン、フルアジナム、ピロキロン、トリシクラゾール、オキソリニック酸、ジチアノン、イミノクタジン酢酸塩、シモキサニル、ピロールニトリン、メタスルホカルブ、ジエトフェンカルブ、ビナパクリル、レシチン、重曹、フェナミノスルフ、ドジン、ジメトモルフ、フェナジンオキシド、カルプロパミド、フルスルファミド、フルジオキソニル、ファモキサドン、フルオピコリド、マンジプロパミド、ベンチアバリカルブ、イソプロピル、エタボキサム、ジアゾファミド等。Strobilurin-based agents; strobilurin-A, metminostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, orisatrobin and the like.
Others; propamocarb hydrochloride, quintozene, hydroxyisoxazole, metasulfocarb, anilazine, isoprothiolane, probenazole, quinomethionate, dithianone, dinocab, diclomedin, fermzone, fluazinam, pyroxylone, tricyclazole, oxolinic acid, dithianone, iminotadine acetate, simoxanil Nitrine, metasulfocarb, dietofencarb, binapacryl, lecithin, baking soda, phenaminosulfur, dodine, dimethomorph, phenazine oxide, carpropamide, fursulfamide, fludioxonil, famoxadone, fluopicolide, mandipropamide, bench avalibcarb, isopropyl, ethaboxam, diazofamide, etc.
殺虫・殺ダニ剤:
有機燐及びカーバメート系殺虫剤;フェンチオン、フェニトロチオン、ダイアジノン、クロルピリホス、ESP、バミドチオン、フェントエート、ジメトエート、ホルモチオン、マラソン、トリクロルホン、チオメトン、ホスメット、ジクロルボス、アセフェート、EPBP、メチルパラチオン、オキシジメトンメチル、エチオン、サリチオン、シアノホス、イソキサチオン、ピリダフェンチオン、ホサロン、メチダチオン、スルプロホス、クロルフェンビンホス、テトラクロルビンホス、ジメチルビンホス、プロパホス、イソフェンホス、エチルチオメトン、プロフェノホス、ピラクロホス、モノクロトホス、アジンホスメチル、アルディカルブ、メソミル、チオジカルブ、カルボフラン、カルボスルファン、ベンフラカルブ、フラチオカルブ、プロポキスル、BPMC、MTMC、MIPC、カルバリル、ピリミカーブ、エチオフェンカルブ、フェノキシカルブ等。Insecticides and acaricides:
Organic phosphorus and carbamate insecticides: fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothione, marathon, trichlorphone, thiomethone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, sathione Cyanophos, isoxathione, pyridafenthion, hosalon, methidathion, sulprophos, chlorfenvinphos, tetrachlorbinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, propenophos, pyraclophos, monocrotophos, azinephosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, Carbosulfan, Benfuracarb, Fracioca Bed, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, and the like.
ピレスロイド系殺虫剤;ペルメトリン、シペルメトリン、デルタメスリン、フェンバレレート、フェンプロパトリン、ピレトリン、アレスリン、テトラメスリン、レスメトリン、ジメスリン、プロパスリン、フェノトリン、プロトリン、フルバリネート、シフルトリン、シハロトリン、フルシトリネート、エトフェンプロクス、シクロプロトリン、トロラメトリン、シラフルオフェン、ブロフェンプロクス、アクリナスリン等。 Pyrethroid insecticides; permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, proprasrin, phenothrin, protorin, fluvinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, Cycloprotonline, trolamethrin, silafluophene, brofenprox, acrinusrin and the like.
ベンゾイルウレア系その他の殺虫剤;ジフルベンズロン、クロルフルアズロン、ヘキサフルムロン、トリフルムロン、テトラベンズロン、フルフェノクスロン、フルシクロクスロン、ブプロフェジン、ピリプロキシフェン、メトプレン、ベンゾエピン、ジアフェンチウロン、アセタミプリド、イミダクロプリド、ニテンピラム、フィプロニル、カルタップ、チオシクラム、ベンスルタップ、硫酸ニコチン、ロテノン、メタアルデヒド、機械油、BTや昆虫病原ウイルスなどの微生物農薬等。 Benzoylurea and other insecticides; diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, metoprene, benzoepin, diafenthiuron, acetamiprid , Imidacloprid, nitenpyram, fipronil, cartap, thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.
殺線虫剤;フェナミホス、ホスチアゼート等。
殺ダニ剤;クロルベンジレート、フェニソブロモレート、ジコホル、アミトラズ、BPPS、ベンゾメート、ヘキシチアゾクス、酸化フェンブタスズ、ポリナクチン、キノメチオネート、CPCBS、テトラジホン、アベルメクチン、ミルベメクチン、クロフェンテジン、シヘキサチン、ピリダベン、フェンピロキシメート、テブフェンピラド、ピリミジフェン、フェノチオカルブ、ジエノクロル等。Nematicides; phenamifos, phostiazates, etc.
Acaricides; chlorbenzilate, phenisobromolate, dicophore, amitraz, BPPS, benzomate, hexothiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentezin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, Pyrimidifen, phenothiocarb, dienochlor, etc.
植物生長調節剤:
ジベレリン類(例えばジベレリンA3、ジベレリンA4、ジベレリンA7)、IAA、NAA等。Plant growth regulator:
Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.
次に実施例を挙げて本発明を更に詳細に説明する。ただし、本発明は実施例に何ら限定されるものではない。
1)製造実施例
1−1)Zが式(6)で表される化合物の製造実施例EXAMPLES Next, an Example is given and this invention is demonstrated still in detail. However, the present invention is not limited to the examples.
1) Production Example 1-1) Production Example of Compound in which Z is Represented by Formula (6)
[製造実施例1]
(Z)−{〔6−(3,4−メチレンジオキシ)フェニルアセチルアミノ〕ピリジン−2−イル}メトキシイミノ−(1−メチル−1H−テトラゾール−5−イル)フェニルメタンの製造(化合物1−a−17)
Preparation of (Z)-{[6- (3,4-methylenedioxy) phenylacetylamino] pyridin-2-yl} methoxyimino- (1-methyl-1H-tetrazol-5-yl) phenylmethane (Compound 1 -A-17)
(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノンオキシム(6.0g,29mmol)(式(31))のアセトニトリル(200ml)溶液に、〔2−クロロメチル−6−(3,4−メチレンジオキシ)フェニルアセチルアミノ〕ピリジン(15.69g,51mmol)(式(32))、及び炭酸カリウム(10.92g,79mmol)を加え、全容を40℃にて16.5時間撹拌した。反応混合物をろ過し、ろ液を濃縮した。得られた残留物を酢酸エチルに溶解後、有機層を水洗し、無水硫酸マグネシウムで乾燥した。溶媒を留去し、得られた残留物をシリカゲルカラムクロマトグラフィー〔展開溶媒:n−ヘキサン:酢酸エチル=3:2(v/v)〕により精製して、(Z)−{〔6−(3,4−メチレンジオキシ)フェニルアセチルアミノ〕ピリジン−2−イル}メトキシイミノ−(1−メチル−1H−テトラゾール−5−イル)フェニルメタン(式(33))を6.32g得た。 To a solution of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone oxime (6.0 g, 29 mmol) (formula (31)) in acetonitrile (200 ml), [2-chloromethyl-6- (3,4-Methylenedioxy) phenylacetylamino] pyridine (15.69 g, 51 mmol) (formula (32)) and potassium carbonate (10.92 g, 79 mmol) were added, and the whole volume was 16.5 at 40 ° C. Stir for hours. The reaction mixture was filtered and the filtrate was concentrated. The obtained residue was dissolved in ethyl acetate, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography [developing solvent: n-hexane: ethyl acetate = 3: 2 (v / v)] to give (Z)-{[6- ( 3.32 g of 3,4-methylenedioxy) phenylacetylamino] pyridin-2-yl} methoxyimino- (1-methyl-1H-tetrazol-5-yl) phenylmethane (formula (33)) was obtained.
製造実施例1と同様の方法により得られた、本発明のオキシム誘導体等を第6表に示す。
1−2)Zが式(7)で表される化合物の製造実施例 1-2) Production Example of Compound in which Z is Represented by Formula (7)
[製造実施例2]
(Z)−(1−メチル−1H−テトラゾール−5−イル) フェニルメタノン−O−{[2−アセトキシ−(4−メトキシフェニル)アセチルアミノ]ピリジン−6−イルメチル}−オキシムの製造(化合物2−a−5)[Production Example 2]
Production of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O-{[2-acetoxy- (4-methoxyphenyl) acetylamino] pyridin-6-ylmethyl} -oxime (compound 2-a-5)
2−(アセトキシ)−(4−メトキシフェニル)酢酸0.6g(2.6mmol)およびトリエチルアミン0.29g(2.9mmol)をトルエン20mlに溶解し、ピバル酸クロライド0.35g(2.9mmol)を加えて室温にて6時間撹拌した。生じた結晶をろ別し、ろ液に(Z)−(1−メチル−1H−テトラゾール−5−イル) フェニルメタノン−O−[2−アミノピリジン−6−イルメチル]−オキシム0.20g(0.64mmol)を加えて室温にて16時間撹拌した後に溶媒を留去し、得られた粗生成物をシリカゲルカラムクロマトグラフィー精製して、目的物である(Z)−(1−メチル−1H−テトラゾール−5−イル) フェニルメタノン−O−{[2−アセトキシ−(4−メトキシフェニル)アセチルアミノ]ピリジン−6−イルメチル}−オキシム0.27gを得た。 0.6 g (2.6 mmol) of 2- (acetoxy)-(4-methoxyphenyl) acetic acid and 0.29 g (2.9 mmol) of triethylamine were dissolved in 20 ml of toluene, and 0.35 g (2.9 mmol) of pivalic acid chloride was dissolved. In addition, the mixture was stirred at room temperature for 6 hours. The resulting crystals were filtered off and (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2-aminopyridin-6-ylmethyl] -oxime 0.20 g ( 0.64 mmol) was added and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel column chromatography to obtain the desired product (Z)-(1-methyl-1H). -Tetrazol-5-yl) Phenylmethanone-O-{[2-acetoxy- (4-methoxyphenyl) acetylamino] pyridin-6-ylmethyl} -oxime 0.27 g was obtained.
[製造実施例3]
(Z)−(1−メチル−1H−テトラゾール−5−イル) フェニルメタノン−O−{[2−フルオロ―(4−メトキシフェニル)アセチルアミノ]ピリジン−6−イルメチル}−オキシムの製造(化合物2−a−7)[Production Example 3]
Production of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O-{[2-fluoro- (4-methoxyphenyl) acetylamino] pyridin-6-ylmethyl} -oxime (compound 2-a-7)
2−(フルオロ)−(4−メトキシフェニル)酢酸エチル0.29g(1.35mmol)をメタノール4mlに溶解し、水酸化カリウム0.13g(2.03mmol)を加えて室温にて1時間半撹拌した。溶媒を減圧下留去して得られた白色固体を塩化メチレン8mlに溶解し、塩化オキサリル0.26g(2.03mmol)を加えて1時間加熱還流した。減圧濃縮した後に塩化メチレン8mlに溶解し、ピバル酸0.14g(1.35mmol)およびトリエチルアミン0.20g(2.01mmol)を加えた。室温にて1時間撹拌後、(Z)−(1−メチル−1H−テトラゾール−5−イル) フェニルメタノン−O−[2−アミノピリジン−6−イルメチル]−オキシム0.14g(0.45mmol)を加えて室温にて29時間撹拌した。溶媒を留去し、得られた粗生成物をシリカゲルカラムクロマトグラフィー精製して、目的物0.19gを得た。 Dissolve 0.29 g (1.35 mmol) of ethyl 2- (fluoro)-(4-methoxyphenyl) acetate in 4 ml of methanol, add 0.13 g (2.03 mmol) of potassium hydroxide and stir at room temperature for 1.5 hours. did. The white solid obtained by distilling off the solvent under reduced pressure was dissolved in 8 ml of methylene chloride, 0.26 g (2.03 mmol) of oxalyl chloride was added, and the mixture was heated to reflux for 1 hour. After concentration under reduced pressure, the residue was dissolved in 8 ml of methylene chloride, and 0.14 g (1.35 mmol) of pivalic acid and 0.20 g (2.01 mmol) of triethylamine were added. After stirring at room temperature for 1 hour, 0.14 g (0.45 mmol) of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2-aminopyridin-6-ylmethyl] -oxime. ) And stirred at room temperature for 29 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel column chromatography to obtain 0.19 g of the desired product.
[製造実施例4]
(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−O−{[2−ジフルオロ−(4−メトキシフェニル)アセチルアミノ]ピリジン−6−イルメチル}−オキシムの製造(化合物2−a−9)
4−メトキシベンゾイル蟻酸エチル0.65g(3.12mmol)を塩化メチレン10mlに溶解し、三フッ化N,N−ジエチルアミノ硫黄0.76g(4.68mmol)を加え、40℃にて6時間半撹拌した。さらに室温にて3日撹拌した後、三フッ化N,N−ジエチルアミノ硫黄0.76g(4.68mmol)を加えて40℃にて7時間半撹拌した。反応混合物を水にあけ、塩化メチレンで抽出した有機層に硫酸マグネシウムを加えて乾燥した後に減圧濃縮し、得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶出液;ヘキサン:酢酸エチル=9:1(v/v))精製して、目的物である2,2−ジフルオロ−(4−メトキシフェニル)酢酸エチル0.44gを得た。
2,2−ジフルオロ−(4−メトキシフェニル)酢酸エチル0.44g(1.91mmol)をメタノール5mlに溶解し、水酸化ナトリウム0.10g(2.48mmol)の水溶液を加えて室温にて7時間撹拌した。溶媒を減圧留去し、2N塩酸で中和した後、酢酸エチルで抽出した。有機層に硫酸マグネシウムを加えて乾燥した後に減圧濃縮することで目的物である2,2−ジフルオロ-(4-メトキシフェニル)酢酸の粗生成物を得た。
2,2−ジフルオロ−(4−メトキシフェニル)酢酸0.23g(1.35mmol)を塩化メチレン5mlに溶解し、ピバル酸クロライド0.18g(1.49mmol)およびN−エチルジイソプロピルアミン0.21g(1.62mmol)を加えて室温にて30分撹拌した後、(Z)−(1−メチル−1H−テトラゾール−5−イル) フェニルメタノン−O−[2−アミノピリジン−6−イルメチル]−オキシム0.14g(0.45mmol)を加えて室温にて一晩撹拌した。溶媒を留去し、得られた粗生成物をシリカゲルカラムクロマトグラフィー精製して、目的物である(Z)−(1−メチル−1H−テトラゾール−5−イル) フェニルメタノン−O−{[2−ジフルオロ−(4−メトキシフェニル)アセチルアミノ]ピリジン−6−イルメチル}−オキシム0.14gを得た。
製造実施例2〜4と同様の方法により得られた、本発明のオキシム誘導体等を第7表に示す。
Preparation of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O-{[2-difluoro- (4-methoxyphenyl) acetylamino] pyridin-6-ylmethyl} -oxime (compound 2-a-9)
0.65 g (3.12 mmol) of ethyl 4-methoxybenzoylformate is dissolved in 10 ml of methylene chloride, 0.76 g (4.68 mmol) of N, N-diethylaminosulfur trifluoride is added, and the mixture is stirred at 40 ° C. for 6 hours and a half. did. Further, after stirring at room temperature for 3 days, 0.76 g (4.68 mmol) of N, N-diethylaminosulfur trifluoride was added and stirred at 40 ° C. for 7 and a half hours. The reaction mixture was poured into water, magnesium sulfate was added to the organic layer extracted with methylene chloride, dried and concentrated under reduced pressure. The resulting crude product was subjected to silica gel column chromatography (eluent; hexane: ethyl acetate = 9: 1). (V / v)) Purification was performed to obtain 0.44 g of ethyl 2,2-difluoro- (4-methoxyphenyl) acetate as a target product.
0.44 g (1.91 mmol) of ethyl 2,2-difluoro- (4-methoxyphenyl) acetate is dissolved in 5 ml of methanol, and an aqueous solution of 0.10 g (2.48 mmol) of sodium hydroxide is added to the solution for 7 hours at room temperature. Stir. The solvent was distilled off under reduced pressure, neutralized with 2N hydrochloric acid, and extracted with ethyl acetate. Magnesium sulfate was added to the organic layer, dried, and then concentrated under reduced pressure to obtain a crude product of 2,2-difluoro- (4-methoxyphenyl) acetic acid as a target product.
0.23 g (1.35 mmol) of 2,2-difluoro- (4-methoxyphenyl) acetic acid was dissolved in 5 ml of methylene chloride, 0.18 g (1.49 mmol) of pivalic acid chloride and 0.21 g of N-ethyldiisopropylamine ( (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2-aminopyridin-6-ylmethyl]- 0.14 g (0.45 mmol) of oxime was added and stirred overnight at room temperature. The solvent was distilled off, and the resulting crude product was purified by silica gel column chromatography to obtain the desired product (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O-{[ 0.14 g of 2-difluoro- (4-methoxyphenyl) acetylamino] pyridin-6-ylmethyl} -oxime was obtained.
Table 7 shows the oxime derivatives of the present invention obtained by the same method as in Production Examples 2 to 4.
[製造実施例5]
(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−O−[2−(シンナモイル)アミノピリジン−6−イルメチル]−オキシムの製造(化合物3−a−1)
製造実施例5と同様の方法により得られた、本発明のオキシム誘導体等を第8表に示す。
Preparation of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2- (cinnamoyl) aminopyridin-6-ylmethyl] -oxime (Compound 3-a-1)
Table 8 shows oxime derivatives of the present invention obtained by the same method as in Production Example 5.
以下の製造実施例中、rac−BINAPは2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフチル(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)を、Pd2(dba)3はPdとジベンジリデンアセトンとの錯体を、THFはテトラヒドロフランを、TBAFはフッ化テトラ−n−ブチルアンモニウム(Tetra-n-butylammonium fluoride)を表す。In the following production examples, rac-BINAP represents 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl (Pd). 2 (dba) 3 represents a complex of Pd and dibenzylideneacetone, THF represents tetrahydrofuran, and TBAF represents tetra-n-butylammonium fluoride.
[製造実施例6]
(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−O−[2−フェニルアミノピリジン−6−イルメチル]−オキシムの製造(化合物4−a−1)
(工程1)
シュレンク反応器に2−ブロモ−6−(t−ブチルジメチルシロキシ)メチルピリジン(0.60g,2.0mmol)、アニリン(0.56g,6.0mmol)、rac−BINAP(0.13g,0.2mmol)、ナトリウム t-ブトキシド(0.29g, 3.0mmol)およびPd2(dba)3(0.08g,0.09mmol)を順次加えた後、真空減圧とアルゴン復圧を3回繰り返した。この混合物にトルエン10mLを加え、80℃で24時間加熱した。反応混合物を室温まで冷却した後、反応混合物へ水を加え、酢酸エチルで抽出した。抽出した有機層を合わせ、飽和食塩水で洗い、硫酸マグネシウムで乾燥した後、減圧下で溶媒を留去した。得られた残渣にTHF(20mL)とTBAFの1M THF溶液(4.1mL)を加え、室温下、17時間攪拌した。反応混合物へ水を加え、1時間放置後、減圧下で溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー (展開溶媒:n−ヘキサン/酢酸エチル=2/1(v/v))により精製し、2−フェニルアミノ−6−ヒドロキシメチルピリジン(0.23g,53%)を得た。
得られた化合物の物性は以下のとおりであった。
1H NMR (300 MHz, CDCl3) δ 3.53 (br-s, 1H), 4.65 (s, 2H), 6.55 (br-s, 1H), 6.66 (d, 1H, J = 7.3 Hz), 6.76 (d, 1H, J = 8.4 Hz), 7.07 (tt, 1H, J = 6.7, 1.9 Hz), 7.29-7.37 (m, 4H), 7.49 (dd, 1H, J = 8.4, 7.3 Hz)[Production Example 6]
Production of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2-phenylaminopyridin-6-ylmethyl] -oxime (Compound 4-a-1)
(Process 1)
In a Schlenk reactor, 2-bromo-6- (t-butyldimethylsiloxy) methylpyridine (0.60 g, 2.0 mmol), aniline (0.56 g, 6.0 mmol), rac-BINAP (0.13 g,. 2 mmol), sodium t-butoxide (0.29 g, 3.0 mmol) and Pd 2 (dba) 3 (0.08 g, 0.09 mmol) were sequentially added, and then vacuum reduction and argon return pressure were repeated three times. To this mixture was added 10 mL of toluene, and the mixture was heated at 80 ° C. for 24 hours. The reaction mixture was cooled to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extracted organic layers were combined, washed with saturated brine, dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. To the obtained residue were added THF (20 mL) and 1M THF solution of TBAF (4.1 mL), and the mixture was stirred at room temperature for 17 hours. Water was added to the reaction mixture, and after standing for 1 hour, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 2/1 (v / v)). To give 2-phenylamino-6-hydroxymethylpyridine (0.23 g, 53%).
The physical properties of the obtained compound were as follows.
1 H NMR (300 MHz, CDCl 3 ) δ 3.53 (br-s, 1H), 4.65 (s, 2H), 6.55 (br-s, 1H), 6.66 (d, 1H, J = 7.3 Hz), 6.76 ( d, 1H, J = 8.4 Hz), 7.07 (tt, 1H, J = 6.7, 1.9 Hz), 7.29-7.37 (m, 4H), 7.49 (dd, 1H, J = 8.4, 7.3 Hz)
(工程2)
室温下、2−フェニルアミノ−6−ヒドロキシメチルピリジン(0.21g,1.1mmol)とジクロロメタン(10mL)の混合物へ塩化チオニル(0.15g,1.3mmol)を加え、室温下で1.5時間撹拌した。減圧下で溶媒を留去し、2−フェニルアミノ−6−クロロメチルピリジン塩酸塩(0.27g,定量的)を得た。
得られた化合物の物性は以下のとおりであった。
1H NMR (300 MHz, CDCl3) δ 4.77 (s, 2H), 6.95-6.98 (m, 2H), 7.26-7.39 (m, 3H),7.44-7.49 (m, 2H), 7.75-7.80 (m, 1H), 10.29 (br-s, 1H). (Process 2)
At room temperature, thionyl chloride (0.15 g, 1.3 mmol) was added to a mixture of 2-phenylamino-6-hydroxymethylpyridine (0.21 g, 1.1 mmol) and dichloromethane (10 mL). Stir for hours. The solvent was distilled off under reduced pressure to obtain 2-phenylamino-6-chloromethylpyridine hydrochloride (0.27 g, quantitative).
The physical properties of the obtained compound were as follows.
1 H NMR (300 MHz, CDCl 3 ) δ 4.77 (s, 2H), 6.95-6.98 (m, 2H), 7.26-7.39 (m, 3H), 7.44-7.49 (m, 2H), 7.75-7.80 (m , 1H), 10.29 (br-s, 1H).
(工程3)
乾燥アセトニトリル10mLと2−フェニルアミノ−6−クロロメチルピリジン塩酸塩(0.27g,1.1mmol)の混合物へ、(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノンオキシム(0.23g,1.1mmol)と炭酸カリウム(0.43g,3.11mmol)を加えた。室温下、この懸濁液を110時間攪拌した。反応液を水に加えた後、酢酸エチルで抽出した。有機層を飽和食塩水で洗い、無水硫酸マグネシウムで乾燥した後、減圧下で溶媒を留去した。得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:n−ヘキサン/酢酸エチル=2/1(v/v))で精製し、(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−o−[2−フェニルアミノピリジン−6−イルメチル]−オキシム(0.22g,54%)を得た。(Process 3)
To a mixture of 10 mL of dry acetonitrile and 2-phenylamino-6-chloromethylpyridine hydrochloride (0.27 g, 1.1 mmol), (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone oxime (0.23 g, 1.1 mmol) and potassium carbonate (0.43 g, 3.11 mmol) were added. The suspension was stirred for 110 hours at room temperature. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 2/1 (v / v)) to obtain (Z)-(1-methyl-1H-tetrazol-5-yl). Phenylmethanone-o- [2-phenylaminopyridin-6-ylmethyl] -oxime (0.22 g, 54%) was obtained.
[製造実施例7]
(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−O−[2−(4,6−ジメチルピリミジル)アミノピリジン−6−イルメチル]−オキシムの製造(化合物4−b−2)
(工程1)
製造実施例6の(工程1)と同様にして2−(4,6−ジメチルピリミジル)アミノ−6−ヒドロキシメチルピリジンを得た。
得られた化合物の物性は次の通りであった。
NMR:1H NMR (300 MHz, CDCl3) δ 2.41 (s, 6H), 3.89 (t, 1H, J = 5.3 Hz), 4.67 (d, 2H, J = 5.3 Hz), 6.58 (s, 1H), 6.83 (d, 1H, J = 7.5 Hz), 7.67 (dd, 1H, J =8.4, 7.5 Hz), 8.06 (br-s, 1H), 8.37 (d, 1H, J = 8.4 Hz). [Production Example 7]
Preparation of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2- (4,6-dimethylpyrimidyl) aminopyridin-6-ylmethyl] -oxime (compound 4 -B-2)
(Process 1)
In the same manner as in Production Example 6 (Step 1), 2- (4,6-dimethylpyrimidyl) amino-6-hydroxymethylpyridine was obtained.
The physical properties of the obtained compound were as follows.
NMR: 1 H NMR (300 MHz, CDCl 3 ) δ 2.41 (s, 6H), 3.89 (t, 1H, J = 5.3 Hz), 4.67 (d, 2H, J = 5.3 Hz), 6.58 (s, 1H) , 6.83 (d, 1H, J = 7.5 Hz), 7.67 (dd, 1H, J = 8.4, 7.5 Hz), 8.06 (br-s, 1H), 8.37 (d, 1H, J = 8.4 Hz).
(工程2)
室温下、2−(4,6−ジメチルピリミジル)アミノ−6−ヒドロキシメチルピリジン(0.28g,1.2mmol)とジクロロメタン(12mL)の混合物へ塩化チオニル(0.17g,1.3mmol)を加え、室温下で8時間撹拌した。反応混合物を水(30mL)とNaHCO3(0.5g)からなる水溶液へ加え、分液した後、クロロホルムで抽出した。抽出した有機層を合わせ、硫酸マグネシウムで乾燥した後、減圧下で溶媒を留去した。得られた残渣をシリカゲルカラムクロマトグラフィー (展開溶媒:n−ヘキサン/酢酸エチル=3/1(v/v))により精製し、2−(4,6−ジメチルピリミジル)アミノ−6−クロロメチルピリジン(0.22g,79%)を得た。
得られた化合物の物性は次のとおりであった。
1H NMR (300 MHz, CDCl3) δ 2.40 (s, 6H), 4.55 (s, 2H), 6.57 (s, 1H), 7.05 (d, 1H, J = 7.0 Hz), 7.69 (dd, 1H, J = 8.4, 7.0 Hz), 7.75 (br-s, 1H), 8.45 (d, 1H, J= 8.4 Hz). (Process 2)
To a mixture of 2- (4,6-dimethylpyrimidyl) amino-6-hydroxymethylpyridine (0.28 g, 1.2 mmol) and dichloromethane (12 mL) at room temperature, thionyl chloride (0.17 g, 1.3 mmol) And stirred at room temperature for 8 hours. The reaction mixture was added to an aqueous solution consisting of water (30 mL) and NaHCO 3 (0.5 g), and the mixture was separated and extracted with chloroform. The extracted organic layers were combined and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 3/1 (v / v)) to give 2- (4,6-dimethylpyrimidyl) amino-6-chloro. Methylpyridine (0.22 g, 79%) was obtained.
The physical properties of the obtained compound were as follows.
1 H NMR (300 MHz, CDCl 3 ) δ 2.40 (s, 6H), 4.55 (s, 2H), 6.57 (s, 1H), 7.05 (d, 1H, J = 7.0 Hz), 7.69 (dd, 1H, J = 8.4, 7.0 Hz), 7.75 (br-s, 1H), 8.45 (d, 1H, J = 8.4 Hz).
(工程3)
製造実施例6の(工程3)と同様にして、(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−o−[2−(4,6−ジメチルピリミジル)アミノピリジン−6−イルメチル]−オキシムを得た。(Process 3)
(Z)-(1-Methyl-1H-tetrazol-5-yl) phenylmethanone-o- [2- (4,6-dimethylpyrimidyl) in the same manner as in Production Example 6 (Step 3). Aminopyridin-6-ylmethyl] -oxime was obtained.
[製造実施例8]
(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−O−[2−(2−ピリジル)アミノピリジン−6−イルメチル]−オキシムの製造(化合物4−b−1)
(工程1)
製造実施例6の(工程1)と同様にして2−ピリジルアミノ−6−ヒドロキシメチルピリジンを得た。得られた化合物の物性は次の通りであった。
NMR:1H NMR (300 MHz, CDCl3) δ 3.51 (br-s, 1H), 4.70 (s, 2H), 6.80 (d, 1H,J = 7.3 Hz), 6.86 (dd, 1H, J = 7.2, 5.0 Hz), 7.38 (d, 1H, J = 8.4 Hz), 7.39 (br-s, 1H), 7.53 (d, 1H, J = 8.2 Hz), 7.61 (dd, 1H, J = 8.4, 7.3 Hz), 7.61 (dd, 1H,J = 8.2, 7.2 Hz), 8.28 (d, 1H, J = 5.0 Hz).
(工程2)
続いて、製造実施例6の(工程2)と同様にして、2−ピリジルアミノ−6−クロロメチルピリジンを得た。得られた化合物の物性は次の通りであった。
1H NMR (300 MHz, CDCl3) δ 4.76 (s, 2H), 7.11-7.16 (m, 2H), 7.77-7.87 (m, 2H),7.97-8.03 (m, 2H), 8.38 (d, 1H, J = 9.0 Hz), 14.04 (br-s, 1H).
(工程3)
製造実施例6の(工程3)と同様にして(Z)−(1−メチル−1H−テトラゾール−5−イル)フェニルメタノン−O−[2−(2−ピリジル)アミノピリジン−6−イルメチル]−オキシムを製造した。
製造実施例6〜8と同様の方法により、本発明のオキシム誘導体等を第9表に示す。
また、製造実施例6〜8の工程1及び工程2と同様にして得られる本発明の中間体化合物(式(10))を、第10−a表及び第10−b表に示す。
Production of (Z)-(1-methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2- (2-pyridyl) aminopyridin-6-ylmethyl] -oxime (Compound 4-b-1)
(Process 1)
In the same manner as in Production Example 6 (Step 1), 2-pyridylamino-6-hydroxymethylpyridine was obtained. The physical properties of the obtained compound were as follows.
NMR: 1 H NMR (300 MHz, CDCl 3 ) δ 3.51 (br-s, 1H), 4.70 (s, 2H), 6.80 (d, 1H, J = 7.3 Hz), 6.86 (dd, 1H, J = 7.2 , 5.0 Hz), 7.38 (d, 1H, J = 8.4 Hz), 7.39 (br-s, 1H), 7.53 (d, 1H, J = 8.2 Hz), 7.61 (dd, 1H, J = 8.4, 7.3 Hz ), 7.61 (dd, 1H, J = 8.2, 7.2 Hz), 8.28 (d, 1H, J = 5.0 Hz).
(Process 2)
Subsequently, 2-pyridylamino-6-chloromethylpyridine was obtained in the same manner as in Production Example 6 (Step 2). The physical properties of the obtained compound were as follows.
1 H NMR (300 MHz, CDCl 3 ) δ 4.76 (s, 2H), 7.11-7.16 (m, 2H), 7.77-7.87 (m, 2H), 7.97-8.03 (m, 2H), 8.38 (d, 1H , J = 9.0 Hz), 14.04 (br-s, 1H).
(Process 3)
(Z)-(1-Methyl-1H-tetrazol-5-yl) phenylmethanone-O- [2- (2-pyridyl) aminopyridin-6-ylmethyl in the same manner as in Production Example 6 (Step 3) ] -Oxime was prepared.
Table 9 shows the oxime derivatives and the like of the present invention by the same method as in Production Examples 6 to 8.
Moreover, the intermediate compound (Formula (10)) of this invention obtained by carrying out similarly to the manufacturing method 6-8 process 1 and the process 2 is shown to Table 10-a and Table 10-b.
次に、本発明の植物病害防除剤の製剤実施例を若干示す。添加物及び添加割合は、これら実施例に限定されるものではなく、広範囲に変化させることが可能である。製剤実施例中の部は重量部を示す。なお、製剤実施例において、「本発明の化合物」は、「本発明のオキシム誘導体等」を意味する。 Next, some preparation examples of the plant disease control agent of the present invention are shown. Additives and addition ratios are not limited to these examples, and can be varied over a wide range. The part in a formulation example shows a weight part. In the formulation examples, “the compound of the present invention” means “the oxime derivative of the present invention and the like”.
製剤実施例1 水和剤
本発明化合物 40部
クレー 53部
ジオクチルスルホサクシネートナトリウム塩 4部
リグニンスルホン酸ナトリウム塩 3部
以上を均一に混合して微細に粉砕して、有効成分40%の水和剤を得る。Formulation Example 1 Wetting agent Compound of the present invention 40 parts Clay 53 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 3 parts or more are uniformly mixed and finely pulverized to hydrate 40% active ingredient Get the agent.
製剤実施例2 乳剤
本発明化合物 10部
ソルベッソ200 53部
シクロヘキサノン 26部
ドデシルベンゼンスルホン酸カルシウム塩 1部
ポリオキシエチレンアルキルアリルエーテル 10部
以上を混合溶解して、有効成分10%の乳剤を得る。Formulation Example 2 Emulsion Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts or more are mixed and dissolved to obtain an emulsion of 10% active ingredient.
製剤実施例3 粉剤
本発明化合物 10部
クレー 90部
以上を均一に混合して微細に粉砕して、有効成分10%の粉剤を得る。Formulation Example 3 Powder A compound of the present invention 10 parts Clay 90 parts or more are mixed uniformly and finely pulverized to obtain a powder of 10% active ingredient.
製剤実施例4 粒剤
本発明化合物 5部
クレー 73部
ベントナイト 20部
ジオクチルスルホサクシネートナトリウム塩 1部
リン酸カリウム 1部
以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。Formulation Example 4 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part or more is pulverized and mixed well, and after adding water and kneading well, granulation drying As a result, granules containing 5% active ingredient are obtained.
製剤実施例5 懸濁剤
本発明化合物 10部
ポリオキシエチレンアルキルアリルエーテル 4部
ポリカルボン酸ナトリウム塩 2部
グリセリン 10部
キサンタンガム 0.2部
水 73.8部
以上を混合し、粒度が3ミクロン以下になるまで湿式粉砕して、有効成分10%の懸濁剤を得る。Formulation Example 5 Suspension Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts or more are mixed and the particle size is 3 microns or less To obtain a suspension containing 10% of the active ingredient.
製剤実施例6 顆粒水和剤
本発明化合物 40部
クレー 36部
塩化カリウム 10部
アルキルベンゼンスルホン酸ナトリウム塩 1部
リグニンスルホン酸ナトリウム塩 8部
アルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物 5部
以上を均一に混合して微細に粉砕後、適量の水を加えてから練り込んで粘土状にした。粘土状物を造粒した後乾燥し、有効成分40%の顆粒水和剤を得る。
3)試験例(トマト疫病防除試験)
素焼きポットで栽培したトマト幼苗(品種「レジナ」、4〜5葉期)に、前記製剤実施例2の乳剤を有効成分100ppmの濃度で散布した。散布後、室温で自然乾燥し、トマト疫病菌(Phytophthora infestans)の遊走子嚢懸濁液を噴霧接種し、明暗を12時間毎に繰り返す高湿度の恒温室(20℃)に4日間保持した。葉上の病斑出現状態を無処理と比較調査し防除価(%)を求めた。本発明では、防除価80%以上を示す化合物を、植物病害防除に有効な化合物とした。
なお、第6表〜第9表において、「活性」項目に「○」が付いてある化合物は、防除価80%以上を示す化合物であり、「X」が付いてある化合物は、防除価80%未満を示す化合物である。Formulation Example 6 Granule wettable powder Compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts or more uniformly mixed Then, after finely pulverizing, an appropriate amount of water was added and kneaded into a clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
3) Test example (tomato plague control trial)
Tomato seedlings (variety “Regina”, 4 to 5 leaf stage) cultivated in an unglazed pot were sprayed with the emulsion of Formulation Example 2 at a concentration of 100 ppm active ingredient. After spraying, it was naturally dried at room temperature, sprayed and inoculated with a zoospore sac suspension of Phytophthora infestans, and kept for 4 days in a high-humidity constant temperature room (20 ° C.) repeating light and dark every 12 hours. The lesion appearance on the leaves was compared with no treatment, and the control value (%) was obtained. In the present invention, a compound having a control value of 80% or more is regarded as an effective compound for controlling plant diseases.
In Tables 6 to 9, a compound with “◯” in the “activity” item is a compound having a control value of 80% or more, and a compound with “X” is a control value of 80 It is a compound showing less than%.
本発明のオキシム誘導体及びその塩は、ごく低薬量で極めて優れた植物病害に対する防除効果を示し、かつ、有用植物に対する薬害の心配がない。また、本発明の植物病害防除剤は、植物病害に対する優れた防除効果を有する。さらに、本発明の化合物は、本発明のオキシム誘導体等を製造する際の中間体として用いられる中間体化合物を提供する。従って、本発明は産業上有用である。 The oxime derivative and the salt thereof of the present invention exhibit an extremely excellent control effect against plant diseases at a very low dose, and there is no fear of phytotoxicity against useful plants. Moreover, the plant disease control agent of this invention has the outstanding control effect with respect to a plant disease. Furthermore, the compound of the present invention provides an intermediate compound used as an intermediate in producing the oxime derivative or the like of the present invention. Therefore, the present invention is industrially useful.
Claims (3)
R2及びR21は、夫々独立して、水素原子、ハロゲン原子、又は無置換若しくは置換基を有するC1〜6アルキル基を表す。
Aは、式(2)又は(3)
で表されるヘテロアリール基を表す。
Dは、式(4)又は式(5)で表されるヘテロアリール基を表す。
Zは、下記式(6)
Q11は、単結合または直鎖C1〜3アルキレン基を表す。
Q1は、置換基を有するC6〜10アリール基、又は無置換若しくは置換基を有するヘテロアリール基を表す。)、
下記式(7)
n2は1〜3のいずれかの整数を表し、n2が2以上の場合、R4同士及びR41同士は同一又は異なっていてもよい。但しR4及びR41の全てが水素原子となることはない。
Jは酸素原子又は硫黄原子を表す。)で表される2価基を表す。
Q2は、無置換若しくは置換基を有するC6〜10アリール基、又は無置換若しくは置換基を有するヘテロアリール基を表す。)、
下記式(8)
下記式(9)
Q4は、C4〜6シクロアルキル基、無置換若しくは置換基を有するC6〜10アリール基、又は無置換若しくは置換基を有するヘテロアリール基を表す。)で表されるいずれかの基を表す。]}An oxime derivative represented by the formula (1) and a salt thereof.
R 2 and R 21 each independently represent a hydrogen atom, a halogen atom, or an unsubstituted or substituted C 1-6 alkyl group.
A is the formula (2) or (3)
The heteroaryl group represented by these is represented.
D represents the heteroaryl group represented by Formula (4) or Formula (5).
Z represents the following formula (6)
Q 11 represents a single bond or a linear C1-3 alkylene group.
Q 1 represents a C6-10 aryl group having a substituent or an unsubstituted or substituted heteroaryl group. ),
Following formula (7)
n2 represents any integer of 1 to 3, and when n2 is 2 or more, R 4 and R 41 may be the same or different. However, not all of R 4 and R 41 are hydrogen atoms.
J represents an oxygen atom or a sulfur atom. Represents a divalent group represented by:
Q 2 represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group. ),
Following formula (8)
Following formula (9)
Q 4 represents a C4-6 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group. ) Represents any group represented. ]}
で表される化合物。Formula (10)
A compound represented by
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008113377 | 2008-04-24 | ||
JP2008113377 | 2008-04-24 | ||
JP2008114390 | 2008-04-24 | ||
JP2008114384 | 2008-04-24 | ||
JP2008114384 | 2008-04-24 | ||
JP2008114390 | 2008-04-24 | ||
JP2008251604 | 2008-09-29 | ||
JP2008251604 | 2008-09-29 | ||
PCT/JP2009/001849 WO2009130900A1 (en) | 2008-04-24 | 2009-04-22 | Oxime derivative, intermediate compound, and plant disease control agent |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013048541A Division JP5770768B2 (en) | 2008-04-24 | 2013-03-11 | Compound |
Publications (1)
Publication Number | Publication Date |
---|---|
JPWO2009130900A1 true JPWO2009130900A1 (en) | 2011-08-11 |
Family
ID=41216641
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010509080A Pending JPWO2009130900A1 (en) | 2008-04-24 | 2009-04-22 | Oxime derivatives, intermediate compounds and plant disease control agents |
JP2013048541A Active JP5770768B2 (en) | 2008-04-24 | 2013-03-11 | Compound |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013048541A Active JP5770768B2 (en) | 2008-04-24 | 2013-03-11 | Compound |
Country Status (2)
Country | Link |
---|---|
JP (2) | JPWO2009130900A1 (en) |
WO (1) | WO2009130900A1 (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2632135T3 (en) * | 2008-01-15 | 2017-09-11 | Bayer Intellectual Property Gmbh | Pesticide composition comprising a tetrazolyl oxime derivative and an active substance pesticide or insecticide |
WO2009115556A1 (en) * | 2008-03-19 | 2009-09-24 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
EP2265119A1 (en) * | 2008-03-19 | 2010-12-29 | Bayer CropScience AG | Fungicide hydroximoyl-tetrazole derivatives |
KR101309978B1 (en) * | 2008-07-02 | 2013-09-17 | 닛뽕소다 가부시키가이샤 | Plant growth accelerator |
WO2010100876A1 (en) * | 2009-03-02 | 2010-09-10 | 日本曹達株式会社 | Tetrazoyl oxime derivative, salt thereof, and plant disease control agent |
CN102725282B (en) * | 2009-12-28 | 2015-12-16 | 拜尔农科股份公司 | Fungicide hydroximoyl-tetrazole derivatives |
BR112012020509B1 (en) * | 2010-02-26 | 2018-01-23 | Nippon Soda Co., Ltd. | TETRAZOLYLXIMAX AND FUNGICIDE DERIVATIVE |
EP2719686B1 (en) | 2010-03-12 | 2015-12-02 | Nippon Soda Co., Ltd. | Process to halogenate a picoline derivative |
JP2013525400A (en) * | 2010-04-28 | 2013-06-20 | バイエル・クロップサイエンス・アーゲー | Fungicide hydroxymoyl-heterocyclic derivative |
US20140005230A1 (en) * | 2011-03-14 | 2014-01-02 | Juergen Benting | Fungicide hydroximoyl-tetrazole derivatives |
Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59157004A (en) * | 1983-02-26 | 1984-09-06 | Yoshio Katsuta | Insecticidal and miticidal agent containing novel 2-phenylpropyl ether derivative and its preparation |
JPS624258A (en) * | 1985-06-29 | 1987-01-10 | Dainippon Jiyochiyuugiku Kk | Insecticidal and miticidal agent containing carboxylic acid ester derivative and production thereof |
JPS62155259A (en) * | 1985-12-27 | 1987-07-10 | Ishihara Sangyo Kaisha Ltd | Aminotrifluoromethylpyridine and its production |
JPH0327359A (en) * | 1989-06-02 | 1991-02-05 | Ciba Geigy Ag | New herbicide |
JPH03232855A (en) * | 1989-11-08 | 1991-10-16 | Ishihara Sangyo Kaisha Ltd | Imide-based compound |
DE4228792A1 (en) * | 1992-08-29 | 1994-03-03 | Hoechst Ag | New piperidinyl:amino-pyridine derivs. - useful as agricultural and technical fungicides. |
JPH06340631A (en) * | 1993-03-17 | 1994-12-13 | Basf Ag | Extermination of harmful life |
JPH0892224A (en) * | 1994-09-16 | 1996-04-09 | Kumiai Chem Ind Co Ltd | 3,5-substituted phenyltriazole derivative and insecticide/ miticide |
JPH11269176A (en) * | 1997-12-10 | 1999-10-05 | Sagami Chem Res Center | Oxime derivative and agrochemical containing the derivative |
WO2000071536A1 (en) * | 1999-05-20 | 2000-11-30 | E.I. Du Pont De Nemours And Company | Heteroaryloxypyrimidine insecticides and acaricides |
WO2003005824A2 (en) * | 2001-07-11 | 2003-01-23 | Bayer Cropscience Gmbh | Substituted 3-heteroaryl (amino-or-oxy)-pyrrolidin-2-ones, method for the production thereof and use thereof as herbicides or as plant growth regulators |
JP2003509342A (en) * | 1999-09-10 | 2003-03-11 | メルク エンド カムパニー インコーポレーテッド | Tyrosine kinase inhibitor |
JP2004507526A (en) * | 2000-08-31 | 2004-03-11 | ファイザー・プロダクツ・インク | Pyrazole derivatives and their use as protein kinase inhibitors |
JP2004131392A (en) * | 2002-10-08 | 2004-04-30 | Sumitomo Chem Co Ltd | Tetrazole compound and application thereof |
JP2004131416A (en) * | 2002-10-10 | 2004-04-30 | Sumitomo Chem Co Ltd | Tetrazole compound and plant disease controlling application thereof |
JP2006515846A (en) * | 2002-12-13 | 2006-06-08 | ニューロジェン・コーポレーション | 2-Substituted quinazolin-4-ylamine analogues as capsaicin receptor modulators |
WO2006072831A1 (en) * | 2005-01-10 | 2006-07-13 | Pfizer Inc. | Pyrrolopyrazoles, potent kinase inhibitors |
US20060217390A1 (en) * | 2005-02-24 | 2006-09-28 | Esmir Gunic | Cycloalkl, aryl and heteroaryl amino isothiazoles for the treatment of Hepatitis C virus |
WO2006114260A1 (en) * | 2005-04-25 | 2006-11-02 | Novartis Ag | Phenylacetylene derivatives having mglur5 receptor affinity |
WO2006129842A1 (en) * | 2005-06-01 | 2006-12-07 | Banyu Pharmaceutical Co., Ltd. | Novel aminopyridine derivative having selective aurora-a inhibitory activity |
JP2007504229A (en) * | 2003-09-02 | 2007-03-01 | メルク エンド カムパニー インコーポレーテッド | Bipyridylamines and ethers as modulators of metabotropic glutamate receptor-5 |
WO2008001076A1 (en) * | 2006-06-26 | 2008-01-03 | Ucb Pharma S.A. | Fused thiazole derivatives as kinase inhibitors |
WO2008006875A1 (en) * | 2006-07-13 | 2008-01-17 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
WO2008006874A1 (en) * | 2006-07-13 | 2008-01-17 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
WO2009020191A1 (en) * | 2007-08-08 | 2009-02-12 | Nippon Soda Co., Ltd. | Tetrazoyloxime derivative and plant disease control agent |
JP5133985B2 (en) * | 2007-05-14 | 2013-01-30 | 日本曹達株式会社 | Tetrazoyl oxime derivatives and plant disease control agents |
-
2009
- 2009-04-22 WO PCT/JP2009/001849 patent/WO2009130900A1/en active Application Filing
- 2009-04-22 JP JP2010509080A patent/JPWO2009130900A1/en active Pending
-
2013
- 2013-03-11 JP JP2013048541A patent/JP5770768B2/en active Active
Patent Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59157004A (en) * | 1983-02-26 | 1984-09-06 | Yoshio Katsuta | Insecticidal and miticidal agent containing novel 2-phenylpropyl ether derivative and its preparation |
JPS624258A (en) * | 1985-06-29 | 1987-01-10 | Dainippon Jiyochiyuugiku Kk | Insecticidal and miticidal agent containing carboxylic acid ester derivative and production thereof |
JPS62155259A (en) * | 1985-12-27 | 1987-07-10 | Ishihara Sangyo Kaisha Ltd | Aminotrifluoromethylpyridine and its production |
JPH0327359A (en) * | 1989-06-02 | 1991-02-05 | Ciba Geigy Ag | New herbicide |
JPH03232855A (en) * | 1989-11-08 | 1991-10-16 | Ishihara Sangyo Kaisha Ltd | Imide-based compound |
DE4228792A1 (en) * | 1992-08-29 | 1994-03-03 | Hoechst Ag | New piperidinyl:amino-pyridine derivs. - useful as agricultural and technical fungicides. |
JPH06340631A (en) * | 1993-03-17 | 1994-12-13 | Basf Ag | Extermination of harmful life |
JPH0892224A (en) * | 1994-09-16 | 1996-04-09 | Kumiai Chem Ind Co Ltd | 3,5-substituted phenyltriazole derivative and insecticide/ miticide |
JPH11269176A (en) * | 1997-12-10 | 1999-10-05 | Sagami Chem Res Center | Oxime derivative and agrochemical containing the derivative |
WO2000071536A1 (en) * | 1999-05-20 | 2000-11-30 | E.I. Du Pont De Nemours And Company | Heteroaryloxypyrimidine insecticides and acaricides |
JP2003509342A (en) * | 1999-09-10 | 2003-03-11 | メルク エンド カムパニー インコーポレーテッド | Tyrosine kinase inhibitor |
JP2004507526A (en) * | 2000-08-31 | 2004-03-11 | ファイザー・プロダクツ・インク | Pyrazole derivatives and their use as protein kinase inhibitors |
WO2003005824A2 (en) * | 2001-07-11 | 2003-01-23 | Bayer Cropscience Gmbh | Substituted 3-heteroaryl (amino-or-oxy)-pyrrolidin-2-ones, method for the production thereof and use thereof as herbicides or as plant growth regulators |
JP2004131392A (en) * | 2002-10-08 | 2004-04-30 | Sumitomo Chem Co Ltd | Tetrazole compound and application thereof |
JP2004131416A (en) * | 2002-10-10 | 2004-04-30 | Sumitomo Chem Co Ltd | Tetrazole compound and plant disease controlling application thereof |
JP2006515846A (en) * | 2002-12-13 | 2006-06-08 | ニューロジェン・コーポレーション | 2-Substituted quinazolin-4-ylamine analogues as capsaicin receptor modulators |
JP2007504229A (en) * | 2003-09-02 | 2007-03-01 | メルク エンド カムパニー インコーポレーテッド | Bipyridylamines and ethers as modulators of metabotropic glutamate receptor-5 |
WO2006072831A1 (en) * | 2005-01-10 | 2006-07-13 | Pfizer Inc. | Pyrrolopyrazoles, potent kinase inhibitors |
US20060217390A1 (en) * | 2005-02-24 | 2006-09-28 | Esmir Gunic | Cycloalkl, aryl and heteroaryl amino isothiazoles for the treatment of Hepatitis C virus |
WO2006114260A1 (en) * | 2005-04-25 | 2006-11-02 | Novartis Ag | Phenylacetylene derivatives having mglur5 receptor affinity |
WO2006129842A1 (en) * | 2005-06-01 | 2006-12-07 | Banyu Pharmaceutical Co., Ltd. | Novel aminopyridine derivative having selective aurora-a inhibitory activity |
WO2008001076A1 (en) * | 2006-06-26 | 2008-01-03 | Ucb Pharma S.A. | Fused thiazole derivatives as kinase inhibitors |
WO2008006875A1 (en) * | 2006-07-13 | 2008-01-17 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
WO2008006874A1 (en) * | 2006-07-13 | 2008-01-17 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
JP5133985B2 (en) * | 2007-05-14 | 2013-01-30 | 日本曹達株式会社 | Tetrazoyl oxime derivatives and plant disease control agents |
WO2009020191A1 (en) * | 2007-08-08 | 2009-02-12 | Nippon Soda Co., Ltd. | Tetrazoyloxime derivative and plant disease control agent |
Non-Patent Citations (4)
Title |
---|
JPN6009025110; BOLM,C. et al: 'Synthesis of chiral 2,2'-dipyridylamines and their use in the copper-catalyzed asymmetric allylic ox' Tetrahedron Letters Vol.45, No.26, 2004, p.5019-5021 * |
JPN6012068633; GOSWAMI, S.: 'N-Bromosuccinimide reactions of some heterocycles in the presence or absence of water: an overview o' Journal of Heterocyclic Chemistry Vol.38, 2001, p.173-178 * |
JPN6012068635; Synthesis of C2-symmetric and unsymmetrically substituted 2,2'-dipyridylamines and crystal structure: 'BOLM, C.' Journal of Organometallic Chemistry Vol.689, No.23, 2004, p.3767-3777 * |
JPN6012068638; KAMENECKA, T. M.: 'Dipyridyl amines: Potent metabotropic glutamate subtype 5 receptor antagonists' Bioorganic & Medicinal Chemistry Letters Vol.15, No.19, 2005, p.4350-4353 * |
Also Published As
Publication number | Publication date |
---|---|
JP2013144699A (en) | 2013-07-25 |
JP5770768B2 (en) | 2015-08-26 |
WO2009130900A1 (en) | 2009-10-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5770768B2 (en) | Compound | |
JP5133985B2 (en) | Tetrazoyl oxime derivatives and plant disease control agents | |
CN102770424B (en) | Tetrazyl 9 oxime derivate or its salt and sterilant | |
KR101327670B1 (en) | Tetrazoyloxime derivative and plant disease control agent | |
JP2010248273A (en) | Oxime compound or salt thereof, and fungicide | |
WO2010137302A1 (en) | Nitrogen-containing heteroaryl derivatives and fungicides for agricultural and horticultural use | |
JP5215321B2 (en) | Oxime ether derivatives and agricultural and horticultural fungicides | |
JP5550913B2 (en) | Tetrazoyloxime derivative and salt thereof, and plant disease control agent | |
JP4726373B2 (en) | Oxime O-ether compounds and agricultural and horticultural fungicides | |
JPWO2009144935A1 (en) | Nitrogen-containing heterocyclic derivatives and agricultural and horticultural fungicides | |
JP5350460B2 (en) | Tetrazoyloxime derivatives and salts thereof, and plant disease control agents | |
JP5542452B2 (en) | Tetrazoyloxime derivatives and salts thereof, and plant disease control agents | |
EP1362850A1 (en) | Oxime ether compound and agricultural or horticultural bactericide | |
JP5322296B2 (en) | Method for using plant disease control agent containing tetrazoyloxime derivative | |
WO2012165305A1 (en) | Bipyridine compound and bactericide | |
JP2007161621A (en) | Nitrogen-containing heterocyclic compound and agricultural/horticultural fungicide | |
JP2011236197A (en) | Tetrazolyl compound or salt thereof and germicide | |
WO2011046082A1 (en) | Oxime ether derivative or salt thereof, and agricultural/horticultural germicide |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130108 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130311 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20131112 |