JP2001089453A - Heteroaryloxy(thio)alkanoic acid amide derivative and germicide for agriculture and horticulture - Google Patents
Heteroaryloxy(thio)alkanoic acid amide derivative and germicide for agriculture and horticultureInfo
- Publication number
- JP2001089453A JP2001089453A JP26661299A JP26661299A JP2001089453A JP 2001089453 A JP2001089453 A JP 2001089453A JP 26661299 A JP26661299 A JP 26661299A JP 26661299 A JP26661299 A JP 26661299A JP 2001089453 A JP2001089453 A JP 2001089453A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- cycloalkyl
- substituted
- thio
- 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
- 150000001408 amides Chemical class 0.000 title claims abstract description 19
- 125000005553 heteroaryloxy group Chemical group 0.000 title claims abstract description 18
- 230000002070 germicidal effect Effects 0.000 title abstract 3
- 238000003898 horticulture Methods 0.000 title abstract 2
- 239000004480 active ingredient Substances 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000000417 fungicide Substances 0.000 claims description 12
- 230000000855 fungicidal effect Effects 0.000 claims description 11
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 6
- 235000009566 rice Nutrition 0.000 abstract description 6
- 230000006378 damage Effects 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- 230000001276 controlling effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- -1 for example Chemical group 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 125000004149 thio group Chemical group *S* 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000231139 Pyricularia Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000012937 correction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 241000209094 Oryza Species 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001330975 Magnaporthe oryzae Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241000221787 Erysiphe Species 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 150000002170 ethers Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012046 mixed solvent Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical group CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 241000221300 Puccinia Species 0.000 description 2
- 241001361634 Rhizoctonia Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- ODCNAEMHGMYADO-UHFFFAOYSA-N 1,4-dichlorophthalazine Chemical compound C1=CC=C2C(Cl)=NN=C(Cl)C2=C1 ODCNAEMHGMYADO-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000000042 2-butynylthio group Chemical group [H]C([H])([H])C#CC([H])([H])S* 0.000 description 1
- PTDNHYVEBIHJBK-UHFFFAOYSA-M 2-chloro-1,3-dimethylimidazol-1-ium;chloride Chemical compound [Cl-].CN1C=C[N+](C)=C1Cl PTDNHYVEBIHJBK-UHFFFAOYSA-M 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JMTALIXYGZVUFA-UHFFFAOYSA-N 3-amino-3,4-dimethylpentan-2-one;hydrochloride Chemical compound Cl.CC(C)C(C)(N)C(C)=O JMTALIXYGZVUFA-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- ITDVJJVNAASTRS-UHFFFAOYSA-N 4,6-dimethoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC)=NC(S(C)(=O)=O)=N1 ITDVJJVNAASTRS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 101100316860 Autographa californica nuclear polyhedrosis virus DA18 gene Proteins 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- 206010039509 Scab Diseases 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000519995 Stachys sylvatica Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 125000005109 alkynylthio group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 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 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、文献未記載の新規
化合物であるヘテロアリールオキシ(チオ)アルカン酸ア
ミド誘導体及びこれを有効成分として含有する農園芸用
殺菌剤に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a heteroaryloxy (thio) alkanoic acid amide derivative which is a novel compound which has not been described in any literature, and a fungicide for agricultural and horticultural use containing the same as an active ingredient.
【０００２】[0002]
【従来の技術】ある種のヘテロアリールオキシカルボン
酸誘導体が生理活性を有することは知られている。例え
ば、特公昭61-4395公報明細書及び国際公開番号WO93/25
540号公報明細書にはヘテロアリール基がベンゾチアゾ
リル基、2-ピリミジニル基である化合物が除草活性を有
することが示されている。また、特開昭63-132867号公
報明細書には、ヘテロアリール基が2-ピリミジニル基、
キノリル基である化合物が殺菌活性を有することが示さ
れている。しかしながら、これらの化合物の殺菌活性は
満足されるものでなく、本発明化合物のような優れた殺
菌活性を有することについては全く記載されていない。BACKGROUND OF THE INVENTION It is known that certain heteroaryloxycarboxylic acid derivatives have biological activity. For example, Japanese Patent Publication No. 61-4395 and International Publication No.WO93 / 25
No. 540 discloses that a compound in which a heteroaryl group is a benzothiazolyl group or a 2-pyrimidinyl group has herbicidal activity. Further, JP-A-63-132867 discloses that a heteroaryl group is a 2-pyrimidinyl group,
Compounds that are quinolyl groups have been shown to have bactericidal activity. However, the fungicidal activity of these compounds is not satisfactory, and there is no description at all that the compounds of the present invention have excellent fungicidal activity.
【０００３】[0003]
【発明が解決しようとする課題】近年、農園芸用殺菌剤
の多用により薬剤に対する耐性菌が出現し、既存の薬剤
では充分な殺菌活性を示さないことがある。また、環境
問題から低濃度で効率良く有害菌を防除できる新しい殺
菌剤が求められている。In recent years, due to the heavy use of fungicides for agricultural and horticultural use, resistant bacteria have emerged, and existing drugs may not show sufficient bactericidal activity. In addition, a new disinfectant capable of efficiently controlling harmful bacteria at a low concentration is demanded due to environmental problems.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、従来知ら
れた殺菌剤に優る殺菌活性を有する薬剤を開発するため
に、種々の新規なヘテロアリールオキシ(チオ)アルカン
酸アミド誘導体を合成し、その生理活性について検討し
たところ、本発明化合物がイネいもち病等に対して優れ
た殺菌活性を有するとともに、有用作物に対しなんら害
を及ぼさないことを見出し、本発明を完成するに至っ
た。DISCLOSURE OF THE INVENTION The present inventors have synthesized various novel heteroaryloxy (thio) alkanoic acid amide derivatives in order to develop a drug having a bactericidal activity superior to conventionally known bactericides. After examining its physiological activity, it was found that the compound of the present invention has excellent bactericidal activity against rice blast and the like, and found that it did not cause any harm to useful crops, thereby completing the present invention. .
【０００５】すなわち、本発明は、(1)一般式[1]That is, the present invention relates to (1) the general formula [1]
【０００６】[0006]
【化2】 [Formula 2]
【０００７】[式中、WはXnによって置換されてもよいヘ
テロアリール基を表し、Aは酸素原子又は硫黄原子を表
し、R1は水素原子、C1〜C6アルキル基又はC3〜C6シクロ
アルキル基を表し、R2は、C1〜C6アルキル基又はC3〜C6
シクロアルキル基を表し、R3は、C2〜C6アルキル基、C3
〜C6シクロアルキル基(該基はハロゲン原子又はC1〜C6
アルキル基によって置換されていてもよい。)、C3〜C6
シクロアルキルC1〜C6アルキル基又はC1〜C4ハロアルキ
ル基を表すか、あるいはR2とR3は互いに結合してこれら
が結合している炭素原子と共に5員〜7員環のシクロアル
キル基(該基はC1〜C6アルキル基によって置換されてい
てもよい。)を形成し、Qはエチニル基、シアノ基、基−
COR4又は基−CH(OH) R4 を表し、R4はC1〜C6アルキル
基、C1〜C4ハロアルキル基又はC3〜C6シクロアルキル基
(該基はハロゲン原子又はC1〜C6アルキル基によって置
換されていてもよい。)を表し、XはC1〜C6アルキル基、
C2〜C6アルケニル基、C2〜C6アルキニル基、C3〜C6シク
ロアルキル基、C1〜C4ハロアルキル基、C1〜C6アルコキ
シ基、C2〜C6アルケニルオキシ基、C2〜C6アルキニルオ
キシ基、C3〜C6シクロアルキルオキシ基、C1〜C4ハロア
ルコキシ基、C1〜C6アルキルチオ基、C2〜C6アルケニル
チオ基、C2〜C6アルキニルチオ基、C3〜C6シクロアルキ
ルチオ基、C1〜C4ハロアルキルチオ基、ハロゲン原子、
フェニル基(該基はC1〜C6アルキル基、C1〜C4ハロアル
キル基、C1〜C6アルコキシ基、シアノ基又はハロゲン原
子によって置換されていてもよい。) 、シアノ基又はニ
トロ基を表し、nは0〜4の整数を表す。]にて示されるヘ
テロアリールオキシ(チオ)アルカン酸アミド誘導体。
(2)(1)項記載のヘテロアリールオキシ(チオ)アルカン酸
アミド誘導体を有効成分として含有する農園芸用殺菌剤
である。Wherein W represents a heteroaryl group which may be substituted by Xn, A represents an oxygen atom or a sulfur atom, R 1 represents a hydrogen atom, a C 1 -C 6 alkyl group or a C 3 -C represents 6 cycloalkyl group, R 2 is, C 1 -C 6 alkyl or C 3 -C 6
Represents a cycloalkyl group, R 3 is a C 2 -C 6 alkyl group, C 3
-C 6 cycloalkyl group (said group halogen atom or a C 1 -C 6
It may be substituted by an alkyl group. ), C 3 ~C 6
Represents a cycloalkyl C 1 -C 6 alkyl group or a C 1 -C 4 haloalkyl group, or R 2 and R 3 are bonded to each other and a 5- to 7-membered cycloalkyl together with the carbon atom to which they are bonded; group (. said group which may be substituted by C 1 -C 6 alkyl group) to form, Q is ethynyl group, cyano group, group -
COR 4 or a group --CH (OH) R 4 , wherein R 4 is a C 1 -C 6 alkyl group, a C 1 -C 4 haloalkyl group or a C 3 -C 6 cycloalkyl group
(Said group may be substituted by a halogen atom or a C 1 -C 6 alkyl group.) Represents, X is C 1 -C 6 alkyl group,
C 2 -C 6 alkenyl group, C 2 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, C 1 -C 4 haloalkyl groups, C 1 -C 6 alkoxy group, C 2 -C 6 alkenyloxy group, C 2 -C 6 alkynyloxy group, C 3 -C 6 cycloalkyl group, C 1 -C 4 haloalkoxy groups, C 1 -C 6 alkylthio group, C 2 -C 6 alkenylthio group, C 2 -C 6 alkynylthio, C 3 -C 6 cycloalkylthio group, C 1 -C 4 haloalkylthio group, a halogen atom,
Phenyl (in which the group C 1 -C 6 alkyl group, C 1 -C 4 haloalkyl groups, C 1 -C 6 alkoxy group, may be substituted by a cyano group or a halogen atom.), A cyano group or a nitro group And n represents an integer of 0 to 4. And a heteroaryloxy (thio) alkanoic acid amide derivative represented by the formula:
(2) A fungicide for agricultural and horticultural use containing the heteroaryloxy (thio) alkanoic acid amide derivative according to the item (1) as an active ingredient.
【０００８】まず、本明細書において用いられる用語に
ついて、以下説明する。なお、本明細書における、例え
ば「C1〜C6」等の表記は、これに続く置換基の炭素数
が、この場合では1乃至6であることを表している。First, terms used in the present specification will be described below. In the present specification, for example, the notation such as “C 1 -C 6 ” indicates that the number of carbon atoms of the substituent following this is 1 to 6 in this case.
【０００９】ハロゲン原子とは、フッ素原子、塩素原
子、臭素原子及びヨウ素原子を示す。The halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
【００１０】C1〜C6アルキル基とは、直鎖又は分岐鎖状
のアルキル基を示し、例えばメチル基、エチル基、n-プ
ロピル基、イソプロピル基、n-ブチル基、イソブチル
基、sec-ブチル基、tert-ブチル基、n-ペンチル基、イ
ソペンチル基、ネオペンチル基、n-ヘキシル基、イソヘ
キシル基、3，3-ジメチルブチル基等を挙げることがで
きる。The C 1 -C 6 alkyl group means a linear or branched alkyl group, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl. Examples thereof include a butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, and a 3,3-dimethylbutyl group.
【００１１】C3〜C6シクロアルキル基とは、例えばシク
ロプロピル基、シクロペンチル基、シクロヘキシル基等
を挙げることができる。The C 3 -C 6 cycloalkyl group includes, for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and the like.
【００１２】C3〜C6シクロアルキルC1〜C6アルキル基と
は、例えばシクロプロピルメチル基、シクロペンチルメ
チル基、シクロヘキシルメチル基等を挙げることができ
る。The C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group includes, for example, a cyclopropylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group and the like.
【００１３】C1〜C4ハロアルキル基とは、ハロゲン原子
によって置換された、直鎖又は分岐鎖状のアルキル基を
示し、例えばフルオロメチル基、クロロメチル基、ブロ
モメチル基、ジフルオロメチル基、ジクロロメチル基、
ジブロモメチル基、トリフルオロメチル基、クロロジフ
ルオロメチル基、ペンタフルオロエチル基等を挙げるこ
とができる。The C 1 -C 4 haloalkyl group refers to a linear or branched alkyl group substituted by a halogen atom, such as fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl. Group,
Examples thereof include a dibromomethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, and a pentafluoroethyl group.
【００１４】C2〜C6アルケニル基とは、直鎖又は分岐鎖
状のアルケニル基を示し、例えばビニル基、1-プロペニ
ル基、アリル基、イソプロペニル基、1-ブテニル基、2-
ブテニル基等を挙げることができる。The C 2 -C 6 alkenyl group refers to a linear or branched alkenyl group such as a vinyl group, a 1-propenyl group, an allyl group, an isopropenyl group, a 1-butenyl group,
Butenyl groups and the like.
【００１５】C2〜C6アルキニル基とは、直鎖又は分岐鎖
状のアルキニル基を示し、例えばエチニル基、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、4-メチル-1-ペンチニル基、3-メチ
ル-1-ペンチニル基等を挙げることができる。The C 2 -C 6 alkynyl group means a linear or branched alkynyl group such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3 -Butynyl group, 4-methyl-1-pentynyl group, 3-methyl-1-pentynyl group and the like.
【００１６】C1〜C6アルコキシ基とは、直鎖又は分岐鎖
状のアルコキシ基を示し、例えばメトキシ基、エトキシ
基、n-プロポキシ基、イソプロポキシ基、n-ブトキシ
基、イソブトキシ基、sec-ブトキシ基、tert-ブトキシ
基、n-ペンチルオキシ基、イソペンチルオキシ基、n-ヘ
キシルオキシ基等を挙げることができる。The C 1 -C 6 alkoxy group means a linear or branched alkoxy group, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec -Butoxy group, tert-butoxy group, n-pentyloxy group, isopentyloxy group, n-hexyloxy group and the like.
【００１７】C2〜C6アルケニルオキシ基とは、直鎖又は
分岐鎖状のアルケニルオキシ基を示し、例えばアリルオ
キシ基、イソプロペニルオキシ基、2-ブテニルオキシ基
等を挙げることができる。The C 2 -C 6 alkenyloxy group means a linear or branched alkenyloxy group, such as an allyloxy group, an isopropenyloxy group or a 2-butenyloxy group.
【００１８】C2〜C6アルキニルオキシ基とは、直鎖又は
分岐鎖状のアルキニルオキシ基を示し、例えば2-プロピ
ニルオキシ基、2-ブチニルオキシ基、3-ブチニルオキシ
基等を挙げることができる。The C 2 -C 6 alkynyloxy group means a linear or branched alkynyloxy group, such as a 2-propynyloxy group, a 2-butynyloxy group or a 3-butynyloxy group.
【００１９】C3〜C6シクロアルキルオキシ基とは、例え
ばシクロプロピルオキシ基、シクロペンチルオキシ基、
シクロヘキシルオキシ基等を挙げることができる。The C 3 -C 6 cycloalkyloxy group includes, for example, a cyclopropyloxy group, a cyclopentyloxy group,
Examples include a cyclohexyloxy group.
【００２０】C1〜C4ハロアルコキシ基とは、ハロゲン原
子によって置換された、直鎖又は分岐鎖状のアルコキシ
基を示し、例えばフルオロメトキシ基、ジフルオロメト
キシ基、トリフルオロメトキシ基、ペンタフルオロエト
キシ基等を挙げることができる。The C 1 -C 4 haloalkoxy group is a linear or branched alkoxy group substituted by a halogen atom, and is, for example, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a pentafluoroethoxy group. And the like.
【００２１】C1〜C6アルキルチオ基とは、直鎖又は分岐
鎖状のアルキルチオ基を示し、例えばメチルチオ基、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、n-ヘキシルチオ基等を挙げる
ことができる。The C 1 -C 6 alkylthio group means a linear or branched alkylthio group, such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group,
Examples thereof include an n-butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, and an n-hexylthio group.
【００２２】C2〜C6アルケニルチオ基とは、直鎖又は分
岐鎖状のアルケニルチオ基を示し、例えばアリルチオ
基、イソプロペニルチオ基、2-ブテニルチオ基等を挙げ
ることができる。The C 2 -C 6 alkenylthio group means a linear or branched alkenylthio group, such as an allylthio group, an isopropenylthio group or a 2-butenylthio group.
【００２３】C2〜C6アルキニルチオ基とは、直鎖又は分
岐鎖状のアルキニルチオ基を示し、例えば2-プロピニル
チオ基、2-ブチニルチオ基、3-ブチニルチオ基等を挙げ
ることができる。The C 2 -C 6 alkynylthio group means a linear or branched alkynylthio group, such as a 2-propynylthio group, a 2-butynylthio group or a 3-butynylthio group.
【００２４】C3〜C6シクロアルキルチオ基とは、例えば
シクロプロピルチオ基、シクロペンチルチオ基、シクロ
ヘキシルチオ基等を挙げることができる。The C 3 -C 6 cycloalkylthio group includes, for example, a cyclopropylthio group, a cyclopentylthio group, a cyclohexylthio group and the like.
【００２５】C1〜C4ハロアルキルチオ基とは、ハロゲン
原子によって置換された、直鎖又は分岐鎖状のアルキル
チオ基を示し、例えばフルオロメチルチオ基、ジフルオ
ロメチルチオ基、トリフルオロメチルチオ基、ペンタフ
ルオロエチルチオ基等を挙げることができる。The C 1 -C 4 haloalkylthio group is a straight or branched alkylthio group substituted by a halogen atom, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, and pentafluoroethyl. And thio groups.
【００２６】ヘテロアリール基とは、窒素原子、酸素原
子および硫黄原子から選ばれる少なくとも1個のヘテロ
原子を含有する単環又は縮合環を示し、例えば、フリル
基、チエニル基、ピロリル基、ピラゾリル基、イミダゾ
リル基、トリアゾリル基、オキサゾリル基、イソオキサ
ゾリル基、チアゾリル基、イソチアゾリル基、オキサジ
アゾリル基、チアジアゾリル基、ピリミジニル基、ピラ
ジニル基、ピリダジニル基、トリアジニル基、ベンゾフ
リル基、ベンゾチエニル基、インドリル基、インダゾリ
ル基、ベンゾチアゾリル基、ベンゾオキサゾリル基、ベ
ンズイミダゾリル基、キノリル基、イソキノリル基、シ
ンノリニル基、フタラジニル基、キノキサリニル基、ナ
フチリジニル基又はベンゾトリアジニル基を挙げること
ができる。The heteroaryl group is a monocyclic or condensed ring containing at least one heteroatom selected from a nitrogen atom, an oxygen atom and a sulfur atom, for example, a furyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group. , Imidazolyl group, triazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, benzofuryl group, benzothienyl group, indolyl group, indazolyl group, Examples thereof include a benzothiazolyl group, a benzooxazolyl group, a benzimidazolyl group, a quinolyl group, an isoquinolyl group, a cinnolinyl group, a phthalazinyl group, a quinoxalinyl group, a naphthyridinyl group and a benzotriazinyl group.
【００２７】一般式[1]で表される本発明化合物の中に
は、分子内に1個又は2〜3個の不斉炭素原子を有してい
るものもあり、そのような化合物には光学異性体が存在
する。純粋な個々のジアステレオマー、エナンチオマー
及びこれらの混合物も本発明化合物に含まれる。Some of the compounds of the present invention represented by the general formula [1] have one or two or three asymmetric carbon atoms in the molecule. Optical isomers exist. Pure individual diastereomers, enantiomers and mixtures thereof are also included in the compounds of the present invention.
【００２８】[0028]
【発明の実施の形態】一般式[1]で表される本発明化合
物の好ましい化合物としては、Wがチアゾリル基、チア
ジアゾリル基、ピラゾリル基、ピラジニル基、ピリダジ
ニル基、ベンゾチアゾリル基、ベンゾオキサゾリル基、
フタラジニル基又はキノキサリニル基で、R1が水素原
子、メチル基又はエチル基で、Aが酸素原子又は硫黄原
子で、R2がメチル基又はエチル基で、R3がエチル基、n-
プロピル基、イソプロピル基、n-ブチル基、イソブチル
基、sec-ブチル基、tert-ブチル基、シクロプロピル
基、シクロペンチル基又はジクロロメチル基で、Qがエ
チニル基、シアノ基、アセチル基又は1-ヒドロキシエチ
ル基で、Xがメチル基、エチル基、tert-ブチル基、トリ
フルオロメチル基、メトキシ基、フッ素原子、塩素原
子、臭素原子又はフェニル基である化合物を挙げること
ができる。BEST MODE FOR CARRYING OUT THE INVENTION As the preferable compound of the compound of the present invention represented by the general formula [1], W is a thiazolyl group, thiadiazolyl group, pyrazolyl group, pyrazinyl group, pyridazinyl group, benzothiazolyl group, benzoxazolyl group ,
A phthalazinyl group or a quinoxalinyl group, R 1 is a hydrogen atom, a methyl group or an ethyl group, A is an oxygen atom or a sulfur atom, R 2 is a methyl group or an ethyl group, R 3 is an ethyl group, n-
Propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclopropyl group, cyclopentyl group or dichloromethyl group, Q is ethynyl group, cyano group, acetyl group or 1-hydroxy Examples of the ethyl group include compounds in which X is a methyl group, an ethyl group, a tert-butyl group, a trifluoromethyl group, a methoxy group, a fluorine atom, a chlorine atom, a bromine atom or a phenyl group.
【００２９】一般式[1]で示される本発明化合物は、例
えば以下に示す製造法に従って製造することができる。The compound of the present invention represented by the general formula [1] can be produced, for example, according to the following production method.
【００３０】＜製造法1＞<Production Method 1>
【００３１】[0031]
【化3】 Embedded image
【００３２】(式中、W、R1、R2、R3、Q及びAは前記と同
じ意味を表す。) 本発明化合物[1]は、一般式[2]で表されるヘテロアリー
ルオキシ(チオ)アルカン酸類を、必要な場合には触媒及
び／又は塩基の存在下に、縮合剤を用いて一般式[3]で
表されるアミン類と反応させることにより製造すること
ができる。この反応は通常、溶媒中で行われる。(Wherein W, R 1 , R 2 , R 3 , Q and A have the same meanings as described above.) The compound [1] of the present invention is a heteroaryloxy group represented by the general formula [2]: The (thio) alkanoic acids can be produced by reacting with an amine represented by the general formula [3] using a condensing agent, if necessary, in the presence of a catalyst and / or a base. This reaction is usually performed in a solvent.
【００３３】使用できる溶媒としては、反応を阻害しな
い溶媒であればよく、例えばペンタン、ヘキサン、ヘプ
タン、シクロヘキサン、石油エーテル、リグロイン、ベ
ンゼン、トルエン又はキシレン等の炭化水素類、ジクロ
ロメタン、ジクロロエタン、クロロホルム、四塩化炭
素、クロロベンゼン又はジクロロベンゼン等のハロゲン
化炭化水素類、ジエチルエーテル、ジイソプロピルエー
テル、エチレングリコールジメチルエーテル、テトラヒ
ドロフラン又はジオキサン等のエーテル類、アセトン、
メチルエチルケトン、メチルイソプロピルケトン又はメ
チルイソブチルケトン等のケトン類、酢酸メチル又は酢
酸エチル等の酢酸エステル類、アセトニトリル又はプロ
ピオニトリル等のニトリル類、又はジメチルスルホキシ
ド、N,N−ジメチルホルムアミド又はスルホラン等の非
プロトン性極性溶媒、あるいはこれらから選択される溶
媒を組み合わせた混合溶媒を用いることができる。The solvent which can be used may be any solvent which does not inhibit the reaction, for example, hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, benzene, toluene or xylene, dichloromethane, dichloroethane, chloroform, Carbon tetrachloride, halogenated hydrocarbons such as chlorobenzene or dichlorobenzene, diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, ethers such as tetrahydrofuran or dioxane, acetone,
Ketones such as methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone, acetates such as methyl acetate or ethyl acetate, nitriles such as acetonitrile or propionitrile, or non-emulsions such as dimethyl sulfoxide, N, N-dimethylformamide or sulfolane Protic polar solvents or mixed solvents obtained by combining solvents selected from these can be used.
【００３４】縮合剤としては、例えば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、N,
N'−ジシクロヘキシルカルボジイミド、カルボニルジイ
ミダゾール、2−クロロ−1,3−ジメチルイミダゾリウム
クロリド等が挙げられる。これらの縮合剤の使用量は、
特に制限されるものではないが、好ましくは、一般式
[2]で表されるヘテロアリールオキシ(チオ)アルカン酸
類に対して1.0〜2.0当量使用される。As the condensing agent, for example, 1-ethyl-3- (3
-Dimethylaminopropyl) carbodiimide hydrochloride, N,
N'-dicyclohexylcarbodiimide, carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride and the like can be mentioned. The amount of these condensing agents used is
Although not particularly limited, preferably, the compound represented by the general formula
It is used in an amount of 1.0 to 2.0 equivalents to the heteroaryloxy (thio) alkanoic acid represented by [2].
【００３５】触媒としては、例えば4−ジメチルアミノ
ピリジン、1−ヒドロキシベンゾトリアゾール等が挙げ
られる。これらの触媒の使用量は、特に制限されるもの
ではないが、必要な場合には、一般式[2]で表されるヘ
テロアリールオキシ(チオ)アルカン酸類に対して10〜30
モル%使用される。Examples of the catalyst include 4-dimethylaminopyridine, 1-hydroxybenzotriazole and the like. The use amount of these catalysts is not particularly limited, but if necessary, 10 to 30 based on the heteroaryloxy (thio) alkanoic acid represented by the general formula [2].
Used in mole%.
【００３６】塩基としては、この型の反応に一般的に用
いられるものが使用できる。例えば水酸化ナトリウム又
は水酸化カリウム等のアルカリ金属水酸化物、水酸化カ
ルシウム等のアルカリ土類金属水酸化物、炭酸ナトリウ
ム又は炭酸カリウム等のアルカリ金属炭酸塩類、又はト
リエチルアミン、トリメチルアミン、N,N−ジメチルア
ニリン、ピリジン、N−メチルピペリジン、1,5−ジアザ
ビシクロ[4.3.0]ノン−5−エン(DBN)又は1,8−ジアザビ
シクロ[5.4.0]−7−ウンデセン(DBU)等の有機塩基等が
挙げられ、好ましくはトリエチルアミン、ピリジン、N
−メチルピペリジン等の第三級アミン類が挙げられる。
これらの塩基の使用量は、特に制限されるものではない
が、必要な場合には、一般式[2]で表されるヘテロアリ
ールオキシ(チオ)アルカン酸類に対して1.0〜2.0当量使
用される。As the base, those generally used in this type of reaction can be used. For example, alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates such as sodium carbonate or potassium carbonate, or triethylamine, trimethylamine, N, N- Organic bases such as dimethylaniline, pyridine, N-methylpiperidine, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN) or 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) And the like, preferably triethylamine, pyridine, N
Tertiary amines such as -methylpiperidine.
The use amount of these bases is not particularly limited, but if necessary, is used in an amount of 1.0 to 2.0 equivalents to the heteroaryloxy (thio) alkanoic acid represented by the general formula [2]. .
【００３７】一般式[2]で表されるヘテロアリールオキ
シ(チオ)アルカン酸類と一般式[3]で表されるアミン類
は一般的には等モル量使用されるが、どちらか一方を1
〜50モル%過剰に使用することもある。The heteroaryloxy (thio) alkanoic acid represented by the general formula [2] and the amine represented by the general formula [3] are generally used in equimolar amounts.
It may be used in an excess of ~ 50 mol%.
【００３８】反応温度は、−50℃〜150℃の範囲、好ま
しくは0℃〜100℃の範囲において行われる。反応時間は
1〜30時間が好ましい。The reaction is carried out at a temperature ranging from -50 ° C to 150 ° C, preferably from 0 ° C to 100 ° C. The reaction time is
1 to 30 hours is preferred.
【００３９】一般式[2]で表されるヘテロアリールオキ
シ(チオ)アルカン酸類は公知の方法[例えば、国際公開
番号WO98/18766号公報明細書に記載の方法]あるいはそ
れに準じた方法で製造することができる。また、一般式
[3]で表されるアミン類は公知の方法[例えば、オルガニ
ック・シンセセス(Organic Syntheses)、第3巻、第88頁
(1955年)；ジャーナル オブ ザ ケミカル ソサイエ
ティ. パーキン トランザクションズ.1(Journal of th
e Chemical Society. Perkin Transactions.1)、第8
巻、第1645頁(1985年)；ザ ジャーナル オブ オルガ
ニック ケミストリ(The Journal of Organic Chemistr
y)、第49巻、第1208頁(1984年)に記載の方法]あるいは
それに準じた方法で製造することができる。The heteroaryloxy (thio) alkanoic acids represented by the general formula [2] are produced by a known method [for example, the method described in International Publication No. WO98 / 18766] or a method analogous thereto. be able to. Also, the general formula
The amines represented by [3] can be prepared by a known method [for example, Organic Syntheses, Vol. 3, p. 88
(1955); Journal of the Chemical Society. Perkin Transactions. 1 (Journal of th.
e Chemical Society.Perkin Transactions.1), 8th
Vol. 1645 (1985); The Journal of Organic Chemistr
y), Vol. 49, p. 1208 (1984)] or a method analogous thereto.
【００４０】＜製造法2＞<Production method 2>
【００４１】[0041]
【化4】 [Formula 4]
【００４２】(式中、W、R1、R2、R3、Q及びAは前記と同
じ意味を表し、Zはハロゲン原子、C1〜C6アルキルスル
ホニル基、ベンジルスルホニル基等の脱離基を表す。)
本発明化合物[1]は、一般式[4]で表されるヘテロアリー
ル化合物を塩基の存在下に、一般式[5]で表されるアル
カン酸アミド誘導体と反応させることにより製造するこ
とができる。この反応は通常、溶媒中で行われる。使用
できる溶媒としては、製造法1に例示したものと同様の
溶媒を使用する事ができる。(Wherein W, R 1 , R 2 , R 3 , Q and A have the same meanings as described above, and Z is the elimination of a halogen atom, a C 1 -C 6 alkylsulfonyl group, a benzylsulfonyl group, etc.) Represents a group.)
The compound [1] of the present invention can be produced by reacting a heteroaryl compound represented by the general formula [4] with an alkanoic acid amide derivative represented by the general formula [5] in the presence of a base. . This reaction is usually performed in a solvent. As the solvent that can be used, the same solvents as those exemplified in Production Method 1 can be used.
【００４３】塩基としては、この型の反応に一般的に用
いられるものが使用できる。例えば水酸化ナトリウム、
水酸化カリウム、炭酸ナトリウム、炭酸カリウム、重炭
酸ナトリウム、水素化ナトリウム又は水素化カリウム等
の無機塩基、又はトリエチルアミン、トリメチルアミ
ン、N,N−ジメチルアニリン又はピリジン等の有機塩基
等が挙げられる。これらの塩基の使用量は、特に制限さ
れるものではないが、必要な場合には、一般式[4]で表
されるヘテロアリール化合物に対して1.0〜2.0当量使用
される。As the base, those generally used in this type of reaction can be used. For example, sodium hydroxide,
Examples thereof include inorganic bases such as potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydride, and potassium hydride, and organic bases such as triethylamine, trimethylamine, N, N-dimethylaniline, and pyridine. The use amount of these bases is not particularly limited, but if necessary, is used in an amount of 1.0 to 2.0 equivalents to the heteroaryl compound represented by the general formula [4].
【００４４】一般式[4]で表されるヘテロアリール化合
物と一般式[5]で表されるアルカン酸アミド誘導体は一
般的には等モル量使用されるが、どちらか一方を1〜50
モル%過剰に使用することもある。The heteroaryl compound represented by the general formula [4] and the alkanoic acid amide derivative represented by the general formula [5] are generally used in equimolar amounts.
It may be used in a molar excess.
【００４５】反応温度は、−50℃〜150℃の範囲、好ま
しくは0℃〜100℃の範囲において行われる。反応時間は
1〜30時間が好ましい。The reaction is carried out at a temperature ranging from -50 ° C to 150 ° C, preferably from 0 ° C to 100 ° C. The reaction time is
1 to 30 hours is preferred.
【００４６】この反応において一般式[5]で表される化
合物は、例えばハロゲン化アルカン酸ハライド類と一般
式[3]で表されるアミン類とを反応させることで製造す
ることができる。In this reaction, the compound represented by the general formula [5] can be produced, for example, by reacting a halogenated alkanoic acid halide with an amine represented by the general formula [3].
【００４７】＜製造法3＞<Production Method 3>
【００４８】[0048]
【化5】 [Formula 5]
【００４９】(式中、W、R1、R2、R3、Q及びZは前記と同
じ意味を表す。) 本発明化合物[1']は、一般式[6]で表されるヘテロアリ
ール化合物を塩基の存在下に、一般式[7]で表されるア
ルカン酸アミド誘導体と反応させることにより製造する
ことができる。この反応は通常、溶媒中で行われる。(Wherein W, R 1 , R 2 , R 3 , Q and Z have the same meanings as described above). The compound [1 ′] of the present invention is a heteroaryl represented by the general formula [6] The compound can be produced by reacting the compound with an alkanoic acid amide derivative represented by the general formula [7] in the presence of a base. This reaction is usually performed in a solvent.
【００５０】使用できる溶媒は、製造法1に例示したも
のと同様の溶媒を使用する事ができ、塩基は製造法2に
例示したものと同様の塩基を使用することができ、塩基
の使用量は製造法2に例示した使用量と同様でヘテロア
リール化合物に対して1.0〜2.0当量使用される。As the solvent that can be used, the same solvents as those exemplified in Production Method 1 can be used. As the base, the same bases as those exemplified in Production Method 2 can be used. Is used in an amount of 1.0 to 2.0 equivalents to the heteroaryl compound in the same manner as in the use amount exemplified in Production method 2.
【００５１】一般式[6]で表されるヘテロアリール化合
物と一般式[7]で表されるアルカン酸アミド誘導体は一
般的には等モル量使用されるが、どちらか一方を1〜50
モル%過剰に使用することもある。反応温度は、−70℃
〜150℃の範囲、好ましくは−50℃〜100℃の範囲におい
て行われる。反応時間は1〜30時間が好ましい。The heteroaryl compound represented by the general formula [6] and the alkanoic acid amide derivative represented by the general formula [7] are generally used in an equimolar amount.
It may be used in a molar excess. Reaction temperature is -70 ° C
The reaction is carried out at a temperature in the range of -150 ° C, preferably -50 ° C to 100 ° C. The reaction time is preferably 1 to 30 hours.
【００５２】この反応において一般式[7]で表される化
合物は、例えば、一般式[5]で表されるアルカン酸アミ
ド誘導体と酢酸ナトリウムとを反応させて得られるアセ
トキシアルカン酸アミド誘導体を脱アシル化することで
製造することができる。In this reaction, the compound represented by the general formula [7] can be used to remove, for example, an acetoxyalkanoic acid amide derivative obtained by reacting the alkanoic acid amide derivative represented by the general formula [5] with sodium acetate. It can be produced by acylation.
【００５３】＜製造法4＞<Production Method 4>
【００５４】[0054]
【化6】 [Formula 6]
【００５５】(式中、W、R1、R2、R3及びAは前記と同じ
意味を表す。) 本発明化合物[1-2]は一般式[1-1]で表されるヘテロアリ
ールオキシ(チオ)アルカン酸アミド誘導体を、酸の存在
下に水和反応を行うことにより製造することができる。
この反応は無溶媒、又は溶媒中で行われる。(Wherein W, R 1 , R 2 , R 3 and A have the same meaning as described above.) The compound [1-2] of the present invention is a heteroaryl represented by the general formula [1-1] The oxy (thio) alkanoic acid amide derivative can be produced by performing a hydration reaction in the presence of an acid.
This reaction is performed without a solvent or in a solvent.
【００５６】使用できる溶媒としては、反応を阻害しな
い溶媒であればよく、例えばジエチルエーテル、ジイソ
プロピルエーテル、エチレングリコールジメチルエーテ
ル、テトラヒドロフラン又はジオキサン等のエーテル
類、アセトン、メチルエチルケトン、メチルイソプロピ
ルケトン又はメチルイソブチルケトン等のケトン類、酢
酸メチル又は酢酸エチル等の酢酸エステル類、アセトニ
トリル又はプロピオニトリル等のニトリル類、又はジメ
チルスルホキシド、N,N−ジメチルホルムアミド又はス
ルホラン等の非プロトン性極性溶媒、あるいはこれらか
ら選択される溶媒を組み合わせた混合溶媒を用いること
ができる。The solvent which can be used may be any solvent which does not inhibit the reaction, for example, ethers such as diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran or dioxane, acetone, methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone. Ketones, acetates such as methyl acetate or ethyl acetate, nitriles such as acetonitrile or propionitrile, or aprotic polar solvents such as dimethyl sulfoxide, N, N-dimethylformamide or sulfolane, or selected from these. A mixed solvent obtained by combining different solvents can be used.
【００５７】酸としては、例えば硫酸、塩酸、ギ酸等が
挙げられる。これらの酸の使用量は、特に制限されるも
のではないが、一般式[1-2]で表されるヘテロアリール
オキシ(チオ)アルカン酸誘導体に対して5〜50モル%使用
される。Examples of the acid include sulfuric acid, hydrochloric acid, formic acid and the like. The use amount of these acids is not particularly limited, but is used in an amount of 5 to 50 mol% based on the heteroaryloxy (thio) alkanoic acid derivative represented by the general formula [1-2].
【００５８】反応温度は、0℃〜150℃の範囲、好ましく
は20℃〜100℃の範囲において行われる。反応時間は1〜
10時間が好ましい。The reaction is carried out at a temperature ranging from 0 ° C. to 150 ° C., preferably from 20 ° C. to 100 ° C. Reaction time is 1 ~
10 hours is preferred.
【００５９】＜製造法5＞<Production Method 5>
【００６０】[0060]
【化7】 Embedded image
【００６１】(式中、W、R1、R2、R3、R4及びAは前記と
同じ意味を表す。) 本発明化合物[1-4]は、一般式[1-3]で示されるヘテロア
リールオキシ(チオ)アルカン酸アミド誘導体を還元剤と
反応させることにより製造することができる。この反応
は通常、溶媒中で行われる。(Wherein, W, R 1 , R 2 , R 3 , R 4 and A have the same meaning as described above.) The compound [1-4] of the present invention is represented by the general formula [1-3] By reacting the heteroaryloxy (thio) alkanoic acid amide derivative with a reducing agent. This reaction is usually performed in a solvent.
【００６２】使用できる溶媒としては、反応を阻害しな
い溶媒であればよく、例えば、ペンタン、ヘキサン、ヘ
プタン、シクロヘキサン、石油エーテル、リグロイン、
ベンゼン、トルエン、キシレン等の炭化水素類、ジクロ
ロメタン、ジクロロエタン、クロロホルム、四塩化炭
素、クロロベンゼン、ジクロロベンゼン等のハロゲン化
炭化水素類、ジエチルエーテル、ジイソプロピルエーテ
ル、エチレングリコールジメチルエーテル、テトラヒド
ロフラン、ジオキサン等のエーテル類、メタノール、エ
タノール、2−プロパノール等のアルコール類又は、水
とアルコール類との混合溶媒を用いることができる。As a solvent that can be used, any solvent that does not inhibit the reaction may be used, for example, pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin,
Hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, chlorobenzene and dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane , Methanol, ethanol, alcohols such as 2-propanol, or a mixed solvent of water and an alcohol.
【００６３】還元剤としては、この型の反応に一般的に
用いられるものが使用できる。例えば、水素化ホウ素リ
チウム、水素化ホウ素ナトリウム、水素化ホウ素カリウ
ム、トリアルキル水素化ホウ素リチウム、トリアルキル
水素化ホウ素ナトリウム又はシアノ水素化ホウ素ナトリ
ウム等が挙げられ、好ましくは水素化ホウ素ナトリウム
が挙げられる。これらの還元剤の使用量は、特に制限さ
れるものではないが、好ましくは、一般式[1-3]で表さ
れるヘテロアリールオキシ(チオ)アルカン酸アミド誘導
体に対して0.5〜2.0当量使用される。As the reducing agent, those generally used in this type of reaction can be used. For example, lithium borohydride, sodium borohydride, potassium borohydride, lithium trialkylborohydride, sodium trialkylborohydride or sodium cyanoborohydride, and the like, preferably sodium borohydride . The amount of these reducing agents used is not particularly limited, but is preferably 0.5 to 2.0 equivalents based on the heteroaryloxy (thio) alkanoic acid amide derivative represented by the general formula [1-3]. Is done.
【００６４】反応温度は、−70℃〜150℃の範囲、好ま
しくは-20℃〜50℃の範囲において行われる。反応時間
は1〜30時間が好ましい。The reaction is carried out at a temperature ranging from -70 ° C to 150 ° C, preferably from -20 ° C to 50 ° C. The reaction time is preferably 1 to 30 hours.
【００６５】[0065]
【実施例】次に、本発明化合物の製造法を具体的に説明
する。Next, the process for producing the compound of the present invention will be described specifically.
【００６６】＜製造例1＞ 2−[1−(4−クロロフェニル)−3−メチルピラゾール−5
−イルオキシ]−N−(1−シアノ−1,2−ジメチルプロピ
ル)プロピオンアミド(化合物番号A−33)の製造 N,N−ジメチルホルムアミド30mlに1−(4−クロロフェニ
ル)−5−ヒドロキシ−3−メチルピラゾール1.0g、炭酸
カリウム1.0gを加えた。この懸濁液に2−ブロモ−N−(1
−シアノ−1,2−ジメチルプロピル)プロピオンアミド1.
2gを加えた。この混合物を80℃で6時間攪拌した後、水
にあけ、酢酸エチルで抽出した。酢酸エチル層を無水硫
酸マグネシウムで乾燥し、減圧下、酢酸エチルを留去し
た。残渣をシリカゲルカラムクロマトグラフィーで精製
し、目的物0.6gを得た。融点41-44℃<Production Example 1> 2- [1- (4-chlorophenyl) -3-methylpyrazole-5
Preparation of -yloxy] -N- (1-cyano-1,2-dimethylpropyl) propionamide (Compound No.A-33) 1- (4-Chlorophenyl) -5-hydroxy-3 in 30 ml of N, N-dimethylformamide 1.0 g of methylpyrazole and 1.0 g of potassium carbonate were added. To this suspension was added 2-bromo-N- (1
-Cyano-1,2-dimethylpropyl) propionamide 1.
2 g was added. The mixture was stirred at 80 ° C. for 6 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.6 g of the desired product. Melting point 41-44 ℃
【００６７】＜製造例2＞ 2−(4−クロロフタラジン−1−イルオキシ)−N−(1−シ
アノ−1,2,2トリメチルプロピル)プロピオンアミド(化
合物番号P-1,P-2)の製造 N,N−ジメチルホルムアミド30mlに2−ヒドロキシ−N−
(1−シアノ−1,2,2−トリメチルプロピル)プロピオンア
ミド0.9gを溶解した。この溶液に60％水素化ナトリウム
0.11gを加えた。室温で30分攪拌後、1,4−ジクロロフタ
ラジン0.84gを加えた。この混合物を室温で3時間攪拌し
た後、水にあけ、ジエチルエーテルで抽出した。ジエチ
ルエーテル層を無水硫酸マグネシウムで乾燥し、減圧
下、ジエチルエーテルを留去した。残渣をシリカゲルカ
ラムクロマトグラフィーで精製し、目的物0.13g(ジアス
テレオマーA、融点170-172℃)、0.36g(ジアステレオマ
ー混合物、融点182-185℃)を得た。<Production Example 2> 2- (4-Chlorophthalazin-1-yloxy) -N- (1-cyano-1,2,2 trimethylpropyl) propionamide (Compound No. P-1, P-2) Production of 2-hydroxy-N- in 30 ml of N, N-dimethylformamide
0.9 g of (1-cyano-1,2,2-trimethylpropyl) propionamide was dissolved. 60% sodium hydride in this solution
0.11 g was added. After stirring at room temperature for 30 minutes, 0.84 g of 1,4-dichlorophthalazine was added. The mixture was stirred at room temperature for 3 hours, poured into water and extracted with diethyl ether. The diethyl ether layer was dried over anhydrous magnesium sulfate, and diethyl ether was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.13 g (diastereomer A, melting point 170-172 ° C) and 0.36 g (diastereomeric mixture, melting point 182-185 ° C) of the target product.
【００６８】＜製造例3＞ 2−(ベンゾチアゾール−2−イルオキシ)−N−(1−イソ
プロピル−1−メチル−2−オキソプロピル)プロピオン
アミド(化合物番号J-14)の製造 テトラヒドロフラン20mlに2−(ベンゾチアゾール−2−
イルオキシ)プロピオン酸0.5g、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0.5gを加
えた。室温で30分間攪拌後、3−アミノ−3,4−ジメチル
−2−ペンタノン塩酸塩0.4g、トリエチルアミン0.2gを
加えた。この混合物を室温で16時間攪拌した後、水にあ
け、酢酸エチルで抽出した。酢酸エチル層を無水硫酸マ
グネシウムで乾燥し、減圧下、酢酸エチルを留去した。
残渣をシリカゲルカラムクロマトグラフィーで精製し、
目的物0.6gを得た。融点133-136℃<Production Example 3> Production of 2- (benzothiazol-2-yloxy) -N- (1-isopropyl-1-methyl-2-oxopropyl) propionamide (Compound No. J-14) 2 to 20 ml of tetrahydrofuran -(Benzothiazole-2-
0.5 g of yloxy) propionic acid and 0.5 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride were added. After stirring at room temperature for 30 minutes, 0.4 g of 3-amino-3,4-dimethyl-2-pentanone hydrochloride and 0.2 g of triethylamine were added. The mixture was stirred at room temperature for 16 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure.
The residue was purified by silica gel column chromatography,
0.6 g of the desired product was obtained. 133-136 ° C
【００６９】＜製造例4＞ 2−(ベンゾチアゾール−2−イルオキシ)−N−(2−ヒド
ロキシ−1−イソプロピル−1−メチルプロピル)プロピ
オンアミド(化合物番号J-15)の製造 メタノール10mlに2−(ベンゾチアゾール−2−イルオキ
シ)−N−(1−イソプロピル−1−メチル−2−オキソプロ
ピル)プロピオンアミド0.35gを溶解した。この溶液に水
素化ホウ素ナトリウム0.08gを氷冷下で加えた。この混
合物を室温で5時間攪拌した後、水にあけ、酢酸エチル
で抽出した。酢酸エチル層を無水硫酸マグネシウムで乾
燥した後、減圧下、酢酸エチルを留去し、目的物0.2gを
得た。屈折率1.5525(20℃)<Production Example 4> Production of 2- (benzothiazol-2-yloxy) -N- (2-hydroxy-1-isopropyl-1-methylpropyl) propionamide (Compound No. J-15) 0.35 g of-(benzothiazol-2-yloxy) -N- (1-isopropyl-1-methyl-2-oxopropyl) propionamide was dissolved. To this solution, sodium borohydride (0.08 g) was added under ice cooling. The mixture was stirred at room temperature for 5 hours, poured into water and extracted with ethyl acetate. After drying the ethyl acetate layer with anhydrous magnesium sulfate, the ethyl acetate was distilled off under reduced pressure to obtain 0.2 g of the desired product. Refractive index 1.5525 (20 ℃)
【００７０】＜製造例5＞ 2−(4,6−ジメトキシピリミジン−2−イルオキシ)−N−
(1−イソプロピル−1−メチル−2−プロピニル)プロピ
オンアミド(化合物番号F−10)の製造 テトラヒドロフラン30mlに2−ヒドロキシ−N−(1−イソ
プロピル−1−メチル−2−プロピニル)プロピオンアミ
ド0.8gを溶解した。この溶液に60％水素化ナトリウム0.
18gを加えた。室温で30分攪拌後、2−メチルスルホニル
−4,6−ジメトキシピリミジン1.0gを加えた。この混合
物を室温で4時間攪拌した後、水にあけ、酢酸エチルで
抽出した。酢酸エチル層を無水硫酸マグネシウムで乾燥
し、減圧下、酢酸エチルを留去した。残渣をシリカゲル
カラムクロマトグラフィーで精製し、目的物0.6gを得
た。融点98-101℃<Production Example 5> 2- (4,6-dimethoxypyrimidin-2-yloxy) -N-
Production of (1-isopropyl-1-methyl-2-propynyl) propionamide (Compound No.F-10) 0.8 g of 2-hydroxy-N- (1-isopropyl-1-methyl-2-propynyl) propionamide in 30 ml of tetrahydrofuran Was dissolved. Add 60% sodium hydride to this solution.
18g was added. After stirring at room temperature for 30 minutes, 1.0 g of 2-methylsulfonyl-4,6-dimethoxypyrimidine was added. The mixture was stirred at room temperature for 4 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.6 g of the desired product. Melting point 98-101 ° C
【００７１】＜製造例6＞ 2−(4,6−ジメトキシピリミジン−2−イルオキシ)−N−
(1−イソプロピル−1−メチル−2−オキソプロピル)プ
ロピオンアミド(化合物番号F−11)の製造 アセトニトリル40mlに2−(4,6−ジメトキシピリミジン
−2−イルオキシ)−N−(1−イソプロピル−1−メチル−
2−プロピニル)プロピオンアミド0.4g、10％塩酸5mlを
加えた。この混合物を還流下2時間攪拌した後、水にあ
け、酢酸エチルで抽出した。酢酸エチル層を無水硫酸マ
グネシウムで乾燥し、減圧下、酢酸エチルを留去した。
残渣をシリカゲルカラムクロマトグラフィーで精製し、
目的物0.2gを得た。融点103-106℃ 次に、一般式[1]で表される本発明化合物の具体例及び
実施例を表1〜表19に示すが、これらに限られるもので
はない。<Production Example 6> 2- (4,6-dimethoxypyrimidin-2-yloxy) -N-
Preparation of (1-isopropyl-1-methyl-2-oxopropyl) propionamide (Compound No.F-11) 2- (4,6-dimethoxypyrimidin-2-yloxy) -N- (1-isopropyl-) was added to 40 ml of acetonitrile. 1-methyl-
0.4 g of 2-propynyl) propionamide and 5 ml of 10% hydrochloric acid were added. The mixture was stirred under reflux for 2 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure.
The residue was purified by silica gel column chromatography,
0.2 g of the desired product was obtained. Melting point: 103-106 ° C. Next, specific examples and examples of the compound of the present invention represented by the general formula [1] are shown in Tables 1 to 19, but are not limited thereto.
【００７２】表中の記号はそれぞれ以下の意味を示す。
Meとはメチル基を示し、Etとはエチル基を示し、Prとは
n-プロピル基を示し、Pr-iとはイソプロピル基を示し、
Buとはn-ブチル基を示し、Bu-iとはイソブチル基を示
し、Bu-sとはsec-ブチル基を示し、Bu-tとはtert-ブチ
ル基を示し、Pr-cとはシクロプロピル基を示し、Pen-c
とはシクロペンチル基を示し、Phとはフェニル基を示
す。また、例えばPh(4-Cl)とは4-クロロフェニル基を示
す。The symbols in the table have the following meanings.
Me represents a methyl group, Et represents an ethyl group, and Pr represents
represents an n-propyl group, Pr-i represents an isopropyl group,
Bu represents an n-butyl group, Bu-i represents an isobutyl group, Bu-s represents a sec-butyl group, Bu-t represents a tert-butyl group, and Pr-c represents cyclobutyl group. A propyl group, Pen-c
Represents a cyclopentyl group, and Ph represents a phenyl group. Further, for example, Ph (4-Cl) indicates a 4-chlorophenyl group.
【００７３】なお、異性体AとはジアステレオマーA、異
性体BとはジアステレオマーBをそれぞれ表し、異性体M
とはジアステレオマー混合物を表す。ジアステレオマー
Aとはシリカゲルカラムクロマトグラフィー又は高速液
体クロマトグラフィー等によって分離された低極性のジ
アステレオマーを示し、ジアステレオマーBとは同様に
分離された高極性のジアステレオマーを示す。It should be noted that isomer A represents diastereomer A, isomer B represents diastereomer B, and isomer M
Represents a diastereomer mixture. Diastereomer
A indicates a low-polarity diastereomer separated by silica gel column chromatography or high-performance liquid chromatography, and diastereomer B indicates a high-polarity diastereomer similarly separated.
【００７４】[0074]
【表1】 【table 1】
【００７５】[0075]
【表2】 [Table 2]
【００７６】[0076]
【表3】 [Table 3]
【００７７】[0077]
【表4】 [Table 4]
【００７８】[0078]
【表5】 [Table 5]
【００７９】[0079]
【表6】 [Table 6]
【００８０】[0080]
【表7】 [Table 7]
【００８１】[0081]
【表8】 [Table 8]
【００８２】[0082]
【表9】 [Table 9]
【００８３】[0083]
【表10】 [Table 10]
【００８４】[0084]
【表11】 [Table 11]
【００８５】[0085]
【表12】 [Table 12]
【００８６】[0086]
【表13】 [Table 13]
【００８７】[0087]
【表14】 [Table 14]
【００８８】[0088]
【表15】 [Table 15]
【００８９】[0089]
【表16】 [Table 16]
【００９０】[0090]
【表17】 [Table 17]
【００９１】[0091]
【表18】 [Table 18]
【００９２】[0092]
【表19】 [Table 19]
【００９３】本発明の農園芸用殺菌剤は、一般式［１］
で示されるヘテロアリールオキシ（チオ）アルカン酸ア
ミド誘導体を有効成分として含有してなる。本発明化合
物を農園芸用殺菌剤として使用する場合には、その目的
に応じて有効成分を適当な剤型で用いることができる。
通常は有効成分を不活性な液体または固体の担体で希釈
し、必要に応じて界面活性剤、その他をこれに加え、粉
剤、水和剤、乳剤、粒剤等の製剤形態で使用できる。有
効成分の配合割合は必要に応じ適宜選ばれるが、粉剤及
び粒剤とする場合は０．１〜２０％（重量）、また、乳
剤及び水和剤とする場合は５〜８０％（重量）が適当で
ある。The fungicide for agricultural and horticultural use of the present invention has the general formula [1]
The heteroaryloxy (thio) alkanoic acid amide derivative represented by these is contained as an active ingredient. When the compound of the present invention is used as an agricultural and horticultural fungicide, the active ingredient can be used in an appropriate dosage form according to the purpose.
Usually, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant and the like can be added to the active ingredient to be used in the form of powders, wettable powders, emulsions, granules and the like. The compounding ratio of the active ingredient is appropriately selected as required, but is 0.1 to 20% (by weight) in the case of powders and granules, and 5 to 80% (by weight) in the case of emulsions and wettable powders. Is appropriate.
【００９４】好適な担体としては、例えばタルク、ベン
トナイト、クレー、カオリン、珪藻土、ホワイトカーボ
ン、バーミキュライト、消石灰、珪砂、硫安、尿素等の
固体担体、イソプロピルアルコール、キシレン、シクロ
ヘキサノン、メチルナフタレン等の液体担体等があげら
れる。界面活性剤及び分散剤としては、例えばジナフチ
ルメタンスルホン酸塩、アルコール硫酸エステル塩、ア
ルキルアリールスルホン酸塩、リグニンスルホン酸塩、
ポリオキシエチレングリコールエーテル、ポリオキシエ
チレンアルキルアリールエーテル、ポリオキシエチレン
ソルビタンモノアルキレート等があげられる。補助剤と
してはカルボキシメチルセルロース等があげられる。Suitable carriers include, for example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. And the like. As the surfactant and dispersant, for example, dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate,
Polyoxyethylene glycol ether, polyoxyethylene alkyl aryl ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned. Examples of the auxiliary include carboxymethyl cellulose.
【００９５】本発明の農園芸用殺菌剤は、これらの製剤
をそのまま、あるいは希釈して茎葉散布、種子処理、土
壌施用、水面施用または育苗箱施用等により使用するこ
とができる。これらの施用量は、使用される化合物の種
類、対象病害、発生傾向、被害の程度、環境条件、使用
する剤型などによって変動する。例えば粉剤及び粒剤の
ようにそのまま使用する場合には、有効成分で１０アー
ル当り０．１ｇ〜５ｋｇ、好ましくは１ｇ〜１ｋｇの範
囲から適宜選ぶのがよい。また、乳剤及び水和剤のよう
に液状で使用する場合には、０．１ｐｐｍ〜１０，００
０ｐｐｍ、好ましくは１０〜３，０００ｐｐｍの範囲か
ら適宜選ぶのがよい。The fungicide for agricultural and horticultural use of the present invention can be used by spraying foliage, seed treatment, soil application, water surface application or nursery box application, or the like after diluting these preparations. These application rates vary depending on the type of compound used, the target disease, the occurrence tendency, the degree of damage, environmental conditions, the dosage form used, and the like. For example, when used as such as powders and granules, the active ingredient may be appropriately selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. When used in the form of a liquid such as an emulsion and a wettable powder, 0.1 ppm to 10,000 ppm is used.
It is appropriate to appropriately select from the range of 0 ppm, preferably 10 to 3,000 ppm.
【００９６】本発明による化合物は上記の施用形態によ
り、藻菌類（Ｏｏｍｙｃｅｔｅｓ）、子嚢菌類（Ａｓｃ
ｏｍｙｃｅｔｅｓ）、担子菌類（Ｂａｓｉｄｉｏｍｙｃ
ｅｔｅｓ）、及び不完全菌類（Ｄｅｕｔｅｒｏｍｙｃｅ
ｔｅｓ）に属する菌に起因する植物の病害を防除でき
る。次に、具体的な菌名を非限定例としてあげる。シュ
ウドペロノスポラ（Ｐｓｅｕｄｏｐｅｒｏｎｏｓｐｏｒ
ａ）属菌、例えばキュウリべと病菌（Ｐｓｅｕｄｏｐｅ
ｒｏｎｏｓｐｏｒａ ｃｕｂｅｎｓｉｓ）、ベンチュリ
ア（Ｖｅｎｔｕｒｉａ）属菌、例えばリンゴ黒星病菌
（Ｖｅｎｔｕｒｉａｉｎａｅｑｕａｌｉｓ）、エリシフ
ェ（Ｅｒｙｓｉｐｈｅ）属菌、例えばコムギうどんこ病
菌（Ｅｒｙｓｉｐｈｅ ｇｒａｍｉｎｉｓ）、ピリキュ
ラリア（Ｐｙｒｉｃｕｌａｒｉａ）属菌、例えばイネい
もち病菌（Ｐｙｒｉｃｕｌａｒｉａｏｒｙｚａｅ）、ボ
トリチス（Ｂｏｔｒｙｔｉｓ）属菌、例えばキュウリ灰
色かび病菌（Ｂｏｔｒｙｔｉｓ ｃｉｎｅｒｅａ）、リ
ゾクトニア（Ｒｈｉｚｏｃｔｏｎｉａ）属菌、例えばイ
ネ紋枯病菌（Ｒｈｉｚｏｃｔｏｎｉａ ｓｏｌａｎ
ｉ）、パクシニア（Ｐｕｃｃｉｎｉａ）属菌、例えばコ
ムギ赤さび病菌（Ｐｕｃｃｉｎｉａ ｒｅｃｏｎｄｉｔ
ａ）。The compounds according to the invention can be used according to the above-mentioned application forms, for example, algal fungi (Oomycetes), ascomycetes (Asc)
omycetes), Basidiomyc
etes), and Deuteromyce
tes) can be controlled. Next, specific bacterial names are given as non-limiting examples. Pseudoperonospora
a) Genus bacteria such as cucumber downy mildew (Pseudope)
ronospora cubensis, Venturia genus bacteria, such as apple scab fungus (Venturiainaequalis), Erysiphe genus bacteria, such as wheat powdery mildew (Erysiphe graminii), Pyricularia (Pyricularia (Pyricularia), Pyricularia (Pyricularia (Pyricularia)) , Botrytis spp., For example, Botrytis cinerea, Rhizoctonia spp., For example, Rhizoctonia solan
i) a bacterium of the genus Puccinia, for example, Puccinia recondit
a).
【００９７】さらに、本発明の化合物は必要に応じて殺
虫剤、他の殺菌剤、除草剤、植物生長調節剤、肥料等と
混合してもよい。次に、本発明の農園芸用殺菌剤の代表
的な製剤例をあげて、製剤方法を具体的に説明する。以
下の説明において「％」は重量百分率を示す。Further, the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary. Next, the formulation method will be specifically described with reference to typical formulation examples of the agricultural and horticultural fungicides of the present invention. In the following description, “%” indicates weight percentage.
【００９８】製剤例１ 粉剤 化合物（Ｊ−１４）２％、珪藻土５％及びクレ−９３％
を均一に混合粉砕して粉剤とした。Formulation Example 1 Dust 2% of compound (J-14), 5% of diatomaceous earth and 93% of clay
Was uniformly mixed and pulverized to obtain a powder.
【００９９】製剤例２ 水和剤 化合物（Ｊ−１４）５０％、珪藻土４５％、ジナフチル
メタンジスルホン酸ナトリウム２％及びリグニンスルホ
ン酸ナトリウム３％を均一に混合粉砕して水和剤とし
た。Formulation Example 2 Wettable powder 50% of the compound (J-14), 45% of diatomaceous earth, 2% of sodium dinaphthylmethanedisulfonate and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to obtain a wettable powder.
【０１００】製剤例３ 乳剤 化合物（Ｊ−１４）３０％、シクロヘキサノン２０％、
ポリオキシエチレンアルキルアリールエーテル１１％、
アルキルベンゼンスルホン酸カルシウム４％及びメチル
ナフタリン３５％を均一に溶解して乳剤とした。Formulation Example 3 Emulsion 30% of compound (J-14), 20% of cyclohexanone,
11% polyoxyethylene alkyl aryl ether,
An emulsion was prepared by uniformly dissolving 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene.
【０１０１】製剤例４ 粒剤 化合物（Ｊ−１４）５％、ラウリルアルコール硫酸エス
テルのナトリウム塩２％、リグニンスルホン酸ナトリウ
ム５％、カルボキシメチルセルロース２％及びクレー８
６％を均一に混合粉砕する。この混合物に水２０％相当
量を加えて練合し、押出式造粒機を用いて１４〜３２メ
ッシュの粒状に加工したのち、乾燥して粒剤とした。Formulation Example 4 Granules Compound (J-14) 5%, lauryl alcohol sulfate sodium salt 2%, lignin sulfonate sodium 5%, carboxymethyl cellulose 2% and clay 8
6% is uniformly mixed and pulverized. The mixture was kneaded by adding an amount of water equivalent to 20%, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules.
【０１０２】次に、本発明の農園芸用殺菌剤の奏する効
果を試験例をあげて具体的に説明する。Next, the effects of the fungicide for agricultural and horticultural use according to the present invention will be specifically described with reference to test examples.
【０１０３】試験例１ イネいもち病予防効果試験 直径７ｃｍの素焼鉢各々に、イネ種子（品種：愛知旭）
を１５粒ずつ播種し、温室内で育成した。第４葉が完全
に展開したイネ苗に、製剤例２に準じて調製した水和剤
を、有効成分濃度が５００ｐｐｍになるように水で希釈
し、１鉢当り１０ｍｌ散布した。風乾後、イネいもち病
菌（Ｐｙｒｉｃｕｌａｒｉａ ｏｒｙｚａｅ）の分生胞
子懸濁液を噴霧接種し、直ちに２５℃の湿室内に２４時
間入れた。その後温室内に移し、接種５日後に第４葉の
病斑数を調査した。数１により防除価を求め、表２０の
基準により評価した。結果を表２１に示した。Test Example 1 Rice Blast Prevention Effect Test Rice seeds (variety: Asahi Aichi) were placed in each of the unglazed pots having a diameter of 7 cm.
Were seeded at a time and grown in a greenhouse. The wettable powder prepared in accordance with Formulation Example 2 was diluted with water so that the active ingredient concentration became 500 ppm, and sprayed 10 ml per pot onto the rice seedling in which the fourth leaf had completely developed. After air-drying, a conidia suspension of rice blast fungus (Pyricularia oryzae) was spray-inoculated and immediately placed in a 25 ° C moist chamber for 24 hours. Thereafter, they were transferred to a greenhouse, and the number of lesions on the fourth leaf was examined 5 days after the inoculation. The control value was calculated according to Equation 1, and evaluated according to the criteria shown in Table 20. The results are shown in Table 21.
【０１０４】[0104]
【数１】 (Equation 1)
【０１０５】[0105]
【表２０】 [Table 20]
【０１０６】[0106]
【表２１】 [Table 21]
【０１０７】試験例２ イネいもち病水面施用試験 直径９ｃｍの白磁鉢に１．５葉期の水稲（品種：愛知
旭）稚苗を３茎ずつ４カ所に移植し、温室内で育成し
た。２．５葉期に製剤例２に準じて調製した水和剤を有
効成分濃度が１０アールあたり1００ｇになるように鉢
に水面施用処理をした。処理１０日後に、イネいもち病
菌（Ｐｙｒｉｃｕｌａｒｉａ ｏｒｙｚａｅ）の分生胞
子懸濁液を噴霧接種し、直ちに２５℃の湿室内に２４時
間入れた。その後、温室内に移し、接種５日後に接種時
の最高位葉の病斑数を調査した。数１により防除価を求
め、表２０の基準により評価した結果を表２２に示し
た。Test Example 2 Rice Blast Water Surface Application Test Rice seedlings (variety: Aichi Asahi) at the 1.5 leaf stage were transplanted into four white spots each at four locations in a white porcelain bowl having a diameter of 9 cm and grown in a greenhouse. The wettable powder prepared according to Formulation Example 2 at the 2.5 leaf stage was subjected to water application to the pot such that the active ingredient concentration was 100 g per 10 ares. Ten days after the treatment, a conidia spore suspension of rice blast fungus (Pyricularia oryzae) was spray-inoculated and immediately placed in a 25 ° C moist chamber for 24 hours. Then, they were transferred to a greenhouse, and five days after the inoculation, the number of lesions on the highest leaf at the time of the inoculation was examined. The control value was determined by Equation 1 and the results of evaluation based on the criteria in Table 20 are shown in Table 22.
【０１０８】[0108]
【表２２】 [Table 22]
【０１０９】試験例３ コムギうどんこ病予防効果試験 直径６ｃｍのプラスチックポット各々に、コムギ種子
（品種：農林６１号）を１０粒づつ播種し、温室内で育
成した。２葉が展開したコムギ苗に、製剤例２に準じて
調製した水和剤を、有効成分濃度が５００ｐｐｍになる
ように水で希釈し、１ポット当たり１０ｍｌ散布した。
風乾後、コムギうどんこ病菌（Ｅｒｙｓｉｐｈｅ ｇｒ
ａｍｉｎｉｓ）の胞子を接種し、温室内で管理した。接
種１０日後にポット全体の第１葉の発病面積を調査し、
表２３の基準により評価した。結果を表２４に示した。Test Example 3 Wheat Powdery Mildew Prevention Effect Test 10 plastic seeds (variety: Norin 61) were sowed in each plastic pot having a diameter of 6 cm, and grown in a greenhouse. A wettable powder prepared according to Formulation Example 2 was diluted with water so that the active ingredient concentration became 500 ppm, and sprayed 10 ml per pot onto the wheat seedling having two leaves developed.
After air-drying, wheat powdery mildew (Erysiphe gr)
aminis) and inoculated in a greenhouse. Ten days after inoculation, the diseased area of the first leaf of the entire pot was investigated,
The evaluation was made according to the criteria in Table 23. The results are shown in Table 24.
【０１１０】[0110]
【表２３】 [Table 23]
【０１１１】[0111]
【表２４】 [Table 24]
【０１１２】[0112]
【発明の効果】本発明の農園芸用殺菌剤は、イネいもち
病、コムギうどんこ病等に対して高い防除効果を有し、
しかも、作物に薬害を生ずることなく、残効性、耐雨性
に優れるという特徴をも併せ持っているため、農園芸用
殺菌剤として有用である。EFFECT OF THE INVENTION The agricultural and horticultural fungicide of the present invention has a high control effect on rice blast, wheat powdery mildew, etc.
In addition, it is useful as an agricultural and horticultural fungicide because it also has characteristics that it does not cause harm to crops and has excellent residual effect and rain resistance.
─────────────────────────────────────────────────────
────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成１２年９月１８日（２０００．９．１
８）[Submission Date] September 18, 2000 (2009.1)
8)
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】請求項３[Correction target item name] Claim 3
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【手続補正２】[Procedure amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】請求項４[Correction target item name] Claim 4
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ａ０１Ｎ 43/56 Ａ０１Ｎ 43/56 Ｄ 43/58 43/58 Ａ Ｅ 43/60 43/60 １０１ １０１ 43/653 43/653 Ｎ 43/66 43/66 43/76 １０１ 43/76 １０１ 43/78 43/78 Ｃ １０１ １０１ 43/824 Ｃ０７Ｄ 231/20 Ｚ 43/836 235/26 Ｃ０７Ｄ 231/20 237/32 235/26 239/34 237/32 239/46 239/34 241/18 239/46 241/44 241/18 249/12 ５０２ 241/44 251/30 249/12 ５０２ 263/58 251/30 277/34 263/58 277/36 277/34 277/68 277/36 277/74 277/68 285/08 277/74 Ａ０１Ｎ 43/82 １０１Ｂ 285/08 １０４ 285/13 Ｃ０７Ｄ 285/12 Ｃ (72)発明者 松本 克則 静岡県磐田郡福田町塩新田408番地の１ 株式会社ケイ・アイ研究所内 (72)発明者 米倉 範久 静岡県磐田郡福田町塩新田408番地の１ 株式会社ケイ・アイ研究所内 (72)発明者 古瀬 勝美 静岡県小笠郡菊川町加茂1809番地 (72)発明者 豊島 淳 静岡県小笠郡菊川町加茂1809番地 (72)発明者 熊倉 和夫 静岡県磐田郡豊田町森下1013番地の６ (72)発明者 村松 憲通 静岡県掛川市葛ヶ丘３丁目15番地の11 Ｆターム(参考） 4C031 EA03 4C033 AD11 AD12 AE08 AE10 AE17 4C036 AD05 AD08 AD19 4C056 AA01 AB01 AC02 AD03 AE03 AF05 CA06 4H011 AA01 BA01 BB09 BB10 BC05 BC07 BC19 BC20 DA02 DA15 DA16 DD01 DD03 DD04 DH03──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) A01N 43/56 A01N 43/56 D 43/58 43/58 AE43 / 60 43/60 101 101 43 / 653 43/653 N 43/66 43/66 43/76 101 43/76 101 43/78 43/78 C 101 101 43/824 C07D 231/20 Z 43/836 235/26 C07D 231/20 237/32 235 / 26 239/34 237/32 239/46 239/34 241/18 239/46 241/44 241/18 249/12 502 241/44 251/30 249/12 502 263/58 251/30 277/34 263 / 58 277/36 277/34 277/68 277/36 277/74 277/68 285/08 277/74 A01N 43/82 101B 285/08 104 285/13 C07D 285/12 C (72) Inventor Katsunori Matsumoto 408-1, Shioda, Fukuda-cho, Iwata-gun, Shizuoka Prefecture Inside the K.I. Research Institute Co., Ltd. (72) Inventor Norihisa Yonekura 408-1, Shioda, Fukuda-cho, Iwata-gun, Shizuoka (72) Katsumi Furuse, Inventor 1809, Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Atsushi Jun, 1809, Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Kazuo Kumakura, Toyota, Iwata-gun, Shizuoka Prefecture 1013, Morishita 6-72 (72) Inventor: Kenmichi Muramatsu 3-15, Kuzugaoka, Kakegawa-shi, Shizuoka 11F term (reference) 4C031 EA03 4C033 AD11 AD12 AE08 AE10 AE17 4C036 AD05 AD08 AD19 4C056 AA01 AB01 AC02 AD03 AE03 AF05 CA06 4H011 AA01 BA01 BB09 BB10 BC05 BC07 BC19 BC20 DA02 DA15 DA16 DD01 DD03 DD04 DH03
Claims (5)
基を表し、Aは酸素原子又は硫黄原子を表し、R1は水素
原子、C1〜C6アルキル基又はC3〜C6シクロアルキル基を
表し、R2は、C1〜C6アルキル基又はC3〜C6シクロアルキ
ル基を表し、R3は、C2〜C6アルキル基、C3〜C6シクロア
ルキル基(該基はハロゲン原子又はC1〜C6アルキル基に
よって置換されていてもよい。)、C3〜C6シクロアルキ
ルC1〜C6アルキル基又はC1〜C4ハロアルキル基を表す
か、あるいはR2とR3は互いに結合してこれらが結合して
いる炭素原子と共に5員〜7員環のシクロアルキル基(該
基はC1〜C6アルキル基によって置換されていてもよ
い。)を形成し、Qはエチニル基、シアノ基、基−COR4又
は基−CH(OH) R4 を表し、R4はC1〜C6アルキル基、C1〜
C4ハロアルキル基又はC3〜C6シクロアルキル基(該基は
ハロゲン原子又はC1〜C6アルキル基によって置換されて
いてもよい。)を表し、XはC1〜C6アルキル基、C2〜C6ア
ルケニル基、C2〜C6アルキニル基、C3〜C6シクロアルキ
ル基、C1〜C4ハロアルキル基、C1〜C6アルコキシ基、C2
〜C6アルケニルオキシ基、C2〜C6アルキニルオキシ基、
C3〜C6シクロアルキルオキシ基、C1〜C4ハロアルコキシ
基、C1〜C6アルキルチオ基、C2〜C6アルケニルチオ基、
C2〜C6アルキニルチオ基、C3〜C6シクロアルキルチオ
基、C1〜C4ハロアルキルチオ基、ハロゲン原子、フェニ
ル基(該基はC1〜C6アルキル基、C1〜C4ハロアルキル
基、C1〜C6アルコキシ基、シアノ基又はハロゲン原子に
よって置換されていてもよい。) 、シアノ基又はニトロ
基を表し、nは0〜4の整数を表す。]にて示されるヘテロ
アリールオキシ(チオ)アルカン酸アミド誘導体。[Claim 1] General formula [1] Wherein, W is represents a heteroaryl group optionally substituted by Xn, A represents an oxygen atom or a sulfur atom, R 1 represents a hydrogen atom, C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl R 2 represents a C 1 -C 6 alkyl group or a C 3 -C 6 cycloalkyl group, and R 3 represents a C 2 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group (the group May be substituted with a halogen atom or a C 1 -C 6 alkyl group.), A C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group or a C 1 -C 4 haloalkyl group, or R 2 And R 3 combine with each other to form a 5- to 7-membered cycloalkyl group (which may be substituted by a C 1 -C 6 alkyl group) together with the carbon atom to which they are attached. , Q is ethynyl group, a cyano group, a group -COR 4 or a group -CH (OH) R 4, R 4 is C 1 -C 6 alkyl group, C 1 ~
C 4 haloalkyl group or C 3 -C 6 cycloalkyl group (said group may be substituted by a halogen atom or a C 1 -C 6 alkyl group.), X is C 1 -C 6 alkyl groups, C 2 -C 6 alkenyl group, C 2 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, C 1 -C 4 haloalkyl groups, C 1 -C 6 alkoxy group, C 2
-C 6 alkenyloxy group, C 2 -C 6 alkynyloxy group,
C 3 -C 6 cycloalkyl group, C 1 -C 4 haloalkoxy groups, C 1 -C 6 alkylthio group, C 2 -C 6 alkenylthio group,
C 2 -C 6 alkynylthio, C 3 -C 6 cycloalkylthio group, C 1 -C 4 haloalkylthio group, a halogen atom, a phenyl group (said group C 1 -C 6 alkyl group, C 1 -C 4 haloalkyl A C 1 -C 6 alkoxy group, a cyano group or a halogen atom.), A cyano group or a nitro group, and n represents an integer of 0-4. And a heteroaryloxy (thio) alkanoic acid amide derivative represented by the formula:
ラゾリル基、トリアゾリル基、オキサゾリル基、イソオ
キサゾリル基、チアゾリル基、イソチアゾリル基、オキ
サジアゾリル基、チアジアゾリル基、ピラジニル基、ピ
リダジニル基、インドリル基、インダゾリル基、ベンゾ
チアゾリル基、ベンゾオキサゾリル基、ベンズイミダゾ
リル基、イソキノリル基、シンノリニル基、フタラジニ
ル基、キノキサリニル基又はナフチリジニル基であり、
Qがシアノ基である請求項1に記載の化合物。2. A pyrazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, and an indazolyl group, each of which W may be substituted by Xn. , Benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, isoquinolyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group or naphthyridinyl group,
2. The compound according to claim 1, wherein Q is a cyano group.
ラゾリル基、トリアゾリル基、オキサゾリル基、イソオ
キサゾリル基、チアゾリル基、イソチアゾリル基、オキ
サジアゾリル基、チアジアゾリル基、2-ピリミジニル
基、ピラジニル基、ピリダジニル基、トリアジニル基、
インドリル基、インダゾリル基、ベンゾチアゾリル基、
ベンゾオキサゾリル基、ベンズイミダゾリル基、キノリ
ル基、イソキノリル基、シンノリニル基、フタラジニル
基、キノキサリニル基又はナフチリジニル基であり、Q
がエチニル基、基−COR4又は基−CH(OH) R4である請求
項1に記載の化合物。3. A pyrazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a 2-pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, each of which may be substituted by Xn. Triazinyl group,
Indolyl, indazolyl, benzothiazolyl,
Benzoxazolyl group, benzimidazolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group or naphthyridinyl group, Q
Is an ethynyl group, a group —COR 4 or a group —CH (OH) R 4 .
ピラゾリル基、トリアゾリル基、チアゾリル基、チアジ
アゾリル基、2-ピリミジニル基、ピラジニル基、ピリダ
ジニル基、トリアジニル基、ベンゾチアゾリル基、ベン
ゾオキサゾリル基、ベンズイミダゾリル基、キノリル
基、フタラジニル基又はキノキサリニル基であり、Qが
エチニル基、基−COR4又は基−CH(OH) R4である請求項1
に記載の化合物。4. each of W may be replaced by Xn,
Pyrazolyl group, triazolyl group, thiazolyl group, thiadiazolyl group, 2-pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, quinolyl group, phthalazinyl group or quinoxalinyl group, Q is ethynyl group, claim 1 is a group -COR 4 or a group -CH (OH) R 4
The compound according to the above.
(チオ)アルカン酸アミド誘導体を有効成分として含有す
る農園芸用殺菌剤。5. The heteroaryloxy according to claim 1, wherein
An agricultural and horticultural fungicide containing a (thio) alkanoic acid amide derivative as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26661299A JP2001089453A (en) | 1999-09-21 | 1999-09-21 | Heteroaryloxy(thio)alkanoic acid amide derivative and germicide for agriculture and horticulture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26661299A JP2001089453A (en) | 1999-09-21 | 1999-09-21 | Heteroaryloxy(thio)alkanoic acid amide derivative and germicide for agriculture and horticulture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001089453A true JP2001089453A (en) | 2001-04-03 |
Family
ID=17433245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26661299A Pending JP2001089453A (en) | 1999-09-21 | 1999-09-21 | Heteroaryloxy(thio)alkanoic acid amide derivative and germicide for agriculture and horticulture |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001089453A (en) |
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1999
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