JP2696342B2 - Amidine derivative, method for producing the same, acaricide and agricultural / horticultural fungicide - Google Patents
Amidine derivative, method for producing the same, acaricide and agricultural / horticultural fungicideInfo
- Publication number
- JP2696342B2 JP2696342B2 JP15839388A JP15839388A JP2696342B2 JP 2696342 B2 JP2696342 B2 JP 2696342B2 JP 15839388 A JP15839388 A JP 15839388A JP 15839388 A JP15839388 A JP 15839388A JP 2696342 B2 JP2696342 B2 JP 2696342B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituent
- lower alkyl
- formula
- represented
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000417 fungicide Substances 0.000 title claims description 10
- 239000000642 acaricide Substances 0.000 title claims description 9
- 230000000855 fungicidal effect Effects 0.000 title claims description 8
- 230000000895 acaricidal effect Effects 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001409 amidines Chemical class 0.000 title description 2
- 125000001424 substituent group Chemical group 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- -1 1- (2-propynyloxy) -N-phenylacetyl 2,6-dichlorobenzamidine Chemical compound 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 201000010099 disease Diseases 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 230000003902 lesion Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 5
- 235000021536 Sugar beet Nutrition 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 244000141359 Malus pumila Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 239000005842 Thiophanate-methyl Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- ZZVVDIVWGXTDRQ-UHFFFAOYSA-N 1-[(4-tert-butylphenyl)methylsulfanyl]-1-butylsulfanyl-n-pyridin-3-ylmethanimine Chemical compound C=1C=CN=CC=1N=C(SCCCC)SCC1=CC=C(C(C)(C)C)C=C1 ZZVVDIVWGXTDRQ-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- SPJLQKZVWZEOOR-UHFFFAOYSA-N 1-chloro-4-(4-nitrophenoxy)-2-propylsulfanylbenzene Chemical compound C1=C(Cl)C(SCCC)=CC(OC=2C=CC(=CC=2)[N+]([O-])=O)=C1 SPJLQKZVWZEOOR-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
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- URYAFVKLYSEINW-UHFFFAOYSA-N Chlorfenethol Chemical compound C=1C=C(Cl)C=CC=1C(O)(C)C1=CC=C(Cl)C=C1 URYAFVKLYSEINW-UHFFFAOYSA-N 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005821 Propamocarb Substances 0.000 description 1
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- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- 229950005488 proclonol Drugs 0.000 description 1
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- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
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- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Epoxy Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は新規なアミジン誘導体、その製造方法及び殺
ダニ剤、農園芸用殺菌剤に関する。The present invention relates to a novel amidine derivative, a method for producing the same, a miticide, and a fungicide for agricultural and horticultural use.
農園芸作物の栽培に当り、作物の病原菌やダニに対し
て多数の防除薬剤が使用されているが、その防除効力が
不十分であったり、薬剤耐性の病原菌やダニの出現によ
りその使用が制限されたり、また植物体に薬害や汚染を
生じたり、あるいは人畜魚類に対する毒性が強かったり
することから、必ずしも満足すべき防除薬とは言い難い
ものが少なくない。従って、かかる欠点の少ない安全に
使用できる薬剤の出現が強く要請されている。In the cultivation of agricultural and horticultural crops, a number of control agents are used against pathogens and mites in crops, but their use is limited due to insufficient control efficacy or the emergence of drug-resistant pathogens and mites. In many cases, it is difficult to say that it is a satisfactory control agent because it is harmful or contaminated to plants, or is highly toxic to humans and fishes. Therefore, there is a strong demand for a drug that can be safely used with few such disadvantages.
本発明の目的は工業的に有利に合成でき効果が確実で
安全に使用できる殺ダニ剤・農園芸用殺菌剤となりる新
規化合物を提供することである。An object of the present invention is to provide a novel compound which can be synthesized industrially advantageously, has a certain effect, and can be used safely and can be used as an acaricide and an agricultural / horticultural fungicide.
本発明は一般式〔Ｉ〕 〔式中、R1は置換基を有するフェニル基、ナフチル基、
又は置換基を有していてもよい含窒素単環ヘテロ環基
を、 R2は、置換基を有してもよい低級アルキル基、低級ア
ルケニル基、低級アルキニル基、式−Xr1で表わされる
基 −COCO基を示し、r1は低級アルキル基、置換基を有した
低級アルケニル基、置換基を有してもよいフェニル基、
又は置換基を有するベンジル基を示す。但し、Ｘが−CO
基を示すとき、r1は置換基を有するベンジル基を示
す。）、 で表わされる基（式中ＹはＯ又はＳ、r2は低級アルキル
基を示す。）を、 R3は、置換基を有してもよい低級アルキル基、置換基
を有してもよい低級アルケニル基、置換基を有してもよ
いフェニル基、置換基を有してもよいベンジル基、又は
ピペリジノ基を、 で表わされる化合物及びその製造方法及び殺ダニ剤・農
園芸用殺菌剤である。The present invention relates to a compound of the formula [I] Wherein R 1 is a phenyl group having a substituent, a naphthyl group,
Or a nitrogen-containing monocyclic heterocyclic group which may have a substituent, R 2 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group which may have a substituent, represented by the formula -Xr 1 Base -COCO group, r 1 is a lower alkyl group, a lower alkenyl group having a substituent, a phenyl group which may have a substituent,
Or a benzyl group having a substituent. Where X is -CO
When a group is represented, r 1 represents a benzyl group having a substituent. ), Wherein Y represents O or S, and r 2 represents a lower alkyl group, and R 3 represents a lower alkyl group which may have a substituent, a lower alkyl group which may have a substituent. An alkenyl group, a phenyl group which may have a substituent, a benzyl group which may have a substituent, or a piperidino group, And a method for producing the compound, acaricide, and a fungicide for agricultural and horticultural use.
本発明化合物の製造方法は次の通りである。 The method for producing the compound of the present invention is as follows.
式中、Halはハロゲンを示し、R1、R2、R3、Ｚは前記
と同じ意味を示す。反応は有機溶媒中所望により、塩基
の存在下、０℃から用いられる。溶媒の沸点までで、１
時間から数10時間行われる。溶媒としては、ベンゼン、
トルエン、クロロホルム、ジクロロエタン、DMF、アセ
トニトリル等が使用できる。 In the formula, Hal represents a halogen, and R 1 , R 2 , R 3 and Z have the same meaning as described above. The reaction is used at 0 ° C. in an organic solvent, if desired, in the presence of a base. Up to the boiling point of the solvent, 1
It takes several hours to several hours. As the solvent, benzene,
Toluene, chloroform, dichloroethane, DMF, acetonitrile and the like can be used.
塩基としては、ピリジン、トリエチルアミン、DBU、
水素化ナトリウム等が使用できる。Bases include pyridine, triethylamine, DBU,
Sodium hydride and the like can be used.
式中、Halはハロゲンを示し、R1、R2、R3、Ｚは前記
と同じ意味を示す。反応は有機溶媒中、所望により脱酸
剤の存在下、−10℃から用いられる溶媒の沸点までで、
１時間から数10時間行われる。 In the formula, Hal represents a halogen, and R 1 , R 2 , R 3 and Z have the same meaning as described above. The reaction is carried out in an organic solvent, optionally in the presence of a deoxidizing agent, from -10 ° C to the boiling point of the solvent used,
It lasts from one hour to several tens of hours.
溶媒としては、DMF、アセトニトリル、THF等が使用で
きる。脱酸剤としては、トリエチルアミン、ピリジン等
が使用できる。また、水素化ナトリウム等であらかじめ
一般式〔IV〕で表わされる化合物のナトリウム塩を製造
したのち、一般式〔Ｖ〕で表わされる化合物と反応させ
ることも可能である。DMF, acetonitrile, THF and the like can be used as the solvent. As a deoxidizing agent, triethylamine, pyridine and the like can be used. It is also possible to prepare a sodium salt of the compound represented by the general formula [IV] in advance with sodium hydride or the like, and then to react with a compound represented by the general formula [V].
式中、Hal、R1、R2、R3、Ｚは前記と同じ意味を示
す。 In the formula, Hal, R 1 , R 2 , R 3 and Z have the same meanings as described above.
反応は有機溶媒中、塩基の存在下−10℃から50℃まで
の温度で数時間から数10時間行われる。The reaction is carried out in an organic solvent in the presence of a base at a temperature of -10 ° C to 50 ° C for several hours to several tens hours.
溶媒としては、ベンゼン、THF、ジエチルエーテル等
が使用できる。As the solvent, benzene, THF, diethyl ether and the like can be used.
塩基としては、トリエチルアミンなどの一級アミン等
が使用できる。As the base, a primary amine such as triethylamine can be used.
（４） さらに本発明化合物は、置換基の種類によって
は、下記反応式あるいは公知と類似の反応を適宜選択す
ることによっても製造することができる。(4) Further, the compound of the present invention can also be produced by appropriately selecting a reaction similar to the following reaction formula or a known reaction depending on the type of the substituent.
いずれの場合も反応終了後は通常の後処理を行うこと
により目的物を得ることができる。 In any case, after completion of the reaction, the desired product can be obtained by performing ordinary post-treatment.
本発明化合物の製造は、IR、NMR、MASS等から決定し
た。The production of the compound of the present invention was determined from IR, NMR, MASS and the like.
〔実施例〕 次に実施例を挙げ、本発明化合物を更に説明する。[Examples] Next, the compounds of the present invention will be further described with reference to Examples.
実施例１ N1−（２−プロピニルオキシ）−Ｎ−フェニ
ルアセチル2,6−ジクロロベンズアミジン（化合物番号1
45）： N1−（２−プロピニルオキシ）−2,6−ジクロロベン
ズアミジン1gをベンゼン10mlに溶解させ、フェニルアセ
チルクロリド0.76gを加え一晩還流させた。Example 1 N 1- (2-propynyloxy) -N-phenylacetyl 2,6-dichlorobenzamidine (Compound No. 1)
45): 1 g of N 1- (2-propynyloxy) -2,6-dichlorobenzamidine was dissolved in 10 ml of benzene, 0.76 g of phenylacetyl chloride was added, and the mixture was refluxed overnight.
冷却後、ベンゼンを減圧留去し、シリカゲルカラムに
て分離精製し、目的物1.1gを得た。After cooling, benzene was distilled off under reduced pressure and the residue was separated and purified by a silica gel column to obtain 1.1 g of the desired product.
m.p〔95−98℃〕 実施例２ N1−エトキシ−Ｎ−クロロアセチル−４−ク
ロロベンズアミジン（化合物番号209）： N1−エトキシ−４−クロロベンズアミジン4gをアセト
ニトリル40mlに溶解させ、トリエチルアミン2.2gを加え
たのち５℃に冷却した。クロロアセチルクロリド2.5gを
０〜10℃で滴下させ滴下終了後室温にて３時間撹拌し
た。Example 2 N 1 -ethoxy-N-chloroacetyl-4-chlorobenzamidine (Compound No. 209): mp [95-98 ° C.] 4 g of N 1 -ethoxy-4-chlorobenzamidine was dissolved in 40 ml of acetonitrile, 2.2 g of triethylamine was added, and the mixture was cooled to 5 ° C. 2.5 g of chloroacetyl chloride was added dropwise at 0 to 10 ° C, and the mixture was stirred at room temperature for 3 hours after completion of the addition.
反応終了後、反応液を氷水に注加し、酢酸エチル抽
出、水洗、硫酸マグネシウムで乾燥ののち、濾別し酢酸
エチルを減圧留去した。残渣をベンゼン溶媒で再結晶を
行ない、目的物2.2gを得た。After completion of the reaction, the reaction solution was poured into ice water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and the ethyl acetate was distilled off under reduced pressure. The residue was recrystallized from a benzene solvent to obtain 2.2 g of the desired product.
m.p〔127−128℃〕 実施例３ N1−エトキシ−Ｎ−フェニルチオアセチル−
2,6−ジクロロベンズアミジン（化合物番号76）： N1−エトキシ−Ｎ−フェニルアセチル−2,6−ジクロ
ロベンズアミジン1gをTHFに溶解させ、ローソン試薬1.6
gを加えたのち60℃で一晩反応させた。mp [127-128 ° C] Example 3 N 1 -ethoxy-N-phenylthioacetyl-
2,6-dichlorobenzamidine (Compound No. 76): 1 g of N 1 -ethoxy-N-phenylacetyl-2,6-dichlorobenzamidine was dissolved in THF, and Lawson reagent 1.6 was dissolved.
After adding g, the mixture was reacted at 60 ° C. overnight.
反応液を氷水にあけ、酢酸エチル抽出、水洗、硫酸マ
グネシウム乾燥後濾別し、酢酸エチルを減圧留去し、残
渣をシリカゲルカラムにて分離精製し目的物0.8gを得
た。The reaction solution was poured into ice water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and filtered. The ethyl acetate was distilled off under reduced pressure, and the residue was separated and purified on a silica gel column to obtain 0.8 g of the desired product.
m.p〔53−９℃〕 実施例４ N1−エトキシ−Ｎ−（４−メトキシフェニル
アセチル）−2,6−ジクロロ−４−エチルスルフィニル
ベンズアミジン（化合物番号335）： N1−エトキシ−Ｎ−（４−メトキシフェニルアセチ
ル）−４−エチルチオ−2,6−ジクロロベンズアミジン
0.5gをジクロロメタン10mlに溶解し、ｍ−クロロ過安息
香酸0.21gを溶解したジクロロメタン溶液5mlを０℃以下
で滴下させた。Example 4 N 1 -ethoxy-N- (4-methoxyphenylacetyl) -2,6-dichloro-4-ethylsulfinylbenzamidine (Compound No. 335): N 1 -ethoxy-N- (4-methoxyphenylacetyl) -4-ethylthio-2,6-dichlorobenzamidine
0.5 g was dissolved in 10 ml of dichloromethane, and 5 ml of a dichloromethane solution in which 0.21 g of m-chloroperbenzoic acid was dissolved was added dropwise at 0 ° C or lower.
１軸間０℃に保ったのち室温にてさらに１時間反応さ
せた。反応液を２％NaOH水溶液中にあけ、ジクロロメタ
ンにて抽出、水洗、硫酸マグネシウム乾燥後、濾別して
ジクロロメタンを減圧留去した。残渣をシリカゲルカラ
ムにて分離精製し、目的物0.4gを得た。After maintaining at 0 ° C. for one axis, the reaction was carried out at room temperature for another 1 hour. The reaction solution was poured into a 2% aqueous NaOH solution, extracted with dichloromethane, washed with water, dried over magnesium sulfate, filtered, and the dichloromethane was distilled off under reduced pressure. The residue was separated and purified on a silica gel column to obtain 0.4 g of the desired product.
m.p〔84−86℃〕 実施例５ N1−エトキシ−Ｎ−（４−メトキシフェニル
アセチル）−2,6−ジクロロ−４−エチルスルホニルベ
ンズアミジン（化合物番号336）： N1−エトキシ−Ｎ−（４−メトキシフェニルアセチ
ル）−４−エチルチオ−2,6−ジクロロベンズアミジン
0.35g、ジクロロメタン10mlに溶解し、ｍ−クロロ過安
息香酸0.3gを溶解したジクロロメタン溶液5mlを０℃以
下で滴下させた。mp [84-86 ° C.] Example 5 N 1 - ethoxy -N- (4- methoxyphenyl acetyl) -2,6-dichloro-4-ethylsulfonyl benzamidine (Compound No. 336): N 1 -ethoxy-N- (4-methoxyphenylacetyl) -4-ethylthio-2,6-dichlorobenzamidine
0.35 g was dissolved in 10 ml of dichloromethane, and 5 ml of a dichloromethane solution in which 0.3 g of m-chloroperbenzoic acid was dissolved was added dropwise at 0 ° C or lower.
以降実施例11と同様に処理して目的物0.25gを得た。 Thereafter, the same treatment as in Example 11 was carried out to obtain 0.25 g of the target product.
m.p〔114−117℃〕 実施例６ N1−（２−プロピニルオキシ）−Ｎ−（４−
アミノフェニルアセチル）−2,6−ジクロロベンズアミ
ジン（化合物番号158）： 鉄粉1.82g、酢酸0.63g、水40mlからなる懸濁液中に、
N1−（２−プロピニルオキシ）−Ｎ−（４−ニトロフェ
ニルアセチル）−2,6−ジクロロベンズアミジン3.3gを
溶解したメチルエチルケトン溶液8mlを70〜75℃にて滴
下した。mp [114-117 ° C] Example 6 N 1- (2-propynyloxy) -N- (4-
(Aminophenylacetyl) -2,6-dichlorobenzamidine (Compound No. 158): In a suspension consisting of 1.82 g of iron powder, 0.63 g of acetic acid and 40 ml of water,
8 ml of a methyl ethyl ketone solution in which 3.3 g of N 1- (2-propynyloxy) -N- (4-nitrophenylacetyl) -2,6-dichlorobenzamidine was added dropwise at 70 to 75 ° C.
３時間後冷却し酢酸エチル200ml加えしばらく撹拌
後、セライトを用いて不溶物を濾別し、酢酸エチル層を
水洗、硫酸マグネシウム乾燥、濾別し酢酸エチルを減圧
留去した。After cooling for 3 hours, 200 ml of ethyl acetate was added, and the mixture was stirred for a while. Insoluble materials were filtered off using celite. The ethyl acetate layer was washed with water, dried over magnesium sulfate and filtered, and ethyl acetate was distilled off under reduced pressure.
残渣をシリカゲルカラムにて分離精製して目的物2.4g
を得た。The residue was separated and purified on a silica gel column to give 2.4 g of the desired product.
I got
▲ｎ23.0 D▼1.5921 実例例７ N1−（２−プロピニルオキシ）−Ｎ−（４−
ヒドロキシフェニルアセチル）−2,6−ジクロロベンズ
アミジン（化合物番号160）： N1−（２−プロピニルオキシ）−Ｎ−（４−アセトキ
シフェニルアセチル）−2,6−ジクロロベンズアミジン1
gをメタノール20mlに溶解させ、炭酸カリウム2gを含む
水溶液10mlを30℃を越えない温度で滴下し、滴下後さら
に２時間撹拌した。▲ n 23.0 D ▼ 1.5921 Example 7 N 1- (2-propynyloxy) -N- (4-
(Hydroxyphenylacetyl) -2,6-dichlorobenzamidine (Compound No. 160): N 1- (2-propynyloxy) -N- (4-acetoxyphenylacetyl) -2,6-dichlorobenzamidine 1
g was dissolved in 20 ml of methanol, and 10 ml of an aqueous solution containing 2 g of potassium carbonate was added dropwise at a temperature not exceeding 30 ° C. After the addition, the mixture was further stirred for 2 hours.
反応液を水にあけ、５％塩酸にてpH4に調整したの
ち、酢酸エチルにて抽出した。水洗、硫酸マグネシウム
乾燥濾別ののち、酢酸エチルを減圧留去して得られた残
渣をシリカゲルカラムにて、分離精製して目的物0.8gを
得た。The reaction solution was poured into water, adjusted to pH 4 with 5% hydrochloric acid, and extracted with ethyl acetate. After washing with water and drying by filtration with magnesium sulfate, ethyl acetate was distilled off under reduced pressure, and the residue obtained was separated and purified on a silica gel column to obtain 0.8 g of the desired product.
▲ｎ23.0 D▼1.5790 実施例８ N1−（２−プロピニルオキシ）−Ｎ−（４−
エトキシカルボニルメトキシフェニルアセチル）−2,6
−ジクロロベンズアミジン（化合物番号166）： N1−（２−プロピニルオキシ）−Ｎ−（４−ヒドロキ
シフェニルアセチル）−2,6−ジクロロベンズアミジン2
gをDMF20mlに溶解し０℃にて60％NaH 0.23gを加えた。
室温で１時間撹拌後再び０℃以下でブロモ酢酸エチル1.
1gを滴下した。▲ n 23.0 D ▼ 1.5790 Example 8 N 1- (2-propynyloxy) -N- (4-
Ethoxycarbonylmethoxyphenylacetyl) -2,6
-Dichlorobenzamidine (Compound No. 166): N 1- (2-propynyloxy) -N- (4-hydroxyphenylacetyl) -2,6-dichlorobenzamidine 2
g was dissolved in 20 ml of DMF, and 0.23 g of 60% NaH was added at 0 ° C.
After stirring at room temperature for 1 hour, ethyl bromoacetate was added again at 0 ° C or lower.
1 g was added dropwise.
室温で３時間撹拌後、飽和食塩水中に反応液をあけ酢
酸エチルにて抽出、飽和食塩水洗浄後、硫酸マグネシウ
ム乾燥、濾別し、酢酸エチルを減圧留去して得られた残
渣をシリカゲルカラムにて分離精製、目的物を2g得た。After stirring at room temperature for 3 hours, the reaction solution was poured into a saturated saline solution, extracted with ethyl acetate, washed with a saturated saline solution, dried over magnesium sulfate, filtered, and the residue obtained by evaporating the ethyl acetate under reduced pressure was purified by a silica gel column. Separation and purification yielded 2 g of the desired product.
m.p〔92−95℃〕 実施例９ N1−エトキシ−Ｎ−（４−メトキシ−α−メ
チルチオフェニルアセチル）−2,6−ジクロロベンズア
ミジン（化合物番号107）： N1−エトキシ−Ｎ−（４−メトキシ−α−クロロフェ
ニルアセチル）−2,6−ジクロロベンズアミジン0.5gをT
HF2mlに溶解し、メチルメルカプタンナトリウム塩水溶
液0.6gを室温にて加え４時間撹拌させた。mp [92-95 ° C.] Example 9 N 1 - ethoxy -N- (4- methoxy -α- methylthiophenyl acetyl) -2,6-dichloro-benzamidine (Compound No. 107): 0.5 g of N 1 -ethoxy-N- (4-methoxy-α-chlorophenylacetyl) -2,6-dichlorobenzamidine
It was dissolved in 2 ml of HF, and 0.6 g of an aqueous solution of methyl mercaptan sodium salt was added at room temperature and stirred for 4 hours.
氷水にあけクロロホルムにて抽出後、水洗、硫酸マグ
ネシウム乾燥、濾別ののち減圧下クロロホルムを留去
し、残渣をシリカゲルカラムにより分離精製し、目的物
0.4gを得た。After opening in ice water and extracting with chloroform, washing with water, drying over magnesium sulfate, and filtration, chloroform was distilled off under reduced pressure, and the residue was separated and purified using a silica gel column.
0.4 g was obtained.
m.p〔102−104℃〕 実施例10 N1−エトキシ−Ｎ−〔4,α−ジメトキシフェ
ニルアセチル）−2,6−ジクロロベンズアミジン（化合
物番号105）： N1−エトキシ−Ｎ−（４−メトキシ−α−クロロフェ
ニルアセチル）−2,6−ジクロロベンズアミジン1gをメ
タノール5mlに溶解し、２時間還流させた。mp [102-104 ° C.] Example 10 N 1 -ethoxy-N- [4, α-dimethoxyphenylacetyl) -2,6-dichlorobenzamidine (Compound No. 105): 1 g of N 1 -ethoxy-N- (4-methoxy-α-chlorophenylacetyl) -2,6-dichlorobenzamidine was dissolved in 5 ml of methanol and refluxed for 2 hours.
メタノールを減圧留去後、シリカゲルカラムにて分離
精製して目的物0.8gを得た。After methanol was distilled off under reduced pressure, the residue was separated and purified by a silica gel column to obtain 0.8 g of the desired product.
mp〔84−87℃〕 実施例11 N1−エトキシ−Ｎ−（１−ラゾリルアセチ
ル）−2,6−ジクロロベンズアミジン（化合物番号29
2）： N1−エトキシ−Ｎ−ブロモアセチル−2,6−ジクロロ
ベンズアミジン0.5gをDMF5mlに溶解し、ピラゾール0.1g
を室温にて加え１時間反応させた。次いで80℃でさらに
１時間撹拌させたのち、氷水中に反応液をあけ酢酸エチ
ルにて抽出、水洗した。硫酸マグネシウム乾燥ののち濾
別し酢酸エチルを減圧留去して得られた残渣をシリカゲ
ルカラムにて分離精製して目的物0.3gを得た。mp [84-87 ° C.] Example 11 N 1 -ethoxy-N- (1-razolylacetyl) -2,6-dichlorobenzamidine (Compound No. 29)
2): 0.5 g of N 1 -ethoxy-N-bromoacetyl-2,6-dichlorobenzamidine was dissolved in 5 ml of DMF, and 0.1 g of pyrazole was dissolved.
Was added at room temperature to react for 1 hour. Next, the mixture was further stirred at 80 ° C. for 1 hour, then the reaction solution was poured into ice water, extracted with ethyl acetate, and washed with water. After drying over magnesium sulfate, the residue was filtered and ethyl acetate was distilled off under reduced pressure. The residue obtained was separated and purified on a silica gel column to obtain 0.3 g of the desired product.
m.p〔49−54.5℃〕 実施例12 N1−エトキシ−N1−エチル−N2−（４−メト
キシフェニルアセチル）−2,6−ジクロロベンズアミジ
ン（化合物番号98）： N1−エトキシ−Ｎ−（α−アセトキシ−４−メトキシ
フェニルアセチル）−2,6−ジクロロベンズアミジン2g
をメタノール15mlに溶解し、水酸化カリウム0.6gを溶解
させたメタノール溶液5mlを室温にて滴下した。mp [49-54.5 ° C.] Example 12 N 1 - ethoxy -N 1 - ethyl -N 2 - (4-methoxyphenyl acetyl) -2,6-dichloro-benzamidine (Compound No. 98): N 1 -ethoxy-N- (α-acetoxy-4-methoxyphenylacetyl) -2,6-dichlorobenzamidine 2 g
Was dissolved in 15 ml of methanol, and 5 ml of a methanol solution in which 0.6 g of potassium hydroxide was dissolved was added dropwise at room temperature.
３時間後、氷水にあけて２％塩酸で中和して、ベンゼ
ンにて抽出、水洗、硫酸マグネシウム乾燥後、濾別して
ベンゼンを減圧留去した。After 3 hours, the mixture was poured into ice water, neutralized with 2% hydrochloric acid, extracted with benzene, washed with water, dried over magnesium sulfate, filtered, and benzene was distilled off under reduced pressure.
残渣をシリカゲルカラムにて分離精製して目的物1.5g
を得た。The residue was separated and purified on a silica gel column to give 1.5 g of the desired product
I got
m.p〔120.5−122.0℃〕 実施例13 N1−（２−プロピニルオキシ）−Ｎ−（４−
メトキシ−α−エトキシイミノ−フェニルアセチル）−
2,6−ジクロロベンズアミジン（化合物番号191）： N1−（２−プロピニルオキシ）−Ｎ−（４−メトキシ
フェニルグリオキシリル）−2,6−ジクロロベンズアミ
ジン1gをエタノール10mlに溶解し、エトキシアミン0.3g
を加え６時間還流させた。エタノールを減圧留去し残渣
をシリカゲルカラムにより分離精製し目的物0.6gを得
た。mp [120.5-122.0 ° C] Example 13 N 1- (2-propynyloxy) -N- (4-
Methoxy-α-ethoxyimino-phenylacetyl)-
2,6-dichlorobenzamidine (Compound No. 191): 1 g of N 1- (2-propynyloxy) -N- (4-methoxyphenylglyoxylyl) -2,6-dichlorobenzamidine was dissolved in 10 ml of ethanol, and 0.3 g of ethoxyamine was dissolved.
Was added and refluxed for 6 hours. Ethanol was distilled off under reduced pressure, and the residue was separated and purified by a silica gel column to obtain 0.6 g of the desired product.
m.p〔132−135℃〕 実施例14 N1−（２−ヒドロキシイミノエトキシ）−
N1−フェニルアセチル−2,6−ジクロロベンズアミジン
（化合物番号５）： N1−（2,2−ジエトキシエトキシ）−Ｎ−フェニルア
セチル−2,6−ジクロロベンズアミジン0.1gをエタノー
ル1mlに溶解し、ヒドロキシアミン塩酸塩0.4gを加え
た。50℃で一晩撹拌したのち氷水にあけ酢酸エチルにて
抽出し、硫酸マグネシウム乾燥濾別後、酢酸エチルを減
圧留去した。残渣をシリカゲルカラムにより分離精製し
て目的物を0.03g得た。mp [132-135 ° C] Example 14 N 1- (2-hydroxyiminoethoxy)-
N 1 -phenylacetyl-2,6-dichlorobenzamidine (Compound No. 5): 0.1 g of N 1- (2,2-diethoxyethoxy) -N-phenylacetyl-2,6-dichlorobenzamidine was dissolved in 1 ml of ethanol, and 0.4 g of hydroxyamine hydrochloride was added. After stirring overnight at 50 ° C., the mixture was poured into iced water, extracted with ethyl acetate, dried over magnesium sulfate and filtered, and the ethyl acetate was distilled off under reduced pressure. The residue was separated and purified by a silica gel column to obtain 0.03 g of the desired product.
▲ｎ26 D▼1.5880 実施例15 N1−メチルスルフィニルメトキシ−Ｎ−フェ
ニルアセチル−2,6−ジクロロベンズアミジン（化合物
番号８）： N1−メチルチオメトキシ−Ｎ−フェニルアセチル−2,
6−ジクロロベンズアミジン0.3gをジクロロメタン15ml
に溶解し、ｍ−クロロ過安息香酸0.16gを溶解したジク
ロロメタン溶液10mlを０℃で滴下した。▲ n 26 D ▼ 1.5880 Example 15 N 1 -methylsulfinylmethoxy-N-phenylacetyl-2,6-dichlorobenzamidine (Compound No. 8): N 1 -methylthiomethoxy-N-phenylacetyl-2,
0.3 g of 6-dichlorobenzamidine in 15 ml of dichloromethane
And 10 ml of a dichloromethane solution in which 0.16 g of m-chloroperbenzoic acid was dissolved was added dropwise at 0 ° C.
室温で一晩撹拌した後、ジクロロメタン100mlを加え
５％炭酸ナトリウム水溶液、次いで水で洗浄したのち硫
酸マグネシウム乾燥、濾別しジクロロメタンを減圧留去
した。After stirring overnight at room temperature, 100 ml of dichloromethane was added, and the mixture was washed with a 5% aqueous solution of sodium carbonate and then with water, dried over magnesium sulfate, separated by filtration and the dichloromethane was distilled off under reduced pressure.
残渣をシリカゲルカラムにて分離精製し、目的物0.25
gを得た。粘稠オイル。The residue was separated and purified on a silica gel column,
g was obtained. Viscous oil.
実施例16 N1−（2,3−エポキシプロポキシ）−Ｎ−フ
ェニルアセチル−2,6−ジクロロベンズアミジン（化合
物番号９）： N1−アリルオキシ−Ｎ−フェニルアセチル−2,6−ジ
クロロベンズアミジン1gをジクロロメタン40mlに溶解
し、ｍ−クロロ過安息香酸0.56gを溶解したジクロロメ
タン溶液15mlを０℃で滴下した。Example 16 N 1 - (2,3-epoxypropoxy) -N- phenylacetyl-2,6-dichloro benzamidine (Compound No. 9) 1 g of N 1 -allyloxy-N-phenylacetyl-2,6-dichlorobenzamidine was dissolved in 40 ml of dichloromethane, and 15 ml of a dichloromethane solution in which 0.56 g of m-chloroperbenzoic acid was dissolved was added dropwise at 0 ° C.
室温で一晩撹拌の後ジクロロメタン200mlを加え５％
炭酸ナトリウム水溶液次いで水で洗浄し、硫酸マグネシ
ウム乾燥、濾別したのちジクロロメタンを減圧留去し
た。After stirring overnight at room temperature, add 200 ml of dichloromethane and add 5%
After washing with an aqueous sodium carbonate solution and then with water, drying over magnesium sulfate and filtration, dichloromethane was distilled off under reduced pressure.
残渣をシリカゲルカラムにより分離精製して目的物1.
1gを得た。The residue is separated and purified by a silica gel column to obtain the target product 1.
1 g was obtained.
m.p〔58.0−59.5℃〕 上記実施例を含めて、本発明化合物の代表例を第１表
に示す。mp [58.0-59.5 ° C] Table 1 shows typical examples of the compound of the present invention including the above Examples.
〔課題を解決するための手段−殺ダニ剤農園芸用殺菌
剤〕 このようにして得られた本発明化合物を実際に施用す
る際には他成分を加えず純粋な形で使用できるし、また
農薬として使用する目的で、一般の農薬のとり得る形
態、即ち、水和剤、粒剤、乳剤、水溶剤、エアロゾル等
の形態で使用することもできる。添加剤および担体とし
ては固形剤を目的とする場合は、大豆粉、小麦粉等の植
物性粉末、珪藻土、燐灰石、石こう、タルク、パイロフ
ィライト、クレイ、鉱物油、植物油等の鉱物性微粉末等
が使用される。液体の剤型を目的とする場合は、ケロシ
ン、鉱油、石油、ソルベントナフサ、キシレン、シクロ
ヘキサン、シクロヘキサノン、ジメチルホルムアミド、
ジメチルスルホキシド、アルコール、アセトン、鉱物
油、植物油、水等を溶剤として使用する。これらの製剤
において均一かつ、安定な形態をとるために、必要なら
ば界面活性剤を加え、水で所定の濃度に希釈して懸濁液
あるいは乳濁液として粉剤、粒剤はそのまま植物に散布
する方法で使用される。 [Means for solving the problem-acaricide agricultural and horticultural fungicide] When the compound of the present invention thus obtained is actually applied, it can be used in a pure form without adding other components, For the purpose of using as a pesticide, it can be used in the form of general pesticides, that is, wettable powders, granules, emulsions, aqueous solvents, aerosols and the like. When a solid agent is intended as an additive or carrier, a mineral powder such as soybean flour, flour or other vegetable powder, diatomaceous earth, apatite, gypsum, talc, pyrophyllite, clay, mineral oil, vegetable oil, etc. Is used. For liquid dosage forms, kerosene, mineral oil, petroleum, solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide,
Dimethyl sulfoxide, alcohol, acetone, mineral oil, vegetable oil, water, etc. are used as solvents. In order to obtain a uniform and stable form in these preparations, add a surfactant if necessary, dilute to a predetermined concentration with water, and spray powders and granules as suspensions or emulsions on plants as they are. Used in a way to
次に、本発明の組成物の実施例を若干示すが、添加物
及び添加割合は、これら実施例に限定されるべきもので
はなく、広い範囲に変化させることが可能である。Next, some examples of the composition of the present invention will be described. However, the additives and the addition ratio are not limited to these examples, and can be changed in a wide range.
実施例17 水和剤 本発明化合物 40部 珪藻土 53部 高級アルコール硫酸エステル 4部 アルキルナフタレンスルホン酸 ３部 以上を均一に混合して微細に粉砕すれば、有効成分40
％の水和剤 を得る。Example 17 wettable powder 40 parts of the compound of the present invention 53 parts of diatomaceous earth 4 parts of higher alcohol sulfate ester 3 parts of alkylnaphthalenesulfonic acid If the above components are uniformly mixed and finely pulverized, the active ingredient 40
% Wettable powder.
実施例18 乳剤 本発明化合物 30部 キシレン 33部 ジメチルホルムアミド 30部 ポリオキシエチレンアルキルアリルエーテル 7部 以上を混合溶解すれば、有効成分30％の乳剤を得る。Example 18 Emulsion 30 parts of the compound of the present invention 33 parts of xylene 30 parts of dimethylformamide 7 parts of polyoxyethylene alkyl allyl ether By mixing and dissolving the above components, an emulsion having an active ingredient of 30% is obtained.
実施例19 粉剤 本発明化合物 10部 タルク 89部 ポリオキシエチレンアルキルアリルエーテル 1部 以上を均一に混合して微細に粉砕すれば、有効成分10
％の粉剤を得る。Example 19 Dust The present compound 10 parts Talc 89 parts Polyoxyethylene alkyl allyl ether 1 part
% Powder.
なお、本発明化合物は単独でも十分有効であることは
言うまでもないが、効力が不十分もしくは弱い病害又は
ダニに対しては各種の殺菌剤や殺虫・殺ダニ剤の１種又
は２種以上と混合して使用することも出来る。Needless to say, the compound of the present invention is sufficiently effective alone, but it is mixed with one or more kinds of various fungicides and insecticides and acaricides against inadequate or weak diseases or mites. It can also be used.
本発明化合物と混合して使用出来る殺菌剤、殺虫剤、
殺ダニ剤、植物生長調節剤の代表例を以下に示す。Fungicides that can be used in combination with the compound of the present invention, insecticides,
Representative examples of miticides and plant growth regulators are shown below.
キャプタン、フォルペット、TMTD、ジネブ、マンネ
ブ、マンゼブ、プロピネブ、ポリカーバメート、TPN、
サイモキサニル、メプロニル、フルトラニル、ベンシク
ロン、オキシカルボキシン、ホチセルアルミニウム、プ
ロパモカーブ、トリアジメホン、トリアジメノール、フ
ェナリモール、トリフルミゾール、トリデモルフ、トリ
ホリン、ブチオベート、ジクロメジン、フェンプロピモ
ルフ、アニラジン、ポリオキシン、メタラキシル、フラ
ラキシル、プロクロラズ、イソプロチオラン、プロベナ
ゾール、ビテルタノール、エタコナゾール、プロピコナ
ゾール、ペンコナゾール、フルシラゾール、ピロールニ
トリン、PCNB、ブラストサイジンＳ、カスガマイシン、
バリダマイシン、イプロジオン、ビンクロゾリン、プロ
シミドン、ベノミル、チオファネートメチル、ヒメキサ
ゾール、塩基性塩化銅、塩基性硫酸銅、MBC、ジエトフ
ェンカルブ、メタンスルホカルブ、キノメチオナート、
ビナパクリル、レシチン、トリクロホスメチル、ジクロ
フルアニド、エクロメゾール、ジチアノン、ストレプト
マイシン、フルアジナム。Captan, Folpet, TMTD, Zineb, Maneb, Manzeb, Propineb, Polycarbamate, TPN,
Thymoxanil, mepronil, flutranil, bencyclone, oxycarboxine, photoiselluminum, propamocarb, triadimefon, triadimenol, fenarimol, triflumizole, tridemorph, triforin, butiobate, diclomedin, fenpropimorph, anilazine, polyoxin, metalaxyl, flalaxil, Prochloraz, isoprothiolane, probenazole, bitertanol, etaconazole, propiconazole, penconazole, flusilazole, pyrrolnitrin, PCNB, blasticidin S, kasugamycin,
Validamycin, iprodione, vinclozolin, procymidone, benomyl, thiophanate methyl, hymexazole, basic copper chloride, basic copper sulfate, MBC, dietofencarb, methanesulfocarb, quinomethionate,
Vinapacryl, lecithin, triclofosmethyl, diclofluanid, echromezol, dithianon, streptomycin, fluazinam.
BCPE、クロルベンジレート、クロルプロピレート、プ
ロクロノール、ジコフォル、フェニソブロモレート、ク
ロルフェナミジン、アミトラズ、BPSS、PPPS、ベンゾメ
ート、シヘキサチン、ポリナクチン、チオキノックス、
CPCBS、テトラジホン、テトラスル、シクロプレート、
カヤサイド、カヤホープ、多硫化石灰、フェンチオン、
ダイアジノン、フェニトロチオン、クロルピリホス、ES
P、バミドチオン、フェントエート、ホルモチオン、マ
ラチオン、ジプテレックス、チオメトン、メナゾン、ジ
クロルホス、アセフェート、ジアリホル、メチルパラチ
オン、エチオン、アルディカーブ、プロポキシュール、
パーメスリン、サイパーメスリン、デカメスリン、フェ
ンバレレート、フェンプロパスリン、ピレトリン、アレ
スリン、テトラメスリン、レスメスリン、パルスリン、
ジメスリン、シクロサール、フルバリネート、機械油、
ヘキシチアゾクス、ジフルベンズロン、ブプロフェジ
ン、フェノキシカルブ、フルベンジミン。BCPE, chlorbenzylate, chlorpropylate, proclonol, dicophor, phenisobromolate, chlorphenamidine, amitraz, BPSS, PPPS, benzomate, cyhexatin, polynactin, thioquinox,
CPCBS, tetradiphone, tetrasul, cycloplate,
Kayaside, Kayahope, polysulfide lime, fenthion,
Diazinon, fenitrothion, chlorpyrifos, ES
P, bamidothion, fentoate, formotion, malathion, dipterex, thiomethone, menazone, dichlorphos, acephate, diarifor, methyl parathion, ethione, aldicarb, propoxur,
Permethrin, cypermethrin, decamesulin, fenvalerate, fenpropasulin, pyrethrin, allesulin, tetramethrin, resmethrin, pulsulin,
Dimethrin, cyclosal, fluvalinate, machine oil,
Hexythiazox, diflubenzuron, buprofezin, phenoxycarb, flubenzimine.
ジベレリン類（例えばジベレリンA3、ジベレリンA4、
ジベレリンA7）IAA、NAA。Gibberellins (eg, gibberellin A 3 , gibberellin A 4 ,
Gibberellin A 7 ) IAA, NAA.
本発明の化合物はアシノワハダニ、ナミハダニ、ミカ
ンハダニ等の各種の植物寄生性ハダニ類に有効であり、
特に各種ハダニの卵・幼虫及び若虫のステージに対して
は優れた殺卵力、殺幼虫力及び殺若虫力を示す。また、
混血動物に対する毒性は低く、安全性の高い薬剤であ
る。The compound of the present invention is effective against various plant parasitic spider mites such as red mite, red mite, mandarin red mite,
In particular, it exhibits excellent ovicidal, larvicidal and nymphalidizing powers against the stages of eggs, larvae and nymphs of various spider mites. Also,
It is a highly safe drug with low toxicity to mixed animals.
又、本発明化合物は農園芸用殺菌剤として広い範囲の
植物病害に対して防除効果を示すが、特に各種作物のう
どんこ病、灰色かび病、べと病、リンゴ・ナシの黒星
病、テンサイの褐斑病、イネのいもち病、ごま葉枯病、
トマト・ジャガイモの疾病などに有効である。The compound of the present invention is effective as a fungicide for agricultural and horticultural use in controlling a wide range of plant diseases, but in particular, powdery mildew, gray mold, downy mildew, scab of apple and pear, and sugar beet of various crops. Brown spot, rice blast, sesame leaf blight,
Effective for tomato and potato diseases.
また、ベンズイミダゾール系薬剤（例えばチオファネ
ートメチル、ベノミル、カルベンダジム）に耐性を示す
キュウリうどんこ病、リンゴ黒星病、テンサイ褐斑病な
どの病害に対しても本発明化合物は有効である。The compounds of the present invention are also effective against diseases such as cucumber powdery mildew, apple scab, sugar beet brown spot which are resistant to benzimidazole drugs (eg, thiophanate methyl, benomyl, carbendazim).
試験例1.ナミハダニに対する効力 ２寸鉢に播種したインゲンの発芽後７〜10日を経過し
た第１本葉上に、有機燐剤抵抗性のナミハダニの雄成虫
を30頭接種したのち、前記薬剤の実施例18に示された乳
剤の処方に従い、化合物濃度が125ppmになるように水で
希釈して散布した。散布３日後に、成虫を除去し、この
３日間に産付された卵に関し、成虫まで発育し得たか否
かを11日目に調査し、殺ダニ有効度を求めた。結果は第
２表の通りである。なお、殺ダニ有効度は、次式より求
めた。Test Example 1. Efficacy against the spider mite On the first true leaf 7 to 10 days after the germination of the kidney bean seeded in a 2 inch pot, 30 male adults of the spider mite, the organic phosphorus resistant, were inoculated with the drug. In accordance with the formulation of the emulsion described in Example 18, the compound was diluted with water so that the compound concentration became 125 ppm and sprayed. Three days after spraying, the adults were removed, and the eggs laid during these three days were examined on day 11 to determine whether they could develop into adults, and the mite-killing effectiveness was determined. The results are shown in Table 2. The acaricidal effectiveness was determined by the following equation.
試験例2.リンゴ黒星病防除試験 素焼きポットで栽培したリンゴ幼苗（品種「国光」、
３〜４葉期）に、本発明化合物の水和剤の所定濃度の薬
液を散布し風乾させた後、リンゴ黒星病菌（Venturia i
naequalis）の分生胞子を接種し、20℃の温室中に保存
した。２週間後に各葉の発病程度を調査基準にしたがっ
て調査し、下記算式より処理区の防除価（％）を算出し
た。その結果を第３表に示す。 Test example 2. Apple scab control test Apple seedlings grown in unglazed pots (variety "Kunimitsu",
At the 3-4 leaf stage), a wet solution of the compound of the present invention was sprayed with a predetermined concentration of the drug solution and air-dried.
naequalis) were inoculated and stored in a greenhouse at 20 ° C. Two weeks later, the disease development of each leaf was examined according to the investigation criteria, and the control value (%) of the treated plot was calculated by the following formula. Table 3 shows the results.
調査基準 罹病指数 病斑面積（％） 0 ０（健全） 1 〜 10 2 11〜 20 3 21〜 30 4 31〜 40 5 41〜 50 6 51〜 60 7 61〜 70 8 71〜 80 9 81〜 90 10 91〜100 試験例3.コムギうどんこ病防除試験 素焼きポットで栽培したコムギ幼苗（品種「農林61
号」、1.0〜1.2葉期）に、本発明化合物の水和剤の所定
濃度の薬液を散布し、葉を風乾させた後、コムギうどん
こ病菌（Erysiphe graminis f.sp.tritici）の分生胞子
を振り払い接種し、22〜25℃の室温に７日間保持して、
発病の状況を調査した。以下に示す基準に従い、各処理
区の罹病指数を求め、防除価算出式より防除価（％）を
算出した。その結果を第４表に示す。Survey criteria Morbidity index Lesion area (%) 0 0 (healthy) 1 to 10 2 11 to 20 3 21 to 30 4 31 to 40 5 41 to 50 6 51 to 60 7 61 to 70 8 71 to 80 9 81 to 90 10 91-100 Test Example 3 Wheat Powdery Mildew Control Test Wheat seedlings (cultivar “Norin 61
No., 1.0-1.2 leaf stage), a wet solution of the compound of the present invention was sprayed at a predetermined concentration, the leaves were air-dried, and then the division of wheat powdery mildew (Erysiphe graminis f.sp. tritici) was performed. Shake and inoculate the spores, keep them at room temperature of 22-25 ° C for 7 days,
The incidence of the disease was investigated. The disease index of each treatment group was determined according to the criteria shown below, and the control value (%) was calculated from the control value calculation formula. Table 4 shows the results.
調査基準 罹病指数 病斑出現状況 0 無発病 1 病斑数（コロニー）１〜３コ 2 〃 ４〜７コ 3 〃 ８〜10コ 4 〃 11コ〜病斑面積40％ 5 病斑面積41〜50％ 6 〃 51〜60％ 7 〃 61〜70％ 8 〃 71〜80％ 9 〃 81〜90％ 10 〃 91〜100％ 試験例4.テンサイ褐斑病防除試験 9cmの素焼きポットで栽培したテンサイ幼苗（品種
「バーレスストリーネ」、５〜６葉期）に、本発明化合
物の水和剤の所定濃度の薬液を散布し、葉を風乾させた
後、テンサイ褐斑病菌（Cercospora beticola）の分生
胞子を噴霧接種し24〜28℃、高湿度に１日間保ってか
ら、23〜30℃の温室に12日間保持して発病の状況を調査
した。以下に示す基準に従い、各処理区の罹病指数を求
め、防除価算出式より防除価（％）を算出した。その結
果を第５表に示す。Survey criteria Morbidity index Lesion appearance 0 No disease 1 Number of lesions (colonies) 1 to 3 2 4 to 7 3 8 to 10 4 11 to 40% of lesion area 5 5% of lesion area 41 to 50% 6 〃 51-60% 7 〃 61-70% 8 〃 71-80% 9 〃 81-90% 10 〃 91-100% Test Example 4. Sugar beet brown spot control test A chemical solution of a predetermined concentration of a wettable powder of the compound of the present invention was sprayed on sugar beet seedlings (variety "burlestree", 5 to 6-leaf stage) cultivated in a 9 cm unglazed pot. After air-drying the leaves, the conidia of sugar beet brown spot fungus (Cercospora beticola) are sprayed and inoculated, kept at 24-28 ° C and high humidity for 1 day, and kept in a greenhouse at 23-30 ° C for 12 days. The incidence of the disease was investigated. The disease index of each treatment group was determined according to the criteria shown below, and the control value (%) was calculated from the control value calculation formula. Table 5 shows the results.
調査基準 罹病指数 病斑出現状況 0 全く発病をみとめない 0.5 １葉当り病斑数３〜５コ 1 葉面積の10％以下に病斑をみとめる 2 同上 20〜40％ 3 同上 41〜75％ 4 同上 76％以上 試験5.キュウリベと病防除試験 温室内で約３週間育苗したキュウリ（品種 相模半
白）幼苗に、本発明化合物の水和剤の所定濃度の薬液を
キュウリ葉裏面に散布し、風乾後、キュウリベと病の罹
病葉から採集した本菌遊走子のうの懸濁液を噴霧接種し
て25℃、湿度100％の接種箱に保持した。接種２日後に
処理キュウリ幼苗を室温23〜26℃、温度70％以上の温室
に移し、２日後に以下の基準にしたがって各キュウリ葉
の発病程度を調査し、下記の算式より処理区の防除価
（％）を算出した。その結果を第６表に示す。Survey criteria Morbidity index Lesion appearance 0 No disease observed 0.5 Lesion number per leaf 3 to 5 1 Lesion found in 10% or less of leaf area 2 Same as above 20 to 40% 3 Same as above 41 to 75% 4 Same as above 76% Test 5. Cucumber and disease control test To a cucumber (variety Sagami Hanjiro) seedling grown in a greenhouse for about 3 weeks, a chemical solution of a wettable powder of the compound of the present invention at a predetermined concentration is sprayed on the back of the cucumber leaf, and air-dried. A suspension of the zoospores of the fungus collected from the diseased leaves of the disease was spray-inoculated and kept in an inoculation box at 25 ° C. and 100% humidity. Two days after inoculation, the treated cucumber seedlings are transferred to a greenhouse at room temperature of 23 to 26 ° C and a temperature of 70% or more, and two days later, the degree of disease of each cucumber leaf is investigated according to the following criteria. (%) Was calculated. Table 6 shows the results.
調査基準 罹病指数 発病程度 0 健全（無発病） 0.5 微小病斑２〜３コ 1 病斑面積割合 10％以下 2 〃 11〜25％ 3 〃 26〜50％ 4 〃 51％以上 防除価算出式 Survey criteria Morbidity index Disease severity 0 Healthy (no disease) 0.5 Small lesions 2 to 3 1 Lesion area ratio 10% or less 2 2 11 to 25% 3 〃 26 to 50% 4 〃 51% or more
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ０１Ｎ 43/10 Ａ０１Ｎ 43/10 Ｃ 43/20 43/20 43/28 43/28 43/40 １０１ 43/40 １０１Ｆ 43/50 43/50 Ｃ 43/52 43/52 43/56 43/56 Ｂ 43/653 43/653 Ｊ 47/06 47/06 Ｅ 47/20 47/20 Ｚ 47/22 47/22 Ｂ 47/24 47/24 Ｅ 47/48 47/48 57/14 57/14 Ｚ Ｃ０７Ｃ 271/10 9451−4Ｈ Ｃ０７Ｃ 271/10 271/28 9451−4Ｈ 271/28 271/60 9451−4Ｈ 271/60 311/29 7419−4Ｈ 311/29 317/40 7419−4Ｈ 317/40 317/44 7419−4Ｈ 317/44 323/40 7419−4Ｈ 323/40 323/52 7419−4Ｈ 323/52 323/62 7419−4Ｈ 323/62 331/14 7106−4Ｈ 331/14 Ｃ０７Ｄ 213/64 Ｃ０７Ｄ 213/64 213/78 213/78 231/12 231/12 Ｅ 233/60 １０４ 233/60 １０４ 233/90 233/90 Ｃ 235/08 235/08 241/18 241/18 241/30 241/30 295/20 295/20 Ａ 303/20 303/20 307/54 307/54 317/30 317/30 333/24 333/24 Ｃ０７Ｆ 9/09 Ｃ０７Ｆ 9/09 Ｕ 9/165 9/165 Ｕ (72)発明者 山田 富夫 神奈川県小田原市高田字柳町345 日本 曹達株式会社小田原研究所内 (72)発明者 高橋 英光 神奈川県小田原市高田字柳町345 日本 曹達株式会社小田原研究所内 (72)発明者 橋本 章 神奈川県小田原市高田字柳町345 日本 曹達株式会社小田原研究所内 (72)発明者 佐野 慎亮 神奈川県小田原市高田字柳町345 日本 曹達株式会社小田原研究所内 (72)発明者 細川 浩靖 神奈川県小田原市高田字柳町345 日本 曹達株式会社小田原研究所内 (56)参考文献 特開 平１−34954（ＪＰ，Ａ) 特開 昭61−68461（ＪＰ，Ａ) 特開 昭59−42357（ＪＰ，Ａ) 特開 昭55−160778（ＪＰ，Ａ) 特開 昭53−2487（ＪＰ，Ａ) 特開 昭58−208263（ＪＰ，Ａ) 特開 昭58−96007（ＪＰ，Ａ) 特開 昭56−167660（ＪＰ，Ａ) 特開 昭47−2145（ＪＰ，Ａ) 特公 昭48−20557（ＪＰ，Ｂ２) 特公 昭43−8014（ＪＰ，Ｂ１) 米国特許4584317（ＵＳ，Ａ) 米国特許4554014（ＵＳ，Ａ) 米国特許3347874（ＵＳ，Ａ) ソビエト連邦特許207239（ＳＵ，Ａ) Ｊ．Ｃｈｅｍ．Ｓｏｃ．Ｐｅｒｋｉｎ Ｔｒａｎｓ Ｉ．Ｖｏｌ．６（1988) ｐ．1313−15，Ｂｕｌｌ．Ｓｏｃ．Ｃｈ ｉｍ．Ｆｒ，Ｖｏｌ．７（1970）ｐ2615 −28 Ｃｏｌｌｅｃｔ．Ｃｚｅｃｈ．Ｃｈｅ ｍ．Ｃｏｍｍｕｎ．Ｖｏｌ．48（２) （1983）ｐ596−607，Ｔｅｔｒａｂｃｄ ｒｃｎ Ｌｅｔｔ．Ｖｏｌ．20（1968) ｐ2421−24 Ｋｙｕｓｈｕ Ｋｏｇｙｏ Ｄａｉｇ ａｋｕ Ｋｅｓｋｙｕ Ｈｏｕｋｏｋ ｕ，Ｎｏ．15（1965）ｐ57−64──────────────────────────────────────────────────続 き Continuation of the front page (51) Int.Cl. 6 Identification number Agency reference number FI Technical display location A01N 43/10 A01N 43/10 C 43/20 43/20 43/28 43/28 43/40 101 43/40 101F 43/50 43/50 C 43/52 43/52 43/56 43/56 B 43/653 43/653 J 47/06 47/06 E 47/20 47/20 Z 47/22 47 / 22 B 47/24 47/24 E 47/48 47/48 57/14 57/14 Z C07C 271/10 9451-4H C07C 271/10 271/28 9451-4H 271/28 271/60 9451-4H 271 / 60 311/29 7419-4H 311/29 317/40 7419-4H 317/40 317/44 7419-4H 317/44 323/40 7419-4H 323/40 323/52 7419-4H 323/52 323/62 7419 −4H 323/62 331/14 7106 −4H 331/14 C07D 213/64 C07D 213/64 213/78 213/78 231/12 231/12 E 233/60 104 233/60 104 233/90 233/90 C 235/08 235/08 241/18 241/18 241/30 241/30 295/20 295/20 A 303/20 303/20 307/54 307/54 317/30 317/30 333/24 333/24 C07F 9/09 C07F 9/09 U 9/165 9/165 U (72) Inventor Tomio Yamada 345 Yanagimachi, Takada, Odawara-shi, Kanagawa Japan Inside the Soda Co., Ltd. Odawara Research Laboratory (72) Inventor Hidemitsu Takahashi 345, Yanagimachi, Takada, Odawara City, Kanagawa Prefecture Japan Soda Co., Ltd. (72) Inventor Shinsuke Sano 345 Yanagimachi, Takada, Odawara City, Kanagawa Prefecture, Japan Odawara Research Laboratory, Soda Co., Ltd. JP-A-1-34954 (JP, A) JP-A-61-68461 (JP, A) JP-A-59-42357 (JP, A) JP-A-55-160778 (JP, A) JP-A-53-2487 (JP, A) JP-A-58-208263 (JP, A) JP-A-58-96007 (JP, A) JP-A-56-167660 (JP, A JP-A-47-2145 (JP, A) JP-B-48-20557 (JP, B2) JP-B-43-8014 (JP, B1) US Patent 4,584,317 (US, A) US Patent 4,540,014 (US, A) U.S. Pat. No. 3,347,874 (US, A) Soviet Union Patent 207239 (SU, A) Chem. Soc. Perkin Trans I. Vol. 6 (1988) p. 1313-15, Bull. Soc. Chim. Fr, Vol. 7 (1970) p2615-28 Collect. Czech. Chem. Commun. Vol. 48 (2) (1983) p596-607, Tetrabcd rcn Lett. Vol. 20 (1968) p2421-24 Kyushu Kogyo Daigaku Ku Keskyu Hookoko, No. 1, p. 15 (1965) p57-64
Claims (6)
又は置換基を有していてもよい含窒素単環ヘテロ環基
を、 R2は、置換基を有してもよい低級アルキル基、低級アル
ケニル基、低級アルキニル基、式−Xr1で表わされる基 −COCO基を示し、r1は低級アルキル基、置換基を有する
低級アルケニル基、置換基を有してもよいフェニル基、
又は置換基を有するベンジル基を示す。但し、Ｘが−CO
基を示すとき、r1は置換基を有するベンジル基を示
す。）、 で表わされる基（式中ＹはＯ又はＳ、r2は低級アルキル
基を示す。）を、 R3は、置換基を有してもよい低級アルキル基、置換基を
有してもよい低級アルケニル基、置換基を有してもよい
フェニル基、置換基を有してもよいベンジル基、又はピ
ペリジノ基を、 で表わされる化合物。1. A compound of the formula [I] Wherein R 1 is a phenyl group having a substituent, a naphthyl group,
Or a nitrogen-containing monocyclic heterocyclic group which may have a substituent, R 2 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group which may have a substituent, represented by the formula -Xr 1 Base -COCO group, r 1 is a lower alkyl group, a lower alkenyl group having a substituent, a phenyl group which may have a substituent,
Or a benzyl group having a substituent. Where X is -CO
When a group is represented, r 1 represents a benzyl group having a substituent. ), Wherein Y represents O or S, and r 2 represents a lower alkyl group, and R 3 represents a lower alkyl group which may have a substituent, a lower alkyl group which may have a substituent. An alkenyl group, a phenyl group which may have a substituent, a benzyl group which may have a substituent, or a piperidino group, A compound represented by the formula:
又は置換基を有していてもよい含窒素単環ヘテロ環基
を、 R2は、置換基を有してもよい低級アルキル基、低級アル
ケニル基、低級アルキニル基、式−Xr1で表わされる基 −COCO基を示し、r1は低級アルキル基、置換基を有した
低級アルケニル基、置換基を有してもよいフェニル基、
又は置換基を有するベンジル基を示す。但し、Ｘが−CO
基を示すとき、r1は置換基を有するベンジル基を示
す。）、 で表わされる基（式中ＹはＯ又はＳ、r2は低級アルキル
基を示す。）で表わされる化合物とHalZR3〔III〕（式
中、Halはハロゲンを示し、 R3は、置換基を有してもよい低級アルキル基、置換基を
有してもよい低級アルケニル基、置換基を有してもよい
フェニル基、置換基を有してもよいベンジル基、又はピ
ペリジノ基を、 で表わされる化合物を反応させることからなる一般式
〔Ｉ−１〕 （式中、R1、R2、R3、Ｚは前記と同じ意味を示す。）で
表わされる化合物の製造方法。2. The general formula [II] (Wherein, R 1 is a phenyl group having a substituent, a naphthyl group,
Or a nitrogen-containing monocyclic heterocyclic group which may have a substituent, R 2 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group which may have a substituent, represented by the formula -Xr 1 Base -COCO group, r 1 is a lower alkyl group, a lower alkenyl group having a substituent, a phenyl group which may have a substituent,
Or a benzyl group having a substituent. Where X is -CO
When a group is represented, r 1 represents a benzyl group having a substituent. ), (Wherein Y represents O or S, r 2 represents a lower alkyl group) and HalZR 3 [III] (where Hal represents halogen, R 3 represents a substituent) A lower alkyl group which may have, a lower alkenyl group which may have a substituent, a phenyl group which may have a substituent, a benzyl group which may have a substituent, or a piperidino group, General formula [I-1] comprising reacting a compound represented by the following formula: (Wherein, R 1 , R 2 , R 3 and Z have the same meanings as described above).
又は置換基を有していてもよい含窒素単環ヘテロ環基
を、 R3は、置換基を有してもよい低級アルキル基、置換基を
有してもよい低級アルケニル基、置換基を有してもよい
フェニル基、置換基を有してもよいベンジル基、又はピ
ペリジノ基を、 で表される化合物とHalR2〔Ｖ〕（式中、Halはハロゲン
を示し、 R2は、置換基を有してもよい低級アルキル基、低級アル
ケニル基、低級アルキニル基、式−Xr1で表わされる基 −COCO基を示し、r1は低級アルキル基、置換基を有した
低級アルケニル基、置換基を有してもよいフェニル基、
又は置換基を有するベンジル基を示す。但し、Ｘが−CO
基を示すとき、r1は置換基を有するベンジル基を示
す。）、 で表わされる基（式中ＹはＯ又はＳ、r2は低級アルキル
基を示す。）で表わされる化合物を反応させることから
なる一般式〔Ｉ−１〕 （式中、R1、R2、R3、Ｚは前記と同じ意味を示す。）で
表わされる化合物の製造方法。3. A compound of the general formula [IV] (Wherein, R 1 is a phenyl group having a substituent, a naphthyl group,
Or a nitrogen-containing monocyclic heterocyclic group which may have a substituent, R 3 is a lower alkyl group which may have a substituent, a lower alkenyl group which may have a substituent, A phenyl group which may have, a benzyl group which may have a substituent, or a piperidino group, And HalR 2 [V] (wherein Hal represents halogen, and R 2 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group which may have a substituent, a group represented by the formula -Xr 1 Group represented -COCO group, r 1 is a lower alkyl group, a lower alkenyl group having a substituent, a phenyl group which may have a substituent,
Or a benzyl group having a substituent. Where X is -CO
When a group is represented, r 1 represents a benzyl group having a substituent. ), (Wherein Y represents O or S, and r 2 represents a lower alkyl group) represented by the general formula [I-1] (Wherein, R 1 , R 2 , R 3 and Z have the same meanings as described above).
ェニル基、ナフチル基、又は置換基を有していてもよい
含窒素単環ヘテロ環基を、 R2は、置換基を有してもよい低級アルキル基、低級アル
ケニル基、低級アルキニル基、式−Xr1で表わされる基 −COCO基を示し、r1は低級アルキル基、置換基を有した
低級アルケニル基、置換基を有してもよいフェニル基、
又は置換基を有するベンジル基を示す。但し、Ｘが−CO
基を示すとき、r1は置換基を有するベンジル基を示
す。）、 で表わされる基（式中ＹはＯ又はＳ、r2は低級アルキル
基を示す。）を示す。〕で表される化合物と、 HN−ZR3 〔VII〕 （式中、R3は、置換基を有してもよい低級アルキル基、
置換基を有してもよい低級アルケニル基、置換基を有し
てもよいフェニル基、置換基を有してもよいベンジル
基、又はピペリジノ基を、 で表わされる化合物を反応させることからなる一般式
〔Ｉ−２〕 （式中、R1、R2、R3、Ｚは前記と同じ意味を示す。）で
表わされる化合物の製造方法。4. A compound of the general formula [VI] (In the formula, Hal represents a halogen, R 1 represents a substituted phenyl group, a naphthyl group, or a nitrogen-containing monocyclic heterocyclic group which may have a substituent, and R 2 represents a substituent. a lower alkyl group which may be, a lower alkenyl group, lower alkynyl group, a group represented by the formula -Xr 1 -COCO group, r 1 is a lower alkyl group, a lower alkenyl group having a substituent, a phenyl group which may have a substituent,
Or a benzyl group having a substituent. Where X is -CO
When a group is represented, r 1 represents a benzyl group having a substituent. ), Wherein Y represents O or S, and r 2 represents a lower alkyl group. And a compound represented by the formula: HN-ZR 3 [VII] (wherein R 3 is a lower alkyl group which may have a substituent,
A lower alkenyl group which may have a substituent, a phenyl group which may have a substituent, a benzyl group which may have a substituent, or a piperidino group, A general formula [I-2] comprising reacting a compound represented by the formula: (Wherein, R 1 , R 2 , R 3 and Z have the same meanings as described above).
又は置換基を有していてもよい含窒素単環ヘテロ環基
を、 R2は、置換基を有してもよい低級アルキル基、低級アル
ケニル基、低級アルキニル基、式−Xr1で表わされる基 −COCO基を示し、r1は低級アルキル基、置換基を有した
低級アルケニル基、置換基を有してもよいフェニル基、
又は置換基を有するベンジル基を示す。但し、Ｘが−CO
基を示すとき、r1は置換基を有するベンジル基を示
す。）、又は で表わされる基（式中ＹはＯ又はＳ、r2は低級アルキル
基を示す。）を、 R3は、置換基を有してもよい低級アルキル基、置換基を
有してもよい低級アルケニル基、置換基を有してもよい
フェニル基、置換基を有してもよいベンジル基、又はピ
ペリジノ基を、 で表される化合物の１種又は２種以上を有効成分として
含有することを特徴とする殺ダニ剤。5. A compound of the formula [I] Wherein R 1 is a phenyl group having a substituent, a naphthyl group,
Or a nitrogen-containing monocyclic heterocyclic group which may have a substituent, R 2 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group which may have a substituent, represented by the formula -Xr 1 Base -COCO group, r 1 is a lower alkyl group, a lower alkenyl group having a substituent, a phenyl group which may have a substituent,
Or a benzyl group having a substituent. Where X is -CO
When a group is represented, r 1 represents a benzyl group having a substituent. ) Or Wherein Y represents O or S, and r 2 represents a lower alkyl group, and R 3 represents a lower alkyl group which may have a substituent, a lower alkyl group which may have a substituent. An alkenyl group, a phenyl group which may have a substituent, a benzyl group which may have a substituent, or a piperidino group, An acaricide comprising one or more of the compounds represented by the formula (1) as an active ingredient.
又は置換基を有していてもよい含窒素単環ヘテロ環基
を、 R2は、置換基を有してもよい低級アルキル基、低級アル
ケニル基、低級アルキニル基、式−Xr1で表わされる基 −COCO基を示し、r1は低級アルキル基、置換基を有した
低級アルケニル基、置換基を有してもよいフェニル基、
又は置換基を有するベンジル基を示す。但し、Ｘが−CO
基を示すとき、r1は置換基を有するベンジル基を示
す。）、 で表わされる基（式中ＹはＯ又はＳ、r2は低級アルキル
基を示す。）を、 R3は、置換基を有してもよい低級アルキル基、置換基を
有してもよい低級アルケニル基、置換基を有してもよい
フェニル基、置換基を有してもよいベンジル基、又はピ
ペリジノ基を、 で表わされる化合物の１種又は２種以上を有効成分とし
て含有することを特徴とする農園芸用殺菌剤。6. A compound of the formula [I] Wherein R 1 is a phenyl group having a substituent, a naphthyl group,
Or a nitrogen-containing monocyclic heterocyclic group which may have a substituent, R 2 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group which may have a substituent, represented by the formula -Xr 1 Base -COCO group, r 1 is a lower alkyl group, a lower alkenyl group having a substituent, a phenyl group which may have a substituent,
Or a benzyl group having a substituent. Where X is -CO
When a group is represented, r 1 represents a benzyl group having a substituent. ), Wherein Y represents O or S, and r 2 represents a lower alkyl group, and R 3 represents a lower alkyl group which may have a substituent, a lower alkyl group which may have a substituent. An alkenyl group, a phenyl group which may have a substituent, a benzyl group which may have a substituent, or a piperidino group, A fungicide for agricultural and horticultural use, characterized in that it contains one or more of the compounds represented by the formula (1) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15839388A JP2696342B2 (en) | 1988-06-27 | 1988-06-27 | Amidine derivative, method for producing the same, acaricide and agricultural / horticultural fungicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15839388A JP2696342B2 (en) | 1988-06-27 | 1988-06-27 | Amidine derivative, method for producing the same, acaricide and agricultural / horticultural fungicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH026453A JPH026453A (en) | 1990-01-10 |
| JP2696342B2 true JP2696342B2 (en) | 1998-01-14 |
Family
ID=15670752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15839388A Expired - Lifetime JP2696342B2 (en) | 1988-06-27 | 1988-06-27 | Amidine derivative, method for producing the same, acaricide and agricultural / horticultural fungicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2696342B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0941988A3 (en) * | 1998-03-10 | 2000-09-20 | Basf Aktiengesellschaft | Benzamidoxime derivatives, intermediates and process for their preparation and their use as fungicides |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE277004T1 (en) * | 1994-12-19 | 2004-10-15 | Nippon Soda Co | BENZAMIDOXIME DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND A BACTERICIDE FOR AGRICULTURE AND HORTICULTURE |
| ATE240039T1 (en) * | 1996-06-04 | 2003-05-15 | Nippon Soda Co | AGRICULTURAL AND HORTICULTURAL ANTIBACTERIAL COMPOSITIONS |
| WO1997046096A1 (en) * | 1996-06-04 | 1997-12-11 | Nippon Soda Co., Ltd. | Agricultural/horticultural bactericidal compositions |
| AU748905B2 (en) * | 1997-09-18 | 2002-06-13 | Basf Aktiengesellschaft | Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides |
| US6417398B1 (en) * | 1997-09-18 | 2002-07-09 | Basf Aktiengesellschaft | Benzamidoxim derivatives, intermediate products and methods for preparing them, and their use as fungicides |
| DE69930325D1 (en) * | 1998-04-30 | 2006-05-11 | Nippon Soda Co | A fungicidal composition for agriculture and horticulture containing a benzamidoxime compound and an acid amide derivative |
| WO2000017156A1 (en) * | 1998-09-22 | 2000-03-30 | Basf Aktiengesellschaft | Novel benzamidoxime derivatives, intermediate products, methods for the production thereof, and their use as fungicides |
| KR100377508B1 (en) * | 2000-04-04 | 2003-03-26 | 서종대 | Portable scooper |
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| WO2003053917A1 (en) * | 2001-12-21 | 2003-07-03 | Nippon Soda Co.,Ltd. | Guanidine compounds and pest controllers |
| DK2559690T3 (en) | 2005-05-10 | 2016-04-25 | Incyte Holdings Corp | Modulators of indoleamine 2,3-dioxygenase and methods of use thereof |
| EP1971583B1 (en) | 2005-12-20 | 2015-03-25 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| WO2008036642A2 (en) | 2006-09-19 | 2008-03-27 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CL2007002650A1 (en) | 2006-09-19 | 2008-02-08 | Incyte Corp | COMPOUNDS DERIVED FROM HETEROCICLO N-HIDROXIAMINO; PHARMACEUTICAL COMPOSITION, USEFUL TO TREAT CANCER, VIRAL INFECTIONS AND NEURODEGENERATIVE DISORDERS BETWEEN OTHERS. |
| GB0720232D0 (en) * | 2007-10-16 | 2007-11-28 | Syngenta Participations Ag | Insecticidal compounds |
| BRPI0915692B8 (en) | 2008-07-08 | 2021-05-25 | Incyte Corp | compounds derived from 1,2,5-oxadiazoles, their solid form, their composition, as well as their uses |
| SG10201803874PA (en) | 2013-11-08 | 2018-07-30 | Incyte Holdings Corp | Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor |
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| US4554014A (en) | 1984-04-20 | 1985-11-19 | Stauffer Chemical Company | O-Aryloxyphenoxyacyl-α-N,N,-dialkylaminooximes and herbicidal methods of use |
| US4584317A (en) | 1984-09-11 | 1986-04-22 | Chevron Research Company | Pesticidal tin amidoximes |
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| FR2524465A1 (en) * | 1982-04-01 | 1983-10-07 | Rhone Poulenc Agrochimie | NEW HERBICIDES DERIVED FROM SULFONIMIDE GROUP PHENOXYBENZOIC ACIDS |
| JPS5942357A (en) * | 1982-09-03 | 1984-03-08 | Ishihara Sangyo Kaisha Ltd | Benzamidoxime derivative and insecticide containing the same |
| GB8422701D0 (en) * | 1984-09-07 | 1984-10-10 | Shell Int Research | Ether herbicides |
| JPS6434954A (en) * | 1987-02-18 | 1989-02-06 | Hokko Chem Ind Co | Benzenecarboximidamide derivative and agricultural and horticultural fungicide |
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| US3347874A (en) | 1963-01-09 | 1967-10-17 | Union Carbide Corp | 5-nitrofuryl-2-amidoximes |
| US4554014A (en) | 1984-04-20 | 1985-11-19 | Stauffer Chemical Company | O-Aryloxyphenoxyacyl-α-N,N,-dialkylaminooximes and herbicidal methods of use |
| US4584317A (en) | 1984-09-11 | 1986-04-22 | Chevron Research Company | Pesticidal tin amidoximes |
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| Title |
|---|
| Ｃｏｌｌｅｃｔ．Ｃｚｅｃｈ．Ｃｈｅｍ．Ｃｏｍｍｕｎ．Ｖｏｌ．４８（２）（１９８３）ｐ５９６−６０７，Ｔｅｔｒａｂｃｄｒｃｎ Ｌｅｔｔ．Ｖｏｌ．２０（１９６８）ｐ２４２１−２４ |
| Ｊ．Ｃｈｅｍ．Ｓｏｃ．Ｐｅｒｋｉｎ Ｔｒａｎｓ Ｉ．Ｖｏｌ．６（１９８８）ｐ．１３１３−１５，Ｂｕｌｌ．Ｓｏｃ．Ｃｈｉｍ．Ｆｒ，Ｖｏｌ．７（１９７０）ｐ２６１５−２８ |
| Ｋｙｕｓｈｕ Ｋｏｇｙｏ Ｄａｉｇａｋｕ Ｋｅｓｋｙｕ Ｈｏｕｋｏｋｕ，Ｎｏ．１５（１９６５）ｐ５７−６４ |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0941988A3 (en) * | 1998-03-10 | 2000-09-20 | Basf Aktiengesellschaft | Benzamidoxime derivatives, intermediates and process for their preparation and their use as fungicides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH026453A (en) | 1990-01-10 |
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