JPH0123472B2 - - Google Patents

Info

Publication number: JPH0123472B2
Authority: JP; Japan
Prior art keywords: parts; compound; formula; halogen atom; present
Prior art date: 1983-03-24
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

Application number

JP4796783A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59175489A (ja

Inventor

Hiroshi Sugyama

Keizo Hosoda

Yoshikazu Kumagai

Masaki Takeuchi

Masanori Okada

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chugai Pharmaceutical Co Ltd

Original Assignee

Chugai Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1983-03-24

Filing date

1983-03-24

Publication date

1989-05-02

1983-03-24 Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd

1983-03-24 Priority to JP4796783A priority Critical patent/JPS59175489A/ja

1984-03-13 Priority to US06/589,018 priority patent/US4596801A/en

1984-03-14 Priority to CA000449586A priority patent/CA1228590A/en

1984-03-16 Priority to AU25806/84A priority patent/AU562226B2/en

1984-03-22 Priority to EP84103191A priority patent/EP0120480B1/en

1984-03-22 Priority to AT84103191T priority patent/ATE28198T1/de

1984-03-22 Priority to DE8484103191T priority patent/DE3464608D1/de

1984-03-23 Priority to BR8401360A priority patent/BR8401360A/pt

1984-03-23 Priority to ES530959A priority patent/ES8604947A1/es

1984-10-04 Publication of JPS59175489A publication Critical patent/JPS59175489A/ja

1985-06-14 Priority to ES544241A priority patent/ES8604194A1/es

1989-05-02 Publication of JPH0123472B2 publication Critical patent/JPH0123472B2/ja

Status Granted legal-status Critical Current

Links

125000005843 halogen group Chemical group 0.000 claims description 12
239000000417 fungicide Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
XAZNOOMRYLFDQO-UHFFFAOYSA-N 4h-3,1-benzoxazine Chemical class C1=CC=C2COC=NC2=C1 XAZNOOMRYLFDQO-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
PKKSAVQQCBTBNZ-UHFFFAOYSA-N amino(diphenyl)methanol Chemical class C=1C=CC=CC=1C(O)(N)C1=CC=CC=C1 PKKSAVQQCBTBNZ-UHFFFAOYSA-N 0.000 claims description 4
230000000855 fungicidal effect Effects 0.000 claims description 4
150000001875 compounds Chemical class 0.000 description 31
201000010099 disease Diseases 0.000 description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 21
239000000203 mixture Substances 0.000 description 16
238000009472 formulation Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
241000221785 Erysiphales Species 0.000 description 8
-1 chloro-α-hydroxybenzyl Chemical group 0.000 description 8
239000004927 clay Substances 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241000209140 Triticum Species 0.000 description 6
235000021307 Triticum Nutrition 0.000 description 6
238000000034 method Methods 0.000 description 6
239000002689 soil Substances 0.000 description 5
240000008067 Cucumis sativus Species 0.000 description 4
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002156 mixing Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000007605 air drying Methods 0.000 description 3
125000005037 alkyl phenyl group Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
230000009969 flowable effect Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000003898 horticulture Methods 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
244000045561 useful plants Species 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
230000002411 adverse Effects 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000003902 lesion Effects 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000009331 sowing Methods 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
230000001225 therapeutic effect Effects 0.000 description 2
239000000230 xanthan gum Substances 0.000 description 2
229920001285 xanthan gum Polymers 0.000 description 2
235000010493 xanthan gum Nutrition 0.000 description 2
229940082509 xanthan gum Drugs 0.000 description 2
OXLXSOPFNVKUMU-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical class CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC OXLXSOPFNVKUMU-UHFFFAOYSA-N 0.000 description 1
GTYUFIQKBPAHPN-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-pyridin-4-yl-4h-3,1-benzoxazine Chemical compound C1=CC(Cl)=CC=C1C1C2=CC=CC=C2N=C(C=2C=CN=CC=2)O1 GTYUFIQKBPAHPN-UHFFFAOYSA-N 0.000 description 1
UTGOCPHGFPSMAO-UHFFFAOYSA-N 4-(4-chlorophenyl)-6-fluoro-2-pyridin-4-yl-4h-3,1-benzoxazine Chemical compound C12=CC(F)=CC=C2N=C(C=2C=CN=CC=2)OC1C1=CC=C(Cl)C=C1 UTGOCPHGFPSMAO-UHFFFAOYSA-N 0.000 description 1
ZOUTVMHARGGMEE-UHFFFAOYSA-N 6-bromo-4-phenyl-2-pyridin-4-yl-4h-3,1-benzoxazine Chemical compound C12=CC(Br)=CC=C2N=C(C=2C=CN=CC=2)OC1C1=CC=CC=C1 ZOUTVMHARGGMEE-UHFFFAOYSA-N 0.000 description 1
FJZSHXHUIBBESX-UHFFFAOYSA-N 6-chloro-4-(4-chlorophenyl)-2-pyridin-4-yl-4h-3,1-benzoxazine Chemical compound C1=CC(Cl)=CC=C1C1C2=CC(Cl)=CC=C2N=C(C=2C=CN=CC=2)O1 FJZSHXHUIBBESX-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
241000221787 Erysiphe Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
241000317981 Podosphaera fuliginea Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
241000221301 Puccinia graminis Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000579741 Sphaerotheca <fungi> Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000002316 fumigant Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 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
239000003350 kerosene Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP4796783A 1983-03-24 1983-03-24 ４ｈ−３，１−ベンゾオキサジン誘導体、その製造法およびそれらを含有する農園芸用殺菌剤 Granted JPS59175489A (ja)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
JP4796783A JPS59175489A (ja)	1983-03-24	1983-03-24	４ｈ−３，１−ベンゾオキサジン誘導体、その製造法およびそれらを含有する農園芸用殺菌剤
US06/589,018 US4596801A (en)	1983-03-24	1984-03-13	4H-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same
CA000449586A CA1228590A (en)	1983-03-24	1984-03-14	4h-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same
AU25806/84A AU562226B2 (en)	1983-03-24	1984-03-16	Pyridyl-benzoxazines
AT84103191T ATE28198T1 (de)	1983-03-24	1984-03-22	4h-3,1 benzoxazinderivate, verfahren zu ihrer herstellung und sie enthaltendes pilztoetendes landwirtschafts- oder gartenprodukt.
EP84103191A EP0120480B1 (en)	1983-03-24	1984-03-22	4h-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same
DE8484103191T DE3464608D1 (en)	1983-03-24	1984-03-22	4h-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same
BR8401360A BR8401360A (pt)	1983-03-24	1984-03-23	Derivado de 4h-3,1-benzoxazina,processo para producao do mesmo,composicao fungicida agricola ou horticola e processo para controle de fungos patogenicos em plantas ou solo
ES530959A ES8604947A1 (es)	1983-03-24	1984-03-23	Un derivado de 4h-3, 1-benzoxazina
ES544241A ES8604194A1 (es)	1983-03-24	1985-06-14	Un procedimiento para producir un derivado de 4h-3,1-benzo- xazina

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4796783A JPS59175489A (ja)	1983-03-24	1983-03-24	４ｈ−３，１−ベンゾオキサジン誘導体、その製造法およびそれらを含有する農園芸用殺菌剤

Publications (2)

Publication Number	Publication Date
JPS59175489A JPS59175489A (ja)	1984-10-04
JPH0123472B2 true JPH0123472B2 (es)	1989-05-02

Family

ID=12790094

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4796783A Granted JPS59175489A (ja)	1983-03-24	1983-03-24	４ｈ−３，１−ベンゾオキサジン誘導体、その製造法およびそれらを含有する農園芸用殺菌剤

Country Status (1)

Country	Link
JP (1)	JPS59175489A (es)

1983
- 1983-03-24 JP JP4796783A patent/JPS59175489A/ja active Granted

Also Published As

Publication number	Publication date
JPS59175489A (ja)	1984-10-04

Publication	Publication Date	Title
HU186351B (en)	1985-07-29	Antidotal or herbicide-antidotal preparations containing substituted dithia-alkylidene-amino derivatives as actor
EP0120480B1 (en)	1987-07-08	4h-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same
JPH0123472B2 (es)	1989-05-02
JPS599521B2 (ja)	1984-03-03	除草剤
JPH0251553B2 (es)	1990-11-07
JPS6011031B2 (ja)	1985-03-22	イミダゾ−ル誘導体の製造方法
JPH0368860B2 (es)	1991-10-30
JPS60136565A (ja)	1985-07-20	アセタ−ル類化合物、その製造法およびそれらを含有する農園芸用殺菌剤
JPH045012B2 (es)	1992-01-30
JPH0466869B2 (es)	1992-10-26
JPH0314827B2 (es)	1991-02-27
JPH02178266A (ja)	1990-07-11	ニコチン酸アニリド系化合物及び該化合物を含有する除草剤
JPH045279A (ja)	1992-01-09	新規なオキシムエーテル誘導体およびそれを有効成分とする除草剤および農園芸用殺菌剤
JPS60126267A (ja)	1985-07-05	シツフ塩基誘導体，その製造法およびそれらを含有する農園芸用殺菌剤
JPS59199677A (ja)	1984-11-12	アセタ−ル類化合物、その製造法およびそれらを含有する農園芸用殺菌剤
EP0122410A2 (en)	1984-10-24	Fungicidal isonicotinanilide acetal derivatives, process for their production and fungicides containing them
JPS6143160A (ja)	1986-03-01	シクロヘキセンジカルボン酸ジアミド類およびこれを有効成分とする除草剤
JPS60252465A (ja)	1985-12-13	２−フエニル−４，５，６，７−テトラヒドロ−２ｈ−インダゾ−ル誘導体、その製造法およびそれを有効成分とする除草剤
JPS59155360A (ja)	1984-09-04	アセタ−ル類化合物、その製造法およびそれらを含有する農園芸用殺菌剤
JPS6176463A (ja)	1986-04-18	Ｎ−アルキルイソニコチン酸アニリド誘導体、その製造法およびそれらを含有する農園芸用殺菌剤
JPS6320428B2 (es)	1988-04-27
JPH0368865B2 (es)	1991-10-30
JPS6148508B2 (es)	1986-10-24
JPS6025968A (ja)	1985-02-08	イソニコチン酸アニリド誘導体およびその化合物からなる農園芸用殺菌剤
JPH0350721B2 (es)	1991-08-02