BG61973B1 - Производни на сулфамоилтриазола и фунгициди, които гисъдържат като активни компоненти - Google Patents

Производни на сулфамоилтриазола и фунгициди, които гисъдържат като активни компоненти Download PDF

Info

Publication number: BG61973B1
Authority: BG; Bulgaria
Prior art keywords: group; general formula; integer; lower alkyl; formyl
Prior art date: 1992-07-14

Application number

BG98647A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG98647A (bg

Inventor

Atsushi Goh

Yoshihiro Usui

Yoshimi Tsutsumi

Yoshie Kirio

Yoshihiro Takayama

Seiichiro Yamada

Masako Yamanaka

Original Assignee

Mitsubishi Chemical Corporation

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.)

1992-07-14

Filing date

1994-03-10

Publication date

1998-11-30

1994-03-10 Application filed by Mitsubishi Chemical Corporation filed Critical Mitsubishi Chemical Corporation

1995-03-31 Publication of BG98647A publication Critical patent/BG98647A/bg

1998-11-30 Publication of BG61973B1 publication Critical patent/BG61973B1/bg

Links

239000000417 fungicide Substances 0.000 title claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 30
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
125000001188 haloalkyl group Chemical group 0.000 claims description 18
WAIIVJKIXMLKTR-UHFFFAOYSA-N 2h-triazole-4-sulfonamide Chemical class NS(=O)(=O)C1=CNN=N1 WAIIVJKIXMLKTR-UHFFFAOYSA-N 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 14
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
125000004438 haloalkoxy group Chemical group 0.000 claims description 13
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
230000000855 fungicidal effect Effects 0.000 claims description 9
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
230000006378 damage Effects 0.000 abstract description 5
230000006735 deficit Effects 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 103
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
239000000460 chlorine Substances 0.000 description 56
125000001309 chloro group Chemical group Cl* 0.000 description 48
239000000243 solution Substances 0.000 description 36
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 31
239000002904 solvent Substances 0.000 description 29
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
-1 methoxy- Chemical class 0.000 description 26
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
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238000000034 method Methods 0.000 description 19
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 19
201000010099 disease Diseases 0.000 description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
238000002360 preparation method Methods 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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238000003756 stirring Methods 0.000 description 13
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235000019341 magnesium sulphate Nutrition 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
239000000126 substance Substances 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
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229910000027 potassium carbonate Inorganic materials 0.000 description 10
239000000047 product Substances 0.000 description 10
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
238000004821 distillation Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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239000000543 intermediate Substances 0.000 description 8
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239000002585 base Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 7
JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 7
AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241000196324 Embryophyta Species 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
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150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
239000000969 carrier Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
101150065749 Churc1 gene Proteins 0.000 description 4
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MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
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102100038239 Protein Churchill Human genes 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
244000061456 Solanum tuberosum Species 0.000 description 4
235000002595 Solanum tuberosum Nutrition 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
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150000002170 ethers Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
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KRGDHNPMWOBKPN-UHFFFAOYSA-N 1h-1,2,4-triazole-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=NC=NN1 KRGDHNPMWOBKPN-UHFFFAOYSA-N 0.000 description 3
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
IXYACKYHUWCLAM-UHFFFAOYSA-M sodium;2-ethylhex-1-ene-1-sulfonate Chemical compound [Na+].CCCCC(CC)=CS([O-])(=O)=O IXYACKYHUWCLAM-UHFFFAOYSA-M 0.000 description 1
MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000003971 tillage Methods 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BG98647A 1992-07-14 1994-03-10 Производни на сулфамоилтриазола и фунгициди, които гисъдържат като активни компоненти BG61973B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP4186869A JPH0632785A (ja)	1992-07-14	1992-07-14	スルファモイルトリアゾール誘導体及びそれを有効成分とする殺菌剤
PCT/JP1993/000939 WO1994001419A1 (fr)	1992-07-14	1993-07-08	Derive de sulfamoyltriazole et bactericide le renfermant comme principe actif

Publications (2)

Publication Number	Publication Date
BG98647A BG98647A (bg)	1995-03-31
BG61973B1 true BG61973B1 (bg)	1998-11-30

Family

ID=16196099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG98647A BG61973B1 (bg)	1992-07-14	1994-03-10	Производни на сулфамоилтриазола и фунгициди, които гисъдържат като активни компоненти

Country Status (7)

Country	Link
US (1)	US5527818A (fr)
EP (1)	EP0603415A4 (fr)
JP (1)	JPH0632785A (fr)
AU (1)	AU662651B2 (fr)
BG (1)	BG61973B1 (fr)
CA (1)	CA2116220C (fr)
WO (1)	WO1994001419A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH11302276A (ja) *	1996-04-26	1999-11-02	Nissan Chem Ind Ltd	スルファモイルトリアゾール誘導体並びに農園芸用殺菌剤
ATE499365T1 (de) *	1997-10-24	2011-03-15	Nissan Chemical Ind Ltd	Sulfamoyl-verbindungen und bakterizide für landwirtschaft oder gartenbau
CN104230914B (zh) *	2014-08-26	2016-08-31	盐城师范学院	1,2,4-三唑类化合物及其制备方法
CN105693638B (zh) *	2016-01-05	2018-12-04	浙江博仕达作物科技有限公司	一种杀菌化合物、杀菌剂组合物和制剂及其应用
CN105669576B (zh) *	2016-02-22	2018-12-04	浙江博仕达作物科技有限公司	一种杀菌化合物、杀菌剂组合物和制剂及其应用
CN106879599B (zh) *	2017-03-24	2018-08-03	浙江博仕达作物科技有限公司	三氮唑磺酸酯类化合物在防治水稻细菌性病害中的应用
WO2018184579A1 (fr) *	2017-04-05	2018-10-11	Dongguan Hec Tech R&D Co., Ltd.	Composé de triazole et son utilisation en agriculture
CN110950812B (zh) *	2018-09-27	2020-11-10	东莞市东阳光农药研发有限公司	三氮唑化合物及其在农业中的应用
CN114516846B (zh) *	2020-11-19	2025-12-02	东莞市东阳光农药研发有限公司	一种三唑类磺酰胺衍生物及其制备方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3682711D1 (de) *	1985-06-18	1992-01-16	Ici Plc	Als fungizide verwendbare heterocyclische verbindungen.
US5045557A (en) *	1987-03-20	1991-09-03	Schering Agrochemicals Ltd.	Imidazable fungicides and use thereof
GB8906965D0 (en) *	1989-03-28	1989-05-10	Schering Agrochemicals Ltd	Fungicides
ES2124705T3 (es) *	1990-08-03	1999-02-16	Chugai Pharmaceutical Co Ltd	Compuesto de triazol.

1992
- 1992-07-14 JP JP4186869A patent/JPH0632785A/ja active Pending
1993
- 1993-07-08 WO PCT/JP1993/000939 patent/WO1994001419A1/fr not_active Ceased
- 1993-07-08 US US08/199,218 patent/US5527818A/en not_active Expired - Fee Related
- 1993-07-08 EP EP93914971A patent/EP0603415A4/fr not_active Withdrawn
- 1993-07-08 AU AU45138/93A patent/AU662651B2/en not_active Ceased
- 1993-07-08 CA CA002116220A patent/CA2116220C/fr not_active Expired - Fee Related
1994
- 1994-03-10 BG BG98647A patent/BG61973B1/bg unknown

Also Published As

Publication number	Publication date
EP0603415A4 (fr)	1995-03-22
CA2116220A1 (fr)	1994-01-20
CA2116220C (fr)	1997-02-04
BG98647A (bg)	1995-03-31
EP0603415A1 (fr)	1994-06-29
WO1994001419A1 (fr)	1994-01-20
US5527818A (en)	1996-06-18
AU662651B2 (en)	1995-09-07
AU4513893A (en)	1994-01-31
JPH0632785A (ja)	1994-02-08

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AU2002327096B2 (en)	2007-11-22	3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
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DK172191B1 (da)	1997-12-22	Plantebeskyttelsesmidler indeholdende 1,2,4,-triazolderivater, fremgangsmåde til beskyttelse af kulturplanter mod phytotoksiske bivirkninger af herbicider, i midlerne indgående triazolderivater eller salte deraf, disses anvendelse og fremstilling.
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CN102336744B (zh)	2014-05-07	取代三唑啉酮醚类化合物及其作为杀菌、杀虫、杀螨剂的用途
WO1992017468A1 (fr)	1992-10-15	Derive de pyridine, sa production, herbicide et procede de desherbage
BG61973B1 (bg)	1998-11-30	Производни на сулфамоилтриазола и фунгициди, които гисъдържат като активни компоненти
JP2009078991A (ja)	2009-04-16	チオフェンカルボン酸誘導体およびその製造方法、並びに殺菌剤
CN102336743B (zh)	2015-01-14	取代三唑啉酮醚类化合物及其应用
JP2000226374A (ja)	2000-08-15	ピラゾリノン誘導体
US5817829A (en)	1998-10-06	Pyrazolecarboxylic acid derivatives and plant disease control agent
JP2002520384A (ja)	2002-07-09	アリールビニルエーテル誘導体およびそれらの除草剤としての使用
HU201531B (en)	1990-11-28	Compositions comprising 1,5-diphenyl-1,2,4-triazole-3-carboxylic acid derivatives for the protection of plants against phytotoxic effect of herbicides and process for producing the active ingredients
EP0945437A1 (fr)	1999-09-29	Dérivés de pyrazolyl acide acrylique et parazolyl acide oximino-acetique, leur préparation et leur utilisation comme fongicides
JP3051356B2 (ja)	2000-06-12	除草性アニリン誘導体
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US5190575A (en)	1993-03-02	5-substituted-2,4-diphenylpyrimidine derivatives and their use
US5270467A (en)	1993-12-14	5-substituted-2,4-diphenylpyrimidine derivatives
JP2004262934A (ja)	2004-09-24	３−フェノキシ−４−ピリダジノール誘導体を含有する除草性組成物
US5349108A (en)	1994-09-20	5-substituted-2,4-diphenylpyrimidine derivatives, their production and use
US5403948A (en)	1995-04-04	5-substituted-2,4-diphenylpyrimidine derivatives, their production and use
JPS63166865A (ja)	1988-07-11	置換されたフエノキシピリジン類
JPH072803A (ja)	1995-01-06	スルファモイルトリアゾール誘導体及びそれを有効成分とする殺菌剤
JPS62463A (ja)	1987-01-06	Ｎ−フエニル−３，４，５，６−テトラヒドロフタルイミド誘導体、その製造方法並びに除草及び植物生長調節用組成物
JP2001011053A (ja)	2001-01-16	３−ピラゾリン−５−オン化合物及びその用途