CS249535B2 - Fungicide and method of its efficient substances production - Google Patents

Fungicide and method of its efficient substances production Download PDF

Info

Publication number: CS249535B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; phenoxybenzaldehyde; water; hydrogen; nitro
Prior art date: 1984-01-17

Application number

CS33785A

Other languages

Czech (cs)

English (en)

Inventor

Jozsef Bakos

Balint Heil

Laszlo Kollar

Szilard Toeroes

Gyula Eifert

Feren Bihari

Janos Szulagyi

Anna Durko

Istvan Kuronya

Istvan Magyari

Katalin Tromfos

Peter Bohus

Laszlo Wohl

Original Assignee

Budapesti Vegyimuevek

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.)

1984-01-17

Filing date

1985-01-17

Publication date

1987-03-12

1985-01-17 Application filed by Budapesti Vegyimuevek filed Critical Budapesti Vegyimuevek

1987-03-12 Publication of CS249535B2 publication Critical patent/CS249535B2/cs

Links

230000000855 fungicidal effect Effects 0.000 title claims abstract description 11
238000000034 method Methods 0.000 title claims description 8
239000000126 substance Substances 0.000 title description 7
238000004519 manufacturing process Methods 0.000 title description 3
239000000417 fungicide Substances 0.000 title description 2
-1 3-formyl-phenoxy Chemical group 0.000 claims abstract description 24
239000000203 mixture Substances 0.000 claims abstract description 18
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
239000000460 chlorine Chemical group 0.000 claims abstract description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052801 chlorine Chemical group 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
239000004480 active ingredient Substances 0.000 claims description 13
IMPIIVKYTNMBCD-UHFFFAOYSA-N 2-phenoxybenzaldehyde Chemical class O=CC1=CC=CC=C1OC1=CC=CC=C1 IMPIIVKYTNMBCD-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 6
150000001555 benzenes Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000003701 inert diluent Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 22
230000000802 nitrating effect Effects 0.000 abstract description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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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 9
239000013543 active substance Substances 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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238000011161 development Methods 0.000 description 7
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238000005160 1H NMR spectroscopy Methods 0.000 description 6
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
241000233866 Fungi Species 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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239000002202 Polyethylene glycol Substances 0.000 description 4
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238000006243 chemical reaction Methods 0.000 description 4
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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239000008187 granular material Substances 0.000 description 4
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238000003359 percent control normalization Methods 0.000 description 4
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BFBADHDKKQLFJK-UHFFFAOYSA-N 3-[2,4-dinitro-6-(trifluoromethyl)phenoxy]benzaldehyde Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1OC1=CC=CC(C=O)=C1 BFBADHDKKQLFJK-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000008272 agar Substances 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
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239000000843 powder Substances 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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239000000080 wetting agent Substances 0.000 description 3
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KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
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241000123650 Botrytis cinerea Species 0.000 description 2
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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241000223218 Fusarium Species 0.000 description 2
235000019738 Limestone Nutrition 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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244000115721 Pennisetum typhoides Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000228452 Venturia inaequalis Species 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
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150000001342 alkaline earth metals Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000010775 animal oil Substances 0.000 description 2
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125000003118 aryl group Chemical group 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
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UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
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DPQYRXNRGNLPFC-UHFFFAOYSA-N 2,4-dichloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1Cl DPQYRXNRGNLPFC-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS33785A 1984-01-17 1985-01-17 Fungicide and method of its efficient substances production CS249535B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU15884A HU193194B (en)	1984-01-17	1984-01-17	Fungicide compositions containing phenoxy-benzaldehyde derivatives as active substances and process for preparing the active substances

Publications (1)

Publication Number	Publication Date
CS249535B2 true CS249535B2 (en)	1987-03-12

Family

ID=10948239

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS33785A CS249535B2 (en)	1984-01-17	1985-01-17	Fungicide and method of its efficient substances production

Country Status (9)

Country	Link
JP (1)	JPS60237038A (de)
CH (1)	CH663409A5 (de)
CS (1)	CS249535B2 (de)
DD (2)	DD233065A5 (de)
DE (1)	DE3501428A1 (de)
FR (1)	FR2558155B1 (de)
GB (1)	GB2154235B (de)
HU (1)	HU193194B (de)
YU (1)	YU6185A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU193467B (en) *	1984-11-12	1987-10-28	Budapesti Vegyimuevek	Fungicidal composition comprising substituted benzoic acid derivative as active substance and process for preparing the active substance
US6028219A (en) *	1995-09-13	2000-02-22	Zeneca Limited	Process for the nitration of diphenylethers
MX2007004400A (es) *	2004-10-13	2007-06-19	Glenmark Pharmaceuticals Sa	Procedimiento para la preparacion de n-(3,5-dicloropirid-a-il)-4- ifluorometoxi-8-metanosulfonamido-dibenzo [b,d] difuran-1-carboxamida.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2050168B (en) *	1979-04-04	1982-11-10	Shell Int Research	Ethynyl compounds as herbicides

1984
- 1984-01-17 HU HU15884A patent/HU193194B/hu unknown
1985
- 1985-01-15 CH CH17985A patent/CH663409A5/de not_active IP Right Cessation
- 1985-01-16 GB GB08501038A patent/GB2154235B/en not_active Expired
- 1985-01-17 DD DD23306585A patent/DD233065A5/de not_active IP Right Cessation
- 1985-01-17 FR FR8500641A patent/FR2558155B1/fr not_active Expired
- 1985-01-17 CS CS33785A patent/CS249535B2/cs unknown
- 1985-01-17 DD DD27262485A patent/DD231345A5/de not_active IP Right Cessation
- 1985-01-17 DE DE19853501428 patent/DE3501428A1/de not_active Withdrawn
- 1985-01-17 JP JP513185A patent/JPS60237038A/ja active Pending
- 1985-01-17 YU YU6185A patent/YU6185A/xx unknown

Also Published As

Publication number	Publication date
DD233065A5 (de)	1986-02-19
DE3501428A1 (de)	1985-07-18
FR2558155B1 (fr)	1987-04-24
CH663409A5 (de)	1987-12-15
HUT37907A (en)	1986-03-28
FR2558155A1 (fr)	1985-07-19
YU6185A (en)	1988-02-29
GB2154235B (en)	1987-07-08
HU193194B (en)	1987-08-28
GB8501038D0 (en)	1985-02-20
JPS60237038A (ja)	1985-11-25
DD231345A5 (de)	1985-12-24
GB2154235A (en)	1985-09-04

Publication	Publication Date	Title
EP0407899B1 (de)	1995-03-01	Aminopyrimidin-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Fungizide
JP3449569B2 (ja)	2003-09-22	トリアゾロピリミジン誘導体
CZ281586B6 (cs)	1996-11-13	Derivát 2-anilinopyrimidinu, způsob jeho přípravy a fungicidní prostředek, který ho obsahuje
US4046906A (en)	1977-09-06	Salts of alkyl 2-benzimidazole-carbamate
CZ294096B6 (cs)	2004-10-13	Benzofenonové sloučeninyŹ způsob jejich výrobyŹ fungicidní prostředky s jejich obsahem a způsob ochrany rostlin
CS247096B2 (en)	1986-11-13	Fungicide agent for using in agriculature and production method of its effective compound
HU194481B (en)	1988-02-29	Fungicide composition containing ethane derivatives and process for producing the active agents
JP3156268B2 (ja)	2001-04-16	イミノチアゾリン誘導体、その製造法、それを有効成分とする除草剤およびその製造中間体
WO1992005158A1 (de)	1992-04-02	4-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltene mittel und ihre verwendung als fungizide
CZ466989A3 (cs)	1998-02-18	Oximetherový derivát, fungicidní prostředek s jeho obsahem a způsob potírání hub
CS249535B2 (en)	1987-03-12	Fungicide and method of its efficient substances production
KR940011460B1 (ko)	1994-12-15	벤조티아지논 화합물의 제조방법
CS220800B2 (en)	1983-04-29	Herbicide means and method of making the active substances
CS248732B2 (en)	1987-02-12	Fungicide agent
HU189528B (en)	1986-07-28	Compositions with fungicide activity and process for preparing substituted succinic acid derivatives as active substances thereof
EP0003430B1 (de)	1982-01-06	Neue 2,6-Dinitrophenylamine, deren Herstellung, diese Verbindungen enthaltende Zusammensetzungen und deren Verwendung als Fungizide
EP0216424A1 (de)	1987-04-01	Imidazole, deren Herstellung und Verwendung als Fungizide
CS411386A2 (en)	1989-09-12	Fungicide and method of its active substances production
JP2503547B2 (ja)	1996-06-05	カルバモイルトリアゾ―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
CA1040642A (en)	1978-10-17	Substituted oxirane compounds
EP0152131B1 (de)	1989-08-23	Carboxamid-Derivate, ihre Herstellung und ihre Verwendung als Fungizidmittel
US5026895A (en)	1991-06-25	Novel (trifluoromethyl)-phenoxy-benzoic acid derivatives, process for the preparation thereof and fungicides containing these compounds as active ingredient
HU206022B (en)	1992-08-28	Fungicidal composition comprising imidazole derivative as active ingredient, process for producing the active ingredient and for applying the composition
JP2993839B2 (ja)	1999-12-27	３−ピロリン−２−オン誘導体、およびこれらを含有することを特徴とする除草剤
DE3102590A1 (de)	1982-08-19	"mikrobizide mittel"