RO103770B1 - Method for preparation of substituted phenyl alkyl formamide - Google Patents

Method for preparation of substituted phenyl alkyl formamide Download PDF

Info

Publication number: RO103770B1
Authority: RO; Romania
Prior art keywords: preparation; compounds; fungicidal; dimethylbutane; formamido
Prior art date: 1988-05-18

Application number

RO13980489A

Other languages

English (en)

Romanian (ro)

Inventor

Mikhailovici Bobylev Mikhail

Mikhailovich Velesevich Sergei

Alexandrovna Eremina Vera

Vladimirovich Perlov Alexandr

Ivanovna Orlova Tatyana

Pavlovich Taschi Valery

Grigorievich Putsykin Jury

Igorevna Akhmatova Natalya

Jurievich Molchanov Oleg

Vladimirovna Bobkova Galina

Nikolaevna Ivanchenko Julia

Arshakovna Rusakova Valentina

Ivanovna Andreeva Elena

Jurievich Tsvetkov Vsevolod

Semenovna Pronchenko Tamara

Original Assignee

Vsesojusny Nii Khim Sredstv Za

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.)

1988-05-18

Filing date

1989-05-18

Publication date

1993-04-15

1988-05-18 Priority claimed from SU884443133A external-priority patent/RU1775394C/ru

1988-05-18 Priority claimed from SU884427664A external-priority patent/RU1775395C/ru

1989-05-18 Application filed by Vsesojusny Nii Khim Sredstv Za filed Critical Vsesojusny Nii Khim Sredstv Za

1993-04-15 Publication of RO103770B1 publication Critical patent/RO103770B1/ro

Links

238000002360 preparation method Methods 0.000 title claims description 42
238000000034 method Methods 0.000 title claims description 12
-1 phenyl alkyl formamide Chemical class 0.000 title claims description 10
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 title description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000012467 final product Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 description 32
150000001875 compounds Chemical class 0.000 description 27
238000011160 research Methods 0.000 description 21
239000005846 Triadimenol Substances 0.000 description 14
201000010099 disease Diseases 0.000 description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
241000196324 Embryophyta Species 0.000 description 12
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 12
241000209140 Triticum Species 0.000 description 11
235000021307 Triticum Nutrition 0.000 description 11
239000013543 active substance Substances 0.000 description 10
241000209219 Hordeum Species 0.000 description 9
235000007340 Hordeum vulgare Nutrition 0.000 description 9
235000001674 Agaricus brunnescens Nutrition 0.000 description 8
ZVHHCHZVHJMAGW-UHFFFAOYSA-N N-[1-(2,4-dichlorophenoxy)-3,3-dimethylbutan-2-yl]formamide Chemical compound CC(C)(C)C(COC1=C(Cl)C=C(Cl)C=C1)NC=O ZVHHCHZVHJMAGW-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000035784 germination Effects 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000463 material Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
244000062793 Sorghum vulgare Species 0.000 description 4
239000008272 agar Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000417 fungicide Substances 0.000 description 4
235000019713 millet Nutrition 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000010899 nucleation Methods 0.000 description 4
230000001629 suppression Effects 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
241000736122 Parastagonospora nodorum Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
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 2
WISVKXCNQOLCJL-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)COC1=CC=C(Cl)C=C1 WISVKXCNQOLCJL-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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000223218 Fusarium Species 0.000 description 2
241000223195 Fusarium graminearum Species 0.000 description 2
239000012267 brine Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
239000004460 silage Substances 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000243 solution Substances 0.000 description 2
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
PYXLGFRIFJEGRL-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4,4-dimethylpent-1-en-3-one Chemical compound CC(C)(C)C(=O)C=CC1=CC=C(Cl)C=C1Cl PYXLGFRIFJEGRL-UHFFFAOYSA-N 0.000 description 1
MUOKXXOKLLKNIE-UHFFFAOYSA-N 4,4-dimethylpent-1-en-3-one Chemical compound CC(C)(C)C(=O)C=C MUOKXXOKLLKNIE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
241000123650 Botrytis cinerea Species 0.000 description 1
HXMNJMPUUZRRMM-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(=C)C(C(C)(C)C)NC=O Chemical compound ClC1=CC=C(C=C1)C(=C)C(C(C)(C)C)NC=O HXMNJMPUUZRRMM-UHFFFAOYSA-N 0.000 description 1
MMHBOANOTOQIMO-UHFFFAOYSA-N ClC1=CC=C(OCC(C(C)(C)C)NC=O)C=C1 Chemical compound ClC1=CC=C(OCC(C(C)(C)C)NC=O)C=C1 MMHBOANOTOQIMO-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241001459558 Monographella nivalis Species 0.000 description 1
241001558145 Mucor sp. Species 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
239000005822 Propiconazole Substances 0.000 description 1
241000520648 Pyrenophora teres Species 0.000 description 1
241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
241001533598 Septoria Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241001123668 Verticillium dahliae Species 0.000 description 1
WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
238000009937 brining Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000013078 crystal Substances 0.000 description 1
235000021186 dishes Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001362 electron spin resonance spectrum Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000693 micelle Substances 0.000 description 1
VATSHOWYLSHEDJ-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-4,4-dimethylpent-1-en-3-yl]formamide Chemical compound O=CNC(C(C)(C)C)C=CC1=CC=C(Cl)C=C1Cl VATSHOWYLSHEDJ-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
235000008935 nutritious Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
230000009466 transformation Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

RO13980489A 1988-05-18 1989-05-18 Method for preparation of substituted phenyl alkyl formamide RO103770B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SU884443133A RU1775394C (ru)	1988-05-18	1988-05-18	1-(4-Хлор-или 2,4-дихлорфенил)-3-формамидо-4,4-диметилпентены-1, обладающие фунгицидной активностью
SU884427664A RU1775395C (ru)	1988-05-18	1988-05-18	1-(2,4-Дихлорфенокси)-2-формамидо-3,3-диметилбутан, обладающий фунгицидной активностью

Publications (1)

Publication Number	Publication Date
RO103770B1 true RO103770B1 (en)	1993-04-15

Family

ID=26666163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
RO13980489A RO103770B1 (en)	1988-05-18	1989-05-18	Method for preparation of substituted phenyl alkyl formamide

Country Status (11)

Country	Link
JP (1)	JPH02504281A (de)
CN (1)	CN1038276A (de)
AU (1)	AU3362489A (de)
CH (1)	CH676597A5 (de)
FR (1)	FR2631624A1 (de)
GB (1)	GB2229437A (de)
HU (1)	HUT49982A (de)
NL (1)	NL8920256A (de)
PL (1)	PL153872B1 (de)
RO (1)	RO103770B1 (de)
WO (1)	WO1989011472A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110407681B (zh) *	2019-08-12	2023-05-02	海南大学	一种脱氢姜酮衍生物、其制备方法及应用

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2011790A (en) *	1934-03-13	1935-08-20	Gordon A Alles	1-(paramethoxyphenyl)-2-formylaminopropanes and method of preparing same
US2368073A (en) *	1943-04-12	1945-01-23	Commercial Solvents Corp	Process for preparing hydroxy amides
AT296242B (de) *	1969-07-21	1972-02-10	Boehringer Sohn Ingelheim	Verfahren zur Herstellung von neuen Formamidderivaten
US3835184A (en) *	1970-07-15	1974-09-10	Boehringer Sohn Ingelheim	Formamide derivatives
JPS4915768B1 (de) *	1970-09-04	1974-04-17
US4147791A (en) *	1972-01-11	1979-04-03	Bayer Aktiengesellschaft	1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants
US4160838A (en) *	1977-06-02	1979-07-10	Janssen Pharmaceutica N.V.	Antimicrobial and plant-growth-regulating triazole derivatives
DE2939350A1 (de) *	1979-09-28	1981-04-30	Basf Ag, 6700 Ludwigshafen	Glykoletheranilide, verfahren zu ihrer herstellung und diese enthaltende fungizide
DE3236522A1 (de) *	1982-05-18	1983-11-24	Bayer Ag, 5090 Leverkusen	Halogenpropargylformamide

1989
- 1989-02-17 CH CH28090A patent/CH676597A5/de not_active IP Right Cessation
- 1989-02-17 JP JP1503855A patent/JPH02504281A/ja active Pending
- 1989-02-17 WO PCT/SU1989/000044 patent/WO1989011472A1/ru not_active Ceased
- 1989-02-17 AU AU33624/89A patent/AU3362489A/en not_active Abandoned
- 1989-02-17 NL NL8920256A patent/NL8920256A/nl not_active Application Discontinuation
- 1989-05-17 PL PL27949089A patent/PL153872B1/pl unknown
- 1989-05-17 HU HU245789A patent/HUT49982A/hu unknown
- 1989-05-18 FR FR8906515A patent/FR2631624A1/fr not_active Withdrawn
- 1989-05-18 CN CN 89104607 patent/CN1038276A/zh active Pending
- 1989-05-18 RO RO13980489A patent/RO103770B1/ro unknown
1990
- 1990-01-17 GB GB9001044A patent/GB2229437A/en not_active Withdrawn

Also Published As

Publication number	Publication date
PL153872B1 (en)	1991-06-28
AU3362489A (en)	1989-12-12
JPH02504281A (ja)	1990-12-06
NL8920256A (nl)	1990-04-02
HUT49982A (en)	1989-12-28
GB2229437A (en)	1990-09-26
CH676597A5 (de)	1991-02-15
WO1989011472A1 (fr)	1989-11-30
FR2631624A1 (fr)	1989-11-24
CN1038276A (zh)	1989-12-27
GB9001044D0 (en)	1990-07-11
PL279490A1 (en)	1990-01-08

Publication	Publication Date	Title
CA1172641A (en)	1984-08-14	Optical isomer of triazolylpentenols, and their production and use as fungicide, herbicide and/or plant growth regulant
CS208796B2 (en)	1981-09-15	Fungicide means and means for regulation of the plant's growth and method of making the active substances
CS236691B2 (en)	1985-05-15	Agent for regulation of plant growth and fungicide agent and production method of its efficient components
DK172423B1 (da)	1998-06-08	Triazolderivater, farmaceutiske og landbrugsmæssige fungicide præparater indeholdende disse og fremgangsmåde til behandling
KR850000338B1 (ko)	1985-03-21	아실화 나프틸아민의 제조방법
JPH0242801B2 (de)	1990-09-26
EP0153284B1 (de)	1989-08-30	Aminoalkanphosphonsäure und Derivate davon als fungizide Mittel
DD202235A5 (de)	1983-09-07	Fungizide mittel
EP0044276A2 (de)	1982-01-20	4-(1H-Azolylmethyl)-1,3-dioxolan-5-on-derivate, Verfahren zu deren Herstellung und deren Verwendung als wachstumsregulierende und/oder mikrobizide Mittel
JPH0359071B2 (de)	1991-09-09
JPS62149667A (ja)	1987-07-03	新規なアゾール誘導体、その製造法及び該誘導体を含有する農園芸用薬剤
EP0115939B1 (de)	1988-08-17	Fungizide Triazole
JPH0232249B2 (ja)	1990-07-19	Kogakukatsuseitoriazoriruarukoorujudotaiojukoseibuntoshiteganjusurusatsukinzai
RU2028052C1 (ru)	1995-02-09	Способ борьбы с грибными болезнями растений
RU1775395C (ru)	1992-11-15	1-(2,4-Дихлорфенокси)-2-формамидо-3,3-диметилбутан, обладающий фунгицидной активностью
RU2835684C1 (ru)	2025-03-03	Способ получения и ростостимулирующая активность [N,N'-бис(диметиламинометил)тиомочевины уксуснокислой]сульфата меди пентагидрата
EP0427168B1 (de)	1996-03-13	Optisch isomeres Triazolylpentenol. Verfahren zur Herstellung und Verwendung als Fungizid, Herbizid und/oder Wachstumsregulator
RU1799868C (ru)	1993-03-07	3-[N-Диметил-N-2-(1,1,5-тригидрооктафторпентоксисульфонил)этил]аммониопропансульфонат в качестве фунгицида и регул тора роста растений
Cole	1957	Some control measures for anthracnose disease of tobacco
US3912497A (en)	1975-10-14	Plant growth regulator
JPH02504281A (ja)	1990-12-06	置換されたフェニルアルキルホルムアミド類及びそれらを基材とする殺カビ製剤
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