Method of fighting true mildew

专利摘要:
There are desclosed compounds of formula: wherein R = H, an alkyl, an alkenyl, an alkynyl, an alkoxyl, a phenyl, a phenoxy, an alkoxycarbonyl, an alkylcarbonyl, a benzoyl or a cyano group; R' and R2 = an alkyl, an alkenyl, an alkynyl, a phenyl, an alkoxycarbonyl, an alkylcarbonyl or a cyano group; or R and R2 together form an orthocondensed benzene ring; X = CH or N. The compounds of formula I are endowed with fungicide activity against phytopathogenous fungi.
公开号:SU1362392A3
申请号:SU843796146
申请日:1984-09-21
公开日:1987-12-23
发明作者:Колле Роберто；Гоццо Франко；Миренна Лунджи
申请人:Монтэдисон С.П.А. (Фирма)；
IPC主号:

专利说明:

113623
The invention relates to chemical methods of plant protection, namely to a method for controlling powdery mildew based on a furyl-1,25A-triazole derivative.
The purpose of the invention is to increase the efficiency of the method.
Example 1. 2,4,5-Triphenyl-3- (1-triazolyl) -furan (compound 1)
ten



15.24 g (0.04 mol) of 1,2,4-triphenyl-3- (1-triazolyl) -butane-1,4-dione is suspended in 100 ml of acetic anhydride.
After adding 1.2 ml of concentrated sulfuric acid, the suspension is heated to reflux.
0
are at room temperature for- 4 hours.
The solution is then removed by evaporation under reduced pressure, and the residue is diluted with 150 ml of acetic anhydride,
After adding 1 ml of concentrated sulfuric acid, the mixture is heated under reflux for 3 hours. After cooling to room temperature, the mixture is poured into 1.5 liters of water and ice with stirring.
After stirring for an additional 30 seconds, the precipitate is collected by filtration, 5 is washed with water until neutral pH and air dried. The product is then recrystallized from isopropyl alcohol to yield 8 g of the desired product (compound 2), mp. 145-.
IR spectrum, cm 1440; 13.70.
Example 3. 2- (4-Chlorophenyl) -3- (1-triazolyl) -4-ethoxycarbonyl
0
 f
1595; 1510; 1460;
for 3 hours. The reaction mixture is post-25 -5-phenyl-furan (compound 3).
After cooling to room temperature. The compound is obtained in 82% yield, using a procedure similar to that described in Example 1, starting from 2-benzoyl-3- (1-tri-30 azolyl) 3- (4-chlorophenyl) ethyl ester ) -propionic acid.
The fish are poured into 1.5 liters of water and ice and kept under stirring. The residue is separated, collected and washed with water until neutral pH and air dried. The solid residue is recrystallized from ethyl alcohol and receive 10 g of the desired product (compound 1), with so pl. 180-182 C.
IR spectrum: 1595; 1500; 1,400; 1440; 1370.
Example 2. 2,5-Diphenyl-3- - (1-triazolyl) -furan (compound 2)
Compound 3 is obtained in the form of a solid crystalline substance with m.p. 142-144 ° C.
35 IR spectrum, cm-: 1720; 1620; 1490 1460; 1440; 1220.
Example 4 Determination of fungicidal activity against cucumber sidia (Sphae.rotheca fuliginea (Schlech) Salmon), Prevention activity.
7.5 g (0.04 mol) of 2- (1-triazolyl) -α-acetophenone is dissolved in 50 ml of dimethylformamide (DMF), the solution is added dropwise to a suspension of 1.92 g of NaH in 50 % inorganic oil and hold at 5 ° C with stirring.
While stirring for 30 s more. At the same temperature, the resulting mixture is added dropwise in nitrogen to a solution containing 8 g (0.04 mol) of 2-bromo-acetophenone in 30 ml of DMF, kept under stirring at 0- 5 ° C. After completion of the addition reaction mixture, Compound 3 is obtained in the form of Tver-; DOG of the crystalline substance with so pl. 142-144 ° C.
IR spectrum, cm-: 1720; 1620; 1490; 1460; 1440; 1220.
Example 4 Determination of fungicidal activity against cucumber sidia (Sphae.rotheca fuliginea (Schlech) Salmon), Prevention activity.
On plants of cucumber varieties Marheter grown in pots in the usual environmental conditions; applied on the lower leaves by spraying the test product in a solution of water - acetone containing 20% acetone (v / v). Then the plants are held
under environmental conditions for 6 days and on the seventh day, an aqueous suspension of conidia Sphaerotheca fuliginea 200,000 conidia (ml) was sprayed onto the front side of the upper leaves. The plants are then returned to room conditions. At the end of the incubation period of the fungi (8 days), the extent of the lesion is calculated using scale indexes.
Research institutes from 100 (healthy plants) to O (fully charged plant).
On Marheter varieties of cucumber plants grown in pots under normal environmental conditions, an aqueous suspension of conidia Sphaerotheca fuliginea 200,000 conidia (ml) is sprayed onto the front of the upper leaves by spraying. After 24 hours after infection, the plants are treated with the test product in a water-acetate solution containing 20% acetone (v / v), spraying both sides of the leaf.
At the end of the incubation period of the fungus (8 days), during which the plants are kept under appropriate environmental conditions, the degree of infection is counted using an index scale at values from 100 (healthy plants) to 0 (fully infected plants).
The results of protective and health compounds are presented in Tables 1 and 2, respectively.
0.1
one
2
Control (water-acetone solution)
0
five
0
five
In Tables 1 and 2, reference is made to the known compounds Z-mercapto-4-metsht-5- (2-furyl) -1,2,4-triazole (24) and 3-mercapto-4-phenyl-5- (2-furyl) -1,2,4-triazole (26).

权利要求:
Claims (1)
[1]
Invention Formula
The method for combating the present powdery mildew of the treatment of plants by the four-1-1,2,4-triazole derivatives, characterized in that, in order to increase the efficiency of the method, a compound of the common furyl -1,2,4-triazole is used. formulas
tps
RI
where R is hydrogen, phenyl, ethoxycarbonyl;
R, is phenyl, 4-chlorophenyl;
R is phenyl, in an amount of 0.1-2 kg / ha.
Table 1
100 100 100
Editor E. Papp
Compiled by N.Kibalova Tehred M. Didyk
Order 6305/58 Circulation 628 Subscription
VNIIPI USSR State Committee
for inventions and discoveries 113035, Moscow, .ZH-35, Raushsk nab. 4/5
Production and printing company, Uzhgorod, st. Project, 4
Table 2
100 100 100
Oh oh
Oh oh
50 50
Proofreader G. Reshetnik

类似技术:

---

公开号 | 公开日 | 专利标题

---

US4130409A|1978-12-19|Triazolyl butandiones

---

EP0092158A2|1983-10-26|Thiazolidine compound and fungicidal composition containing it

---

SU1362392A3|1987-12-23|Method of fighting true mildew

---

US5371106A|1994-12-06|3,4-diaryl-5|-furan-2-one based compounds with fungicidal activity

---

SU1452456A3|1989-01-15|Method of controlling growth of grain crops

---

JPH05194431A|1993-08-03|2-aryl-2-cyano-2-|ethyl-1,2,4-triazole compound

---

US4094985A|1978-06-13|Fungicidal isothiazoles

---

US4038285A|1977-07-26|1-|-4-arylimidazoles and 1-|-3-aryl-1,2,4-triazoles

---

US4276302A|1981-06-30|Miticidal 2-|-imidazolines

---

US5021442A|1991-06-04|Fungicide azolyl-derivatives

---

EP0272679B1|1992-11-04|Fungicide azolyl-derivatives

---

US4284791A|1981-08-18|Combating fungi with N-chloroacetyl-N-|-alanine esters

---

KR900005678B1|1990-08-06|Process for preparing -|-keto-derivatives having fungicidal activity

---

US4073925A|1978-02-14|Fungicidally effective imidazoles and use thereof against fungal pests

---

US4940724A|1990-07-10|Azolyl-derivatives having fungicidal activity

---

US5464836A|1995-11-07|Benzophenones having an antifungal activity

---

CS224622B2|1984-01-16|Microbicide

---

US4169838A|1979-10-02|Pyrazolyltriazole herbicides

---

KR900007336B1|1990-10-08|Process for preparing benzo-triazole

---

US4560694A|1985-12-24|Fungicidal alkylene|-bis-heterocyclyl-biguanides

---

HU193875B|1987-12-28|Process for producing pyridazinone derivatives of antifungal activity

---

US4073901A|1978-02-14|Metal complexes of N-trityl-azoles for combatting fungi

---

US4049820A|1977-09-20|Substituted urazole and thiourazole compounds as agricultural fungicidal agents

---

US5268383A|1993-12-07|Heterocyclic derivatives of alkoxyacrylates with a fungicidal activity

---

US5470863A|1995-11-28|Oximic derivatives with a fungicide activity

同族专利:

---

公开号 | 公开日

---

IT1161927B|1987-03-18|

---

EP0123931B1|1988-12-21|

---

EP0123931A3|1986-02-12|

---

DE3475708D1|1989-01-26|

---

IT8320406D0|1983-03-31|

---

EP0123931A2|1984-11-07|

---

JPS59184177A|1984-10-19|

---

CA1226292A|1987-09-01|

---

SU1243624A3|1986-07-07|

---

US4594353A|1986-06-10|

引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

RU2172314C2|1995-09-13|2001-08-20|Нихон Байер Агрокем К.К.|Chloropyridyl carbonyl derivatives and acid addition salts thereof, and agent for controlling phyropathogenic fungi|US3557005A|1967-07-14|1971-01-19|Procter & Gamble|Detergent compositions containing 3-substituted 2,5 diphenyl-heterocycle brighteners|

---

US4144347A|1978-06-26|1979-03-13|Riker Laboratories, Inc.|3--2-nitrobenzofurans|

---

DE2839388A1|1978-09-11|1980-03-27|Siegfried Ag|IMIDAZOLYLVINYLAETHER AND THEIR USE|

---

DE2944223A1|1979-11-02|1981-05-27|Basf Ag, 6700 Ludwigshafen|FUNGICIDAL ENTRIAZOLES, THEIR PRODUCTION AND USE|

---

US4352808A|1980-12-12|1982-10-05|Schering Corporation|3-Aralkyloxy-2,3-dihydro-2-benzothiophenes and related derivatives, their use as antimicrobials and pharmaceutical formulations useful therefore|

---

EP0079856A1|1981-11-12|1983-05-25|Ciba-Geigy Ag|Microbicidal triazolyl-vinyl esters|

---

JPS58150566A|1982-03-03|1983-09-07|Yoshitomi Pharmaceut Ind Ltd|Novel imidazole derivative|

---

GB2122997B|1982-07-05|1985-08-14|Erba Farmitalia|Imidazoles|

---

IT1161237B|1983-04-26|1987-03-18|Montedison Spa|1,4-DICHETONES-UNSATURATED FUNGICIDE ACTIVITIES|DE3417467A1|1984-05-11|1985-11-14|Bayer Ag, 5090 Leverkusen|CYCLIC AZOLYLVINYL ETHER|

---

US4871758A|1987-03-18|1989-10-03|Schulman Jerome M|Pharmacologically active cholinergic compositions, and methods for making same and use thereof in treating disease|

---

CA1317588C|1988-02-29|1993-05-11|Tohru Ueda|Imidazole derivatives, process for production thereof, and use thereof|

---

GB0919194D0|2009-11-02|2009-12-16|Lytix Biopharma As|Compounds|

---

RU2567553C1|2014-09-18|2015-11-10|Государственное бюджетное образовательное учреждение высшего профессионального образования "Санкт-Петербургская государственная химико-фармацевтическая академия" Министерства здравоохранения Российской Федерации |2-[3--1-phenyl-1h-1,2,4-triazole-5-yl] hexanoic acid and method of its manufacturing|

法律状态:

优先权:

---

申请号 | 申请日 | 专利标题

---

IT20406/83A|IT1161927B|1983-03-31|1983-03-31|FURANO-DERIVATIVES WITH FUNGICIDE ACTIVITY|

---