专利摘要:
Compounds having the general formula <CHEM> are described, wherein: R<1> is selected from F, Cl, Br, CF3, phenyl, C1-C2 alkoxy, C1-C2 haloalkoxy, alkylthio and haloalkylthio, wherein halogen means F, Cl, Br; R<2>is selected from H, F, Cl, Br, CF3; R<3>, R<4> and R<5>, which may be the same or different, are H, C1-C4 alkyl or C3-C6 cycloalkyl, on condition that R<5> is different from R<3> when R<4> is H; Y is selected from H, CH3, OH, CN, F; n is 1 or 2;m is 0 or 1;X is O or S; Rf is selected from C1-C5 polyfluoroalkyl, C2-C4 polyfluoroalkenyl, polyfluoroalkoxyalkyl and polfluoroalkoxyalkenyl, each of them containing at least two fluorine atoms and, optionally, other halogen atoms selected from Cl and Br; Z is CH or N. b
公开号:SU1676447A3
申请号:SU884356765
申请日:1988-11-04
公开日:1991-09-07
发明作者:Колле Роберто;Камаджи Джованни;Ратти Джузеппина;Гаравоглиа Карло;Миренна Луиджи
申请人:Президенца Дел Консильо Деи Министри Уффичио Дел Министро Пер Ил Координаменто Делле Инициативе Пер Ла Ричерка Сиентифика Е Текнологика (Фирма);
IPC主号:
专利说明:

The invention relates to a method for producing new 1,2,4-triazole derivatives, which have an immunizing effect against fungal pathogenesis and can be used in agriculture.
The aim of the invention is the synthesis of new triazolyl derivatives, which have a more effective immunizing effect against fungal pathogenesis
Example I, 1- (1,2,4-Triazolyl) -2-hydroxy-2- (4-chlorophenyl) -3-methyl-4- (1,1,2,2-tetrafluoroethoxy) butane (compound 1 ) „
Potassium tertibutylate (0.1 g) is added to 1- (1,2,4-triazolyl) -2- (4-chlorophenyl) -2,4-dioxy-3-methylbutane (1 g) dissolved in anhydrous tetrahydrofuran (5 ml), anhydrous dimethyl sulfoxide (10 ml), anhydrous tert-butanol (10 ml) in a nitrogen atmosphere at -10 ° C,
After creating a vacuum in the apparatus, tetrafluoroethylene is introduced into it, the whole mixture is kept in the atmosphere
V4 o

VI

with
for 20 hours at room temperature. The reaction mixture is then poured into water and extracted with methylene chloride,
 The extract is washed with water, dried on anhydrous sodium sulphate and evaporated. “The product obtained in this way is analyzed by chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate in a ratio of 3: 3 and then 1:10
0.2 g of whitish oil is separated, which corresponds to the indicated: structure
Infrared spectrum (v,): 3300, 1280, 1220, 1120.
NMR H (60 MHz), tetramethylsilane in CUCI, j: 0.90 (d, 3N); 2.80- 3.10 (m, 1H); 3.20-3.80 (m, 2H); 4.40 (d, 1K); 5.10 (s, 1H); 5.30 (d, 1H); 5.60 (t „t ,, 1H); 6.90-7.30 (m, AH); /-50-/.90 (m, 2H) C
Examples 2-4 s In accordance with the method described in example 1, compounds 2-4 were obtained, the spectroscopic data of which are the following
Compound 2 - 1- (1,2,4-triazolyl) -2-hydroxy-2- (2,4-dichlorophenyl) -3-methyl--4 (1,1,2,2-tetrafluoroethoxy) butane „
Infrared spectrum (-),): 3300, 1220, 1120, 1060, 1030,
NMR spectrum n (60 MHz), tetramethylsilane in CDClj, &amp; 0. 0.60 (d, 3N); 2.80-3.20 (m, 1H); 3.80-4.50 (m, 2H); 4.55 (d, 1H); 4, f5 (s, 1H); 5.35 (d, 1H); 5.60 (t.TO, 1H); 6.80-7.40 (m, 3N); /, 55 (s, 1H); 7.65 (s, 1H) „
Compound 3 - 1- (1,2,4-triazolyl) -2-hydroxy-2- (2,4-dichlorophenyl) -3-methyl-4- (1,1,2,2-tetrafluoroethoxy) - reKcaiu
Infrared spectrum (-cm): 3400, 1280, 1220, 1120.
NMR spectrum H (60 MHz), tetramethylsilane in CDC13, Y: 0, / 5 (d, 3N); 1.00 (t, 3N); 2.05 (quo, 2H); 2.90-3.40 (m, 1H); 4.30-4.70 (m, 1H); 4.75 (d, 1H); 5.30 (s, 1H); 5.65 (d, 1H); 5, / 6 (t.TO, 1H); /, 00-7.65 (m, 3N); /, / 5 (s, 1H); /, 95 (s, 1H) 0
Compound 4 - 1- (1,2,4-triazolyl) -2-OXY-2- (4-chlorophenyl) -3-3-dimethyl-4- (1,1,2,2-tetrafluoroethoxy) butane. Infrared spectrum (,): 3120, 3100, 1120, 1100 „
NMR spectrum N (60 MHz), tetramethyl silane in CDClj, $: 1.05 (s, 3N); 1.10 (s, 3N); H./O (d. 1H); 4.15 (d, 1H);
4.55 (d, 1H); 4.90 (s, 1H); 5.10 (d, 1H); L, 5 (T.T., 1H); /.10-/.55 (m, 4H); /, / 0 (s, 1H),: 7.90 (s, 1H).
Example 5: Determination of immunizing effect on powdery mildew of cucumbers (Sphacrotheca fuliginea (Schlech) Salmon).
Preventive action.
Cucumber plants of the Marketer variety, grown in seedlings in a conditioned medium, are sprayed from the lower leaf surfaces with test compounds in a water-acetone solution containing 20% acetone. The percentage ratio of volumes) “Then the plants are kept in conditioned medium for 1 day after which the upper leaf surfaces sprayed with an aqueous suspension of conidia Sphaerotheca fulihine.a (200,000 conidia / ml). After this, the plant is again placed in a conditioned medium.
At the end of the incubation period of this fungus (8 days), the degree of infection is determined in accordance with an assessment scale index ranging from 100 (healthy plant) to 0 (completely infected plant).
Therapeutic effect.
Marketer variety cucumber plants grown in seedlings in conditioned medium are sprayed from the top of the leaves with an aqueous suspension of conidia Sphaerotheca fuliginea (200,000 conidia / ml). 24 hours after infection, the plants are treated with the test compounds in an aqueous acetone solution containing 20% acetone ( percentage ratio of volumes) by spraying both leaf surfaces
At the end of the incubation period of the fungus (8 days), during which the plants are in a conditioned medium, the degree of infection is determined in accordance with the rating scale indices ranging from 100 (healthy plant) to 0 (completely infected plant)
Example 6 Determination of the immunizing effect on wheat powdery mildew (Erysiphe Grami-. Nis D.C.).
Preventive action.
Leaf of wheat variety Irnerio grown in seedlings
in an conditioned medium, treated by spraying both surfaces of the leaves with test compounds in a water-acetone solution containing 20% acetone (volume ratio) g
After standing for 1 day in a conditioned medium at 20 ° C and a relative humidity of 70%, both surfaces of the leaves of the plants are sprayed with Erysiphe Graminis water suspension (200,000 conidia / ml). After standing for 24 hours in a moisture-saturated medium at 21 ° The plant is placed in a conditioned medium for growing the fungus.
At the end of the specified time period (12 days), the degree of infection is determined in accordance with a rating scale index ranging from 100 (healthy plant) to 0 (completely infected plant).
Therapeutic effect
Leaves of wheat variety Irnerio, grown in seedlings in conditioned medium, are sprayed on both leaf surfaces with an aqueous suspension of Erysiphe Graminis (200,000 conidia / ml). After standing for 24 hours in an environment saturated with moisture at 21 ° C, the leaves are treated with the test compounds in a water-acetone solution containing 20% acetone (percentage ratio of volumes) by spraying both surfaces of the leaves.
At the end of the incubation period (12 days), the extent of infection is immediately determined in accordance with an assessment scale index ranging from 100 (healthy plant) to 0 (completely infected plant). "
Example /. Determination of immunization against linear wheat rust (Puccinia Graminis Rers).
Preventive action
Leaves of wheat, variety Irnerio, grown in seedlings in a conditioned medium, are treated by spraying both surfaces of leaves with test compounds in a water-acetone solution containing 20% acetone (% volume ratio). After standing for 1 day in a conditioned medium at 23 ° C and relative humidity
0
five
0
% 0, the plants are sprayed on both leaf surfaces with a mixture of Puccinia Graminis spores in talc (100 spores / 5 g of talc) o
After standing for 48 hours in a moisture-saturated environment at 21 ° C, the plants are placed in an conditioned medium for growing the fungus,
At the end of the specified period of time (14 days), the degree of infection is immediately determined in accordance with an assessment scale index ranging from 100 (healthy plant to 0 (fully infected plant) „
Therapeutic action "Leaves of wheat variety Irnerio grown in seedlings
in conditioned medium, spray both sides of the leaves with a mixture of Puccimia Graminis spores in talc (tOO mg spores / 5 g of talc), after standing for 48 hours in medium,
5 saturated with moisture, when the leaves are treated with the test compounds in a water-acetone solution containing 20% acetone (weight ratio) by spraying both surfaces of the leaves0
.In the end of the incubation period (14 days), the extent of infection is immediately determined in accordance with an assessment scale index ranging from 100 (healthy plant) to 0 (completely infected plant).
Example 8. Determination of fungicidal action against Ticchi on latura in Blon (Venturia inaegua-lis / CKe / wint).
Preventive action, Starking leaf Blon varieties grown in seedlings
c in a greenhouse, sprayed on both surfaces with test compounds in a water-acetone solution containing 20% acetone (percentage volume ratio). POSLR staying in
0 for 1 day in a conditioned environment at 20 ° C and a relative humidity of / 0%, plants are uniformly sprayed with an aqueous suspension of conidia Venturia inaegualis
c (200,000 conidia / ml) “After standing for 2 days in a moisture-saturated environment at 21 ° C, the plants are placed in a conditioned medium for growing the fungus
At the end of this period (14 days), the degree of infection is immediately determined in accordance with the rating scale indices ranging from 100 (healthy plant) to O (completely infected plant).
Therapeutic effect
Leaf blon Starking cultivars grown in seedlings in a greenhouse are sprayed evenly with a water suspension of conidia Venturia inaeguyalis (200,000 conidia / ml), after standing for 2 days in an environment saturated with moisture, the leaves are treated with the tested compounds in an aqueous-acetone solution j, containing 20% acetone (volume ratio), by spraying both surfaces of the leaves
At the end of the incubation period (14 days), the extent of infection is immediately determined in accordance with an assessment scale index ranging from 100 (healthy plant) to 0 (completely infected plant) with
The results are shown in the table.
As can be seen from the results of the tests presented in the table, the compounds of this general formula, compared with the known azolyl derivatives, show a more effective fungicidal effect, especially with respect to phytopathogenic fungi affecting grain crops, industrial and horticultural crops.
The following are examples of plant diseases that can be controlled with the proposed compounds:
Erysiphe graminis (in cereals); Sphaerolhea fuliginea (in pumpkin crops, for example,
have cucumbers);
Puccinia (in cereals); Septoria (in cereals): Helminthosporium (in cereals); Phynchosporium (in cereals); Podosphaera leucotricha (in Blon); Dncinula necator (in grapes); Venturia inaegualis (in Blon); Piricularis oryzae (in rice); Botrytis cincrea;
Fusarium (in cereals) and other diseases.
Compounds of this general formula have an immunizing effect of a therapeutic and prophylactic nature, are fully compatible with the plants to be protected. In addition, these compounds are characterized by systemic properties. These properties allow the substances in question to penetrate into the vascular systems of plants and act even on individual plots (for example, in leaves) that are removed from the place where they were brought (for example, the roots)
权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining triazolyl derivatives of the general formula
H RS
C-C-CH-X-CF2-CHF2
CH2 R5
about
.ts
where R is chlorine;
RJ is hydrogen or chlorine; Rq-Rj is the same or different and is hydrogen or C -C alkyl, provided that R is different from R when R. is hydrogen; Y - HE; X - oxygen,
characterized in that the compound of the general formula
T
s-ss-hn
CH2-N (I
Ј WN
where R.-RC X and Y have the indicated values,
is reacted with tetrafluoroethylene in aprotic alcohol and alcohol solvents in the presence of catalytic amounts of SPL1 base at a temperature from -Hi (to room temperature.
Compound of formula
Cl-jg C- (CH2) 2-0-C2H5
I N CH2-NQ
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同族专利:
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引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题

DE2918894A1|1979-05-10|1980-11-20|Bayer Ag|FLUORINATED 1-TRIAZOLYL-BUTANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|
DE3175673D1|1980-11-19|1987-01-15|Ici Plc|Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them|
JPS6346070B2|1982-11-02|1988-09-13|Pfizer|
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IT1204773B|1986-01-23|1989-03-10|Montedison Spa|FUNGICIDAL AZOLYL DERIVATIVES|
IT1198240B|1986-12-23|1988-12-21|Agrimont Spa|FUNGICIDAL AZOLYL DERIVATIVES|
AU615887B2|1986-12-23|1991-10-17|Agrimont S.R.L.|Fungicide azolyl-derivatives|
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NZ270418A|1994-02-07|1997-09-22|Eisai Co Ltd|Polycyclic triazole & imidazole derivatives, antifungal compositions|
IT1273509B|1995-04-07|1997-07-08|Zambon Spa|AZOLIC COMPOUNDS FOR ANTI-MYCOTHIC ACTIVITY FOR HUMAN AND VETERINARY USE|
IT1283038B1|1996-02-28|1998-04-07|Zambon Spa|AZOLE COMPOUNDS WITH ANTI-Fungal ACTIVITY FOR HUMAN AND VETERINARY USE|
IT1296925B1|1997-12-05|1999-08-03|Zambon Spa|PROCEDURE FOR THE PREPARATION OF COMPOUNDS WITH ANTI-Fungal Activities|
IT1296924B1|1997-12-05|1999-08-03|Zambon Spa|INTERMEDIATE DIOLIC COMPOUNDS FOR THE PREPARATION OF COMPOUNDS WITH ANTI-Fungal ACTIVITY|
法律状态:
优先权:
申请号 | 申请日 | 专利标题
IT8722560A|IT1232943B|1987-11-09|1987-11-09|FUNGICIDAL AZOLYL DERIVATIVES.|
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