Method of producing derivatives of 1,2,4-thiadiazole

专利摘要:
The invention provides the acaricidal thiadiazoles of the formula: (where: R' and R2, which may be the same or different, are each hydrogen, optionally-substituted alkyl of 1 to 10 carbon atoms, or optionally-substituted phenyl, or R1 is alkylthio of 1 to 6 carbon atoms: R is an ester-forming group: Y is oxygen or sulphur: and the carbamate grouping is in the 3- or 4-position on the phenyl ring), processes for their preparation and compositions containing them.
公开号:SU1450744A3
申请号:SU864027329
申请日:1986-04-15
公开日:1989-01-07
发明作者:Джон Вест Петер；Георг Хант Расселл；Алистайр Гейтс Дункан
申请人:Фбс Лимитед (Фирма)；
IPC主号:

专利说明:

 ate about
4ib 4
 S
The invention relates to a method for producing 1,2,4-thiadiazole derivatives of the general formula
shs
0
OR
(I)
where RI is C — C3 alkyl, phenyl, ethylthio R — C — C4 alkyl, 0 -azopropylbenzyl, 1,1-dimethylproparGSh1,
moreover, the carbamate group is in the 3 or 4 position of the phenyl ring, the compounds (I) can be used in acarcidal compositions.
The aim of the invention is to obtain new derivatives of 1,2,4-tiad11-azole with high acaricidal activity.
Example 1. Isopropyl 3- (3-n-propyl-1, 2, 4-thiadiazol-5-yloxy) fesch-carbamate.
a) 3-n-Propyl-5- (3-aminophenoxy) -1,2,4-iadiazole.
A solution of 32.7 g of 3-aminophenol in 700 ml of dimethylformavd is mixed and slowly processed 9 g of sodium hydrate (80%) and then heated to. A solution of 48.9 g of 3-n-propyl-5-HLOR-1,2,4-thiadiazole in 150 ml of di-methylformamide is then added dropwise and the mixture is then heated to 80 ° C with stirring for 5 hours. 3 liters of water are added and stirred for 1/2 hour, then the product is extracted in diethyl ether (about 1 l for 4 washes). After drying overnight with magnesium sulfate, the solution is filtered and evaporated and 5% aqueous salt is added. acid to form the hydrochloride salt. The aqueous solution of the salt is then extracted with diethyl ether and sodium bicarbonate is added to the aqueous phase to pH 3. After further extraction with dimethyl ether and chromatography, the desired product is obtained in the form of an oil.
b) 3-n-Propyl-5- (3-isocyanato-phenoxy) -1,2,4-thiadiazole.
Phosgene is passed for 650 hours in 650 ml of toluene with the formation of a saturated solution. 15.7 g of the product of step (a) is added to it, the mixture is stirred and heated under reflux for 1 hour. Rust
0
five
five
0
0
five
0
five
0
five
The vortex is then evaporated to give 13.4 g of the desired product.
c) Isopropyl S3- (3-n-propyl-1,2,4-β-thiadiazol-4-yloxy) phenyl carbamate. The product of stage (b) of 4.17 g is heated under reflux for 2.5 hours with 400 MP of isopropanol. Upon evaporation of the solvent and recrystallization from petroleum ether, the desired product is obtained with a yield of 57%, so pl. 64 ° C.
Example 2-12. The following compounds of formula (I) in which the carbamate group is in position 3 of the phenolic ring, are obtained from using methods analogous to example 1.
The indicators for examples 2-20 are given in table. one.
Examples 21-24. The following compounds of formula (I) in which the carbamate group is in position 4 of the phenyl ring are prepared by methods analogous to example 1 (Table 2).
Example 25. A composition of a 40% suspension concentrate of the compound of Example 1 is obtained by mixing the following ingredients, may. %: Polyphon H (sodium salt sulphonated Craft lignin - Westco Corp.) 2
Pluroni P75
(block copolymer.
ethylene oxide and propylene oxide) 3 Xanthan
gum0,2
Formaldehyde 0.2
Water ° Rest
Analogous 40% of the composition was also prepared and contained each of the compounds of examples 2-25 in the same way as the analogous compositions, respectively, containing 0.5} 5; 10, - 20; 50 and 85% by weight of the compound of Example 1 with corresponding changes in the amount of water used.
Example A. From the leaf plate of the first true leaves of the dwarf French legume plants Phascolus vulgaris, discs are cut (diameter 2 s). The disks are placed on wet three-centimeter tape.
filter paper and 10-15 adult female mites (Tetranychus cinnabarinus) are placed on each disk. They lay eggs for 24 hours and then remove them. The discs are placed by immersion in the compounds of the examples listed below at various concentrations, which are obtained by dissolving the appropriate amount of the compound in 2 m of acetone plus 5% Atlox 1025 A (polyethylene oxide sorbitolate condensate) wetting agent and the solution is diluted with water containing a wetting agent Sinperonik N (oxyethylene-ionylphenol condensate) for preparing an aqueous composition containing 0.5 ml / l Sineronic N, 20 ml / l acetone and 1 ml / l Atlox 1025A.
Each treatment is repeated two times and the number of hatched eggs is determined for 8 days.
The results show the lowest degree of deposition at which the tests were carried out and at which the listed compounds killed at least 75% of the eggs (Table 3).
The data show that the compounds of example 1 kill at least 75% of the eggs of ticks at a treatment rate of 0.64-160 mph. Known 1,2,4-thiadiazole derivatives used
in acarecid formulations, kills the eggs of ticks in a percentage of 51-100% at a treatment rate of 0.05%, which is equivalent to 500 million.

权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining 1,2,4-thiadiazole derivatives of the general formula
where R - - C-Sz-alkyl, phenyl, ethylthio, R - C, -C4-alkyl, (T azopropylbenzyl, 1,1-dimethylpropargil,
wherein the carbamate group is in the 3 or 4 position of the phenyl ring, characterized in that the 1,2,4-thiadiazole derivative of the general formula
R,
one
M P ff
s, where B4 has the indicated meanings, is reacted with the corresponding alcohol ROH, in which R has the indicated meanings.
Table
Table 3
Continued table. one
Continued table. 3
71A50744
Continued table. 3
160
.four
26
four
8 Continued table. 3
20 21 23
64
160
64

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引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

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CH550538A|1971-08-31|1974-06-28|Ciba Geigy Ag|COMMERCIAL MEANS FOR CONTROL OF HARMFUL MICRO-ORGANISMS.|

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DE3431272A1|1984-08-25|1986-03-06|Bayer Ag, 5090 Leverkusen|SUBSTITUTED PHENYL UREAS|WO2003059897A1|2002-01-17|2003-07-24|Sumitomo Chemical Company, Limited|Thiadiazole compounds and use thereof|

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DE60227714D1|2002-11-08|2008-08-28|Sumitomo Chemical Co|1,2,4-THIADIAZONE COMPOUNDS AND THEIR USE|

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AU2004282018B2|2003-10-15|2009-07-23|Sumitomo Chemical Company, Limited|1,2,4-thiadiazole compounds and pests controlling composition containing the same|

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CN103214474B|2013-05-02|2016-04-27|南开大学|One class contains the 5-methyl isophthalic acid of 4,5-thiazoline carboxylic ester, 2,3-thiadiazoles derivative and its production and use|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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GB858509752A|GB8509752D0|1985-04-16|1985-04-16|Acaricides|

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