前苏联专利SU1678212A3 Method for preparation thiazolotriazole sulfonamides

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专利摘要:
The invention provides certain herbicidal thiazolotriazole sulphonamides, processes for their preparation, and compositions containing them, the compounds being of the formula: <CHEM> where: R<1> and R<2> which may be the same or different, each represent hydrogen, hydroxy, halo, cyano, substituted or unsubstituted alkyl, alkoxy, alkenyloxy, alkynyloxy, aryl, aralkyl, heteroaryl or carbamoyl, or a group -COR<a> or -CO2R<a> or where R<a> is hydrogen or alkyl: or R<1> and R<2> together represent an alkylene chain of 3 or 4 carbon atoms: R<3> represents a substituted or unsubstituted aryl, heterocyclyl or benzheterocyclyl group; and R<4> represents hydrogen, an alkali-metal atom, an ammonium group, a substituted or unsubstituted alkyl, alkenyl, alkynyl, acyl, alkoxycarbonyl or aralkyl group, a heterocyclic group, or a group of the formula: <CHEM> where R<1> and R<2> are as defined hereinbefore. h
公开号:SU1678212A3
申请号:SU874202481
申请日:1987-04-29
公开日:1991-09-15
发明作者:Стюарт Гейтс Питер
申请人:Шеринг Агрокемикалз Лимитед (Фирма)；
IPC主号:

专利说明:

This invention relates to new thiazolotriazole sulfonamides of the general formula
Uw w
where RI is hydrogen, lower alkyl, unsubstituted or substituted by halogen or lower alkoxycarbonyl;
R2 is hydrogen or lower alkyl;
Ps - phenyl, substituted by halogen, lower alkyl, trifluoromethyl-, nitro-, alkoxy- or alkoxycarbonyl radical, or
benzothiophenyl radical,
having herbicidal activity.
The purpose of the invention is to obtain new thiazolotriazole sulfonamides having a higher activity compared with the known structural analogue, prometrine.
The invention is illustrated by the following examples, in which the following notation is used: Me is methyl, Et is ethyl, Pr is propyl, you are butyl, Ph is phenyl.
EXAMPLE 1: No.- {2-Chloro-6-methylphenyl) -6-methylthiazolo 3,2-Ь 1,2,4 triazole-2-sulfonamide.
but. 3-Benztiltio-5-mercapto-1,2,4-triazole.
ABOUT
h
00
yu ho
WITH
Sodium methylate (35.1 g) is added in portions to 3,5-dimercapto-1,2,4-triazole (86.4 g) in methanol (400 ml) while stirring the system and cooling to 5-15 ° C. under nitrogen atmosphere. After stirring for 5 minutes, benzyl chloride (79.7 g) is added dropwise to the resulting derivative for 1 hour at 5-10 ° C. Then the resulting mixture is stirred for 20 hours at ambient temperature, then filtered. The precipitate is washed with a small amount of methanol cooled with ice and then with water to obtain 83.2 g of the desired product, m.p. 199-201 ° C.
c, 2-benzylthio-b-methyltmazolo 3,2-L 1,2,4 trimazo.
The product from the stage (22.3 g) and chloroacetone (9.6 g) are heated in ethanol (120 ml) under reflux conditions for 22 hours. The solution is then concentrated in vacuo and the residue is stirred with a mixture of ether and aqueous solution. sodium bicarbonate. The ether layer is separated, washed with water, dried over magnesium sulfate and concentrated in vacuo to give 24.1 g of the desired product as an orange oil.
c.6 Metiptazolo 3,2-L 1,2,4 triazole-2-sulfonyl chloride,
Chlorine gas at a temperature of less than 5 ° C m for 0.5 h is slowly passed through a stirred mixture of the product from stage b (13 g) with acetic acid (50 ml) and water (50 ml). The resulting mixture is stirred for 15 minutes, then filtered and the precipitate is washed with water and then with petroleum ether (bp) to form, after drying over calcium chloride, 7.9 g of the desired product, mp 125-129 ° C. After washing ether get pure product, so pl. 133-134 ° C.
d.M- (2-Chloro-8-methylphenyl) -b-methylthiazolo 3,2-L 1,2,4 tri.azol-2-sulfonamide.
The product from step (2.0 g) is added in portions to 2 chloro-6-methylanmine (1.3 g) in pyridine (8 ml) with stirring and cooling to 5-10 ° C. After standing for 4 days at room temperature, the mixture was treated with ether and dilute hydrochloric acid. The precipitate is filtered off and washed with dilute hydrochloric acid, water and then ether to form 1.9 g of crude product. By recrystallization from ethanol, 1.0 g of pure product is obtained, mp. 201-203 ° C.
PRI mme R 2. M (2-chlorophenyl) -6-methylthiazolo 3,2-L 1,2,4 triazole-2-sulfonamide.
but. 6-Methylthiazolo 3,2-L 1,2,4 Triazol-2-sulfonyl chloride (alternative route).
Sulfuryl chloride (9.7 g) in dichloromethane (5 ml) is added dropwise to a stirred mixture of the product from example 1 in (5.0 g) in dichloromethane (40 ml) containing
wet silica gel (12 g silica gel 60-120 mesh plus 1.2 ml of water) at 5-10 ° C. The resulting mixture was stirred for 2 hours at 5 ° C, then filtered and the filtrate was concentrated in vacuo. The residue obtained is treated with petroleum ether (b.p. 40-60 ° C) to form 2.8 g of crude product, m.p. 115-125 ° C
B. 2-Chlorophenyl-b-methylthiazolo) 3,2-L 1,2,4 triazole-2-sulfonamide,
The product from step a (3.0 g) is added in portions to 2-chloroaniline (10 g) while stirring and cooling to 5-10 ° G. The mixture is stirred for 20 hours at ambient temperature. Ether is added.
and the water and after 5 minutes of stirring the precipitated solid is filtered and washed with water and ether. The product yield of 3.4 so pl. 172-174 ° C. PRI me R s 1-118
The compounds of formula (1) were prepared by methods similar to those described for the steps of Examples 1 and 2 described below (see, Table 1). Note 61. M- (Benzo L thiophen-4-yl) 6-methylthiazolo 3.2 L 1,2,4 triazole-2-sulfoiamide,
The product (1.1 g) from the step of Example 1 is added in portions with stirring to 4-amine obenzo L-thiophene (0.7 g) in dimethylaniline (4 ml). The resulting mixture was allowed to stand for 3 days before being treated with dilute hydrochloric acid and ether. The precipitated solid is isolated by filtration, washed with dilute hydrochloric acid, water and ether and dried to give 1.4 g of crude product. The resulting solid is treated with a dilute ammonia solution, filtered, and the filtrate is acidified. The precipitated product is filtered off, washed with water and ether and dried to form 0.8 g of the desired product, m.p. 205-209 ° C,
Girbitsidny example A (before germination).
The seeds of the weed species listed below were sown in anodized aluminum bowls 19 cm long, 9.5 cm wide and 6 cm deep, containing sterilized sandy clay. The soil in the bowls was watered with water and then sprayed with the compounds of the examples listed below, used in the solution-suspension system (1: 1 volume ratio) of acetone and wetting agent,
which is a solution (2 g per 1 l) of loloxy ethylene monolaurate (20 mol).
The concentration of each test compound and the volume of use was calculated in such a way as to ensure the desired application rate of the compound in 450 liters per hectare. After 3-4 weeks of growth in a room with controlled conditions (20 ° C; relative humidity 75-95%; artificial lighting for 14 hours per day), a visual assessment was made of the use of herbicides.
All the differences from the untreated control experiment were attributed with the corresponding indices according to which: 0 - no effect. 1 - 1-24%; 2-effect 25-69%; 3- effect 70-89% and 4-effect 90-100%.
The results obtained in Table 2 were obtained, where the following letters were used to designate weed species;
a - PoLygonum Lapathifolium (mountaineer grungy)
b - Galium aparine (tenacious bed-bed) with - Chrysanthemum segetum (gold flowers) d - Alopecurus myosuroides (fox of mouse-tail) e - Elymus repens (creeping weeds) f- Avena fatua (oatsug)
g - Abutilon theophrasti (Teofrasta)
h - Cyperus rotundus (sedge purpurna) I - Pharbitls purpurea (ipome) j - Echlnochloa crus-galli (chicken millet) k - Setaria viridis (foxtail) e - Solanum nigrum (black nightshade).
Herbicidal example B (after germination).
Seeds of the plant varieties listed below were sown on sterilized clay-sandy soil contained in anodized aluminum plates 19 cm in size (length) x 9.5 cm (width) x b cm (depth). Then the soil was watered with water and the bowls were placed in a room with controlled conditions (20 ° С; relative humidity 75-95%, artificial light 14 hours a day). After 14 h or 21 days after sowing (depending on the type of plants, but when most plants reached the stage of 2–3 true leaves), the foliage of the seedlings was sprayed with compounds of the examples listed below, formed as
solution-suspension systems (volume ratio 1: 1) of acetone and a wetting agent, which is a solution (2 g per liter) of polyoxyethylene monolaurate (20 mol).
The concentration of each test compound was calculated so that it provides the desired rate of application of the compound in 450 liters per hectare. After 2-3 weeks of growth, a visual assessment of the herbicidal action was carried out in a room with controlled conditions.
The following indices were assigned to any differences from the untreated control experiment: 0 - no effect; 1- effect 1-24%; 2 - effect 25-69%; 3 - the effect of 70-892 and 4 - the effect of 90-100 / :.
The results are shown in table 3.
Comparative example. The known herbicide (prometrin) was tested in experiments with the herbicidal compounds of Examples A and B, above, which gave the results shown in Table 4.
A comparison of the above results shows a higher activity of the proposed compound compared with prometrin.

权利要求:
Claims (1)
[1]
Invention Formula
1, Method for preparing thiazolotriazole sulfonamides of general formula
R, V-N-N R
that
2 5 N
S07NHR:
where R 1 is hydrogen, lower alkyl, unsubstituted or substituted by halogen or lower alkoxycarbonyl;
R2 is hydrogen or lower alkyl;
Yaz - phenyl, substituted by halogen, lower alkyl, trifluoromethyl-, nitro. an apoxy or alkoxycarbonyl radical, or a benzothiophenyl radical, characterized in that the thiazolotriazole sulfonyl halide of the general formula
R
R, fs NI S02Ha
where RI and R2 are as defined; HaL - halogen, subjected to interaction with the amine of the general formula NHzRa. where Pz has the indicated meanings in the presence of an organic base.
Table 1
Continuation of table 1
Continued-table 2
H --o .-- 1.and, | tA Ы..В
one
1 1 1 1 1 1 1
0.5 0.5 1
0.5 0.5
one
one
one
one
2.5
one
one
2.5
ABOUT
four
2
one
2
four
3
2
2
2
four
3
ABOUT
four
four
2
four
3
2
ABOUT
ABOUT
ABOUT
2
2
3
four
four
four
four
ABOUT
4 2 4 О 4 4 2 2 4 3 4 О 4 4 О 4
3 o
O 4 4 O 3 4 4 3
4 4 4 4 3 O 4 4 4 4 4 4 4 4 4 2 3 3 3 2 4 4 4 O 3 2 4 3
2 o
2 О О 3 4 2 О 2 О О 3 2 О 4 О О О О О О О О О О 2 2 3 2
2.5
2.5
2.5
one
one
one
one
0.5
one
2.5
4 3 2 3 2 2 О 3
3 3
2 3 3 3 3 3 3 3
2
3 3 3 2 4 4 2 4 1
3 o 2 1
O 2 O 1 3 2
About About 1
ABOUT
about about about 1 about about about about
2 2 О 4 О 2 4 О О О О О О
oh oh
2 o
3 4 O 2 2 1 3 3 2 2 3 3 2 4
4 O 4 3 3 2 O 3 4 1 2 3 4 4 4
2 3 О О О О О О О О О 4 О О 4
3 О 4 О О О О О 3 О 2 2 О О 3
LTD
about 1 1
2 About About 1 3
eleven
four
2 О 4 3 2 О 2 О 1 3 О 2 2 3 О
O 2 O O O O 2 O 2 O 4 O O 4
4 О 4 4 2 О О О 2 2 О О 4 4 2
O 2 O 2 O 2 2 O 2 O 2
About About 4
4 2 4 2 О О О О 2 О О 2 2 2 3
4 3 2
4 4 4
4 4 4 4 4 О О О 4 4 4 2 4 4
Table 3
2
eleven
O 1 o
one
oh oh
one
4 4 4 2 4 4 4 4 4 1
2 2 1
About About 1 1 2 1 1
2 2 1 1 2 2 2 2 2 1
3 2 1 2 1 3 2 2 1 3
3 2 1 1 1 2 2 2 2 3
4 4 2 3 4 4 3 3 2 4
-Table 4

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法律状态:

优先权:

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