前苏联专利SU1355125A3 Method of producing thiocyanopyrimidine derivatives

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专利摘要:
The invention relates to substituted pyrimidine, in particular, thiocyanopyrimidine derivatives of the general formula R — S — C — C — N — C — N —C — S — C 5 N, where R C, —C, -alkyl-, X — halogen, which have biological activity and can be used in agriculture. The goal is to create more active substances of the specified class. Their synthesis is carried out from the corresponding trihalo pyrimidine and alkali metal or ammonium thiocyanate in an organic acid medium. Tests have shown that they have a higher activity against sulfur mold, tomato rot, phytophthora and mildew than the known 2-chloro-4-methyl-6-thiocyanopyrimidine and N- (n-fluorophenyl) -dichloromelamide, and it turns out phytotoxic effects on cultivated plants. 9 tab. g D3 S oo ate ate
公开号:SU1355125A3
申请号:SU853873458
申请日:1985-03-15
公开日:1987-11-23
发明作者:Исикава Катсутоси；Симотори Хитоси；Иида Нобору；Озава Судзи；Инами Сунити
申请人:Мицуи Тоацу Кемикалз Инкорпорейтед (Фирма)；
IPC主号:

专利说明:

The invention relates to methods for the preparation of thiocyanon-mrdine derivatives - new biologically active compounds that can be used in agriculture.
The purpose of the invention is to obtain new thiocyanopyrimidine derivatives having a higher fungicide action against plant pests, such as phytophthora and mildew, which do not have a phytotoxic effect on cultivated plants.
Synthesis of 2,4-dichloro-5-metsh1tio-6-tisedianopyrimidina (compound 1).
Example. In a 50 ml four-necked flask equipped with a thermometer, a reflux condenser and a stirrer, 2.30 g (0.010 mol) of 5-methylthio-2-4,6-trichloropyrimidine and 15 ml of formic acid are placed. While the contents were stirred at room temperature, 1.07 g (0.011 mol) of potassium thiocyanate was added. Then the resulting mixture is heated, stirred at 50 ° C. Hours.
After cooling, the reaction mixture is poured into a large amount of water.
EXAMPLE 4 The same procedures were carried out as in Example 1, except that instead of 1. 07 g (0.011 mol) of potassium thiocyanate, the solid which had been precipitated was collected by filtration and dried. Half-30 0.84 g (0.011 mol) of thiocyanate
2.34 g of crude ammonium crystals are obtained. Get 2.30 g. Uncleaned
move 92.9%). Part of untreated cris-.
tallas recrystallized from ethyl
acetate, which gives a purified product,
35 purified product, mp. 143-144 ,. In tab. 1 shows the properties of soybean crystals (yield 91.3%). A portion of the crude recrystallized crystals are decomposed from ethyl acetate to give
mp.143-144.5 p.
Calculated,%: C, 28.58, H, 1.20, C1, 28.12, N, 16.67, S, 25.43.
CeHyCljN S.
Found,%: C 28.83, H 1.04, C1 28.35, N
16.63, s 25.22.
C1
15 AI,
C1-G
40
5-SCN
in the same way synthesized.
The compounds obtained by the proposed method can be used as herbicides in agriculture and horticulture. Usually, these compounds are mixed with a carrier and, if necessary, with other auxiliary components. When used, such mixtures are processed into ready-to-eat forms, usually used in the form of agricultural and horticultural fungicides, containing active ingredients in the range of 0.01-90% by weight, for example, dusty (concentration of active ingredients 1-10% by weight) , dusts with larger particles (concentration of active
Sch3
IR (KBG): 2160 ().
C-NMR, S, CDC1,, TMS TMS, ppm: 17.7 (C-1); 105.5 (C-2); 125.7 (C-5); 159.8 (0-3); 166.0 (0-4); 171.3 (0-6).
Note 2. In the 5-liter flask: a four-bulb flask equipped with a thermometer, a reflux condenser, and a megaalka, 2.30 g (0.010 mol) of 5-methylthio-2,4,6-trichloropyrimidine and 20 ml of acetic acid are charged. While stirring the contents at 50 ° C, 1.5 g (0.015 mol) of potassium thiocyanate was added. Then
the resulting mixture is heated with stirring at 50 ° C for 10 hours. After cooling the reaction mixture, it is poured into a large amount of water. The precipitated solid is collected by filtration and su-. chat 2.32 g of crude crystals are obtained (yield 92.1%). A part of the crude crystals are recrystallized from ethyl acetate and a purified product is obtained, mp 143-144.5 ° C.
Example 3: The same procedures as in Example 2 are carried out, except that propionic acid is used as the solvent for the reaction instead of acetic acid. 2.28 g of crude crystals are obtained (yield 90.5%) . A portion of the crude crystals is recrystallized from ethyl acetate to give purified
product, mp. 143-144,5 p.
EXAMPLE 4 The same procedures as in Example 1 were carried out, except that 0.84 g (0.011 mol) of thiocyanate was used instead of 1. 07 g (0.011 mol) of potassium thiocyanate.
ammonium. Get 2.30 g. Uncleaned
crystals (yield 91.3%). A portion of the crude recrystallized crystals are decomposed from ethyl acetate to give
in the same way synthesized.
The compounds obtained by the proposed method can be used as herbicides in agriculture and horticulture. Typically, these compounds are mixed with a carrier and, if necessary, with other auxiliary components. When used, such mixtures are processed into ready-to-eat forms, usually used in the form of agricultural and horticultural fungicides, containing active ingredients in the range of 0.01-90% by weight, for example, dusty (concentration of active ingredients 1-10% by weight) , dusts with larger particles (concentration of active
ingredients 1–10 wt.%), micronegrals (active ingredient concentration 1–25 wt.%), granules (active ingredient concentration 2–30 wt.%), wettable powder (con-i
concentration of active ingredients 20–80 wt.%, oily suspensions (concentration of active ingredients 10–70 wt.%), means used for fumigation (concentration of active ingredients 10–70 wt.%), microcapsules (concentration of active ingredients 10- 80% by weight), spreadable formulations (concentration of active ingredients 20-80% by weight), and the like.
The mixtures are applied in an amount of 0.2-4 kg / ha (preferably 0.5-2 kg / - / ha), based on the active ingredient.
A wettable powder containing 30% of Compound 1 as an active ingredient is obtained by grinding and mixing 300 mash. Of Compound 1, 440 mash. diatomaceous earth.
(grain size O, -O, 25 mm) and 0.5 mach. soybean oil.
Microgranules.,
Microgranules containing 5% of Dinene 3 as the active ingredient are prepared by mixing 5 wt.h. in a V-blade mixer. Compounds 3, crushed in a jet mill, 94.5 mach. h, grams of zero calcium carbonate (grain size 0.3-0.6 mm and 0.5 mash. soybean oil.
The recipe is able to spread along the surface to be treated.
The spreading formulation, containing 40% of compound 4, is obtained by means of fine grinding in a 40 m.p. connections 15 ma.ch. ethylene glycol, 0.5 mAh
fO
i5
200 ma.ch. gypsum (magnesia, kaolin), 20 products supplied by the foreign company
25 ma.ch. sodium lignosulfonate,
15 ma.ch. sodium alkyl benzene sulfonate
(number of carbon atoms in alkyl
groups 10-15) and 20 ma.h, ethylene-,,.
nonylphenyl ether (naphthalene concentration); 0.2 math. Takeda Chemical Industries Ltd - organic iodine compound, 3 ma.h. Demo l-N (the product of the foreign company Kao Cor Poreyshn is a special product of polymerization of polyoxyethylene half 5-10).
Granules.
Granules containing 10% of Compound 2 as an active ingredient are prepared by mixing 10 wt.h. connections 2, 62 math. bentonite, 20 ma.ch. talc, 2 ma.ch. sodium dodecylbenzene sulfonate and 1 wt. h. sodium lignosulfonate; a certain amount of water is added to the mixture and then the mass is granulated on a granulating extruder in a known manner.
Dust
Dust containing 2% of compound 2. As an active ingredient is obtained by grinding to a homogeneous mixture and mixing 20 parts by weight. connections 2, 5 ma.h. calcium stearate, 5 ma.ch. powdered silica gel, 200 wt. diatomaceous earth (kieselguhr), 300 ma.ch. gypsum and 470 ma.ch. talcum powder
Coarse Dust ..
Coarse dust containing 5% of Compound 1 as an active ingredient is obtained by mixing 5 wt.h in a V-shaped paddle mixer. Compound 1 milled in a jet mill, 94.5 May, h granulated calcium carbonate
,

3551254
(grain size O, -O, 25 mm) and 0.5 mach. soybean oil.
Microgranules.,
Microgranules containing 5% of compound 3 as an active ingredient are obtained by mixing in a V-blade mixer, 5 wt.h. Compound 3, milled in a jet mill, 94.5 parts by weight, granulated calcium carbonate (grain size 0.3-0.6 mm and 0.5 parts by weight of soybean oil.
The recipe is able to spread along the surface to be treated.
The spreading formulation, containing 40% of compound 4, is obtained by means of fine grinding in a sand mill of 40 wt. compounds 4, 15 ma.ch. ethylene glycol, 0.5 mph
fO
i5
,,
Takeda Chemical Industries Ltd - organic iodine compound, 3 ma.ch. Demo LN (product of the foreign company Kao Corporation - special product 1
0
five
about livinilpyrrolidone and 41, 7 May .ch. water. I
Test I. Algae leafiness (Alternaria mail).
The young shoots of blony (cultivated variety Star King) are placed in 200 ml Erlenmeyer flasks and processed with a pistol (1.0 kg / cm) to give 50 ml of a chemical formulation for a 3 branches. Each test compound was prepared as a wetting powder, then diluted with water to a predetermined concentration. The branches are then allowed to dry in air, after which they are sprayed and inoculated with a suspension of spores of Alternaria mali, which are cultivated in advance, for 7 days in growth medium in the form of vegetable juice, V-S. Next, incubate for 3 days at 23-25 C and humidity of 95%. The number of damages per 1 branch is calculated with respect to the 3 branches in each group and is determined as a reference value in accordance with the following equation:
The number of injuries - SRI in the treated group
1 - 100
The number of damage to research institutes in the untreated group
about
0
Control - by size
Compounds A and B are used as controls for comparison.
- Control Compound A: 2-Chloro-4-methyl-6-thiocyanopyrimidine (described in Hakugaku Fasshi 83, 1086 (1963). Control Compound B: N- (n-fluorophenyl) -dichloromelaimide (a commercially available anti-stain agent leaves Aiternaria (Alternaria mail).
The results are shown in table 2. As can be seen from the table. 2, 2-chloro 4-methyl-benthio-iphenrimidine has no significant effect; The proposed compounds are more active and compared to N- (n-fluorophenyl) dichloramelemide.
Test 2. Cured sulfur mold (Botrytis cinerea).
Cucumber plants (Sagami Hanjiro cultivar in the seed stage appearance stage), which are cultivated each separately in pots in a greenhouse, are sprayed so that 3 p1 pots have 20 ml of a chemical formulation of a certain concentration, obtained as a wetting powder, then diluted with water. the required concentration using a spray gun (1.0 kg / cm). The plants are then air dried.
From Botrytis cinerea, previously cultured on medium before PDA cultivation, a spore suspension is prepared. This suspension is spread and inoculated onto cucumber plants in pots. The cucumber plants inoculated in this way are immediately inhibited in a greenhouse at a temperature of 22-24 ° C and a humidity of 95% for 5 days. After this, the extent of damage to the seeds is examined, the following scale is applied: Indicator Percent of the damaged surface of the sheet
About 1 2
0%
1-10% 11-25%
326-50%
A51% and Bbrtie
Damage indicators for all these shares are determined and the mean-response is calculated.
five
0
five
0
five
0
45
value for each group of plants in the form of damage indicators. The group consists of 3 pots, each with 5 plants.
When performing this, for comparison, the applied compounds A and C are used.
The control compound C: methyl-1-butylcarbamoyl-2-benzimidazolecarbonate is a means of combating gray mold (Botrytis cinera).
The results are shown in the table.
From Table 3, it can be seen that the control compound 2-chloro-4-methyl-6-thiocyanopyrimidine does not have any significant effect, as does methyl-1-butylcarbamoyl-2-benzimide; angry carbamate. Thus, the proposed compounds are more active.
Test 3. Tomato rot (Phytophtora infestans).
Tomato plants (cultivated Sekaiichi cultivar about 25 cm tall), which are cultivated in pots in a greenhouse, are sprayed so that 3 pots have 50 ml of a chemical formulation of a certain concentration. To prepare the recipe, a wetting powder is prepared from the test compound, which is then diluted with water to a predetermined concentration and applied with a spray gun. The plants are then air dried. A suspension of zoospores (mobile spores) is prepared from Phytophtora infestans, cultivated in advance for 7 days on potato pieces. Tomato plants, previously sprayed with a liquid chemical formulation, are sprayed and dried with a suspension of zoospores. A sample of the plants is incubated for 6 days at 17–19 ° C with a humidity of 95% and above. The extent of the development of the lesion is then examined.
The following estimates apply:
Damage rate
Proceed infected leaf surface
About 1
2
0%
1-5% 6-25%
26-50%
51 and above
Damage rates are determined for all leaves, except for the newly developed 2 leaves, in this way, by which the mean values are calculated as damage indicators for each of the groups.
After carrying out the indicated test, control compounds A and D are used for comparison.
Control compound D: zinc-ethylenebis (dithiocarbamate) is a compound commercially available as a means to combat tomato rot (Phytophtora infestans) and potato rot (Phytophtora infestans).
The results are shown in table 4.
As can be seen from Table 4, the proposed compounds are superior in active, 2-chloro-4-methyl-6-thiocyanopyrimidine and zinc-ethylene bis (dithiocarbonate) - a means for controlling phyto-. fluorine.
Test 4. Potato rot (Phytophtora infestans).
Potatoes (cultivated variety Danshaku, plants about 25 cm high), which are cultivated each separately in pots in a greenhouse, are sprayed so that 3 pots contain 50 ml of the chemical composition of a certain concentration (the test compound is prepared as a wetting powder which is then diluted with water to a certain concentration, and applied using a spray gun (1.0 kg / cm). The plants are then dried in air. A zoo spore suspension is prepared from Phytophtora infes- - tans, which is pre-cultivated in 7 days in pieces Rtofel. Potato plants that are sprayed with a chemical formulation are sprayed and inoculated with a zoospore suspension. Test plants are incubated for 6 days At-17-19 ° C and humidity -95%. After that, the degree of damage to the plants is examined. 3. When conducting a test, control compounds A and D are used. The results are shown in Table 5.
five
0
50
five
0
5 0 5 s
As can be seen from Table 5, the proposed compounds are superior in activity to 2-chloro-4-methyl-6-thiocyanopyrimidine and zinc-ethylenbis (dithiocarbamate) - a means of controlling phytophtora (potato rot).
Test 5. Mildew - false, meager growth of cucumbers (Pseudope-ronospora cubensis).
Cucumber plants (cultivated variety Sagami-Hanji at the stage of appearance of two leaves) are cultivated each separately in pots in the greenhouse; after which they are sprayed so that 30 ml of the chemical formulation, a predetermined concentration is consumed for 3 pots (test compound is prepared as a wetting agent powder, which is then diluted with water to a certain concentration, and using a spray gun (1.0 kg / cm). Then the plants are dried in air. Spores of Pseudoperonospora cubensis are harvested from affected areas of cucumber leaves infected with with ice (downy mildew of cucumber). A spore suspension is prepared using the Pseudoperonospora cubensis spores collected in this way and deionized water. The cucumber plants in pots are sprayed and inoculated with a suspension of spores inoculated in this way, the cucumber plants are immediately incubated with 17 spraying spores. C and humidity
, 95% 24 hours, then transferred to a greenhouse with a temperature of 18-27 ° C). After 7 days, the extent of the damage is assessed. The same performance indicators are used as in test 3.
When performing this test, the controls were compounds A and E.
The control compound E: M- (tri-chloromethylthio) 4-cyclohexene-1,2-icar boksimid - a means of combating false
powdery mildew of cucumbers (Pseudopero Pospora cubensi s).
The results are shown in Table 6.
From Table 6 it can be seen that the control compound, 2-chloro-4-metsh1-6-thiocyanopyrimidine, did not show significant activity, as well as N- (trichloromethylthio) -b-cyclohexene-1-, I - Dicarboximide. Thus, the proposed compounds are more active.
.913
Fe test. Mildew is a powdered cucumber mold (Sphaerothe-sa fuliginea).
Cucumber plants at the stage of development of 2 leaves, cultivated each separately in pots in a greenhouse, are sprayed so that 30 ml of a chemical formulation of a known concentration is consumed for 3 pots (a wetting powder is prepared from the test compound, which is then diluted with water required concentration. When applied, use a spray gun (1.0 kg /
/ cm), then the plants are dried on
the air. Sphaerotheca fuliginia spores are harvested from diseased areas of cucumber leaves infected with a mildew of powdered cucumber mold. A spore suspension is prepared using Sphaerotheca fuliginea spores and deionized water collected in this way. Potted cucumber plants are sprayed and inoculated with a spore suspension. Inoculated TAPMs by cucumber plants are placed in a greenhouse (temperature 18-27 s). After 8 days, the extent of damage is examined. Performance indicators are the same as in trial 3.
When conducting this test, comparing the application5 of the compound A and F.
Control compound F; Dimethyl-4-4 -o-phenylene bis (3-thioallophenate) is a remedy for mildew - a piston-shaped cucumber mold (Sphaerotheca fuliginea). The results are shown in table 7.
Test 7. Pest Rice (Pyricularia pryzae).
The seedlings of rice plants (cultivated cultivar Sasanishiki at the stage of development of 5-6 sheets), which are grown in pots in a greenhouse, are sprayed so that 30 ml of a chemical formulation of a predetermined concentration is used on 3 pots (a wetting powder is prepared from a sample of the test compound with its subsequent dilution with water to a predetermined concentration). It is applied using a piercing gun (1.0 kg / cm). The plants are further dried in air. Pyricularia oryzae, which is pre-cultured on growth media,.
25
ten
rice straws are used to spray and inoculate paddy rice seedlings in a humidification chamber, where the humidity and temperature is 24-128 C. After the seedlings in the humidification chamber, for 7 days, the extent of damage is examined using the following scale ratings:

Estimated figure
ABOUT
Damage number
Not

five
0
five
11-2 per sheet
23-5 per sheet
36-10 per sheet
411 and more
In each pot, 10 leaves are selected in no particular order. The damage rate is determined for each sheet in the manner indicated above. Then the average value calculated as the damage rate for each test group is determined. . When conducting this test--. control compounds A and G are not accepted for comparison;
Control compound G; 0-ethyl-S, 5-diphenyldithiophosphate is a means for combating the pest of rice plants (Pyricularia oryzae).
The results are shown in table 8.
Test 8. Mildew (false nuchos dew) of the vine (Plas-: mopara viticola), -
Young grapevine plants (cultivated variety neomuskat ,,, plant aged 2 years), cultivated in pots, sprayed so that 2 pots have 100 ml of a chemical formulation of a predetermined concentration (from each compound a wetting powder is prepared subsequent dilution with water to a certain concentration). After applying the spray gun (1.9 kg / cm), the plants are further dried in air. Plasmopara viticola collected from the affected areas of the vine, which is infected with mildew (downy mildew). Spore suspension
1113
prepared using Plasmopara viticola so collected and deionized water. A spore suspension is sprayed and inoculated with grapevine plants. After 24 hours of soaking the grape plants inoculated in this way in a humidification chamber (humidity 90%, temperature 18-20 ° C), they are transferred to a greenhouse (18-25 ° C) in order to accelerate the development of the disease. you days later. Performance indicators are the same as in trial 3.
When performing this test, control compounds A and D are used for comparison.
The results are shown in table.9.
As tests have shown, the thiocyanopyrimidine derivatives of formula 1 obtained by the proposed method are more active than the known (2-chloro-4-methyl-6-thiocyanopyrimidine and K- (p-fluorophenyl) -dichlororimide) with respect to gray mold , tomato rot, phytophthora and mildew; in addition, they do not exert a phytotoxic effect on cultivated plants.
2512

权利要求:
Claims (1)
[1]
Invention Formula
The method of producing thiocyanopyrimidine derivatives of general formula 1
X
5I
where R is C, - C, is alkyl
X is a halogen atom, which is different in that it is a pyrimidine derivative of general formula II.
X
xV
SR
where R and X have the indicated meanings, are reacted with a thiocyanate of the general formula III
. MSC N
where M is alkali metal or ammonium in the environment of an organic acid.
to
tr s h o to
H
tXJ
in
in in
1U
and
H
Sh
OK
. g
S -.
VO
en CT
cho
ъ
ate
about
m m
and II
g
g
15
1355125
16 Table2
Table 3
17
1355125
18 Table. four
Table5
one
2 3
4 5
Control (Compound A)
Control (compound F)
Not processed
Table
t "
and

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同族专利:

公开号 | 公开日

HU194693B|1988-03-28|

GB2157683B|1987-07-22|

DD234864A5|1986-04-16|

CA1236462A|1988-05-10|

DD246022A5|1987-05-27|

CH663021A5|1987-11-13|

RO91593B|1987-07-31|

DE3509437C2|1988-07-28|

IN162075B|1988-03-26|

NL8500741A|1985-10-16|

SU1514238A3|1989-10-07|

IL74568D0|1985-06-30|

JPH0635450B2|1994-05-11|

FR2561241B1|1987-12-11|

HUT36675A|1985-10-28|

IL74568A|1988-04-29|

GB2157683A|1985-10-30|

FR2561241A1|1985-09-20|

IT1185067B|1987-11-04|

PL252376A1|1985-12-17|

JPS60193970A|1985-10-02|

IT8519921D0|1985-03-15|

KR870000676B1|1987-04-06|

US4774335A|1988-09-27|

KR850006191A|1985-10-02|

PL140597B1|1987-05-30|

DE3509437A1|1985-10-03|

ES541265A0|1985-12-01|

TR22405A|1987-04-13|

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引用文献:

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US20050032060A1|2001-08-31|2005-02-10|Shishir Shah|Arrays comprising pre-labeled biological molecules and methods for making and using these arrays|

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法律状态:

优先权:

申请号 | 申请日 | 专利标题

JP59049218A|JPH0635450B2|1984-03-16|1984-03-16|Thiocyanopyrimidine derivative, its production method and agricultural / horticultural fungicide|

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