Method of preparing mono-5-substituted 3-chloro-4h-1,2,6-thiadiazin-4-ones

专利摘要:
Selected mono-5-substituted-3-chloro-4H-1,2,6 thiadiazin-4-ones having the general formula <IMAGE> are described which are useful for control of fungal disease in plants.
公开号:SU828966A3
申请号:SU792706053
申请日:1979-01-03
公开日:1981-05-07
发明作者:Джозеф Пик Клинтон；Нельсон Гарниш Вэйн；Ллойд Дэвидсон Брус
申请人:Фмк Корпорейшн (Фирма)；
IPC主号:

专利说明:

exothermic, a solution of one; of the reagents, it is slow to apply to a solution of another reagent, and for controlled air supply: external cooling is used. Example 1. Synthesis of 3,5-dichloro-4H-1,2, 6-thiadiazin-4-one. A 50 ml flask with a volume of 50 ml is poured with 20 ml of anhydrous solution, and the flask is flushed with a stream of dry nitrogen. The purging with nitrogen is continued even at the time of the addition of 6.3 g of 3,4,4,5 tetrachloro-4H-, 2,6-dna | Ias: non. In the course of 0.5 h of the irikap van1 process, the temperature of the reak: a non-syllable is maintained at a vapor pressure of 10 ± 1 ° C. After the addition, the reaction mixture is stirred at 10 ° C for 2 (and then at 64 to i right room temperature. Then the mixture IB is fed by npi stirring. In 60 leagues ice. The resulting mixture is filtered and the cake is washed with water and dried, yielding 2.2 g of the yellow-yellow 3,5-dichloro-4H-1,2,6-thiadiazia 4-one, etc., 81–82 ° C. Sppez 3-, chloro-5-phenoxy-4H-1, 2,6-tlad: 11 azip-4-one. The solution of pathenichenoxide is obtained by adding 1.0 g of caustic soda to 2.4 g of fe: {ol in 25 ml of warm dsnip water. This mixture is stirred for 5 minutes, after which B 1 water t To a suspension of 4.6 g of finely ground 3.5-dichloro-4P-1,2,6-thiadiazin-4oia in 75 ml.: 1 nstil; 1) water in a flask with a volume of 250 ml. After 15 minutes, the temperature of the mixture rises to 32 ° C. After having been exchanged for 1 hour at room temperature, take an orange of filter color and filter cake rinsed with water. As a result of recrystallization of pz 120 ml of ethanol, 4.2 g of fluffy, light yellow needles of 3-chloro-5-phenoxy-4H-1,2,6-T1iadiazin-4-opa are obtained, and the pl. 121 -122 ° C (according to Giver and Tromnen, melting point 122.3-123.5 ° C). The PC spectrum confirms the intended structure. Found,%: C 44.94; H, 2.26; N 11.63. Cgl-IsCINaOzS. Calculated,%; C, 44.92; H 2.09; N 11.64. Example 3. Siitez Z-chloro-5- (4-chlorophenoxy) -4H-1,2,6-thiadnazin-4-one. As described in method 2, method 2, (2 g of sodium-P-chloro-fluoride is reacted with 4.6 g of 3,5-dichloro-4P-1,2,6-thiadiazip-4-one. Neociiene, ny product з 45 ml then; | uola. By; | 4.3 g of pushy yellow needles of 3-chloro-5- (4-chlorophenoxy) 4H-1, 2,6-thiadiazpi-4-one, t. pl .149-15GS. IR spectrum corresponds to the expected structure. Found,%: C 39.59; H 1.66; N 10.21. CgHsCINgOaS. Calculated,%: C 39.29; H 1.46; N 10.18. Analogues are obtained for compounds of the formula I, nr: iveden; these are given in Table 1. The results of experiments with a 1-step solution of this and And test of growth of micelles are given in Table 2, where X means png ation germination CHOP (at 40 for 1 h mn) above 40%. O - less than 40% ingnbirozanie Nspytyzaemye denote organisms in Table; tse amgzhsirivedenpym cipher, T and G .1 H TABLE 1
connections: eP1
Chlorine
Fsnoksp
4 Л1ст11лфсм1а; -сС11
4 Tre-r-Booth. | Fe110x11
4-L1STO with 11 fs11 hydroxy
.-Ч1-Б V; ч; 1; с11фсногССИ
4 floor1) ks carbo :: ilfe11ox11
-i-Ltsst ;; lami 11of0 J1; c11
4-itrophene: gSS1
4-1 lianofsioksi
.1-Ftorfeioks11
4-Chlorfsnoxy
3-Chlorophenoxy
2-Chl rfenox
4-Brompheiox11
3.4-Dphlorphenoxy
2,4-day, (orfs1yuksn
2 /) - Di.orfs11oxy
2,3-DichlorfsiokS11
3,5-Dichlorfe 110 Oxy
3-Mstilfs 1ox
: -Ms-GlfchCh () KS
2.4-DimeG 1phenoxy
2,6-D1 mstplefe1yuks11
3,5-D11metplfs1Yuksi
.. miifepoxy
4-Amiinofen (ks11gpdrpkhlorid
-82 -123
-: 138
--164,5
144-146 -124.5 122-112 .5
10.5177-179 -185 184-188 186-140
8.5-151 149-105 103-83 81.5 -149.5 148-159 .5
.) 7.5-118 116-129
27, .o-136 .5
135-135, 5
134-102, 5
101-78
76-133 .5
32.5-127
25.5-127, 5
126300
above 300
higher
6 Continuation of table I
Mpgibiropaiis ip- ,,
p rgan “sporeI I:, g; o, orovimii growth mtseln
shs ro VJ AS ss PL EP up,:; FS lr PO PU RS but her
1) the extent of Tai.iiiiibi 2
AS: Alternaria solani
BC: Botrytis cinerea
CC: Cladosporium cucumerinu
EP Erysiphe polygoni
FS Fusarium solani HO Helminthosporium oryzae PL Plytophtora mtestana PO Pyricularia oryzae PU: Pythium ultimum
RS - Rhizoctonia solani SF: Selerotinia fructicola UP Uromyces phaseol
VI Venturia inaegualis
where R is lower alkyl, halogen, lower alkoxy, OXI-, nitro, cyano, amino, carboxyl, lower acyl, lower acylamino, lower alkoxycarbonyl, carbonyl (lower) alkyl, lower, alkylureido, phenylureido, trihalomethyl , cyano (lower) alkyl, phenyl (“izsha) alkoxy-, carbonyl-OXY-, (LOW alkyls; BUT: carboxyloxy, phenylaminocarbonyloxy-, lower alkylgroup, lower alusulfyl, lower alkylsulfoyl; n 1-3; in case - halogen,,
a compound of the formula

权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining mono-b-substituted 3-chloro-4H-1,2,6-thiadiazi, n-4-ones of the general formula
ABOUT
C1.A, x
T t
where X is a naphthoxy or fanxy group of the general formula
C1
€ 1
T
and reacting with a compound of the formula MX, where M is an alkali metal and X is as defined above.
The source of information, irin the attention of experts:
I, Weingand-Hilgetag. Methods of excierism in organic chemistry. M., “Himi, 1968, p. 316.

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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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EP0363316B1|1988-09-30|1992-12-16|Ciba-Geigy Ag|Biocides to protect materials and for water systems|

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RU2151145C1|1994-04-11|2000-06-20|Санкио Компани Лимитед|Intermediate compound for synthesis of heterocyclic compounds showing antidiabetic activity|

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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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US05/782,860|US4097594A|1977-03-30|1977-03-30|Mono-5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-one antifungal agents|

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