Method of producing aromatic compounds

专利摘要:
The invention relates to novel compounds of formula I: <CHEM> wherein the symbols have the significances given in the description, the synthesis thereof and to the use of compounds of formula I for the control of pests such as insects mites and ticks.
公开号:SU1402252A3
申请号:SU853926394
申请日:1985-07-17
公开日:1988-06-07
发明作者:Артур Хенрик Клив
申请人:Сандос А.Г. (Фирма)；
IPC主号:

专利说明:

ten
The invention relates to a method for producing new compounds - aromatic compounds of the general formula
Y
R YrHQ -OCHRi-CHRj-Z-C-JT -Rj
where R. is Cj-Cg-alkyl or C -C-alkene;
Wj is oxygen or sulfur;
R, is hydrogen or C, -C-alkyl;
R is hydrogen;
R, - C, -C4-alkyl;
I - oxygen or sulfur; X, X is oxygen or sulfur, or rpyn-j a NH, and if X is oxygen or sulfur, then X is the group NH, or N is C, is alkyl; if X is an NH group, then X is an isloride or sulfur that is active against a wide range of harmful substances - fleas, ticks, flies, cockroaches.
The aim of the invention is to search for new compounds with increased insecticidal activity, revamping the activity of the known 25 compounds in structure and application. Example 1, Ethyl-N-2- 4- (l-methylproduct) phenoxy ethyl / carbamate.
To pre-washed O, 106 g (4.4 mmol) of sodium hydride in 5 ml of rahidrofuran (THF) and 5 ml (DMF) of diethylformamide at room temperature was added 1.0 g (4.4 mmol) of ethyl-N- 2- (4-hydroxyphenoxy) ethyl carbonate in 5 ml (THF) of tetrahydrofuran. The mixture was stirred at room temperature for 1.5 hours and then cooled at -5 ° C. To the mixture was added 0.72 g (5.3 mmol) of 1-methylpropyl bromide in 2 ml of THF, then another 5 ml of MP was added. The reaction mixture allowed to warm slowly to room temperature, and then heated for 18 hours at 60. The reaction mixture is cooled to room temperature, poured into water and the mixture is extracted three times with ether. The combined ether layers are washed with water until neutral, then with brine and dried over calcium sulfate. The solvent was distilled off under vacuum and the product was purified by preparative thin layer chromatography to give the title compound (compound A-13, Table 2).
NMR spectrum (CDCl1): 0.93 (m, 3N,. CH (CH3) -0); 1.23 (t and d, 6H, CH, CH, CH (CH,) - 0 - and); 1.56 (m, 2H, CHjCH CH (CH) -O-); 3.47 (m, 2H, methylene next to NH-); 4.03 (m
35
40
45
50
55
0
five
Q
five
0
five
0
five
5H, methylene and methyl next to -0-); 5.07 (broad array, 1I, NH) and 6.77 (with, aromatic protons) cpn.d.
Compounds were prepared analogously,. Listed in table.2-4.
Table 2 shows the compounds of the general formula in which R ,.
Table 3 lists the compounds of the general formula where R 2 is boyl,.
Example 1. Compounds A-6, A-15 and A-17 are tested for contact activity on house flies according to the following procedure.
Musca domestica larvae at the third age stage, which move after feeding, individually treat 1 µl of the test compound in acetone locally at different dose levels. Additional larvae treated identically with 1 µl of acetone serve as controls. The larvae were kept in closed containers for 7 days at a 31 and 16-hour photoperiod. The effect of the experiment is expressed as AU 5J, which is the dose in micrograms per larva required to cause an effect on 50% of the tested insects. Observed effects include direct (acute) toxicity (larval death), delayed toxicity (death of pupae), and juvenile hormonal activity: violation of the complete hatching of adults, inhibition of chitin, destruction of the cuticle, and pupation anomalies. Each of the test compounds listed has a 030 μg / / larva.
Example 2: Compounds A-1, A-15, A-18 and A-19 were tested on yellow low-temperature mosquitoes according to the following procedure.
The larvae of Aides aegypti in the late fourth stage (usually 5 days after hatching from the eggs) are placed in plastic containers with 50 ml of tap water, into which 50 µl of the acetone dilution of the test compound was applied at the concentrations tested. A few drops of liver powder suspension are added as a source of nutrition. The containers are closed and vented at a 28, 16-hour photoperiod until all the larvae or pupae either die or hatch as adults. The effect of experience is expressed as EC, which is represented by 1D
This is the concentration in ppm required to cause a 50% effect on insects. Observed effects include direct toxicity (larval death) and juvenile hormonal activity: pupal mortality and the impossibility of complete hatching of adults. Each of these test compounds has an EC of 0.0010 ppm.
PRI me R 3. The activity of compounds A-6, A-18 and A-19 was tested by swallowing cockroaches (Prussians) according to the following procedure.
Prepared food is prepared by mixing the test compound with dog food at the test dose levels. 100 nymphs of Blattella germanica are placed in the cage. Water and shelter were provided and the feed of the processed dog food was maintained and maintained. The control was the experience with unprocessed dog food. The cages are stabilized at a 28, 16-hour photoperiod and 50% relative humidity. Cockroaches are observed for the development of normal and abnormal adults. Normal adults are those who have fully developed wings with a normal flat shape. A percentage of reproducibility control is also observed. At 10 ppm, each of these compounds gives 100% reproducibility control.
EXAMPLE 4 Compounds A-1 and A-6 were tested on cat fleas according to the following procedure.
The internal donations of glass Petri dishes (20 mm mm plates) are treated with 1 ml of acetone dilution of the test compound at the concentrations tested. Approximately 1 hour after treatment, 1/8 teaspoon of a diluted flea medium consisting of 50% sterilized sand and 50% finely chopped flea food is placed in each cup. In each bowl
Q
five
5 o
n c
0
five
52
The cups are placed on five week-old larvae of the last age of the cat flea (ctepocephalides felis), covered and stored at 27 and 80% relative humidity for 35 days. 35 days after treatment, the number of adult fleas, pupae and larvae is counted. The effect of the experiment is expressed as the percentage inhibition of hatching of adults. At a dose of 3.5–10 mg / ml or 0.0005 mg / ft of glass surface, each of the above compounds gives 100% control of hatching of adults.
Data on biological activity are given below in table.1.

权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining aromatic compounds of the general formula
Y
- W-Q-OCHRi-START J-J-C-Z -113
where R is C-Cg-alkyl or C-C-alkene;
W is oxygen or sulfur;
R, is hydrogen or C, -C-alkyl;
R is hydrogen;
R — C, —C — alkyl;
I - oxygen or sulfur; X, X is oxygen or sulfur, or NH group. Moreover, if X is oxygen or sulfur, then X is NH or N - C, - C is j-alkyl, if X is NH, then X is oxygen or sulfur; characterized in that the compound of the general formula
Y, D
H-v- -ocHRi-oaRj-j: - with -x -m,
where W, R ,, R, R, X, I and X have the indicated meanings;
reacting with compound RQ, where R has the indicated meanings; Q is halogen or mesyl.
Table 1
Continuation of table 1
A-20
A-23
A-24
IN 1
AT 2
AT 4
B-30
C-3
Standard phenoxy-carb
RR3 about
IIIIR
(sn2) w-sn-o-s-1tsG
“2
R-W-f --W CH, -CH2-X-C-X-CH, CH
.
Shz-S CH-SNo
SNS
SNS CH: 2 C-CHO
SNS
СНз-С СН-СН2-СНг о СНз
A-5 SNg CH-CH-CHNg-SNg
0.054
0,00067
Oh 050
0,008
0,0029
0,00078
0.012
0.069
0.1 1
table 2
CH
.
oh oh oh
293
Oh ohh oh
267
Oh NH Oh
279
Oh NH Oh
307
Oh ohh oh
293
ni IIiimJIlIIi lLlI
Oh ohh oh oh
Oh ohh oh oh
Oh ohh oh oh
Oh ohh oh oh
Oh ohh oh oh
b .2 CH CH3
7 СЯЗ-СНг-СНг-СН
SNS
8 CHz-CH2-CH CHd CHji 9 CHa-CH CH-CH
(Mo
10 sns-sn-sn2-sn:
SNS
11 СНз-С112-СНз-СН2 о о NH оо
bij
12 CHj-СНг-СН2-СН2-СН о о ш о о
SNS
13 СНз-С СН-СНо о ш о о
II
SNS SNZ
14 CH3-CH2-C CH-CH2 o NH 4 oO
СНз 15 СНз-СН2-СН0000NH
A-16
Sn-Sn-Sn.2
SNS
A-17 CH3-CH2-CH CH3
A-18 CH3-CH2-CH CH3
A-19 CH3-CH2-CH
SNS
A-20 Sch-CH-CH
I
SNS
A-21 sns-sn: -sn2
SNS
1402252
8 Continuation of table 2
lIIi lLlI
 T
8,281
296
295
294
309
295
310
307
307,281
Oh NH Oh Oh
Oh NH Oh Oh
Oh NH Oh Oh
Oh NH Oh Oh
Oh NH Oh Oh
about NH oo
oh oh oh
oh oh oh
oh nh oo
000NH
0000NH293
oh oh oh SNH298
S o o SNH314
S About About ONH297
SO NH OO
297
S About About ONH309
Nz-S Sh-SNg SNz
ai3-CH2-CH
СНз СНз-СНг-СН
CH3 CH3-C3I2-CH
SNS
СНз-СНг-СН СНз
СНз-СНг СНз
 n
M + NE
CHj-CHg-CH-W-С31з
I TIlLlLl IT
6 I 7 00
S oh nh
309
About About NH OS
298
S About NH OS
314
S About NH SS
330
о о S оNH298
S O S ONH314
Table 3
-L G -CH-CH2-X-C-x -Rz
Note. (1) (2) (K) -form: (oi.) 19, 103 (in methanol), for example, from (5) - (+) - 2-butanol through (R) -2- (4) -1- methylpropoxy (phenoxy) ethanol. (8) -form: (сЛ) п ° 1 9.78 °, for example from (R) - (-)
butanol through (5) -2- (4) -1-methylpropoxy (phenoxy) ethanol.
R-0
II, O CHR1 CHR 2 X R 3
(1) H
(1) H
(1) H
(1) H
CH j-CHCCHj) CHCCH,) - CH 2,
) (CHj) C CH-CH5,
0
0
NH
0
C, H,
C, H
iC, H,
iC, H,
307 307 307 307

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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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US63195984A| true| 1984-07-18|1984-07-18|

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