Method of insect control

专利摘要:
The compounds of the formula (I) <IMAGE> (I) in which X denotes CH2 or O, R1 denotes (subst.) pyridyl or (subst.) pyrimidyl, R2 and R3 denote alkyl or alkenyl or R2 and R3 denote an alkylene chain, R4 denotes -H, -CN, -CCl3, -C 3BOND CH, alkyl, F, or -C(S)-NH2, R5 denotes pyridyl, furyl, thienyl, phthalimidyl, di(C1-C4)alkylmaleimidyl, thiophthalimidyl, dihydrophthalimidyl or tetrahydrophthalimidyl, which may all be substituted, or substituted phenyl, or R4 and R5-together with the carbon atom bridging them-denote an optionally substituted indanyl, cyclopentenoyl or cyclopentenyl radical, have advantageous insecticidal, acaricidal and nematocidal properties.
公开号:SU1618274A3
申请号:SU874202456
申请日:1987-04-24
公开日:1990-12-30
发明作者:Херберт Шуберт Ханс；Зальбек Герхард；Людерс Вальтер；Кнауф Вернер；Вальтерсдорфер Анна
申请人:Хехст Аг (Фирма)；
IPC主号:

专利说明:

R-Si-CH, -X-CH, -. R,
I CH (1)
where X is oxygen or methylene;
R (- 2-chloropyripin-5-yl, 2-methoxy-pyridin-5-yl, 2 (5) -ethoxy-pyridine-5 (2) -yl, 2 (2,2,2-three - fluoroethoxy) -pyridine 5-yl, 2-ethoxy-pyridin-5-yl;
with an organometallic compound of the formula
Me-CHz-CH2-CHz-R2 (III);
b) a silane of the formula CH,
I
}
 O4
R -Si-CH, -X
I CH.
(Iv) or
CH,
Rj-Si-CHj -X-Me
(V)
in the presence of catalysts based on transition metals of groups I and VIII, preferably Cu, Br, NiCl .; h) formula silane
sn
3
with an alkylating agent of the formula Y-CHX-R2 (VI)
in the presence of a base; c) silane formula
CH
3
 R.-Si-CHJ I 2 CH,
(Vii)
with the compound of the formula:
HX-CHi-R2 (VIII) in the presence of a base, or with an organometallic compound of the formula Me-X-CH2-R2; (IX) g) a silane of the formula
CH.
Rf-Si-CH2-Me
(X)
CH
3
with the compound of the formula:
Y-CHj, -CH2.-R2; (XI)
d) formula silane
CH
3
R -Si-CH -CH2-Y CH,
(Xii)
with organometallic compound Me-CH2-Rj; e) silane formula
ch3
Y-Si-CH2-X-CHa-Rz
ch3
(Xiv)
with organometallic compound R gMe (XV); g) silane formula

R, -Si-CH2-X-CH2-Y CH,
(Xvi)
with an organometallic compound of the formula
Me-R2 (XVII)
CH2 I 3
R-Si-H
(Xviii)
ten
CH

with an olefin of formula
CH CHi-CH -R;,. (XIX) in the presence of a catalyst - a complex compound of Group VIII elements such as HzPtCl, Co2 (CO) в, Rh4 (CO), a; 1g4 (CO) 1g, RhClLP (C6H5-). The ratio of catalyst and reagents depends on the catalyst. For example, for H PtClg
it is in the range of 1: 10-10: 1; i) silane formula
CH.
I 3
R, -Si-Me
CH,
(Xx)
with compound of formula
Y-CHi-CH-CH2-R2. (XXI)
In formulas II-XXI, X, R and R2 have the indicated value, Me is the equivalent of an alkali or alkaline earth metal, preferably Li, Na, K, Mg is a nucleophilically removable group, preferably a helogen or a sulfonate.
The reaction temperature is from -75 to, preferably from -75 to + 105 ° C. The starting materials are usually taken: but in equimolar amounts. The reaction is carried out in the presence of dilute
l, the nature of which is determined by the nature of the reagents.
Suitable diluents are aliphatic and aromatic hydrocarbons, for example pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene and xylene; diethyl and dibutyl ethers, glycol dimethyl ether, diglycol dimethyl ether, tetrahydrofuran, and dioxane; all possible mixtures of these solvents. Method h) unlike other methods of synthesizing compounds of the general formula I, is preferably carried out
without diluent. However, it can
carry out in the presence of solvents such as cyclohexane, petroleum ether, benzene, toluene, tilol, etc.
 16 When using compounds (IV) and (VIII), other diluents can also be used. Ketones are also suitable in these cases, for example acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate; : nitriles, for example acetonitrile and, propionitrile; amides, for example: dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, as well as dimethyl sulfoxide, tetramethylsulfone, and hexamethylphosphoric triamide.
Inorganic bases are used as bases, for example, alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal hydrides, carbonates or bicarbonates, as well as organic bases, for example pyridine, triethylamine, NN-diisopropylethylamine or diazabacycloctane.
20 After 3 days, the death of insects is 100% when using compounds 1-23, and when using the known compound (4 methylphenyl) -dimethyl-G (3-phenoxybenzyl) -oxymethyl-siphon and, if necessary, purifying an amount of 0.35 g / ha and 0.5 kg / ha of the compound (I) are carried out respectively at 65 and 75%. in the usual way, for example, by means of Example 3. Strongly affected solvent boiling (under known Pseudocoocus citri bean plants under reduced pressure) and (Phaseolus vulgaris) are sprayed over
thirty
then by-distillation or chromatography, or by distributing the crude product between the two phases and the subsequent conventional treatment.
Example 1. A mixture of 18.2 g (0.09 mol) of 2-ethoxy-5-bromopyridine (obtained from 2.5%) is poured onto 2.4 g (0.10 mol) of magnesium shavings in 10 ml of anhydrous tetrahydrofuran (THF). dibromopyridine and sodium methylate in DMSO), 11.4 (0.12 mol) of chlorodimethylsilane and 50 ml of anhydrous THF. A highly exothermic reaction occurs. The reaction will be more complete if the mixture is boiled under reflux for 2 hours. Then the mixture is poured -4-5 and 9. It is poured into water and extracted multiple times with n-hexane. The extracts are washed with water and saturated sodium chloride solution, dried and evaporated, the residue is distilled. 7 g (43%) of 2-ethoxy- 0 of 5-dimethyl-silylpyridine are obtained in the form of the procedure of Example 2. Then the plants are kept for 7 days in a greenhouse at 20-25 ° C and the number of dead insects is determined.
35
40
100% insect death is established for compounds j-6,14-16, 20.
Example 4. The leaves of the beans (Phaseolus vulgaris) are treated according to the method of Example 2 and placed in the same processed larvae of the Mexican bean beetle (Epilachna varivestic) in a surveillance chamber. After 48 hours, 10% of the larvae die by using compounds 1,2,
Thus, this method is highly effective at low doses.

权利要求:
Claims (4)
[1]
Invention Formula
colored oil with so kip. 140-150 C (7 mm Hg).
A mixture of 3.6 g (20 mmol) of 2-ethoxy-5-dimethyl-silylpridine and 4.2 g (20 mmol) of 3-allyldiphenyl ether is mixed with two drops of a 30% solution of hexachloroplatinic acid in isopropanol. After a slight heat274
The exothermic reaction proceeds. The resulting crude product was distilled in a spherical tube and 3.6 g (46) of (2-ethoxypyridin-5-yl) -dimethyl-3- (3-phenoxyphenyl) propyl-silane were obtained.
0
de colorless oil with t.kip. 230 C (0.15 mm Hg), p 1.5618.
According to this procedure, the following compounds of formula (I) are presented in the table.
Example
[2]
2. Strongly infected with tl (Aphis craccivora) plants go-.
5 powders of Narbonne (Vicia faba / ava) are sprayed up to the stage of beginning splitting with aqueous emulsions containing the content of compound (I) YuOOrrt in the amount of 0.4 kg / ha (compound I).
0 After 3 days, the death of insects is 100% when using compounds 1-23, and when using the known compound (4 methylphenyl) -dime- with t-G (3-phenoxybenzyl) -oxymethyl-5, the amount of 0.35 g / ha and 0.5 kg / ha, respectively, 65 and 75%. Example
[3]
3. Strongly affected Pseudocoocus citri bean plants (Phaseolus vulgaris) are sprayed according to
method of example 2. Then the plants are kept for 7 days in a greenhouse at 20-25 ° C and the number of dead insects is determined.
5 and 9.
100% insect death is established for compounds j-6,14-16, 20.
Example
[4]
4. The leaves of the beans (Phaseolus vulgaris) are treated according to the method of Example 2 and are placed in the same processed larvae of the Mexican bean beetle (Epilachna varivestic) in a surveillance chamber. After 48 hours, 10% of the larvae die by using compounds 1,2,
5 and 9.
Thus, this method has a high efficiency at small. doses.
5 and 9.
Invention Formula
A method of combating insects by treating plants or their biotope with a trimethylsilane derivative, characterized in that, in order to increase the efficiency of the method, a compound of the general formula is used as a trimethylsilane derivative
CH,
R, -Si-CHz-X-CH2-R2,
ch3
where X is oxygen or methylene;
K, -2-chloro-pyridin-5-yl, 2-methoxy-pyridin-5-yl.
ICh
) sun „
CH,
n
CH,
P
CH,
m
about
and
about
|
about
N-
C1
CH-M-
°
-
ABOUT
ten
|
eleven
Kl
about
2 (5) -ethoxy-pyridin-5-yl, 2- (2,2,2-trifluoroethoxy) -pyridin-5-yl, 2-ethoxy-pyrimidine-5-yl;
R-3-phenoxy-phenyl, 3-phenoxy-4-fluoro-phenyl, 3- (4-fluoro-phenoxy) -4-fluoro-phenyl, 6-phenoxypyridin-2-yl, amounts of 0.35 and 0, 5 kg / ha.
o-cho;
T.kip.01, Ј 230 С - 1.5618
about
KG.0 15 220 ° С
Bp 235 С
vOVF About
F
T.KWr.0i2 230 ° C
© ® ®
T.kipo | 230 - 235 ° С
T.Kip "0 Od 205-210aS
Bp 02. 235- - 240 ° С
YuG
-about
T.kip.0 (g 220 ° C
(O) o
T.kil.042. 225- - 230 ° С
Bp 005-210- 220 ° C
YuG
ABOUT
Boiling point, 210-220 ° C0

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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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DE3618354|1986-05-31|

---