SU689597A3 - Insectoacariocidenematocide agent - Google Patents

Description

(54) INSECTOACARICIDONEEMATIC MEANS, if necessary, in the presence of an acid acceptor or ammonium salts and, if necessary, in the presence of a solvent or diluent. Preparable compounds are preferably prepared using suitable solvents and diluents. In this case, almost all inert organic solvents are used. These preferably include aliphatic and aromatic, if necessary chlorinated hydrocarbons such as benzene, toluene, xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, or an ether such as diethyl ether and dibutyl ether, dioxane, ketones for example, acetyl, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, as well as nitriles such as aceto and propionitrile. All common acid binders, preferably alkaline carbonates and alcohols, for example sodium and potassium carbonate, methylate or ethylate, aliphatic, aromatic or heterocyclic amines, for example triethylamine trimethylamine, dimethylaniline, dimethyl benzylamine and pyridine can be used as acid acceptors. The reaction temperature may vary widely. The process is carried out at a temperature from 0 to 100 ° C, preferably 20 ° C. The reaction proceeds at normal pressure.

R

Example

 S74

C H

 S66

 S74

5CjHj

0CjH -H

7C., Hg

8SgNz

Table 1

Output

Indicator

% refracted

g

1.5102

G.24 1.5080

four

- L, 5570

1.5057 1.4929 1.4992 1, 6969 For carrying out the proposed method, the starting compounds are used in an equimolar ratio. The reagents are combined in one of the indicated solvents in the presence of an acid acceptor and stirred at elevated temperature to supplement the reaction for one or several hours. The mixture is then mixed with an organic solvent, e.g. toluene, and the organic phase is processed in conventional manner by washing, drying and distilling the solvent. Example. -l S shy-szn, - // yo- (oc, Hs) 2 300 ml of acetonitrile, 13.8 g (0.1 mol) of 2-iso-propyl-5-oxypyrimidine, 20, 7 g (0.15 mol of potassium carbonate and 18, -8 g (0.1 mol) of O, 0-diethylthionophosphoric acid diester chloride, are stirred for 2 hours at 45 ° C. Then the reaction mixture is poured into 400 ml of toluene and washed twice, each time with 300 ml of water. The toluene solution is dried over sodium sulfate and evaporated under vacuum. The residue is distilled under high vacuum. 17.4 g (62% of theory) of O, 0-diethyl-O- (2-isopropylpyrimidine) -5-yl-thionophosphoric acid ester are obtained as a brown oil with a P of 1.4970. In a similar manner, compounds of formula 1 shown in Table 1 can be prepared. one.

9CgHj

UC2 H

n (i

10СзНд

.-2 tig

) 11 Cj Ps,

r 1,5643

2

1.5827

ii 1.5028

The 5-hydroxypyrimidine used as starting compounds can be prepared as follows.

A solution of 49.5 g (0.45 mol) of 5-methoxypyrimidine, 38 g (0.68 mol) of potassium hydroxide in a mixture of 80 ml of water and 170 ml of methanol is heated in an autoclave for 3 hours to 190 ° C. The methanol is then distilled off in vacuo, the residue is mixed with 50 ml of ice-cold water and the solution is brought to pH 4.5 with cooling. And by addition of concentrated hydrochloric acid. After 30 minutes, the crystallized product is filtered off with suction and in this way 30 g (70% of theory) of 5-hydroxypyrimidine are obtained as a crystalline powder with a melting point. with a slightly brown color.

Similarly, the following compounds of the formula

.9.

presented in table. 2. -Table2

PRI me R 2.

Experience with Phaedon larvae.

Solvent: 3 wt. including acetone.

Emulsifier: 1 weight. including alkylaryl polyglycol ether.

In order to obtain an active drug, start 1 wt. including it is mixed with the indicated amount of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

The active agent is sprayed before the formation of drops.

(known)

oJxOCjHs

H

SCjHT-n ISO-S U

,

CH,

(known) K - S

(j7-o- - (oc, H5),

cabbage leaves (B assica oEefacea) and planted on them larva of horseradish leaf beetle (Phaedon cochEeariae).

After this time, the killing degree is determined in%. At the same time, 100% means that all the larvae are dying, and 0% means that not a single larva has been killed.

Active principle, concentration, time of assessment and results are given.

in tab. 3 ..

Table3

0.01

100 0,001

about

100

0.01,100 0.001

PRI me R J. experience with vetranychufe (steady).

Solvent: 3 wt. including acetone. Emulsifier; 1 weight. including alkylaryl polyglycol ether.

To obtain the drug acting 1% start weight. h. it is mixed with. The specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

The active agent is sprayed to form a bean plant (Phascotub),

 Continuation of table 5

Which .eo of all stages of development is severely affected by a spider mite (Tetranvchus urticote.

After this time, the degree of damage is determined in percent.

At 100% - means that all ticks are euthanized, and 0% means that no ticks are killed.

50 The active principles, their concentrations, the time of determination and the results are shown in Table. four.

A4 table

PRI me R 4. Experience. Test insects: 6 1yrMei & Gapag PB.

Solvent: acetone.

2 wt. h. active beginning absorb in 1000 about. including solvent. The solution thus obtained is diluted with a solvent to the desired concentration.

2/5 ml of active ingredient is served in a Petri dish. At the bottom of the petri dish is a filter paper with a diameter of approximately 9.5 cm. The petri dish remains open until the solvent has completely evaporated. Depending on the condensation $

Q ll / OCzH5

H- / ЗСзН7-а

0,002 - SzN, - L

zo

CH, (known)

xCzHs

Op

m:

OCjHj

0,002

CHj (known)

V

- jK7-f) g iso

0,002

L n, -f J -o-P {oCaH5) z 0.002

Tl-o-:

"X-sns

t / w-cjh; 0,002

P / OCjH7-lOJ

SNS-f WOi / OCiHs

0,002

UHC Hg-WO

Table 4 favor

The amount of the active ingredient per 1 m of filter paper is different. Then 25 experimental insects are fed into the Petri dish and the dish is covered with a glass lid.

The condition of the experimental insects is checked after 3 days.

The degree of killing is determined in percent. In this case, 100% means that all experimental insects are euthanized, and 0% means that not one experimental insect is killed.

Active principle, their concentration, experimental animals and the results are shown in Table. five.,

Table 5

100 100 100

50

LOW / WOW -

} / UHCjH7 Examples Experience LD, Ltd. Experimental insects sTbEatLo orientd i ".

Solvent; acetone.

2 .weight. h. active beginning absorb 100 vol. h. The solution thus obtained is diluted with further solvent to the desired concentration.

2.5 GSH solution of the current beginning is served in a Petri dish. The bottom of the petri dish is filter paper with a diameter of approximately 9.5 cm. | The petri dish is left open until the solution is completely volatilized. Depending on the concentration Jx-OC Hj W / 5СзН7-п

iz-С Е -, -) -N

SNS (known)

  and wo-CjHyHf Vo-P (oCHN) g

N -l s

iso-C t {VO-P (

and ..- SzNH / Uo-lc

  / OSNTOS Fri-and

PRI me R 6. Experience with the maximum concentration.

Test nematodes: WeEo-idogyne incognita.

Solvent: 3 wt. h, acetone.

Emulsifier: 1 weight. including alkylaryl polyglycol ether.

In order to obtain an active drug, start 1 wt. the active ingredient is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Supplement table, 5

irizimi :.

100

0,002

100 0,002

The amount of active start per 1 m of filter paper is different. Then about 25 experimental insects are served in a Petri dish.

5 and close it with a glass lid.

The condition of the experimental insects is checked after 3 days. The degree of killing is determined in percent. At the same time 100% means

0 that all HaceKONOje experimental animals were euthanized, and 0% that no experimental insect was killed.

The active principles, their concentrations, experimental animals and the results are given in Table. b.

Table

0.02

100 100 100

The preparation of the active principle is intensively mixed with the soil strongly affected by experimental nematodes. At the same time, the concentration of the active principle in the preparation plays practically no role, the decisive factor is only the amount of the active principle per unit volume of soil, which is indicated in parts per million. The treated soil is filled into pots, planted with lettuce, and the pots are left to stand at the greenhouse temperature.

After 4 weeks exploring the damage of the roots of lettuce nematodes

and determine the degree of effect of the active principle in percent. 100% means that there is no lesion, and 0% that the lesion is as high as that of the control plants.

ots

 SC3H7

/.)

(known} .Hs).

, - (o-1 ° C,

xn

- about

«Zh, 1L, | / ogN5

Hj / TSH-SZH

, os, „,),

-yoJc ° V

L / OCzHs

V

v

J / OCzHs

Cjhs

with "SC / 7A.

CH,

0., - / -VoJx ° “5

 jj / WlCjHT-UJO

, c, -y,

Vjo

eleven

L xOCjH,

-O- shs t-sh.

g

s /

irjS

KCh5

- -OCzHs

CHj-fX-o- - Z S

imciHs

in untreated, however, affected soil.

The effective principles, the amount of application and the results of the experiment are given in Table 7.

Table

0

ioo

100

100

100

100

100

100

100

100

100

100

100

i

HosSN-7 SHCjHj

 ShNSNSNS4N9 -izo

11 / OSNN7

iraCjH7-u3o

and

(Wo-p- (oSgN5) h

 A X OSSNt-RCD

...- szn - Wo-RS 7

Ln

-SzN, - (y 0-P- (ONzz) 2

WO

and

,; - nn. And OSgNz CjHi-f / -0-P

g /

Example. Experience with limiting 1 centering (insects living in the soil).

Experimental insects: living in

soil larvae TenebfiQ moEitor.

Solvent; 3 wt. including acetone.

Emulsifier: 1 weight. including alkylaryl polyglycol ether.

In order to obtain an active drug, start 1 wt. including it is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

The preparation of the active principle is intensively mixed with the soil. At the same time, the concentration of the active principle in the preparation plays practically no role, the decisive factor is

SSNz

3 C

° X, i-CH (CH3b

SgNzO -s

known)

Continuation of table 7

100 100

100

100 100

100 100

only the amount of active ingredient per volume unit of soil, which is indicated in parts per million (mg / l). The soil is filled with pots and allowed to stand at room temperature.

After 24 hours, the experimental insects are fed into the treated soil, and after a further 2-7 days, the degree of action of the active principle is determined in percent by counting dead and living insects. In this case, 100% means that everything: the insects are euthanized, and 0% means that there are the same number of insects as in untreated soil.

The effective principles, the amount of application and the results are shown in Table. eight..

Table

I

OSGYA5

/

0-P

SC3H7

SznH

w

SNS

(Favorite) CH-fToJio la

II /

CHj

CH w

 -KG- ° ™

CHj

SNS W

"-Snc L-o-K SNZ

SNZ / OSSNt Example. Experience with extreme concentration (systemic action) Insect experimental: Phaeolon tochttariae. Solvent; 3 wt. including acetone. Emulsifier: 1 weight. including alkylaryl polyglycol ether. To obtain a drug active start 1 wt. including it is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. The preparation of the active principle is intensively mixed with the soil. At the same time, the concentration of the active principle practically does not play any role in the preparation, the decisive factor is only the amount of the active principle per unit volume of soil, which is indicated in parts per million (mg / l).

-CCH3 "s

sn

Cjhso

p-s., сCjHsO Н

(from 9)

0 | xOSgN5

TT-V- scjH wo - CjH, N

Syaz

(uiteomw)

Continued Table 8 2

100

100

100 The treated soil is filled into pots and planted with cabbage (braasica osep ceO}). Thus, the action begins to enter the leaves through the plant roots. To confirm the systemic effect, after these 7 days, the insects are planted on the leaves. After another 2 days, the insects are counted dead insects. From the number of dead insects, the systemic effect of the active principle is determined. 100% means that all experimental insects are killed, and 0% means that the number of living experimental insects is the same sokim as in the untreated soil. Active principles, their number and the results are shown in Table. 9. Sheets a9

Sn L 1

 VO-PIOC HSJZ

CH;} -C /

:: s „h o-1--: ;;

3 T7 / CCH

 / Shz

g-sn-;

CHj

t t

PRI me R 9. Experience with maximum concentration (systemic action).

Experimental insect: / MyzuS reg5-1 soy

Solvent: 3 wt. including acetone.

Emulsifier: 1 weight. including alkylaryl polyglycol ether.

In order to obtain an active drug, start 1 wt. it is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

The preparation of the active principle is intensively mixed with the soil. At the same time, the concentration of the active principle in the preparation plays practically no role, the decisive factor is only the amount of the active principle per unit volume of soil, which is indicated in parts / million. Then, HvOCoHs

OR:

G1

CHj

(honestly)

t N -l S

П-Зч // II

(

Continued e 2abl. 9

ZIIII-.

2

100 100 100

100 100

the botanized soil is filled into pots and cabbage (brocssico oteracea) is planted in it;

5 plant roots in the leaves.

To confirm the systemic action, after the expiration of 7 days, the indicated experimental insects are planted on the leaves. After a further 2 days

0 count killed insects. The systemic action of the active principle is determined from the number of dead insects. At the same time, 100% means that all experimental insects are killed, and 0% means that the number of live insects is the same as in untreated soil.

Effective principles, quantity

0 application and the results are shown in Table. ten.

Table 10

100 V - 3 „/ СНз h / h h 0-СН. a, °

l

CHjHf) g kg ll OCjHs

1T

shit

Claims (2)

The claims Insektoakaritsidonematotsidnoe means comprising deystvuk Zeh beginning based on pyrimidine derivatives of phosphoric acids and an additive from the group of solid and liquid of supports, characterized in that, in order to increase insecticide akarntsidnoy activity and manifestations nematicide aktivyosti, it comprises, as the pyrimidine derivatives of phosphoric acid compounds of general formula 100 100 1 p lo; oken e ta6l, O 2 where K is alkyl Cj - Cj; Sj is methyl, ethyl. C, Cj-alkoxy; C - Cd-: alkylamino or phenyl; hydrogen, methyl, propyl or phenyl; X - sulfur, oxygen; in an amount of 0.1-95 wt.%. Sources of information taken into account in the examination 1, US Patent No. 2754243, cl.424-200, published. 1956 2. Published for the Federal Republic of Germany 2360877, cl. C 07 R 9/18, published, 1975 (prototype).