SU597318A3 - Insecticide-acaricide-nematocide composition - Google Patents

Description

The invention relates to chemical means of combating insecticides, mites and nematodes. —Wow, namely, the use of insecticylacaricidal nematode based on phosphorus acid derivatives. An insecticide-acyancide-nematocidal agent is known, the active 1; 1 st substance of which is O, 0-dimethyl-0-7-chloro-benz-xoxazole- (3) -yl-thionophosphoric acid I, but its activity is insufficient. Also known is 0-ethyl-O-5-chloroben zizoxazole- (3) -yl-thionoethanephosphonic acid 2, which has insecticidal and acaricidal properties. For the purpose of finding new insecticide-acaricide-nematocylic agents, possessing a high insecticidal, acarius activity, a preceding and nematocidal compound is taxed using the formula (I) with 1–3 carbon atoms from the genus; R, is ethyl, .1 alkoxy with 1-3 carbon atoms; Esters of 6-chlorobenzisoxaol-ONE-PHOSPHORIC (PHOSPHONIC) ACID of formula (I) are prepared by reacting 6-chloro-3-hydroxybenzisoxazole with thio-benzophosphoric (phosphonic) acid esters in the presence of acid acceptors or alkaline-alkaline-earth metal halides with phosphoric acid B in the presence of acid or alkaline-alkaline earth metal halides with phosphoric acid B or phosphoric acid B in the presence of acid or alkaline alkaline earth metal salts of t-ionophosphoric (phosphonic) acid necessary in the presence of a diluent or solvent. The reaction temperature can be varied in the range of 0-120 ° C, preferably 40-60 ° C. The reaction is carried out at normal pressure. For carrying out the process, 6-chloro-3-hydroxy-benzisoxazole is preferably taken in 10-20% excess. Examples of the preparation of the proposed compounds. Example 1. Preparation of a compound of the formula O-P (OSI) 2 A mixture of 61 g (0.36 mol) of 6-chloro-3-hydroxybenzisoxazole in 500 ml of acetonitrile and 54 g (0.39 mol) of potassium carbonate is stirred for 30 minutes at temperature of 50 ° C. 48 g (0.3 mol) of 0,0-dimethylthionophosphoric acid diester chloride are added dropwise to the mixture at 50 ° C and stirred at this temperature for 1 h, and then overnight at room temperature. It is then poured into water and the resulting oil is extracted with toluene. The organic phase is washed with water, and then twice 2n. sodium hydroxide solution and rinse with water until no medium reacts. After drying over sodium sulfate, the solvent is distilled off. 63 g (72.5% of theory) of O, 0-dimethyl-O-b-chlorobenzisoxazole- (3) -yl-thionophosphoric acid layered ether are obtained in the form of an oil. By recrystallization from a mixture of petroleum ether: ether (5: 1), pale yellow crystals are obtained with a mp. . Analogously to Example 1, the compounds of the formula C1 „can be obtained. 1. Forms of drug use are common. The preparations contain 0.1-95% by weight, preferably 0.5-90%, of the active principle. The concentration of the active principle in ready-to-use preparations can be varied over a wide range of 0.0001-10%, preferably 0.01-1.0%. The compounds proposed as the active beginning can be used by the method of distribution of the substance in an extremely low volume (UZV) when it is possible to apply preparations with the content of the active principle up to 95 or 100%. The effectiveness of the following compounds is visible,: from the following example Example 8 p A. Experience with flies Ce / -ai E Solvent: 3 weight.h. acetone. Emulsifier: 1 weight.h. alkyl aryl polyglycol ether. In order to obtain an active drug, start 1 wt. it is mixed with the solvent and emulsifier, then the concentrate is diluted with water to the desired concentration. 1 cm of the active drug is pipetted onto a circle of filter paper approximately 7 cm in diameter, which is placed on the opening of a glass vessel with fruit flies placed in not approximately 30 (Cegs titis cap-iiaia) and covered with a glass plate. After the time specified in table. 2, determine the degree of killing. At the same time, 100% means that all flies have been euthanized, and 0% not a single fly has been euthanized. The results are shown in Table. 2. Example B. Experience with Pbaedon leaf beetle larvae. Solvent: 3 parts by weight. acetone, emulsifier: 1 weight. including alkylapylpolystyrene ester. In order to obtain a preparation of the current onset, 1 weight.h. it is mixed with a solvent and an emulsifier, then the concentrate is diluted with water to the desired concentration. A preparation of the active principle is sprayed with cabbage leaves (B as51ca oEgasea) before formation of drops and the larvae of the horseradish leaf (phaedon cochBeap above) are placed on them. After the time specified in table. 3, determine the degree of killing. At the same time, 100% means that all the larvae are killed; 0% - no larvae are euthanized. The results are shown in Table. 3. PRI me R B. Experience with cicada EusceE s Solvent: 3 weight.h. acetone, emulsifier: 1 weight.h. alkyl aryl polyglycol ether. In order to obtain a preparation of the current onset, 1 weight.h. it is mixed with a solvent and an emulsifier, then the concentrate is diluted with water to the desired concentration. The drug of the beginning of the beginning is sprayed with beans (Vicia fa la) to the moisture content of dew and the soil of cicadas (EusceEis bi iboitus) on them. After the time specified in the table. 4, determine the degree of killing. In this case, 100% means that all cicadas are euthanized, 0% means that no cicada is euthanized. The results are shown in Table. 4.o PRI me R G. Experience with spider mites {stable) Tet runvcfius Solvent: 3 weight.h. acetone, emulsifier: 1 weight.h. alkylaryl polyglycol ether. In order to obtain a preparation of the current onset, 1 weight.h. it is mixed with solvent 1 and an emulsifier, then the concentrate is diluted with water to the desired concentration. The preparation of the active principle is sprayed, before the formation of droplets, of the bean plants (PhaseoEos VU Cg-aris), which have reached a height of approximately 10 to 30 cm. These plants are severely affected by common grass and bean spider mites (Tetgapvchiv Uhiicae) in all stages of its development. After the time specified in table. 5, the killing degree is determined. At the same time 100%

means that all of the cobwebs are clever; 0% - nn one tick does not die

The results obtained in Pobedil in table. five.

PRI me R D. Experience with pre. concentration (living in the soil of insects). Experimental insects: ground litters -PiiOfbiu anlic ua

Solvent; 3 weight hours acetone, emulsifier: 1 weight.h, alkylaryl polyglycol ether.

For the preparation of the active ingredient, 1. it is mixed with a solvent, an emulsifier is added, then the concentrate is diluted with water to a concentration that is clear. The preparation of the active principle is tiathally mixed with the earth. At the same time, the concentration of the active principle in the preparation practically does not play a role, the decisive is the weight amount of the dekestvuyuschego beginning per unit volume of the earth. The earth is loaded into pots and left to stand at room temperature.

After 24 hours, experimental insects are placed in the cultivated land after 2–7 days, by counting the dead and living insects (in percent), the effectiveness of the active principle is determined. Efficiency is 100% if all insects are euthanized, and 0% if there are as many insects alive as there are in untreated land (in control),

The results obtained are shown in Table. 6

PRI me R E. Experience with the maximum concentration (living in a pose of insects). Experimental insect: larva in 3eh4J e Tepe brio mo EH or-.

Solvent: 3 weight, h. acetone, emulsified atrium: 1 ae c, h al k il il ar il p cl of glycol ether.

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

The preparation of the active principle is thoroughly mixed with the earth. At the same time, the concentration of the active principle E practically does not play a decisive role; the weight quantity of the active principle per unit volume of the earth is decisive. loaded into the mountains; 1pc and left to stand at room temperature.

After 24 hours, the experimental insects are placed in the cultivated land, and after 2–7 days, the efficiency of its beginnings is determined by counting the dead and living insects (in percent). Efficiency is 100% if all of them are euthanized, and 0% - if as many insects remain alive as there are in the untreated earth (in the control).

Received 11 penyjii; ghats at the wedge; n tab. 7

EXAMPLE, Experience with limiting ko ;; centration, Experimental nemato; 1y:

 с t о 1 d о g з п е i п с о о п. t. oi

Solvent: 3 carried, h, acetone, emulsifier: 1 weight. H. alkyl aryl polyglycol ether.

To obtain the drug, the current start 1 weight.h. it is mixed with a solvent; an emulsifier is added, then the concentrate is diluted with water to the desired concentration.

The preparation of the active principle is thoroughly mixed with the ground / heavily infected with the floor of the patient. At the same time, the concentration of the active principle in the preparation practically does not play a role, the decisive factor is the amount of the active principle on the bulk unit). The harrow, the processed glass is loaded into pots, and the lettuce is kept ropijjKi in the greenhouse npi-; temperature 27s.

After 4 weeks, the roots of the lettuce hfover goat on nematode nos. 1 (yellow) and og; determine the effectiveness of its effective beginning. Effectiveness is equal to 100%, if there is no damage, and 0 °, if the damage is as high as the control pacTeiiiiH in the untreated, but taki-M in the same way infected.

The results are shown in Table 8.

p 3. Experience with ,,,. PONT to S-iiophiCus trrcinats about p; t; We know that we are e-g i u 5. Solvent; acetone.

2 weight parts the current beginning of the solution YT in 100.-g. solvent. Semi1. thus, the solution is diluted with a PRG solution to the desired concentration of Gn t r a p i, 2, -5 ml of the solution of active starter pipetted onto filter paper with a diameter of approximately 9.5 cm in the petri lump. The petri dish is left open until the solvent has completely dissipated. In the head -; simost1-; from the concentration of the solution of the beginning of the current amount of the beginning of 1 m of filter paper is different. Then about 25 HaceKOMiiJX test subject guards are placed in a Petri gull and covered with a glass curl. Three days after the start of the experiment, the degree of mortification of the fcIX was determined. At the same time, 100% means that all the test-asectomy are euthanized; 0% - no insect is killed.

The results are shown in Table 9.

Pr 15 .1 eRI, Experience with mosquito larvae. Experiments FiaceKOf ibie: Aedes aeo-ypi.-j. Solvent: 99 wt.h. ace top, emulsifier: 1 weight.h. benzyloxydiphenyl polyglycol ether.

Received; T drug acting start 2 weight.h. it is dissolved ij 1 uOO Ob. h. pacTBOpsiTejiSi, —– —–––––––––––––––– ––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––; perfect

Aqueous preparations, diptyzu and beginnings rriviKafi: f; noF-ieija every Starsan Ave 1, a friend; but Kok mosquitoes.

iiGiib y, ep11; aleipl. With; rror-i 1,007; O1i {чтоЧ ет ет ет что в в в в в11; - - - и и у у::: пен пен пен пен пен пен пен пен пен пен пен ping jnf4H -uca. not at; .1 rchia.

in tab. ten.

11 p and; ep K, OitHT with a parasite -; mi lyche1 kag. and; --- ll. PaoTnopKiejfbc -i L Q

, 1: reparata existing rchala. lo ns. — averaging 2 hours; 1It is the degree of death DJiRiiHH. At 3TON1 100% of the lake :: Tachee; that ij:.: e jii-i-sHHKH are u-yuscheny, Oi - that neither

: results: UAH; in taol. eleven.

LOCAL ChROLL-; With A1L IN OO i-iilCBKTH

1.R | Adajeg High) -: IsletiDI |: Oh, Akarititsyu W:; G: -iai Odin aktiv1l: O1L5Yu. ro active substance is mixed with the solvent containing the emulsifier. Received: I have thus dissolved the concentrate; are the water jjo of the desired concentration,

Active principle

SgIz O-PX

S ocghj

S

Known

- 2

Active principle

-Q

Ci / WA..iiN g I 11

O- P (OSI 3) 2

(Known)

C1

0-P (OSgN5) 2 (Known)

f 1

table 2

The degree of killing after 1 day, 1

100 85

ABOUT

.00 iOO 90

T a 6 l and c a

Killing Degree

Concentration deistose 3 days. vuyutsdego beginning%

100 100

100 100

about

100 100 100

13 Active principle Concentration of active principle,%

14

Continuation of table 4

100 100 100 Killing degree I after 3 days,%

Number 3

100

100

70

100

100

70

 -f

O - PlOClis) (known}

Cocklice action in all cases x 0.1

Table 5

 The degree of killing for I expiration 2 DN8,%

85,100

IS

About- PfOCIbla (Iebeshnoe) g 5

Number 9

Concentration of the general start of 20 ppm.

Active Start - ™ ..

хЦ

.N

О - Р (ОНЗз) 2 (MzVestnay)

C1

ABOUT

  - to

° | - OC2H5

S (Izvestnaye)

№ 2

№ 4

№ 5

 9

The concentration of active start was 5 ppm.

sixteen

Table 6

The degree of killing,%

50

100

100

Table 7

The degree of killing,%

100

100

100

100

17

Active principle

C1

 I

0-P (OSPs) g (Known) C1

Kg, -.,

t-gneu r-o:

X

EXTREME

(11 Zestnoe) f 2

№ 4

 five

Concentration of the active pumping 10 h, ppm

18

Table

The degree of killing, 100

100

100

acting shchalo

Degree of killing,

„, 0

.. i

Ci --- X 3

0 ™ P (specialty 51g

(Known)

№ 1

№ 2

100

100

ABOUT

100 100 100

100 100 100

nineteen

Active principle

№ 4

№ 7

Number 9

№ 5

20

Continuation of table 9

Concentration is valid Degree of killing,% of beginning expression,% solution,

100 100 100

100 100 100

100 100 100

100 100

100

100 100 100

21

Active principle

Concentration of the active principle in the solution, ppm

22

Table 10

Degree of killing,

about - r1osn5) g

(Known)

100

90

ABOUT

 one

№ 2

№ 4

№ 7

 9

 five

100

100

90

100 100

100 90

100

100

80

100 100

80

100 90

0.1 0.01

100 90

0.1 0.01

23

Active principle

24

Table 11

Concentration of active principle, h / m-mon.

100 10

.00 0.

() 2 (Known)

№ 2

№ 1

f. 3

V 6

№ 7

Number 9

100 30 10

100 100 100

100 10

100 50

100 30 10

1 00 50 50

100

100 10 100

100

100 100 10

100 30 10

100 100 100

100

100 10 100

100 10

Claims (2)

100 100 25 Formula invention insecticides, acaricides, nematocidal agent based aktiBno-active principle - the derivatives of phosphorus acid and an additive selected from the group: nosital, diluent and filler characterized in that, with tsejiMUdnjiMccg drink vgilpni insecticidal, akaritsidlyu usilkmip jinucivinwrw, tnogo and nematocidal action it contains as derivatives of phosphorus acids a compound of the general formula Yu {.JV T f nn 0-Р, in which R is alkyl with 1–3 atoms, and carbon; ; ethyl, alkoxn with 1 to 3 carbon atoms, the content of the active principle being 0.1-95 wt.%. Sources of information received in t-, t attention to examination and: i. patent of Germany No. 1253713, cl. 12p 3, 1968. 2. Patent of France No. 2182229, cl. C 07 T 9/16, 1974.