DEP0007677MA - - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

Registration date: May 20, 1952. Advertised on December 22, 1955

GERMAN PATENT OFFICE

The invention relates to an insect control agent which is characterized by a content of dimethylamino-monoisopropylaminofluorophosphine oxide as an active ingredient.

It is known that many bis (mono- or dialkylamino) fluorophosphine oxides are effective insecticides. This means that they are in sufficient concentration when they are used on plants enter their sap flow through the leaves and ίο roots and thereby the whole plant make toxic to sucking insects without harming the plant itself. The limbs of this However, class of compounds show great fluctuations in terms of their rate of absorption in the Plants, their rate of evaporation, their rate of decomposition, toxicity to insects and toxicity to mammals and humans. For example, this is bis (dimethylamino) fluorophosphine oxide an insect control chemotherapeutic agent used for many types of insects, particularly aphids, is fatal. But this compound is a liquid with a high vapor

509 600/223

P 7677 IVa / 451

pressure, namely of 0.36 mm Ug at 25 ^r , which quickly leads to losses as a result of evaporation before absorption and as a result of evaporation after absorption AnIaL! gives what is dangerous for its use as a Spritznut tel by inexperienced workers.

Bis- (monoisopropylamino) -iluorphosphine oxide, the properties of which are described in the earlier patent 895 228, is also an effective chemotherapeutic insect control agent and has the significant advantage over bis- (dimethylane) ino) -iluorphosphino. \ Yd that it is a very much lower Vapor pressure (the pure compound is a solid substance melting at 65 ⁰ with a vapor pressure of 0.0025 mm Hg at 25 ⁰ ) and that it is much less toxic to mammals. However, it is more slowly absorbed in plants and decomposes into non-toxic compounds much more quickly, reducing its usefulness in some applications.

; POC1 -} B-HF

(C ₃ H ₇ ) NH

be prepared, where H is a tertiary base.

ICs can also be produced by the reaction of phosphorus

PC) Cl ₁₁ ■; (CH ₃ I ₂ NH 13 (C ₃ H ₇ ) NH,

and treating the product obtained with a strong aqueous solution of sodium or ammonium fluoride be prepared, whereupon the isopropylamine hydrofluoride formed as an intermediate, the The chlorine atom on the phosphorus atom is exchanged for a fluorine atom.

It has now been found that the dimethylaminomonoisopropylamino-fluorophosphine oxide excellent properties as a systemic insecticide which does not derive from the properties of the above-mentioned known compounds were to be foreseen. While its toxicity to mammals is within the toxicity for Mammals of the above-mentioned compounds, its insecticidal effect is just as great and often much greater than that of bis (dimethylamino) fluorophosphine oxide, and its effect is more lasting than bis (dimethylamino) fluorophosphine oxide or bis (monoisopropylamino) fluorophosphine oxide.

The new compound can be prepared by reacting the corresponding in an inert organic solvent, e.g. chloroform, dissolved chlorine compound with the hydrofluoride of a tertiary base, which is at least as strong as pyridine and e.g. methyl-dibutylamine can be, according to the equation

: POF + B-HCl

(C ₃ H ₇ ) NH

(CH ₃ ), N _x

-> / P OCl + 2 (C ₃ H ₇ ) NH ₂ H Cl

(C ₃ H ₇ ) NH

(CH ₃ ), N

(CH _{: i} ) ₂ NPOCl, -} 2 (C ₃ H ₇ ) NH> ^ POCl + (C ₃ H ₇ ) NH ₂ -HCl

(C ₃ H ₇ ) NH

treated, whereupon the product obtained with a strong aqueous solution of sodium or Animoniumiluorid is treated. This Procedure is illustrated by the following example.

To 81 g of pure dimethylaminodiclilorphosphine oxide dissolved in 300 ecm of carbon tetrachloride were added (10 g of isoptopylamine with stirring at a temperature of 35 to 40 ". After 30 minutes a solution of 40 g of potassium fluoride in 38 ecm of water was added and the mixture at kept 60 ° during ί hours with good stirring. After cooling to 30 'with the addition of 50 cc of water, the organic layer was separated and fractionally distilled.

The part boiling at qo ° (mercury pressure approx 1.5 mm) was the desired connection

oxychloride (ι mol), which is dissolved in an inert organic solvent, with dimethylamine _{(1 mol) go} and isopropylamine (3 mol) according to the equation

According to a modification of this process, dimethylamino-dichlorophosphine oxide can first be prepared according to the known method Process are produced. 1 mole of this compound can then be mixed with 2 moles of monoisopropylamine according to the equation

Dimethylamine - monoisopropylamino - fluorophosphine oxide and weighed 47 g.

The fluorine was determined according to the method \ 'on Urich (Hei. Chem. Acta, 25, 1115-25, 1942) with an accuracy within 1 ° / _0th This gave a molecular weight of 170 (0.5). After acid hydrolysis (30 minutes in η-hydrochloric acid at 25 ° and subsequent distillation from excess alkali), the total amine gave an equivalent weight of 83.7 or a molecular weight of 167.4.

The new compound is a colorless liquid that can be mixed with water. She gets in very slowly hydrolyzed aqueous solution.

In order to demonstrate the usefulness of the compound for controlling insects on plants, A number of experiments were carried out, some of which are listed below:

600/221

P 7677 IYal451

Table I.

Percent mortality of Megoura vicise (Buckton) on bean plants sprayed 2 days previously Hours were locked up. Temperature 22 °; approximately 60 insects per plant.

Insecticide concentration
in ° / ₀ des

active
Constituent

Percent mortality in 48 hours

Bis (dimethylamino) fluorophosphine oxide

Bis (monoisobpropylamino) fluorophosphine oxide

Dimethylamino-monoisopropylamino-fluorophosphine oxide

water

0.10
0.05

0.10
0.05

0.10

0.05

51.7
31.4

67.2
25.0

100.0

89.6
4.4

Table II

Bean seed plants sprayed with diluted solutions. The plants were populated with Aphis fabae Scopoli before spraying. Temperature 22 ⁰ ; approximately 100 insects were planted per plant.

Insecticide concentration
in ° / ₀ des

active
Constituent

Percent mortality after

Hours 20 hours

Bis (dimethylamino) fluorophosphine oxide

Bi s- (monoisopropylamino) fluorophosphine oxide

Dimethylamino-monoisopropylamino-fluorophosphine oxide 0.016
0.008
0.004
0.002

0.016
0.008
0.004
0.002

0.016
0.008
0.004
0.002

water

51.6
36.3

2.4

0.0

5.4
0.9

i, 4
0.0

100.0

75, o
26.7
23.8

2.0
0.0

99.5

100.0

99.0

83.9

100.0

95.5

9i, 5

87.6

100.0

100.0

100.0

99.2

6.9 12.6

Table III

Percent mortality of Macrosiphoniella sanborni (Gilette) on 24 hours on chrysanthemum plants were locked up. These were injected beforehand in the interstices. The temperature during the uo The duration of the experiment was 22 °. Almost 100 insects were set up per plant in each experiment.

Insecticide concentration

in Vo

of the active
Constituent

Percent mortality after days after injection

Bis (dimethylamino) fluorophosphine oxide

Bis (monoisopropylamino) fluorophosphine oxide

Dimethylamino-monoisopropylamino-fluorophosphine oxide water

0.10
0.05

0.10
0.05

0.10
0.05

100.0
100.0

100.0
90.6

100.0
100.0

6.5

84.5
30.3

38.5
33, i

9 ⁶ > 4
100.0

12.5

3
6.5

43.2
21.4

100.0
97, i

5.7

34.4
2.2

14.0

74.5
78, i

6.4

14.3

12.3 2.6

8.1 39- ¹

₄ I, 2

9.2

509 600/223

P 7677 IVa / 45 I.

Table IV

Percent mortality of Colorado's rufomaculalc (Wilson), the 2nd) hours were placed on chrysanthemum plants. These were in between injected beforehand. The temperature was 22 ° throughout the experiment. Nearly 70 insects per plant were used in the experiment.

111 since th combat aids

concentration

in %

of the active
Constituent

Percentage 'mortality
days after spraying

His- (Diniet hylainiIHi) - (Iuorphosphinoxyd

Bis- (Mo! IoisopiOpylamino) -fluorophosphine oxide

Diniet hylanüiio-nionoisopropylamino-fluorophosphinoxyd.

water

Ks is obviously not possible, with biological experiments a strict hierarchy between the different insecticides as the result will likely depend on the variety the plan / .e, the kinds of insects, the temperature, the humidity and other conditions. However, it is possible to derive from the tables, dal.l in the experiments on two types of plants and four types of insects the initial activity of the new compound is more than equivalent compared to the two other compounds tested, and dal.l proved the effect of the new compound because was more persistent.

With regard to the toxicity to mammals, an experiment showed that.! the minimum, lethal dose for in! Raperilonal injection for bis- (I) imethylaniino) -iluorphosphiiioxyd 1 to 2 mg / kg body weight guinea pigs, mice, KaIt ( ¹ H, with ßis- (MonoisopropvlaininoJ-fluororphosphiiHixyd 25 to 50 mg / kg body weight guinea pigs, mice, rats and in the The new compound was 7.5 mg / kg body weight guinea pigs and 10 mg / kg body weight rats.The new compound therefore holds an intermediate position between the two known compounds.

The new compound can be applied to the aerial parts of the plants as an aqueous solution, advantageously with a content of a common wetting agent.

0.10
0.05

0.10

0.05

0.10
0.05

100.0
100.0

100.0
68.2

100.0
100.0

4.2

85.0
'59 .2

3 ».ο
36.1

100.0
100.0

0.0

17.9
20.7

8.5
8.6

100.0
85.0

ι τ, 6

6.3

0.0

4.2 0.0

38.7
87.2

2.1

8.8 3.2

3.4 2.1

73.3 12.5

4.6

Claims (1)

PATENT CLAIM: It can be added to the soil as irrigation water or nutrient solution, making up the absorption effective through the plant roots, or by injection into the growing plant. For this Applications, prior dilution may be unnecessary. Water is the most economical diluent for the compound, but so are other liquid diluents or solid diluents can be used. Such diluents can Be inert or fertilizers or other substances that have a beneficial effect on the plants exercise. The new compound can also be used in admixture with any other pesticide compatible with the new connection. The preparation of the compound to be used according to the invention is within the scope of the present Registration not claimed. Insect control agents marked by a content of dimethylamino-monoisopropylamino-fluorophosphine oxide as an active ingredient.