DE1210618B - Nematodicidal agents - Google Patents

Description

GERMAN

PATENT OFFICE

EDITORIAL

German class: 451-9 / 02

Number:
File number:
Registration date:
Display day:

Sch 28308IV a / 451
August 11, 1960
February 10, 1966

This invention relates to nematodicidal agents, and more particularly to synergistic nematodicidal agents Agents containing 1,3-dichloropropene.

It is known that methyl isothiocyanate, allyl isothiocyanate, cyclohexyl isothiocyanate and 1,3-dichloropropene have nematodicidal effects. However, it has not yet been recognized that quite certain mixtures, as they are described in the present invention, a synergistic one Effect, i.e. a far higher effectiveness than that of the individual components.

The use of mixtures of active ingredients is per se common in pest control. The combination of mixtures, the individual components of which each develop their specific effectiveness proceed according to the known properties of the individual components; a synergistic effect however, a mixture is never predictable. The discovery of the mixtures according to the invention must can therefore be described as surprising.

On the other hand, in the field of pest control, the control of nematodes has just emerged turned out to be a difficult problem as these pests are very difficult to control and only very specifically veinicht of certain substances, while the majority of the hitherto known insecticides is ineffective.

It was therefore quite impossible to choose from the multitude of known insecticides, even if these z. B. Mixtures of allyl mustard oil and chlorinated hydrocarbons concern any conclusions to infer a nematodicidal activity.

It has already been proposed to control beet nematodes in addition to agents such as calcium cyanamide to use at the same time or alternately with these mustard oils, with the latter only should serve as attractants or incentives. In addition, these agents have the great disadvantage of reaction together.

It has now been found that mixtures consisting of +0 from 95 to 65 percent by weight 1,3-dichloropropene and 5 to 35 percent by weight allyl, η-butyl, n-hexyl or cyclohexyl isothiocyanate, act synergistically and have an unexpectedly high effectiveness as nematodicides that is higher than that of the individual components.

These mixtures can therefore be used to control nematodes and to treat the contaminated Soil can be used.

To prove the good effectiveness of the invention Preparations were carried out according to the following procedure:

Nematodicidal agents

Applicant:

Schering Aktiengesellschaft,

Berlin 65, Mullerstr. 170/172

Named as inventor:

Clare Burton Kenaga, Lake Geneva, Wis .;

Raymond Peter Seven, Wheaton, JIl. (V. St. A.)

Claimed priority:
V. St. v. America September 1, 1959
(83.7 368)

The product to be tested wild in Ν, Ν-dimethylformamide dissolved in at least 5% concentration. A End of the test tube (12 cm long, about 2.5 cm Duichmesser) wildly corked, with approx. 57 g of a black loam soil, previously adjusted to a moisture content of 20% and passed through a No. 12 (US Standard Sieve Series) was filled. the Earth is evenly distributed in the pipe by lightly tapping it so that it has a height of about 8.6 to Occupies 8.9 cm. A layer of 0.64 cm of dry sea sand is then added. The ones to be examined Nematodes are obtained from an oatmeal culture using the Baermann method with the addition of physiological eggs Saline solution (0.85% NaCl) was taken instead of distilled water. The concentration the nematode should be roughly between 12,000 and 15,000 nematodes per cubic centimeter in one Volume from 35 to 50 ml. With the help of a dropper bottle, 4 to 6 drops of the neroatode suspension ' (3000 to 5000 nematodes) evenly distributed over the surface of the sand. Another A 0.64 cm high layer of dry sea sand is added and mixed with 1 ml of physiological saline solution moisturizes.

A polyethylene film is placed over the open end of the tube and a cork inserted so far until he touches the sand.

The tube is turned over and the first cork is removed. Use a glass rod to make a small indentation made in the earth and put the solution to be tested in this well.

The preparation to be tested is added in concentrations of 5000, 4000, 3000 μg etc. After adding

609 507/330

1 21Q 618

the connections to be tested is; the open end of the pipe covered with a thin polyethylene film and corked. All treatments are three times repeated. The tubes are in the dark at 27 ° C in an upright position (nematodes at the top of the tube) stored for 48 hours.

The sea sand, which contains the nematodes, is used to determine the effectiveness of the compounds. contains, from the The tube is removed, 10 ml of physiological saline solution are added and the saline solution is decanted into a glass. The evaluation of the experiment was made by counting the number of nematodes that were present in the wild Controls are required to obtain a hundred live nematodes. The number received will be used as a reference base for the calculation of the treated nematodes. The following results were obtained using Panagellus redivivus as test nematodes.

example 1

This example shows the syneigistic effect of Allyl isothiocyanate and 1,3-dichloropropene mixtures. Table A shows the results obtained when allyl isothiocyanate and 1,3-dichloropropene alone be used. Table B shows the results of the blends. The attempts were made in the above described manner carried out. The dosage is given in micrograms per test tube every attempt. The level of synergism is indicated by the increase in the percentage kill, which is obtained beyond the theoretical one.

Table A.

Nematodicidal effect of
Allyl isothiocyanate and 1,3-dichloropropene

Allyl isothiocyanate Mortification
0 / 1,3-dichloropropene Mortification
0 / dosage
ü ^ gpro /O dosage
in μg per ver /O Test tube 0 search tube 48 75 0 1425 43 150 0 1350 39 225 0 1275 36 300 0 1200 31 375 0 1125 25th 450 14th 1050 21 525 975

Table B.
Allyl isothiocyanate and 1,3-dichloropropene

Allyl 1,3-Tue 1425 isothio chlorine 1350 cyanate propene 1275 Dosage in μg 1200 per test pipe 1125 75 1050 150 975 225 300 375 450 525

salary
to Allylisothio
cyanate
in the
mixture
in weight
percent

10
15th
20th
25th
30th
35

Theoretical
Mortification,
based

on

additive
effect

48

43,

39

36

31

25th

35

Actually
liche
Mortification

59
58
53
67
75
62
54

Synergis
mus

The following examples show the synergistic effect of 1,3-dichloropropene and various Isothiocyanates. The experiments were carried out in the same way as in Example 1. In any case shows. Table A shows the results obtained using the individual components in the indicated dosages, while Table B shows the effect of the mixtures.

11

15th

14th

31

44

37

19th

Example 2 Table A.

Nematodicidal effects of cyclohexyl isothiocyanate and 1,3-dichloropiopene

X ₅ cyclohexyl isothiocyanate 20th 300 Mortification 1,3-dichloropropene Mortification dosage 400 Vo dosage 7o ü ^ g 500 in με Per Per Test tube 0 Test tube 10 0 25th 0 900 40 1200 1500

Table B Cyclohexyl isothiocyanate and 1,3-dichloropropane

Allyl 1,3-bi
chlorine-
propene 900 salary Theore did
sax
liche
away
killing Sy-
ner-
gis-
mus isothio
cyanate
30 Thu
ization
in με per test pipe 1200 of allyl
isothio
cyanate
in the
mixture
in Ge
weight tables
Mortification,
based
on the
additive
effect 7o 35
300 1500 percent 7o 19th 9 400 25th 10 37 12th 500 25th 25th 58 18th 25th 40

Example 3 Table A.

Nematodicidal agent of n-butyl isothiocyanate and 1,3-dichloropropene

■ n-butyl isothiocyanate Mortification
7o 1,3-dichloropropene Mortification
0 / dosage
in μκ per 0 dosage
in μg per / 0 Test tube 0 Test tube "" 10 300 6th 900 25th 400 1200 40 500 1500

Table B n-Butyl isothiocyanate and 1,3-dichloropropene

n-butyl isothio
cyanate

1,3-dichloro propene

Dosage in μg per test tube

300
400
500

900 1200 1500

Salary.

of n-butyl isothio cyanate in the

Mix in

Weight percent

25 25 25

Theoretical kill based on the additive effect

0 / / 0

10 25 46

Example 4 Table A.

Nematodicidal effects of n-hexyl isothiocyanate and 1,3-dichloropropene

n-hexyl isothiocyanate Mortification
0 / 1,3-dichloropropene Mortification
0 / dosage
in μg per /O dosage
in μg per / 0 Test tube 0 Test tube 2 300 0 900 10 400 0 1200 32 500 1500

Table B.

Nematodicidal effect of the mixture of n-hexyl isothiocyanate with 1,3-dichloropropene

n-hexylisothio
cyanate

1,3-dichloro
propene

Dosage in μg
per test pipe

900
1200
1500

Content of n-hexyl isothio cyanate in the mixture

in

Weight percent

25 25 25

Theoretical kill based on the additive effect

O/

/ 0

2 10 32

in conjunction with carriers or "diluents that facilitate distribution. As a solvent can e.g. Examples include: odorless kerosene, ketones, esters, alcohols, chlorinated hydrocarbons and various low boiling petroleum fractions. The preparations can be used as emulsions, Dispersions and in other forms. The application rate of the to be applied The preparation varies, of course, with the type of

ίο contagion and the character of each one area to be treated, but application rates of approximately 19 to 950 l / ha are satisfactory. In field trials to combat contamination of Heterodera schichtii on sugar beets gave a preparation containing 20 parts of allyl isothiocyanate, 48 parts of dichloropropene and 32 parts of 1,2-dichloropropane and corresponding hydrocarbons, and applied at 80 l / ha, a yield of 18 tonnes of sugar beet per hectare, compared to one

ao untreated control with a yield of 10 t per hectare.

These experiments described show only some embodiments of the present invention, and it goes without saying that many variations are still possible, all of which fall within the scope of the present Invention fall.

30th

The 1,3-dichloropropene used in the above experiments was a commercial product sold by sold by Shell Chemical Co. under the trade name "DD" and about 90% 1,3-dichloropropene and contains about 10% of other corresponding chlorinated hydrocarbons, of which 1,2-dichloropropane is the main component.

The preparations according to the invention cannot only be used in undiluted form graze, but they can also be used

Claims (1)

Claim: Nematodicidal agents containing a mixture consisting of 95 to 65 percent by weight 1,3-dichloropropene and 5 to 35 percent by weight of allyl, η-butyl, n-hexyl or cyclohexyl isothiocyanate. Considered publications:
German patent specifications No. 438 400, 700 772,
1008 045, 1032 968;
British Patent No. 473,769;
U.S. Patent Ni. 2,865,803. Eligible patents considered:
German Patent No. 1134 241. 609 507/330 2.66 © Bundesdruckerei Berlin