DE1670312C3 - Substituted 2-carbamoyloxyphenyl-4-methyl-1,2,4-oxadiazolidine-33-diones - Google Patents

Description

O C - - N

R ¹

some substances are listed below:

in

in which R ^{1 is} an alkyl radical with 1 to 4 carbon atoms or the benzyl radical or the cyclohexyl radical and R ^{2 is} hydrogen or R ¹ and R * are the methyl radical, except when prepared according to the process according to patent! 6 70 299.

2. Herbicide containing a solid or liquid carrier and a compound according to claim 1.

CHj-N

C-

Il ο

It is known that 2-chloro-4,6-bis- (ethylamino) -2-triazine (DE-AS 10 11 904) to be used as a herbicide. However, the effect is not satisfactory, and besides, some become Cultures, e.g. B. rice, damaged by the active ingredient.

It has been found that 2-carbamoyloxyphenyl-4-methyl-1,2,4-oxadiazolidine-3,5-diones of the general Formula i

■ l "ι

in which R ^{1 is} an alkyl radical having 1 to 4 carbon atoms or the benzyl radical or the cyclohexyl radical and R ^{2 is} hydrogen or R · and R ^{2 are} the. Means methyl radical, have a good herbicidal effect, which is surprisingly better than that of the known active ingredients.

The compounds according to the invention can be prepared in a simple manner from substituted N-phenyl-N-hydroxyureas and chlorocarbonic acid esters or phosgene be prepared, it being possible for the N-phenyl-N-hydroxyureas in turn to be prepared, for example, from the corresponding isocyanates and substituted phenylhydroxylamines.

The following experimental data are intended to explain the preparation of the compounds according to the invention. In the The parts given in the examples are parts by weight.

example 1

10.4 parts of 2- (3-hydroxyphenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione (melting point: 175 "C) are dissolved in 50 parts of acetone, to which 3 drops of triethylamine have been added, suspended and treated with 3 parts of methyl isocyanate. Under

Ii

L in

R ¹

CH,

CH,

C ₂ H ₅

1-C3H7

C4H9

Benzyl

Cyclohexyl

CH ₃

126 < 'C 80 ° C 11Γ 125 ' ¹ C 'C 110 ° C 124 ^C I.W 'C 'C.

JO The compounds according to the invention can be used as agents for influencing plant growth in the form of solutions, emulsions, suspensions or dusts. The forms of application depend entirely on the intended use; in each case they should ensure a fine distribution of the ensure effective substance.

Medium to high mineral oil fractions are used to produce solutions that can be sprayed directly Boiling point, such as kerosene or diesel oil, also coal tar oil and oils of vegetable or animal origin, also cyclic hydrocarbons, such as tetrahydronaphthalene, and alkylated naphthalenes into consideration.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders) by adding water. To the In the preparation of emulsions, the substances as such or dissolved in a solvent can be homogenized in water using a wetting agent or dispersant. However, it is also possible to prepare concentrates consisting of active substance, emulsifier or dispersant and possibly solvent, which are suitable for dilution with water. The application can also be made as granules.

Water-soluble salts can also be used in the form of their aqueous solution.

An addition of insecticides, fungicides, bactericides and other herbicides is just as possible as that Mixture with fertilizers.

Dusts can be produced by mixing or grinding together the active substances with one Carrier material are produced.

The following examples show the use of the compounds according to the invention.

Example 2

In the greenhouse the plants were barley (Hordeum vulgare), wheat (Triticum sativum), rice

(Oryza saliva), field mustard (Sinapis arvensis), nettle (Urtica urens), chickweed (Stellaria media), chamomile (Matriearia ehamomilla), white goose foot (Chenopodium album), annual bluegrass (Poa snnua). Black foxtail (Alopecurus myosuroides) and chicken millet (Panicum crus galli) with a height of 2 to 17 cm with the active ingredients 2- (3-N ₁ N-dimethylcarbamoyloxypheny |) -4-methyI-1,2,4-oxadiazoIidin-3, 5-dione (I) and ^ ö-dinitro ^ -selcbutylphenyl acetate (II) at an application rate of 1.5 kg of active ingredient per hectare, dispersed with sodium lignosulfonate in 500 liters of water per hectare

After 3 to 4 weeks, the following result was found:

Active ingredient

I II

wheat

barley

Mustard

Small stinging nettle

Chickweed

chamomile

White goosefoot

Einj. Bluegrass

Black foxtail

Chicken millet

0 = no effect.
100 = total effect.

0 to 10
0 to 10
10

90 to! 00
90 to 100
90 to 100
90

90 to 100
80 to 90
80 to 90
80

0 to 10 10

20 to 30 90
90

80 to 90 80
90

0
10
10 to 20

Example 3

IV 2- (3-N-Isopropylcarbamoyloxyphenyl) -4-methyll, 2,4-oxadiazolidine-3,5-dione

each dispersed in 500 liters of water per hectare treated. The test result is from the table below to see:

15th

Pots 8 cm in diameter were filled with loamy Sandy soil filled with seeds of maize (Zea mays), barley (Hordeum vulgare), wheat (T hicum sativum). Rice (Oryza sativa), cotton (Gossypium sp.) And weeds and grass weeds, such as white goosefoot (Chenopodium album), nettle (Urtica urens), mustard (Sinapis arvensis), chickweed (Stellaria media), chamomile (Matricaria chamomilla), annual bluegrass (Poa annua) and chicken millet (Panicum crus galli) sown. The soil was then treated with the active ingredient 2- (3-N, N-dimethylcarbamoyloxyphenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione (I) at an application rate of 2 to 3 kg of active ingredient per hectare, dispersed treated with sodium lignosulfonate in 500 liters of water per hectare.

After 4 weeks it was found that the weeds and grass weeds at I had almost completely died, o while maize (Zea mays), barley (Hordeum vulgare), wheat (Triticum sativum), rice (Oryza sativa) and Cotton (Gossypium sp.) Continued to grow without damage.

B e i s ρ i e I 4 "

In the greenhouse the seeds of Solarium tuberosum, Hordeum vulgare, Triticum sativum, Sinapis were grown arvensis, Poa annua, Alopecurus myosuroides, Apera spica venti and Echinochloa crus-galli sown and the t> o So prepared soil with 1.5 kg / ha each of the active ingredients

I 2- (3-N-methylcarbamoyloxyphenyl) -4-niethyl-

1,2,4-oxadiazolidine-3,5-dione
II 2- (3-N-ethylcarbamoyloxyphenyl) -4-methyl · h;

1,2,4-oxadiazolidine-3,5-dione
III 2- (3-N-butylcarbamoyloxy-phcnyl) -4-methyl-

1.2.4-oxadiazolidine-3,5-dione

Active ingredient

III

IV

Solanum tuberosum 0 0 0 0

Hordeum vulgar 0 0 0 10

Triticum sativum 0 0 0 0

Sinapis arvensis 90 90 90 100

Poa annua 75 75 75 85

Alcpecurus myosuroides 75 80 75 80

Apera spica venti 80 80 80 90

Echinochloa crus-galli 70 75 75 80

0 = without damage. 100 = total damage.

Example 5

An agricultural area overgrown with Zea mays, Triticum sativum, Hordeum vulgare, Sinapis arvensis, Galium aparine, Poa annua, Alopecurus myosuroides and Echinochloa crus-galli was grown at a height of ~ j to 18 cm at 1 kg / ha of the active ingredients

2- (3-N-MethylcarbamoyIoxyphenyI) -4-methyl-1,2,4-oxadiazolidine-3,5-dione
II 2- (3-N-Ethylcarbamoyloxyphenyl) -4-methyl-1,2,4-oxadiazoIidin-3,5-dione

III 2- (3-N-Butylcarbamoyloxyphenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione

IV 2- (3-N-Isopropylcarbamoyloxyphenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione

each dispersed in 500 liters of water ^: · ε ha treated. The result can be seen in the following table:

JO

Active ingredient 0 Il III IV I. 0 0 0 5 Zea mays 0 0 5 5 Triticum sativum 90 0 5 5 Hordeum vulgar 75 90 95 95 Sinapis arvensis 75 80 80 80 Galium aparine 75 80 85 85 Poa annua 70 80 85 90 Alopecurus myosuroides 75 80 80 Echinochloa crus-galli 0 = without damage. 100 “Total damage.

Example δ

An agricultural trial area covered with Gossypium hirsutum, Zea mays, Sinapis arvensis, Stellaria media, Lamium, amplexicaule and Echinochloa crus-galli overgrown at a height of 3 to 15 cm was, was with 2 kg / ha of the active ingredients

I 2- (3-N-isopropylcarbamoyloxyphenyl) -4-methyi-

1,2,4-oxadiazolidine-3,5-dione
II 2- (3-N-Benzyicarbamoyloxyphenyl) -4-methyll, 2,4-oxadiazolidine-3,5-dione

I11 2- (3-N-Cyclahexylearbamoyloxyphenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione

IV 2- (3-N-Methylcarbamoy | oxy-phenyl) -4-methyl-1 _t 2,4-oxadia2o | idine-3,5-dione

dispersed in 500 liters per hectare treated. The plants Gossypium hirsutum and Zea mays were grown using the sub-leaf method injected. The test result can be seen from the following table:

Active ingredient 5 II III IV I. 0 5 5 0 Gossypium hirsutum 90 5 0 0 Zea mays 85 90 90 80 Sinapis arvensis 80 90 85 80 Stellaria media 80 85 85 75 Lamium amplexicaule 70 70 75 Echinochloa crus-galli

15th

20th

0 = without damage,
i 00 = total damage.

Example 7

A test area with Sinapis arvensis, Chenopodium album, Urtica urens, Stellaria media, Matricaria chamomilla, Galinsoga parviflora, Poa annua and Alopecurus myosuroides was sown on same day with

2- (3-N-Isopropylcarbamoyloxy-phenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-dione

JO treated The application rate was 10 kg / ha of active ingredient, dispersed in 500 liters of water per ha. After 4 to 5 weeks, all the plants were completely dead.

Example 8

An agricultural area covered with Sinapis arvensis, Galinsoga parviflora, Chenopodium album, Matricaria chamomilla, Avena fatua, Poa annua and Alopecurus myosuroides was overgrown with

I 2- (3-N-IsopropylcarbamoyIoxyphenyl) -4-methyl-

1,2,4-oxadiazolidine-3,5-dione
II 2- (3-N-ButylcarbamoyIoxyphenyl) -4-methyl-1, 2,4-oxadiazolidine-3,5-dione

III 2- (3-N-EthylcarbamoyIoxy-phenyI) -4-methyl-1,2,4-oxadiazolidine-3,5-dione

IV 2- (3- (N-MethyIcarbamoyIoxyphenyl) -4-methyl-1,2,4-oxadiazoIidin-3,5-dione

and in comparison with

V 2-chloro-4,6-bis- (ethyIamino) -S-ir. ^; izin

treated. At the time of spraying, the plants were 3 to 8 cm tall. The application rate amount per 5 kg of active ingredient per hectare dispersed in 500 liters of water per hectare. After 6 to 7 days one could observe that the weeds and grass weeds treated with the active ingredients I to IV cause greater damage than the plants treated with Compound V. After 4 weeks, almost all of the plants were gone completely dead.

Claims (1)

Claims: all the crystals dissolve after a while, a new precipitate falls out, which is sucked off and dried. 10.5 parts of 2- (3-N-MethyIcarbamoy | oxyphenyl) -4-methyl-1,2,4-oxadiazoli- 1. Substituted α-carbamoyloxyphenyl- ^ methyl-1 ^ 4-oxadiazolidine-3 ^ -diones of the general formula 5 din-3,5-dione; M.p. 126 "C Compounds according to the invention are CHj-N C-O Il c OR ¹ Il / Ο —C-N (I)