DE1276400B - Selective herbicide - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. Cl .:

German class:

Number:
File number:
Registration date:
Display day:

AOIn

C 07c

45 1 - 19/02

12 ο-16; 12 ο-17/03; 12O-25

P 12 76 400.0-41 (B 79246)

November 7, 1964

29th August 1968

It is known that propionic acid-3,4-dichloroanilide to be used for selective weed control on various crops using the post-emergence method. This connection has the disadvantage that when required for practical use In some cases, damage to crop plants occurs and, on the other hand, an often insufficient amount herbicidal effect on various weeds, e.g. B. Scirpus spp. and Dactylis glomerata will. ίο

It is also known to use methoxyurea derivatives, e.g. B. the l-phenyl-S-methyl-S-methoxyurea, for Use weed control. This active ingredient has the disadvantage that the effect is great occurs slowly and also the amount that is still tolerable for the cultivated plants for weed control often not enough.

It has been found that acid anilides of the formula

in which R 1 and R _{2 are} chlorine or methyl and R _{3 is} an isobutyric acid or cyclopropanecarboxylic acid radical, in a mixture in a weight ratio of acid anilide to urea derivative such as 1: 1 to 10: 1 with urea derivatives of the formula

in which Ri and R _{5 are} hydrogen, chlorine, bromine or 4 <> methyl, a good herbicidal effect against weeds and grass weeds while at the same time having a good selective effect on useful plants, e.g. B. rice, cereals, carrots, celery and potatoes have.

Mineral oil fractions, for example, are used to produce emulsions that can be sprayed directly of medium to high boiling point, such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, as well as cyclic hydrocarbons such as tetrahydronaphthalene and alkylated naphthalenes, considering which selective herbicide

Applicant:

Aniline & Soda Factory in Baden

Corporation,

6700 Ludwigshafen

Named as inventor:

Dr. Adolf Fischer, 6704 Mutterstadt; Dr. Gustav Steinbrunn, 6721 Schwegenheim

the active ingredients according to the invention optionally using suitable auxiliary solvents, eg. B. Xylene, may be added. Solutions in low-boiling solvents such as alcohols, ketones, ethers or low-boiling hydrocarbons or chlorinated hydrocarbons are less suitable for direct use rather than in combination with suitable emulsifying agents for the purpose Manufacture of concentrates for the preparation of aqueous emulsions. In the aqueous work-up forms they are preferably emulsions and dispersions. The substances will as such or in one of the above-mentioned solvents, preferably by means of wetting or dispersing agents, homogenized in water. Cation-active emulsifiers or dispersants are examples Quaternary ammonium compounds called, as anion-active dispersants for example soap, Soft soap, aliphatic long-chain sulfuric acid monoesters, aliphatic or aromatic sulfonic acids, long-chain alkoxyacetic acids, as nonionic dispersants, for example polyethylene ^ ether of fatty alcohols and polyethylene oxide condensation product. On the other hand you can also look Active ingredient, emulsifier or dispersant and optionally solvent-based concentrates which can be diluted with water before use.

Dusts can be produced by mixing or grinding the active substances together be made with a solid carrier. Examples include: calcium carbonate, Talc, diatomaceous earth, calcium phosphate,

809 598/558

Boric acid, flour, cork flour, coal and other materials. On the other hand, the substances also by means of a volatile solvent on the * Carriers are applied. In this way it is possible to obtain granules that can be sprinkled.

The various application forms can in the usual way by adding substances that Improve distribution, adhesion, rain resistance and penetration, such as Fatty acids, resins, wetting and emulsifying agents, glue or alginates, the various uses be adjusted.

The biological spectrum of activity can also be broadened by adding substances bactericidal, fungicidal or plant growth-influencing, in particular herbicidal properties as well as by mixing with fertilizers.

The following examples illustrate the use of the herbicides according to the invention.

example 1

In the greenhouse the plants were Zea mays (maize), Hordeum vulgare (barley), Triticum vulgare (Wheat), Seeale cereale (rye), Daucus carota (carrots), Sinapis arvensis (field mustard), Chenopodium album (white goose foot), Urtica urens (small nettle) and Poa annua (annual Bluegrass) at a height of 3 to 15 cm with the following agents 1 = 2 kg / ha cyclopropanecarboxylic acid - 3 - chloro-4-methylanilide,

II = 2 kg / ha isobutyric acid 3,4-dichloroanilide,

III = 2 kg / ha l-phenyl-S-methyl-S-methoxy urine

material,

IV = 2 kg / ha 1 - (3 '- chlorine - 4' - methylphenyl) -

3-methyl-3-methoxyurea, V = 1.6 kg / ha cyclopropanecarboxylic acid 3-chloro

4-methylanilide,

VI = 1.6 kg / ha isobutyric acid - 3.4 - dichloroanilide, VII = 0.4 kg / ha 1 - phenyl - 3 - methyl - 3 - methoxy-

urea,
VIII = 0.4 kg / ha 1 - (3 '- chloro - 4' - methylphenyl>

S-methyl-S-methoxyurea, IX = 1.6 kg / ha of cyclopropanecarboxylic acid 3-chloro-4-methylanilide + 0.4 kg / ha l-phenyl-3-methyl-3-methoxyurea,

X = 1.6 kg / ha of cyclopropanecarboxylic acid 3-chloro-4-methylanilide + 0.4 kg / ha l- (3'-chloro-4'-methylphenyl) - 3 - methyl - 3 - methoxyurea,

XI = 1.6 kg / ha isobutyric acid - 3.4 - dichloroanilide + 0.4 kg / ha l-phenyl-S-methyl-S-methoxyurea

treated. The agents were emulsified in 500 l / ha of water. 1 to 2 days after treatment the plants began to die off from the leaf tips, and after 10 to 14 days it became the herbicidal effect listed in the table below was found.

I. II III IV V Active ingredient VII 0 VIII 0 IX 0 X 0 XI 10
until 20 10
until 20 20th 10
until 20 0
until 10 VI 0
until 5 0 0 0 0 Corn 20th 20th
until 30 20th
until 30 20th 0
until 10 0
until 10 0 0 0 0 0 10 10 20th 20th 0 0
until 10 until 5 0 barley until 20 until 20 until 5 0 0
until 5 5 0
until 5 10 until 5 20th 20th 20th
until 30 20th
until 30 0
until 10 until 10 0 0 0 0 0
until 5 wheat 10
until 20 5
until 10 20th 20th 0
until 10 0
until 10 40 30th
up to 40 100 90
until 100 0 70 70 90
until 100 90
until 100 60
up to 70 0
until 5 50
up to 60 50 100 90
until 100 100 rye 50 65 90
until 100 90
until 100 40
until 50 60
up to 70 50 40
until 50 100 100 100 70 70 100 100 60 60 40
until 50 40 90
until 100 80
until 100 100 Carrots 50 60 70
up to 80 60
up to 70 40 60
up to 70 100 60 Mustard White goosefoot ... Small stinging nettle ... annual bluegrass

0 = no damage.
100 = total damage.

The experiment shows that the mixtures IX, X and XI in comparison to the individual components V, VI, VII and VIII a better plant tolerance with an excellent herbicidal Have an effect. The individual components I, II, III and IV show with an application of 2 kg / ha Active ingredient compared to mixtures IX, X and XI when applying 2 kg / ha total one Similar herbicidal effects, but much more severe damage in maize, cereals and carrots.

Example 2

In the greenhouse, clay-containing soil was poured into plastic pots 8 cm in diameter and then Oryza sativa (rice), Panicum crus galli (chicken millet), Dactylis glomerata (hogweed), Scirpus spp. (Cornices), Amaranthus (Amaranth),

Rumex acetosa (sorrel) and Alisma plantago (frog spoon) sown.

After the rice has reached a height of 20 to 25 cm, the weed plants about a height of

When they reached 5 to 10 cm, they were treated with the following Treated active ingredients:

I = cyclopropanecarboxylic acid-B-chloM-methyl-

anilide, II = l-phenyl-3-methyl-3-methoxyurea,

III = isobutyric acid S ^ dichloroanilide

IV = 1- (4'-bromophenyl) -3-methyl-3-methoxy urine

material,

V = 1- (3 ', 4'-dichlorophenyl) -3-methyl-3-methoxyurea.

It was applied as a dispersion in 5001 Water per hectare. After 48 hours a layer of water of about 3 cm was on the surface of the Given rice and weed pots. The water layer of 3 cm was continuously flowing in Water kept at the same level until the end of the experiment. Started 1 to 2 days after treatment the weeds to die off from the leaf tips, and after 14 days the following became herbicidal Effect determined:

Application rate in kg / ha

0.5

Active ingredient
II

III

0.5

rice

Chicken millet knuckleweed.,

Cornices

Amaranth. Sorrel frog spoon

0 10 10 15

25 15 15

70 70 65 75 60 70

10

70 to 70 to

70 70 to

70 60 to

10 to 20
40 to 50
60 to 70
40 to 50
30 to 40

50
40 to 50

40 ■

100

80 to 90

70
90 to 100

15 10

15 25 15

70 70 65 80 65 65

15th

70 to 80 70 to 80 70 to 80

80

70 60 to 70

continuation

Application rate in kg / ha active ingredient

IV

0.5

0.5

rice

Chicken millet knuckleweed.

Cornices

Amaranth. Sorrel frog spoon

25 25 25 15 25 15

20th

50 to 50 to 40 to

40 40 to

40

90 to 80 to

0
25th
35
25th
20th
30th
20th

20 to 30 50 to 60

40 to 50 60 to 70 40 to 50

40 to 50

100 90 to 100

90 80 to 90

90

90

continuation

Application rate in kg / ha active ingredient

I + II 0.5 + 0.5 II + III
0.5 + 0.5

III + IV
0.5 + 0.5

I + V 0.5 + 0.5

rice

Chicken millet knuckleweed ..

Cornices

Amaranth .. sorrel frog spoon.

0 55 55 50 50 55 50 0
55
55
50
55
50
50

0
55
55
50
50
50
50

0 55 55 50 55 50 50

It turns out that the agents according to the invention both have a surprising effectiveness against Weeds as well as, in particular, have a selective effect, which is due to the components of the mixture was not expected.

Example 3

The plants Zea mays (maize), Hordeum vulgare (barley), Triticum sativum were grown in the greenhouse (Wheat), Daucus carota (carrots), Sinapis arvensis (field mustard), Chenopodium album (white goosefoot) and Urtica urens (small stinging nettle) at a height of 3 to 15 cm with the following means treated:

I = 1.8 kg / ha cyclopropanecarboxylic acid 3-chloro

4-methylanilide

II = 1.8 kg / ha of isobutyric acid 3,4-dichloroanilide III = 0.2 kg / ha of 1- (3 ', 4'-dichlorophenyl) -3-methyl-3-methoxyurea

IV = 0.2 kg / ha l-phenyl-S-methyl-S-methoxy-

urea

V = 1.8 kg / ha cyclopropanecarboxylic acid 3-chloro

4-methylanilide + 0.2 kg / ha l- (3 ', 4'-dichloro-

phenyl) -3-methyl-3-methoxyurea
VI = 1.8 kg / ha isobutyric acid 3,4-dichloroanilide

+ 0.2 kg / ha l-phenyl-S-methyl-S-methoxy-

urinary stolf
VII = 1.0 kg / ha cyclopropanecarboxylic acid 3-chloro

4-methylanilide
VIII = 1.0 kg / ha l-phenyl-S-methyl-S-methoxy-

urea
IX = 1.0 kg / ha isobutyric acid-3,4-dichloroanilide X
XI

1.0 kg / ha cyclopropanecarboxylic acids-chlorine-

4-methylanilide + 1.0 kg / ha 1-phenyl-

3-methyl-3-methoxyurea

1.0 kg / ha isobutyric acid-3,4-dichloroanilide

+ 1.0 kg / ha l-PhenyW-methyM-methoxy-

urea

The agents were dispersed in 500 liters of water each Hectares applied. Plants started from the leaf tips 1 to 2 days after treatment to die off, and after 10 to 14 days the herbicidal listed in the table below became Effect noted.

I. 10 II 10 III IV 0 V 10 Active ingredient VII VIII IX X 10 XI 10 10 10 0 0 10 VI 10 10 10 10 10 Corn until 20 5 10 10 10 20th barley 10 0 0 10 10 until 20 10 10 until 10 0 10 10 10 wheat 0
until 10 5 5 5 0 0
until 10 5 60 70 0 20th 100 until 10 10 10 5 90 90 Carrots up to 70 30th until 30 5 50 80 50 until 100 until 100 50 60
up to 70 30th 90
until 100 100 up to 60 up to 60 90 90
until 100 Mustard 60
up to 70 70 40 20th
until 30 100 40
until 50 80 50 90
until 100 90
until 100 40
until 50 60
up to 70 40 20th 80 100 40
until 50 80
to 90 40
until 50 80 80
to 90 White goosefoot 30th 100 30th 60
up to 70 30th Small stinging nettle 90
until 100 annual bluegrass.

0 = no damage.
100 = total damage.

Claims (1)

Claim: Selective herbicide, characterized in that it contains an acid anilide formula 1: 1 to 10: 1 with a urea derivative of the formula HO CH ₃ NR ₃ in which Rj and R5 are hydrogen, bromine, chlorine or Mean methyl. in which Ri and R2 are chlorine or methyl and R3 mean an isobutyric acid or cyclopropanecarboxylic acid radical, in a mixture in the weight ratio of acid anilide to urea derivative such as Papers considered: Journal of Agric. Food Chem., 8 (1960), p. 261 to 266;
Journal of Economic Entamology, 53, pp. 887 bis 892