DE1642318C3 - Herbicide - Google Patents

Description

The invention relates to a herbicide that is characterized is 3 - (p - bromophenyl) -1 - methoxy due to a content of at least one of the compounds - 1 - methylureaT, 3 - (3,4 - dibromophenyl) 1 - methoxy - 1 - methylureaT or 3 - (3 - bromine 4 - methylphenyl) -1 - methoxy -1 - methylurea T.

The herbicides according to the invention can be used in corn or potato fields for control of weeds such as Digitaria Setaria, Echinochloa, Sorghum halepense seedlings, Portulaca oleracea, Amaranthus, Xanthium, Abutilon theophrasti medio, Ipomoea, Chenopodium album and Ambrosia artemisiifolia. Excellent results are achieved when using one of the three active ingredients in potato fields. The weeds are destroyed without damaging the potato plants

The active ingredients used in the herbicides according to the invention can be mixed with anionic, cationic or nonionic surfactants. About these surfactants include, for example, sodium alkylnaphthalene sulfonate, Sodium and potassium oleate, amine salts of oleic acid such as morpholine and dimethylaminohelates, the sulfonated animal and vegetable oils, such as sulfonated fish and castor oils, the sulfonated petroleum oils, sulfonated acyclic hydrocarbons, sodium lignosulfonate and other wetting, dispersing and emulsifying agents.

The surfactant content of the herbicide is generally 0.1 up to 15% by weight, based on the weight of the whole herbicide.

The herbicides are commonly used on the spot or area from unwanted plant growth referred to as "weeds", i.e. plants that grow in an undesired place, protected should be, as a spray, in granulated or pelletized Form or applied as dust. This application can be applied directly to the area to be treated and the weeds there are carried out during the period of infestation to the weeds destroy, but, if desired, also before an expected infestation to prevent it. One can spray the herbicides according to the invention in aqueous form onto the foliage or by spraying Apply directly to the soil surface. On the other hand, you can also use dry powder preparations Dust directly on the plants or on the ground.

The application of granules is an effective way to control weeds before they emerge growing plants with minimal damage to foliage. The application of pellets, by hand or with machines, is an effective method of achieving a complete Destruction of unwanted plant growth on fences, under power lines and on the like Places.

The active compound is applied in an amount sufficient to achieve the desired control. The amount in which the active ingredient is in the means in the actual application form located in the control of weeds changes with the type of application that is used controlling weeds, purposes of application, and similar variables.

In general, the herbicides according to the invention contain, when applied in the form of a dust, Granules, pellets or an injection medium about 0.5 to 85% by weight of the urea compound. The applied The amount of the active ingredient is 0.28 to 112 kg / ha.

The herbicides according to the invention can fertilizers, other herbicides, pesticides, such as Insecticide and Fungicide and common pesticide diluents.

The active ingredients used in the herbicides according to the invention can be prepared by reacting the corresponding phenyl isocyanate with the corresponding N-alkyl-O-alkylhydroxylamine. This reaction is conveniently carried out by gradually adding the isocyanate in an inert liquid to a solution of the amine in the same liquid. Solvents such as xylene, toluene, dioxane, hexane, ether, acetone or water can be used. In general, temperatures from 0 to 130 ^° C. are satisfactory. On the other hand, the amine can also be added to the isocyanate.

The production of the active ingredients used according to the invention is not claimed here

■ Example 1

A preparation that is dispersible in water is produced by first adding the following ingredients mixes and then grinds in a hammer mill and then in a jet mill:

3-6 (p-Bromophenyl) -l-methyl-1-methoxyureaT (F. 88.5-

89.5 ° C) 40.00%

Alkyl naphthalene sodium sulfonate ... 1.75%
Low viscosity methyl cellulose .... 0.25%
Attapulgite 58.00%

The preparation is used for a combined control of weeds before and after emergence in Potato fields are used. The mixture is used in an amount of 3 kg of active ingredient per hectare in 1701 Water on an accrued stock of Setaria, Digitaria, Sorghum halepense, Amaranthus and Chenopodium album. Excellent weed control with a long-lasting effect is obtained on the weeds until the leaves of the potato plants shade most of the ground.

Example 2

A preparation which is dispersible in water is produced by adding the ingredients listed below mix first and then finely pulverize until all particles are substantially smaller than 50 microns are:

3 4

3- (3-Bromo-4-methyJphenyl) - The agents according to the invention are known

I-methyl-1-methoxyurea 3,4-dichloro derivative with regard to the degree of damage

(M.p. 82.5 - 85.5 ° C) 75.00% of the sorghum plants superior.

Sodium dodecylbenzenesulfonate 1.75%

Sodium lignosulfonate 1.00% 5 Comparative experiment 2

'Diatomaceous earth 22.25% herbicidal effectiveness against Bromus secalinus

This mixture is used before emergence ^{in wheat after puffing}

in an amount of 3 kg of active ingredient per hectare of potato. Wheat and Bromus secalinus are planted in soil

field. Excellent control of 10 is obtained and it is left in the greenhouse for 8 days. Then you bring

Digitaria, Setaria, Echinochloa crusgalli, Amaranthus, the active substances to be tested on the plants and the

Stellaria and Poa annua. The potato plants are ground on. 3 weeks later you check the results

not damaged nits visually. The numbers and letters have the

". . -, same meaning as in test report 1.

A preparation which is dispersible in water is made _k ^ _ha wheat bromus

by placing the following components in a secalinus

Tube mill or sand mill mixes together until

the insoluble components all essentially have one

Particle sizes below 5 microns have: 20 3- (p-bromophenyl) -1-4.5 9C IOC

,, methyl-1-methoxyurea

3- (3,4-dibromophenyl) -l-methyl-

l-methoxyurea (F.100-3- (3-bromo-p-to IyI) -I-4.5 2 B 10B

J ₀₂ OQ 24.00% methoxy-1-methylurea

Sodium Lignosulfonate '.'.'.'.'....... 15 ^ 00% 3- (3,4-Dibromophenyl) -1-4.5 4C 10C

Hydrated attapulgite 1.75% ^{2: i} methyl-1-methoxyurea

Sodium pentachlorophenolate 0.70% 3- (3,4-dichlorophenyl) -l- 4.5 8 C IOC

Disodium phosphate 0.90% methoxy-1-methylurea

Water 57.65% 3-p-chlorophenyl-1-4.5 IOC 9 C

This preparation is used in an amount of 30 methoxy-1-methylurea
of 2.5 kg of active ingredient per hectare in 1501 water in maize fields, both as a means of combating, with the exception of the p-bromophenyl derivative, those of weeds before emergence and after the active ingredients according to the invention are both comparative with emergence. In the growing crops, the weed seedlings are destroyed with regard to the damage to wheat. Man 35 lay
also maintains a good long-term control of the weeds. Digitaria, Setaria, Sor- comparative experiment 3 are well combated
ghum halepense, Amaranthus, Abutilon theophrasti _ · ή wt

Comparative experiment 1
Herbicidal activity against Digitaria
in sorghum culture before emergence

Sorghum and Digitaria seeds are placed in pots with 12.5 cm of soil and treated with those to be tested Links. After 16 days, the results are checked by visual observation. The results are given in the following way: Numbers from 0 to 10 indicate the degree of efficiency, 0 means no damage, 10 means that all plants are damaged. In the letters B = plant burns; C = chlorosis and necrosis and G = growth inhibition.

45

₅ o

and from
3- (3,4-dichlorophenyl) -l-methoxy-1-methyl-urea

Soil that is infected with the fungus Rhizoctonia Solani is poured into 0.5 l containers. The connections to be tested are mixed with the upper, 5 cm thick layer of soil in an amount of 37 kg per hectare. Then you plant cotton and beans. After approximately 2 weeks, the plants are checked for fungal attack checked.

Pilzbckäni fun

kg / ha Sorghum Digitaria 3- (p-bromophenyl) -l-me-
ethyl 1-methoxyurea 0.28 6C 1OC 3- (3-bromo-p-tolyl) -l-
methoxy-1-methylurea 0.28 0 1OC 3- (3,4-dibromophenyl) -l-
methyl-1-methoxyurea 0.28 4C 1OC 3- (3,4-dichlorophenyl) -l-
methoxy-1-methylurea 0.28 1OC 1OC 3-p-chlorophenyl-l-meth-
oxy-1-methylurea 0.28 2G 1OC

65

3- (p-Bromophenyl) -l-methyl-1-100

methoxyurea

3- (3,4-dichlorophenyl) -1-methoxy-0

1-methylurea

If you inoculate diluted nutrient solutions in the following Table of derivatives mixed with a drop of a spore suspension of Rhizopus nigricans, incubated for 4 days at 24 C and determines the mycelial growth compared to an active ingredient-free control solution, the following results are obtained:

Active ingredient- 3- (p-bromophenyl) -l-methyl-l- 3- <p-chlorophenyl) -l-

Concentration methoxy urea methyl -] - metho. ^v .y-

urea

600 ppm no mycelial growth no effect

500 ppm no mycelium growth no effect

250 ppm no mycelial growth no effect

The p-bromophenyl derivative according to the invention accordingly has a desirable fungicidal side effect, the the means of comparison are absent.

Claims (1)

Claim: Herbicide, characterized in that it contains at least one of the compounds 3- (p-Bromophenyl) -l ~ methoxy-1-methyl urea, 3 - (3,4 - dibromophenyl) - 1 - methoxy -1 - methylurea and 3 - (3 - bromo -4 - methylphenyl) -1 -methoxy-1-methylurea ".