DE3045770A1 - UREA DERIVATIVE, METHOD FOR THE PRODUCTION THEREOF AND HERBICIDES THAT CONTAIN THIS - Google Patents

Description

Shell Internationale «ι 'S Π / ζ 7 7 Π

1Α-54 173 JU ^ D // U

description

Urea derivative Process for its production and herbicidal agents containing it

The invention relates to urea derivative, a method too

j its production and herbicidal agents that contain it.

In US-PS 2,655,447 an extraordinarily wide class of urea derivatives with herbicidal properties is described. ben. For over 25 years since these compounds were made, there has been much research into their uses of ureas as hematides. Probably the most important urea derivative is the compound 3- (4-isopropylphenyl) -1,1-dimethylurea, under the trade name "Isoproturon" on sale is. This compound is widely used in Europe to control weeds in winter crops. Its main advantage is that it is extremely effective against a wide variety of weeds and both Pre-emergence and post-emergence herbicide, both in autumn as well as can be used in spring. Their main disadvantage is that there are some economically important weeds in particular, perennial broad-leaved weeds, perennial grass weeds, sticky weeds and speedwell are not controlled

will.

It has now been shown that a certain phenylurea derivative which is not expressly mentioned in US Pat. No. 2,655,447, in which the phenyl ring has two special substituents has particularly favorable herbicidal properties.

130050 / 0A08 _{/ 2}

ORIGINAL INSPECTED

The invention therefore relates to the compound of the formula

M-CO- N (CH ₃ ) ₂

i.e. 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea. This compound is particularly suitable for combating before or after the emergence of weeds in crops how maize, barley or especially wheat grow. As can be seen from the data given in Examples 4 and 5, has this compound has clear advantages over the commercially available herbicide isoproturon for combating Weeds in wheat.

The invention also relates to a method for producing the Compound of the formula I, which is characterized in that the aniline of the formula II or a hydrohalide thereof

(II)

implements, with either

a) a Dimethylcarbamoylhalogenid, vorzugaeise -Chlorid, or

b) Phosgene (COCIp) with formation of the isocyanate of the formula

NCO

(III)

130Q50 / 0A08

and at least a portion of the isocyanate reacts with diethylamine.

Process variant (a) can be carried out with or without a solvent. Suitable solvents include hydrocarbons and halogenated hydrocarbons _# eg benzene, toluene or carbon tetrachloride. This process variant is preferably carried out under essentially anhydrous conditions. Since the reaction is a condensation reaction in which hydrogen halide is eliminated, it is preferably carried out in the presence of a dehydrohalogenating agent; organic or inorganic bases are suitable; Sodium acetate has proven to be particularly suitable when working without the use of a solvent, and organic bases such as triethylamine or pyrridine are suitable when a solvent is used. The reaction is preferably carried out at a temperature in the range from 0 to 80 ^° C., advantageously at room temperature, and the reaction mixture can be worked up by customary processes.

Variant (b) is advantageously carried out in the presence of a solvent, for example a hydrocarbon such as toluene, at a temperature in the range from 80 to 120 ^° C .; the reaction can simply be carried out at the reflux temperature of the solvent used. If appropriate, the isocyanate of the formula III formed can be isolated from the reaction mixture, but it is preferably reacted in situ with dimethylamine. This reaction is conveniently carried out at a temperature in the range from 0 to 30 ° C., simply at room temperature. The desired product can be isolated in any suitable manner.

The invention further relates to a herbicidal composition which the compound of the formula I together with a suitable carrier

130050/0408

ORIGINAL INSPECTED

contains. In a method of controlling undesirable plants in one site, the compound or a Agent according to the invention applied to the site.

In some cases it can be advantageous to mix the compound according to the invention with one or more compounds having herbicidal activity, for example in order to change the spectrum of activity. Thus, the compound according to the invention can be mixed with other herbicides with a broad spectrum of action such as 2- (4-chloro-6-ethylamine »-s-triazin-2-ylamino) -2-methylpropionitrile (trade name" Cyanazine ") or with more specific herbicides with narrower ones Spectrum of activity such as herbicides against wild oats of the aniline type _f as described in GB-PS 1 164 160, for example ethyl N-benzyl-N- (3,4-dichlorophenyl) -2-aminopropionate (trade name "Benzoylpropäthyl") and the racemic Mixture or (-) isomer of isopropyl or methyl N-benzoyl-N- (3-chloro-4-fluorophenyl) -2-aminopropionate (trade names "Flampropisopropyl" and Flampropmethyl ").

A carrier in an inventive composition is any substance with which the active ingredient is formulated to be applied to the site to be treated for example _t a plant, seed or Bode ^ or its storage: to facilitate transport or handling. A carrier can be a solid or a liquid, including substances which are usually gaseous but have been compressed into a liquid, and any conventional carrier used in the preparation of herbicidal compositions can be used.

Suitable solid supports include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earth, magnesium silicates _/ for example talc; Magnesium aluminum silicates such as attapulgites and vermiculites; Aluminum silicates, for example kaolinites montmorillonites and mica, calcium carbonate, calcium sulfate; synthetic hydrated

130050/0408

/ 5

Silicon oxides and synthetic calcium or aluminum silicates; Elements _J, for example carbon and sulfur; natural and synthetic resins such as coumarone resin, polyvinyl chloride and styrene polymers and copolymers - _$ solid polychlorophenols, bitumen, waxes such as beeswax, paraffin wax, and chlorinated mineral waxes and solid Düngemitteljz.B. Superphosphates.

Suitable liquid carriers include water, alcohols, for example isopropanol and glycols; Ketones, for example acetone, methyl ethyl ketone ,. Methyl isobutyl ketone and cyclohexanone; Ether, aromatic or aliphatic hydrocarbons, for example benzene, tuluene and xylene; Petroleum fractions, for example kerosene and light mineral oils; chlorinated hydrocarbons _/ e.g. carbon tetrachloride, perchlorethylene and trichlorethylene. Mixtures of different liquids are often suitable.

Agricultural products are often manufactured in a concentrated form, which is then diluted by the consumer before application. The presence of small amounts of a carrier which is a surface-active agent ₍ facilitates this process of dilution. Thus, preferably at least one carrier in the agent according to the invention is a surface-active agent. For example, the agent can contain at least two carriers, at least one of which is a surface-active agent is.

A surfactant can be an emulsifier, a dispersant, or a wetting agent; it can be nonionic or ionic. Examples of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and ligninsulphonic acids, the condensation products of fatty acids or aliphatic amines or amides _/ contain at least 12 carbon atoms in the molecule, with ethylene oxide and / or propylene oxide; Fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol; Condensates of these substances with ethylene oxide and / or propylene oxide; Condensation products of fatty alcohols or alkyl phenols, e.g. p-octyl

130050/0409

/ 6 ORIGINAL INSFECTED

phenol or p-octyl cresol with ethylene oxide and / or propylene oxide; Sulfates or sulfonates of these condensation products; Alkali or alkaline earth salts, preferably sodium salts of Sulfur or sulfonic acid esters ^ containing at least 10 Carbon atoms in the molecule e.g. sodium lauryl sulfate, sodium sec-alkyl sulfate, Sodium salts of sulfonated castor oil and sodium alkylarylsulfonates such as sodium dodecylbenzenesulfonate and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

The agents according to the invention can be produced, for example, as wettable powders, dusts, granulates, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders usually release 25, 50 and 75% by weight of active ingredient and usually 3 to 10% by weight of a dispersant and, if necessary, 0 to 10% by weight of stabilizer (s) and / or others in addition to the solid inert carrier Additives such as penetrants or tackifiers. Dusts are usually produced as stick concentrates with a composition similar to that of a wettable powder but without a dispersant and are diluted in the field with other solid carriers to form an agent which usually contains 0.5 to 10% by weight of active ingredient. Granules are usually produced in such a way that they have a particle size between 0.152 and 1.676 mm and can be produced by agglomeration or impregnation processes. In general, granules contain 0.5 to 25% by weight of active ingredient and 0 to 10% by weight of additives such as stabilizers, modifiers for the slow release of the active ingredient and binders. Emulsifiable concentrates usually contain, in addition to a solvent and, if necessary, cosolvents, 10 to 50 % (w / v) active ingredient, 2 to 20% (w / v) emulsifiers and 0 to 20 % w / v. other additives such as stabilizers, penetrants and anti-corrosion agents. Suspension concentrates are usually composed so that a stable, non-settling, flowable product is obtained and usually contain 10 to 75% by weight of active ingredient, 0.5 to 15% by weight of dispersant, 0.1 to 10% by weight of 96% by weight

130050/0408

ORiGfNAL INSPECTED

Suspending agents such as protective colloids and ihlxotrope means 0 "to 10 wt -% of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrants and tackifier, and water or an organic Flüssigkeit.in is insoluble, the active ingredient is substantially;. Certain organic solids or inorganic salts may be be dissolved in the agent to help prevent settling or as an antifreeze for water.

Aqueous dispersions and emulsions, e.g. agents obtained by diluting a wettable powder or a concentrate according to the invention with water ^ are also available within the scope of the invention. The emulsions can be in the form of a water-in-oil or an oil-in-water emulsion

and have a thick mayonnaise-like consistency.

The compositions according to the invention can contain other ingredients, for example other compounds with insecticidal or fungicidal properties contain.

The invention is illustrated in more detail by the following examples.

example

Preparation of 5- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea

7.4 g of 3-methyl-4-isopropylaniline and 0.5 g of anhydrous sodium acetate were stirred together as a mixture of solids and 5.4 g of dimethylcarbamoyl chloride were added over the course of 15 minutes. The mixture was left to stand at room temperature overnight, then treated with water and then / methylene chloride extracted. After drying over magnesium sulfate, the solvent was evaporated and the resulting solid was evaporated recrystallized from a mixture of hexane and TQluol.

130050/0408 / ⁸

3 | 5 g of the desired product were obtained, mp 153 to 154 ^° C.

Analysis CHN

for C ₁₅ H ₂₀ N ₂ O 70.9 9.1 12.7 found 69.9 9.1 12.1

Example 2

Alternative process for the preparation of the compound according to the invention

5 g of 3-methyl-4-isopropylaniline (80 % pure) in 150 ml of toluene were heated to reflux temperature while bubbling COCl ₂ gas through the solution for approximately 1.5 hours and then dry nitrogen gas to remove excess COCIp · after cooling 5 g of dimethylamine in 20 ml of toluene were added to the reaction mixture at room temperature. The toluene was evaporated, to the residue was added hexane and the precipitate _f 5 _t 5 g of the desired product _t removed by filtration. After recrystallization from a mixture of hexane and toluene, the desired product had a melting point of ⁰

B eis ρ i e ... l 3

This example shows the preparation of the starting substance 3-methyl-4-isopropylaniline.

186 g of 3-methylaniline were dissolved in 600 ml of sulfuric acid (85% by weight). The mixture was heated to 8O ⁰ C and 120 g of isopropyl alcohol was added. The mixture was ^{stirred at 80 °} C. for 6 hours. After this time the mixture was poured onto ice and ammonium hydroxide added until the mixture was neutral. Then diethyl ether was added and the ether extract was evaporated. The residue was distilled, 110 g of the desired

130050/0408

/ 9

Product received, boiling point 100 ° C. at a pressure of 3.25 mbar.

example

Selective herbicidal activity of the compound according to the invention

Comparative experiment a)

In this experiment, the selective herbicidal effectiveness of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea in Wheat compared to that of the commercial wheat herbicide Isoproturon, 3- (4-isopropylphenyl) -1,1-dimethylurea. The pre-emergence trials were on wheat, the Triticum vulgar variety Sappo, and the post-emergence trials performed on the Maris Huntsman variety. The weed species examined were: common couch grass. Agropyron repens (Co); Wild oats, Avena fatua / ludoviciana (Wo); Ryegrass, Lolium multiflorum (Rg); Annual bluegrass, Poa annua (Pa); Ostrich grass, Agrostis tenuis (Bt); Bulrush, Alopecurus myosuroides (Am); Windhalm, Apera spica venti (Wg); Chickweed, Stellaria media (St); Speedwell, Veronica persica (Sw); Sticky herb Galium aparine (Gg); Knotweed, Polygonum lapathifolium (Pp); red dead nettle, Lamium purpureum (Dn); Field mustard, Sinapis arvensis (Ck); Chamomile, Matricaria spp (Mw); Shepherd's purse, Capsella bursa pastoris (Sp); Poppy seeds, Papaver rhoeas (Po).

The active ingredients to be examined were available as emulsifiable concentrates containing 20% by weight of active ingredient, 10% by weight of mineral oil, Prepared emulsifiers and xylene as solvents. Each concentrate was diluted with water and the test plants were sprayed with amounts of 6.0, 2.0, 0.6, 0.2, 0.06 and 0.02 kg / ha of active ingredient. There were four repetitions for each dose carried out and tests carried out both before emergence and after emergence. When trying before the emergence was untreated soil in which the Seeds were found and in the experiments after emergence

T3Q050 / 04Q8

traded soil _t in which there were seedlings used as a comparison. After 21 days, in the test after emergence and 28 days, in the test before emergence, the effect of the active ingredients was assessed visually on a scale from 0 to 9; a rating of indicates growth as in the untreated control and a rating of 9 indicates death of the plant. For this rating, an increase of one unit on the linear scale corresponds to an approximately 10-bit increase in effect.

The results obtained were subjected to probit analysis whereby a computer calculates the parameters a and b

in a relationship of the form:

Probit (percentural response) = a + b log (dose).

With the help of the resulting curve, the respective doses for a specific response can be calculated. In this example, a GID _cn value, ie the dose required to produce a 50% response to the active ingredient, was calculated for each species.

A selectivity factor for each weed compared to wheat is calculated:

GID _Kn wheat S electivity factor = ——

weed

The greater the selectivity factor, the more selective it is the herbicide works.

Finally the ratio of selectivity factor for the compound according to the invention calculated for the selectivity factor for isoproturon. A value greater than 1 indicates that the compound according to the invention acts more selectively than Isoproturon. The results are given in Table I, where the compound of the invention as A and isoproturon as I. referred to as.

130050/0408

Table I.

Plant
zenart Try before emergence A. Selective! -;
data factor A. relationship
the Selekti
vity factor
ren Try after emergence A. Selectivity
factor A. Proportions
the selecti
Vitality Facto
ren wheat ^GID 50 Ζ 1.67 I. - - ^GID 50 1.67 I. - - Co
Where
Bg
Pa
Bt
At the
Wg
St.
Sw
Gg
Pp
Dn
Ck
Mw
Sp
Po I · " 1.05.
0.59.
0.16
0.08.
0.02
0.18
0, lU
0.18
0.91
0.2U
0.10
0.08 - 1.6
• 2 8
9 3
20 9
83 5
9.3
11>
9.3
18th
TjO
i6; 7th
20.9 2.7
l _f 3
0 5
10.
i>
0.8
3; 6
2.6
2.1
2.0
2.9
wb I. 0.61
0.19
0J21
0.03
0 ', 02
O _r o6
0.07
o _f o6
0 _f 27
0, U6
0.07
0.18
o _r oo6
0.5
0.015
0.001 - 2.7
8.8
8 ^ 0
55: 7
83; 5
27.8
23.9
27.8
6.2-
3 ', 6
23.9
?, 3
176.2
3 ₃ ; u
105.7 0.8
hi ■ '
U ₇ O
° il
0.6
13th
u, o
.5.2
3.5
2.3
I?
2, U
7.5 1.23 0.6
2.1
17.6
20.5
61.5
12.3
11.2
2.6
0.7
³ F ³
8i2
7 _f 2 1.69 1.81
12.1
10.6
33.8
21.1
U2.3
U2 3
211
1.5
0.7
6.8
Uli
96! 7
UiI
1U | 2 1.99
O ₁ OO
0.07
0.06
0.02
0.10
0.11
0, U8
1.87
0.37
0.15
0.17 0.93
0, lU
0.16
0.05
0.08
O.OU "
0 OU
o; o8
1.10
2JU2
0.25
0, ul
0.011
0, 'l2
0.11
0.001

ΧΣ) CIi

Table I shows the following:

1. The connection according to the invention is opposite 9 of the 12 examined before emergence and compared to 11 of the 15 weed species examined more selectively after emergence.

2. The compound of the invention is significantly more effective than isoproturon against commercially important weeds such as couch grass (a perennial grass weed) _; Sticky herb and speedwell.

3. The compound according to the invention is on average 1.8 times as high selective as isoproturon when applied before emergence and 2.5 as selective as isoproturon when applied Apply after emergence.

Comparative experiment b)

A second experiment was carried out in which the selective herbicidal activity of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea has been compared to two other commercially available urea herbicides, namely 3- (3-chloro-4-methoxyphenyl) -1,1-dimethylurea (Chlorotoluron) and 3- (3-chloro-4-methylphenyl) -1,1-dimethylurea (Metoxuron). The procedure used in this pre-emergence experiment was the same as in comparative experiment a) for the experiment before emergence described with the modifications given below. The weed species examined: common couch grass, Agropyron repens (Co); Wild oats, Avenafatura / Ludoviciana (Wo); Ryegrass, lolium multiflorum (Rg); annual bluegrass, Poa annua (Pa); woolly honeydew grass, Holcus lanatus (Yo); Bulrush, Alopecurus myosurd-des (At the); Sugar beet, Beta vulgaris (Sb); Chickweed, Stellaria media (St); Speedwell, Veronica persica (Sw); Bindweed, Convolvulus arvensis (Cv); Knotweed, Polygonum lapathifolium (Pp); Field mustard, Sinapis arvensis (Ck). During this attempt,

130050/0408

the visually estimated the results of treatment after 20 days and these test results were as given above in Comparative Experiment _a)} is converted to the selectivity factors, with the exception that was used in this case, chlorotoluron as a standard. That is, the selectivity factor as obtained for the two compounds to be investigated for the individual weed species was divided in each case by the selectivity factor for chlorotoluron, the ratio for chlorotoluron was then set equal. The results are given in Table II, where the compound according to the invention is again designated as A, chlorotoluron as C and metoxuron as M.

130050/0408

/ 14

Table II

Plant
zenart ^GID 50 - C. M. A. Selectivity factor M. A. Ratio of selectivity
factors M. A. wheat 2.11 2.13 C. - - C. - - Co
Where
Rg
Pa
Yo
At the
Sb
St.
Sw
Cu
Pp
Ck 1.71
1.58
0.51
0.19
0.19
0.33
0.5U
0.03
0, U5
0.25
1.28
0.67 3.23
0 82
0 U9
0122
0.19
0 87
0, U6
0.03
0.29
0.15
O ₇ 6U
0 _f 2U 1.36
0 58
0, UU
0.11
0, lU
0.26
0.17
0.03
0.19
U, U8
0.90
0.10 - o, U8
1 88
3, lU
7.00
1J77
3.35
51.33
5.31
10.27
2, ul
6 _; 12th 1.57
3 ^ 67
U 8U
19.36
15.21
8.19
12.53
71 »00
11.21
0 U8
2.37
21.30 - 0.39
1, Uo
0.76
0.63
0.73
0.28
0.86
0.73
1.13
1.22
1, U6
2, -OU 1.28
27U
1.17
1 7U
1.37
1J28
3) 20
1.01
2.39
0.06
1, UU 1.23
1.3U
U lU
11.11
11.11
6.39
3.91
70.33
U, 69
8JUU
1.65
3.15 HHHHHHHHHHHH
oooooooooooo
oooooooooooo "... .,. 1.00 0.97 2.0U
Average . '' 1

(JI CD

As can be seen from Table II, the inventive Compound on average more than 2 times as selective as either Chlorotoluron or Metoxuron if they were prior to emergence be applied in wheat.

Example 5

Field evaluation of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea

The effectiveness and spectrum of activity of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea after emergence was with that of 3- (4-isopropy $ henyl) -1, 1-dimethylurea f (isoproturon) in a total of 7 field trials in winter cereals in Great Britain. The trials were in fields with normal commercial winter wheat and winter barley, in which naturally occurring grass weeds and / or broadleaf weeds were present ^ carried out.

The preparations of the compound according to the invention in the form of a suspension concentrate containing 500 g / l and of isoproturon containing 50 g / l S.C. (Hytan 500 L) were diluted with water and each in a comparable amount of four Doses applied for each attempt. There were doses of 1.58, 2.10, 2.63 and 4.2 g of active ingredient per hectare according to the 3/4, 1, 1 1/4 or 2 times the recommended dose of 2.1 kgfei / ha isoproturon as a post-emergence herbicide on winter cereals upset in spring. In three experiments (5, 6, and 7), the compound according to the invention with the addition of one Spray aid applied to improve the properties of the agent. The spray aid was in the form of a mixture with the compound according to the invention in the tank in one Ratio of 2 parts of compound (a.m.) to 1 part of spray aid on a weight / volume basis. applied.

Areas of 10 by 3 meters were applied and each treatment was carried out 3 times in different statistically distributed blocks. The funds were being used on every area

1300 50/0408

ORIGINAL INSPEGTED / ¹⁶

a gas pressure sprayer for small areas, which sprayed a volume of 417 l / ha. details with regard to the state of development of the useful plants and the application conditions for each experiment are in Table III given.

Assessing the health of crops and the effectiveness of chemical treatments against grasses and broadleaf weeds was done one to three months after treatment. The effects on the crops were carried out visually according to the EWRC 1-9 scale, with the value O having no effect and the value 9 being Dying of the useful plants means. The evaluation of the weeds includes the estimation of the percentage cover of broad-leaved weeds in general and of species of the predominant weeds found in all test pieces found. The grass weeds were rated by counting the panicles in 6 or 8 equal areas of 0.5m + and converting these values to numbers for the individual flowers 0.5 m in each area. The weed species examined were: a) broad-leaved weeds - speedwell, Veronica persica (Sw); Vogelmjare, Stellaria media (St); Chamomile, matricaria spp. (Kw); Sticky herb, Galium aparine (Gg); red dead nettle, Laminium pxpurea (Dn) and b) grass weeds - bulrush, alopecrus myrosuroides (Am); Wild oats, Avena spp. (Where). Depending on the The crop plants were climatic conditions 138 to 169 days after treatment with the aid of a combination harvester harvested and the grain weight of the crops determined.

The results of the field trials are given in Table IV below. The values given are mean values for the the effects investigated in the various field tests, i.e. from the results for the various field tests in each case the mean is calculated. The stated effect on the crops is the mean value on the EWRC scale

130050/0408 / 17

ORIGINAL INSPECTED

by visual evaluation in 7 trials. The values given for the effectiveness against weeds relate to the percentage reduction in weed growth compared to the comparison areas according to the methods specified above, The effectiveness values against all broad-leaved weed species in the experiment are also given, and this one The mean value for all weed species in this experiment is given under the heading "Total Dicotylidons" as percentage reduction in plant growth compared to comparison. The weight of the crops is given as percentage of the harvested weight of comparison fields, which was set at 100%.

13O0S0 / 0A08 _{/ 18}

ORIGINAL INSPECTED

Table III

Ö cn ο

attempt
No. Useful plant
ze - variety sowing
date
(Year toi »
her) Aufbrin
gungsda
tum Developing
3ungsstu ~
feather tempera
tur at
Apply Damp
activity
salary
<#) Humid
■ equi-
valent Tc content
'of the Bo
dens
(*) 1 W. wheat Sportsman 26 »Sept. 26th of March CD 10.7 * 27.1 26.0 3U 2 W. Barley Sonja Oct 10 28, Feb. A, F 6 ° 28.1 23 _f 5 29 3 W. wheat M. Hobbit 9 _% Oct. 3 March A, D 5 ° 28.3 31 _; 2 UU 1" W wheat Hustler ¹ T * Oct. 3 March Α, Ε V ° 22.3 33 _f 5 Ul 5 W. wheat Flanders Oct 3rd of April A. 9.9 ° 38.6 36.1 52 6th W. wheat Flanders Oct 11 3rd of April C, D, G 10.0 ° 18.6 16.9 18th 7th W. wheat Mitob bit Oct. 18 3rd of April B _S D 10.0 ° l6jl l6.8 16

Development status

A - 5 unfolded leaves (Setzling 'B - 5 unfolded leaves fSetzling _< C - 7 unfolded leaves (Setzling, D - ·' main shoot and 2 stalks E - main stalk and 3 stalks F - main stalk and 4 stalks

Stalk stage stalk stage stalk stage

G -

Pseudo-stem erection (stem elongation stage)

CO CD

cn

CD

Table IV

ο »

OI

ο α »

Witksankettgs-

link

dose

(kg am / ha) EMRC scale

3- (3-methyl-lt-isopropylphenyl) -1,1-dimethyl alcohol

1.58 "2.10 2.63 U, 20

3 (-3-isopropylphenyl) - 1.58 -1,1-dimethylurea 2.10

2.63 k , 20

comparison

2.2 2.3 2f

2.2

2.1 2.0 2.2

2.6

Effectiveness against weeds

79.1
8T 2
93.2
97.7

85.9
90.3
93 _; 5
97.9

Where

19-27.6

33.0 53 _; 2

21.7 3H, 0 36 1 H8 9

broad-leaved weeds

75 _r 3 80.2 85.5 89.7

50.0 ^ 3.6 52.9

96.2
97.6
98.8
9'9.8

Mw

9 ^, 1
9 ^, 5
98.0

95.1

99.2

100.0

87.7

56.0
7O _r 6
67.0
92.8

8.0

² r5
20.3
21.0

Dn

65.2
53.8
66.8
77.3

72.0

Total dicotylidon

82.2 85.0 9O ₇ I.

70.1 72.9 73, U.

78.7

Harvest weight (%) based on the

129.9 138 8 1111.8 136.1

13U.8 136; 6 130.1

100

CTJ

CD

Claims (6)

Claims 1.} 3- (3-Methyl-4-isopropylphenyl) -1,1-dimethylurea. 2. Preparation of the compound according to claim 1, characterized in that the aniline is the Formula I. (D or a hydrohalide thereof reacts with either a) a dimethylcarbamoyl halide or b) Phosgene and the isocyanate of the formula II formed CH, NCO (II) at least partially reacted with dimethylamine. 3. The method according to claim 2, characterized in that that stage a) is carried out in the presence of a dehydrohalogenating agent. 130050/0408 ORIGINAL INSPECTED / 2 "30A5770 4. The method according to claim 2 or 3, characterized in that step a) using Performs dimethylcarbamoyl chloride. 5. Herbicidal agent, characterized in that it, as an active ingredient, the compound according to claim 1, optionally together with one or more carriers ^ contains. 6. Means according to claim 5, characterized in that that it comprises at least two carriers, at least one of which is a surfactant. 6226 130050/0408