DE1542889B2 - Agent for combating weeds based on phenylurea Hoechst AG, 6000 Frankfurt - Google Patents

Description

R,

R ₁ -O-

-NH- CO- N

R2

(R ₁ - O) _ni

NH - CO - N

in

20th

wherein Ri is a haloalkyl or halocycloalkyl or haloalkenyl or halocycloalkenyl radical with 1 to 5 carbon atoms,

/? i = 1 or 2,

R4 = halogen, the alkyl, alkoxy or trifluoro

methyl radical,
/ 7 ₂ = 0 to 3,
R2 = hydrogen or an alkyl radical with 1 to

4 carbon atoms,
R3 = an alkyl or alkoxy radical, each with 1 to 4 carbon atoms,

mean, with the proviso that / 7i = 2 if / 72 = 0.

30th

The subject of German patent 15 68 515 is, inter alia, the use of Halogenälkyloxy- or haloalkenyloxy ureas of the general formula

40

_{where Ri is a C 2} -C ₂ -alkyl or C _{2 -C 3} -alkenyl radical occupied by fluorine and / or chlorine, R _{2 is} hydrogen or a methyl radical and R3 is a methyl or methoxy radical, as herbicides.

It has now been found that urea derivatives of the following general ones can also be used with similar success Formula can use:

50

55

wherein Ri is a haloalkyl or halocycloalkyl or haloalkenyl or halocycloalkenyl radical with 1-5 carbon atoms,

/ 7i = 1 or 2, e, o

R4 = halogen, the alkyl, alkoxy or trifluoro

methyl radical,
/ 7 ₂ = 0-3,
R ₂ = hydrogen or an alkyl radical with 1 to 4 carbon atoms,

R3 = an alkyl or alkoxy radical each having 1 to 4 carbon atoms, with the proviso that / 7i = 2 when / 7 ₂ = O.

The new active ingredients are obtainable analogously to the reactions mentioned in patent 15 68 515.

Almost without exception, they are crystalline compounds. You can recrystallize from the common organic solvents are cleaned.

The new compounds have a good effect against weeds and are gentle in their properties towards a number of important crops such as beets, potatoes, corn, and cotton Cereals are superior to known urea derivatives.

The application forms are dusts, scattering agents or spraying agents, optionally also in combination with fertilizers. Corresponding dusts or grit are distributed in the form of a uniform, free-flowing dust or granules are obtained if the active ingredients are mixed with finely divided, solid substances, z. B. talc, natural clays, pyrophyllite or diatomaceous earth mixes.

So-called wettable powders are wettable preparations that contain wetting and dispersing agents and are used, for. Am Water are uniformly dispersible. The present active ingredients can be used for the purposes mentioned use. Corresponding emulsion concentrates can also be obtained by dissolving the active ingredient in an organic solvent. Such preparations can also contain wetting agents in order to to achieve good suspension or emulsion in water prior to application.

Another application form of the present active ingredients consists in their mixture with fertilizers, whereby fertilizing and at the same time herbicidal agents are obtained. If necessary, you can also use other herbicidal substances are mixed, provided they are chemically compatible; possibly you can also use other biocidal products, e.g. B. insecticides, fungicides, ovicides, soil disinfectants, Add acaricides for appropriate combined effects.

The herbicides can be used as herbicidal active ingredients, for. B. contain the following compounds:

N- [3-methyl-4- (l ', 2'-dichlorovinyloxy) phenyl] -

N'-methylurea, m.p. 156-158 ° C,
N- [3-methyl-4- (l ', 2'-dichlorovinyloxy) phenyl] -

Ν ', Ν'-dimethylurea, melting point 181-183 ° C,
N- [3-methyl-4- (l ', 2'-dichlorovinyloxy) phenyl] -

N'-methyl-N'-methoxyurea,

Mp. 111-113 ° C,
N- [3-methoxy-4- (l ', 2'-dichlorovinyloxy) phenyl] -

Ν ', Ν'-dimethylurea, melting point 171-183 ° C,
N- [3-methoxy-4- (1 ', 2'-dichlorovinyloxy) phenyl] -

N'-methyl-N'-methoxyurea, m.p. 85-87 ° C, N- [3- (l ', 2'-dichlorovinyloxy) -4-chlorophenyl] -

N'-methylurea, m.p. 182-186 ° C,
N- [3- (1 ', 2'-dichlorovinyloxy) -4-chloro-phenyl] -

Ν ', Ν'-dimethylurea, melting point 192-195 ° C,
N- [3- (l ', 2'-dichlorovinyloxy) -4-chloro-phenyl] -

N'-methyl-N'-methoxyurea,

M.p. 162-164 ° C,
N- [3- (r, 2'-dichlorovinyloxy) -4-methyI-phenyl] -

N'-methylurea, m.p. 171-173 ° C,
N- [3- (l ', 2'-dichlorovinyloxy) -4-methyI-phenyl) -

Ν ', Ν'-dimethylurea, melting point 192-193 ° C,
N- [3- (l ', 2'-dichlorovinyIoxy) -4-methyl-phenyl] -

N'-methyl-N'-methoxyurea,

M.p. 126-129 ° C,
N- [3-methyl-4- (l M'-difluoro-2 ', 2'-dichloroethoxy) -

phenyI] -N'-methylurea, melting point 138 ° C,

N- [3-methyl-4- (l ', l'-difluoro-2', 2'-dichloroethoxy) -

phenyl] -N'-methoxyurea, mp 105- 106 ⁰ C, N- [3-methyl-4- (l ', l'-difluoro-2', 2'-dichloräthoxy). -

phenyl] -N ', N'-dimethylurea, melting point 140 ° C, N- [3-methyl-4- (l', l'-difluoro-2 ', 2'-dichloroethoxy) phenyl] -N'- methyl-N'-methoxyurea,

Mp. 77-79 ° C,
N- [3-methyl-4- (l ', 1' -difluor-2 ', 2'-dich! Orethoxy) -

phenyl] -N ', N'-diethylurea, melting point 114-115 ° C, N- [2-methyl-4- (1 ', 1' -difJuor-2 ', 2'-dichloroethoxy) -

phenyl] -N'-methylurea, m.p. 159-161 ⁰ C, N- [2-methyl-4- (1 ', 1'-difluoro-2', 2'-dichloroethoxy) -

phenyl] - N ', N'-dimethylurea, mp 95-96 ⁰ C, N- [2-methyl-4- (l M.' difluoro ^ '^' - dichloräthoxy) -phenyl] -N'-methyl -N'-methoxyurea,

Mp. 71 ° C,
N- [3- (l ', 1' -difluoro ^ '^' - dichloroethoxyM-methyl-

phenyl] -N'-methylurea, m.p. 162-163 ° C, N- [3- (l ', r-difluoro-2', 2'-dichloroethoxy) -4-methylphenyl] -N ', N'-dimethylurea ,

M.p. 117-119 ° C,
N- [3- (l M '-Difluor ^' ^ '- dichloroethoxyH-methylphenyl] -N'-methyl-N'-methoxyurea,

Mp. 89-91 ° C,
N- [3-trifluoromethyl-4- (l ', l'-difluoro-2', 2'-dichloroethoxy) -phenyl] -N'-methylurea,

Mp. 138-140 ⁰ C,
N- [3-trifluoromethyl-4- (r, l'-difluoro-2 ', 2'-dichloroethoxy) phenyl] -N', N'-dimethylurea,

Mp. 167-169 ° C,
Np-trifluoromethyl ^ -ii'.l'-difluor ^ '^' - dichloro-

ethoxy) -phenyl] -N'-methyl-N'-methoxy-

urea, m.p. 60-62 ⁰ C,
N- [3-chloro-4- (l ', 1' -difluoro ^ '^' - dichloroethoxy) -

phenyl] -N'-methyl urea, melting point 137-138 ° C, N- [3-chloro-4- (1 ', 1' -difluoro-2 ', 2'-dichloroethoxy) -

phenyl] -N'-methoxyurea, m.p. 118 ° C, N- [3-chloro-4- (l ', 1' -difluoro-2 ', 2'-dichloroethoxy) -

phenyl] -N ', N'-dimethylurea, melting point 145 ° C, N- [3-chloro-4- (1 M'-difluoro-2 ', 2'-dichloroethoxy) -phenyl] -N'-methyl-N'-methoxyurea,

Mp 92-93 ° C,
N- [2-chloro-4- (1 ', 1' -difluoro-2 ', 2'-dichloroethoxy) -

phenyl] -N'-methylurea, m.p. 156-158 ° C, [2-chloro-4- (l ', 1' -difluoro-2 ', 2'-dichloroethoxy) -

phenyl] -N ', N'-dimethylurea, m.p. 92-94 ° C, [2-chloro-4- (l ', l' -difluoro-2 ', 2'-dichloroethoxy) -phenyl] -N'-methyl-N'-methoxyurea,

Mp. 54-55 ° C,
N- [3- (l ', 1' -difluoro ^ '^' - dichloroethoxyH-chloro-

phenyl] -N'-methylurea, m.p. 137-139 ° C, N-p-il'.l'-difluoro ^ '^' - dichloroethoxyH-chlorophenyl] -N ', N'-dimethyl urea,

M.p. 115-117 ° C,
Np-O'.r-Difluor ^ '^' - dichloroethoxyH-chlorophenyl] -N'-methyl-N'-methoxyurea,

Mp 96-98 ° C,
N- [3- (l ', 1' -difluoro ^ '^' - dichloroethoxyH-chloro-

phenyl] -N ', N'-diethylurea, m.p. 74-76 ° C, N- [3- (l', l'-difluoro-2 ', 2'-dichloroethoxy) -4-bromo-

phenyl] -N'-methylurea, m.p. 157-158 ° C, N- [3- (l ', l'-difIuor-2', 2'-dichloroethoxy) -4-bromo-

phenyl] -N ', N'-dimethylurea, melting point 112 ° C, N- [3- (r, l'-difluoro-2 ', 2'-dichloroethoxy) -4-bromophenyl] -N'-methyl-N'-methoxyurea,

Mp. 94-97 ° C,
N- [3- (l ', l'-difluoro-2', 2'-dichloroethoxy) -4-bromophenyl] -N ', N'-diethylurea, melting point 105-106 ° C,

N- [3-methoxy-4- (l ', l'-difluoro-2', 2'-dichloroethoxy) -

phenyl] -N'-methylurea, m.p. 149 ° C, N- [3-methoxy-4- (l ', 1' -difluoro-2 ', 2'-dichloroethoxy) -

phenyl] -N ', N'-dimethylurea, melting point 159 ° C, N- [3-methoxy-4- (l ', l'-difluoro-2', 2'-dichloroethoxy) -phenyl] -N'-methyl-N'-methoxyurea,

Mp 92-93 ° C,
Np-ChloM-il'.l'-difluor ^ '^' - dichloroethoxy) -

5-methyl-phenyl] -N'-methylurea, m.p. 168 ° C N- [3-chloro-4- (l ', l'-difluoro-2', 2'-dichloroethoxy) -5-methyl-phenyl] -N ', N - dimethylurea,

M.p. 145-147 ° C,
N- [3-chloro-4- (l ', 1' -difluoro-2 ', 2'-dichloroethoxy) -5-methyl-phenyl] -N'-methyl-N'-methoxy-

urea, m.p. 105 ° C,
N- [bis-3,4- (1 ', 1' -difluoro ^ '^' - dichloroethoxy) -

phenyl] -N'-methyl urea, melting point 136 ° C, N- [bis-3,4- (l ', 1' -difluoro-2 ', 2'-dichloroethoxy) -phenyl] -N', N'-dimethylurea,

Mp. 128-130 ° C,
[Bis-3,4- (l M'-difluoro-2 ', 2'-dichloroethoxy) -phenyl] -

N'-methyl-N'-methoxyurea, m.p. 69-70 ° C, N- [bis-3,4- (l ', l'-difluoro-2', 2'-dichloroethoxy) phenyl] -N ', N'-diethylurea, melting point 51-53 ° C,

example 1

In a cold frame experiment, the preparations were

N- [3-chloro-4- (l ', r-difluoro-2', 2'-dichloroethoxy) -

phenyl] -N'-methylurea (I), N- [3-chloro-4- (l ', l'-difluoro-2', 2'-dichloroethoxy) -

phenyl] -N ', N'-dimethylurea (II) and N- [3-chloro-4- (1', 1 '-difluoro-2', 2'-dichloroethoxy) phenyl] -N'-methyl- N'-methoxyurea (III)

on their herbicidal effectiveness and their gentle effect on a number of cultivated plants checked. For this purpose, seeds of the weeds were used

Mustard
Chickweed
Dog chamomile
Ragwort

and the crops

pea

Broad bean

Broad bean

carrot

Summer rye

Spring barley

Spring wheat

oats

Corn

Rice (mountain rice)

cotton

Sinapis arvensis Stellaria media Anthemis arvensis Senecio vulgaris

Pisum sativum Vicia faba Phaseolus vulgaris Daucus carota Seeale cereale Hordeum distichum Triticum aestivum Avena sativa Zea mays Oryza sativa and Gossypium sp.

sown in boxes filled with humus, sandy loam; the soil surface was using the same day injected aqueous suspensions of the preparations mentioned. The evaluation took place after 5 weeks, where the plants were rated in the usual way on the basis of visual inspection. The received Values were then converted into% degree of damage

expected. Served as a means of comparison

for the cotton

N-S ^ -Dichlorophenyl-N'.N'-dimethylurea

(Diuron, IV)
for the vegetables

N-4- (p-chlorophenoxy) -phenyl-N ', N'-dimethyl-

urea (chloroxuron, V)

Table 1

for the cereals

NM-chlorophenyl-N'-methyl-N'-methoxyurea (Monolinuron, VI)

The following table initially gives an overview of the weed effects of the preparations used. The application rate is given as kg of active ingredient per hectare.

Pre Degree of damage at kg active ingredient per ha 1.2 kg / ha 5.0 kg / ha Test plant Application rate 1.2 kg / ha 5.0 kg / ha ready Test plant Application rate 60% 95% 0.6 kg / ha 85% 100% 0.6 kg / ha 95% 100% Chickweed 70% 100% 100% I. Mustard 50% 90% 90% 100% 90% 100% II 80% 100% 100% 90% 100% 100% III 80% 80% 90% 100% 80% 100% IV 80% 90% 100% 70% 100% 100% V 60% 85% 95% 90% 90% 100% VI 75% 95% 100% Ragwort 80% 100% 100% I. Dog chamomile 70% 70% 100% 90% 90% 95% II 80% 100% 100% 80% 100% 100% III 60% 85% 100% 100% 80% 95% IV 90% 95% 100% 70% 100% 100% V 75% 90% VI 80%

The values given show that substances I-III according to the invention in their action on emergent dicotyledonous weeds are approximately in the same range as the known ones Comparison means. The concentration sufficient for normal weed control is in the

Table 2

Effect on crops

Usually between 0.6 and 1.2 kg of active ingredient per hectare. But if you compare the results of this experiment on the cultivated plants tested, it clearly shows that the gentle action of the claimed compounds is better than that of the comparison means.

Preparation test plant

Application rate

0.6 kg / ha 1.2 kg / ha

5.0 kg / ha

Preparation test plant application rate

0.6 kg / ha 1.2 kg / ha 5.0 kg / ha

I. cotton 0% 0% 0% I. II 0% 0% 0% II IV 10% 30% 40% IV

carrot

0% 10% 40% 0% 0% 10% 0% 20% 40%

preparation Test plant: pea
0.6 kg / ha 1.2 kg / ha 5.0 kg / ha Test plant: broad bean
0.6 kg / ha 1.2 kg / ha 5.0 kg / ha Test plant:
0.6 kg / ha Broad bean
1.2 kg / ha 5.0 kg / ha I.
II
V 0% 0%
0% 0%
10% 30% 10%
20%
40% 0% 0%
0% 0%
20% 20% 10%
30%
40% 0%
0%
0% 0%
0%
20% 0%
0%
55% preparation Test plant: rye
0.6 kg / ha 1.2 kg / ha 5.0 kg / ha Test plant: barley
0.6 kg / ha 1.2 kg / ha 5.0 kg / ha Test plant:
0.6 kg / ha wheat
1.2 kg / ha 5.0 kg / ha

I. OO / o 0% 0% 0% 0% 20% OO / o 0% OO / o II 0% 0% 30% OO / o 200/0 25% 0% 0% 10% III 0% 0% 3OO / o 0% 30% 40% OO / o 0% 20% VI 30% 800/0 100% 30% 600/0 90% 400/0 700/0 100 / o

Preparation Test plant: oats. Test plant: maize

0.6 kg / ha 1.2 kg / ha 5.0 kg / ha 0.6 kg / ha 1.2 kg / ha

5.0 kg / ha

Test plant: rice

0.6 kg / ha 1.2 kg / ha 5.0 kg / ha

I. OO / o 0% 10% OO / o OO / o 0% 0% OO / o 10% II 0% 0% 10% OO / o OO / o 10% 0% 10% 20% III 0% 0% 0% OO / o OO / o 0% 0% 20% 3OO / o IV 30% 60% 100 / o 200/0 30% 50% 30% 50% 90%

In particular, I and II surpass on cotton, peas, field beans and French beans, II on carrots, and all 3 claimed compounds I-III on cereals the comparison means clearly in terms of their gentle effect. Thereby also lead clear Overconcentrations may lead to less damage.

The clear advantage of the compounds mentioned lies in their compared to the respective comparison means Perfectly improved protection, especially on cotton and French beans, continues on rye, wheat, oats, corn and a number of other crops.

Example 2

N- [3-methyl-4- (1 M'-difluoro-2 ', 2'-dichloroethoxy) -

phenyl] -N'-methyl-N'-methoxyurea (VII)
N- [3-methyl-4- (1 ', 1' -difluoro-2 ', 2'-dichloroethoxy) -

phenyl] -N ', N'-dimethylurea (VIII)
N-4-chlorophenyl-N'-methyl-N'-methoxyurea

(Monolinuron, IX)
N ^ -Chlorophenyl-N'-methyl-N'-isobutinyl urea

(Buturon, X)

Mixed product of 5% 2-chloro-4,6-bisethylaminos-triazine (simazine) and 22.5% 2-methylmercapto-4-isopropylamino-6- (3'-methoxy) -propylaminos-triazine (XI)

The weeds
Mustard
Chickweed
Dog chamomile
and white goosefoot

Sinapis arvensis
Stellaria media
Anthemis arvensis
Chenopodium album

10

as well as the crops
Spring wheat
Spring barley
oats

Rice (mountain rice)
sugar beet
and broad bean

20th

25th

30th

35

Triticum aestivum
Hordeum distichum
Avena sativa
Oryza sativa
Beta vulgaris
Vacia faba

were sown in boxes in homous, sandy loam soil. On the same day the soil surface became sprayed with an aqueous suspension of preparations VII and VIII. 2 in cereals were used as comparison agents frequently used urea preparations IX and X as well as a triazine mixed product that can also be used in cereals; the first-mentioned comparative agent IX can also be used in field beans.

After the treatment, the boxes were placed in a cold frame, where they were 6 weeks until the evaluation of the Attempt stopped.

The following table gives an overview of the test results; the application rates are given in kg of active ingredient per ha; the rating values determined are converted into »degree of damage in %".

preparation Degree of damage to active ingredient per hectare 1.2 kg / ha 2.5 kg / ha 0.6 kg / ha Weeds *) 73% 100% VII 54% 89% 100% VIII 76% 99% 100% IX 92% 100% 100% X 92% 100% 100% XI 90%

*) The table shows the average value for all four above-mentioned weed species for all preparations.

Table 3

Effect on crops

Preparation test plant: wheat

0.6 kg / ha 1.2 kg / ha 2.5 kg / ha

Test plant: barley

0.6 kg / ha 1.2 kg / ha 2.5 kg / ha

Test plant: oats

0.6 kg / ha 1.2 kg / ha 2.5 kg / ha

VII 0% 0% 0% 0% 0% 0% 0% 0% 0% VIII 10% 10% 20% 0% 0% 30% 0% 0% 10% IX 20% 50% 95% 20% 40% 50% 40% 80% 100% X 65% 80% 90% 55% 95% 100% 60% 90% 100% XI 84% 90% 100% 70% 90% 100% 80% 85% 100%

Preparation test plant: rice

0.6 kg / ha 1.2 kg / ha 2.5 kg / ha

Test plant: sugar beet

0.6 kg / ha 1.2 kg / ha 2.5 kg / ha

Test plant: broad bean

0.6 kg / ha 1.2 kg / ha 2.5 kg / ha

VII 0% 0% 0% 0% 0% 20% 0% 0% 0% VIII 0% 0% 0% 100% 100% 100% 0% 10% 20% IX 80% 95% 100% 95% 100% 100% 50% 60% 80% X 40% 55% 70% 100% 100% 100% XI 70% 80% 90% 100% 100% 100%

A comparison of the individual preparations showed that the claimed compounds VII and VIII hardly inferior to the comparison agents in their weed effects; these destroyed at one application rate of 1.2 kg / ha active ingredient all weeds, while the new compounds in the same dosage the Weeds were consistently very badly damaged and also completely destroyed with increased application rates.

At 1.2 kg / ha, the comparison agents severely or very severely damaged all of the cereal types mentioned In contrast, substances according to the invention were completely sparing at 1.2 and 2.5 kg / ha on wheat, barley, oats and rice or almost completely. Likewise, the broad bean was not or hardly damaged by the new substances, while comparative means IX damaged this crop very severely. One of the most claimed

909 511/3

20th

25 In experiment 1 (see. Table 4) showed that the substance of the invention protects the crop plant excellent VII Zukkerrübe while the closely related substance XIII almost destroyed the sugar beet. The results of experiment 2 (cf. Table 5) show that substance II according to the invention caused no or almost no damage in both rice and soybeans, even in overdoses, while the comparison substance XIV caused the crops mentioned in dosages required for weed control completely destroyed. The same applies to the results of Experiment 3 (cf. Table 6), in which the compound XII according to the invention was extremely gentle on the cultivated plant bean and only slightly damaged it even in considerable overdoses, while the closely related compound XV completely destroyed the bean.

The examples cited demonstrate that substances according to the invention have considerable application technology Have advantages over the non-halogenated reference substances.

Substances VII also spared the sugar beet at the application rates mentioned, while all comparison agents almost completely destroyed this plant species.

The advantage of the claimed substances is that they clearly protect various crops such as wheat, barley, oats, rice, field beans, and in some cases also sugar beet, in application rates in which a number of important arable weeds are destroyed or severely damaged, while comparative | ₀ preparations that are frequently used in the cultures mentioned cause them much more damage.

Example 3

In 3 experiments, which had been designed according to a similar scheme, the invention Active ingredients

VII = N-3-methyl-4- (r, l'-difluoro-2 ', 2'-dichloroethoxy) -phenyl-N'-methyI-N'-methoxy-

urea,
II = N-3-chloro-4- (l ', l'-difIuor-2', 2'-dichloroethoxy) -phenyl-N'.N'-dimethylurea and

XII = N-3-trifluoromethyl-4- (l ', l'-difluoro-2', 2'-di-

chloroethoxy) phenyl-N'-methyl urea

with the otherwise identical, but unsubstituted comparison substances in the alkoxy group on the phenyl nucleus

XIII = N-S-methyl ^ -ethoxyphenyl-N'-methyl-

N'-methoxyurea,

XIV = N-3-chloro-4-ethoxyphenyl-N ', N'-dimethyl-

urea and

XV = N-S-trifluoromethyM-ethoxyphenyl-

N'-methylurea

compared by testing their weed effects and crop tolerance.

For this purpose, seeds of weeds and cultivated plants were sown in pots, the pots were after Sowing sprayed with suspensions of the preparations to be tested dissolved in water in various dosages and then placed in the greenhouse. Four weeks after the treatment, the effect was noted, it is given in Tables 1-3 below as the degree of damage in%.

Table 5

Comparison of the pre-emergence effects of II and XIV on crops and weeds

Table 4 1 weeds VII and XIII on Dosage in kg / ha Comparison of the pre-emergence effects of VfI a. i. Crops and 1.25 0.62 XIlI Plant species 1.25 0.62 0 0 90 85 Crop plant 95 85 sugar beet 100 90 95 90 Weeds 90 80 100 100 Sinapis 85 70 100 95 Stellaria 95 85 100 90 Matricaria 93.0 82.0 95 85 Chenopodium 98.0 88.0 Poa Average Weed effect

Plant species

Dosages in kg / ha a.i.

II

10.0 5.0 2.5

1.25

XIV

2.5

1.25

Crop plant
rice
soy

Weeds
Echinochloa
Poa

Amaranthus
Chenopodium
Stellaria
Matricaria
Sinapis

Average
Weed effect

10 10 0 0 100 85 15th 0 0 0 100 100 95 90 85 95 90 100 100 90 100 90 100 95 85 100 100 100 90 85 95 90 100 100 100 100 95 100 100 95 100 90 100 95 85 100 100

99.3

95.7

89.3

98.6

93.6

11 12

Table 6

Comparison of the pre-emergence effects of XII and XV on crops and weeds

Plant species Dosages in kg / ha a.i.

XII XV

20.0 5.0 2.5 5.0 2.5

Crop plant
French bean 10 0 0 100 100

Weeds Sinapis Stellaria Chenopodium Anthemis Poa

Average 93.0 80.0 96.0 90.0

Weed effect

95 75 90 80 90 75 100 90 95 90 100 95 100 90 100 100 85 70 90 85

Claims (1)

Claim: Herbicidal agent, characterized by a content of haloalkyloxy or Haloalkenyloxy-phenylureas of the general formula (R ₁ -O) ,,, NH-CO-N