DE1542889A1 - Means for combating weeds - Google Patents

Description

Subject of the patent ,, ...... (patent application P 15 42 874.7

= Fw 5062) are agents for combating weeds which are characterized by their content of haloalkyloxy- or haloalkenyloxy-arylureas of the general formula

wherein R _{1 is} a haloalkyl or haloalkenyl radical with 1-4 carbon atoms, R _{2 is a} gasoline or an alkyl radical with 1-4 carbon atoms and R "denotes an alkyl or alkoxy radical with 1-4 carbon atoms in each case"

It has now been found in a further embodiment of this subject that you can also use urea derivatives of the following general formula with similar success:

^H 2

nh-co-n:

* 3

BAD ORJG! ΓW

009884/2117

wherein R ^ is a haloalkyl or ^ alogencycloalkyl or

Haloalkenyl or halocycloalkenyl radical with 1-5 C atoms

η .. = 1 or 2,

Rl = halogen, the alkyl, alkoxy or trifluoromethyl radical,

n ₂ = o - 3,

R ₂ = hydrogen or an alkyl radical with 1-4 C atoms,

R "= an alkyl or alkoxy radical each having 1-4 C atoms, with the proviso that η., Β is 2 when n ₂ = 0

is.

The new active ingredients are analogous to those in the patent. ·· ... «··. ·· (Patent application P 15 42 874.7. (Fw 5062)) mentioned reactions available.

Almost without exception, they are crystalline compounds. You can by recrystallization from the usual organic Solvents are cleaned.

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

The application forms are the same as those in the above-mentioned patent. They can be used as dust, grit or Spray agents, if necessary also in combination with fertilizers, can be used. Appropriate dust or grit be in the form of a uniform, free-flowing; Dust or granules obtained when using the active ingredients finely divided, solid substances, e.g. talc, natural clays. Pyrophyllite or diatomaceous earth mixes.

009884/2117

So-called wettable powders are wettable preparations that network » and dispersants and, for example, uniformly in water are dispersible. The present active ingredients can be used for the purposes mentioned. It can also be appropriate Prepare emulsion concentrates by dissolving the active ingredient in an organic solvent. Such preparations can also contain wetting agents to achieve a good suspension or emulsion in water prior to application.

Another application of the present active ingredients consists in their mixture with fertilizers, thereby fertilizing and at the same time herbicidal agents are obtained. If necessary, they can also be mixed with other herbicidal substances, so far they are chemically compatible; if necessary, you can also use other biocidal products, e.g. insecticides, fungicides, Add ovicides, soil disinfectants, acaricides to achieve appropriate combined effects.

The herbicides can contain, for example, the following compounds as herbicidal active ingredients:

N- ^ 3 ~ methyl-4- (1 ', 2' -dichlorvinyloxy) -phenyl ^ -N '-methylurea M.p. 156-158 ° C. Calc .: 25.8 # Cl 10.2 ^ N

Found: 25.8 # Cl 10.4 # N

N- / 3-Methyl-4- (1 ', 2 · -dichlorovinyloxy) -phenylI-N', N '-dimethylurea M.p. 18I - 183 ° C Calc .: 2k, 6 # Cl 9.7 # N

Found: 24.3 # Cl 9.7 $> N

N- / 3-methyl-4- (1 ^f , 2 '-dichlorovinyloxy) -phenylJ-N' -methyl-N 'methoxyurea m.p. 111-113 ° C boron .: 23.2 $ Cl 9.2 $> N

Found: $ 23.2> Cl 9.0 h N.

N- / 3-methoxy - / + - (1 ·, 2'-dichlorovinyloxy) -phenyl7-N '"N" -dimethylurea Mp. 171-173 ° C. Calc .: 23.2 £ Cl 9.2 # N

Found: 23.4 i * Cl 9.4 # N

0098-84 / 21 17

BAD ORJGjNAL

. N- / 3-methoxy-4 · (1 x, 2'-dichlorvinyloxy) -phenyl7-N * -methyl-N '- methoxyurea mp. 85 - 87 ⁰ C. Calc .: 22.1 $> Cl 8.7 # N

Found: 22.1 # Cl 8.9 # N

N- / 3- (1 ', 2'-dichlorovinyloxy) - ^ - chlorophenylJ-N · -methylurea pp. 182-186 ° C Calc .: 36.0 $> Cl 9.5 # N

Found: $ 36.0> Cl 9.3 # N

N- / 3- (1 ·, 2'-dichlorovinyloxy) -4-chloro-phenyl7-N ', N'-dimethyl urea Mp. 192-195 ° C. Calc .: 3 ^, 4 ^ Cl 9 >> 0 ^ N

Found: 33.8 # Cl 9.3 ^ N

methoxyurea m.p. 162-164 ° C. Calc .: 32.7 % Cl 8.6 # N

Found i 32.4-6 Cl 8.8 % N

N- ^ 3- (1 ', 2'-dichlorovinyloxy) - ^ - methyl-phenylJ-N ^! -methyl-

Calc .: 25.8 # Cl 10.2 "Found: 25.6 $> Cl 10.0 # N

urea m.p. 171-173 ° C. Calc .: 25.8 # Cl 10.2 "^ N

N- / 3- (1 ', 2 ^! -Dichlorovinyloxy) -4-methyl-phenyl) -N ·, N ♦ -dimethylurea "Mp. 192-193 ° C Calc .: 24.6 # Cl 9.7 # N

Found: 24.6 <£ Cl 9.9 # N

N - ^ - (I ', 2'-dichlorovinyloxy) -4-methyl-phenyl7-N'-methyl-N ¹ -methoxyurea m.p. 126-129 ° C Calc .: 23.3 ^ Cl 9.2 ^ N

Found: 23.3 % Cl 9.0 # N

N- / 3-methyl-4- (1 ', 1'-difluoro-2 ^f, 2'-dichloräthoxy) -phenylJ-N · - methylurea mp 138 ⁰ C Ber.:8,9 ^ N.

Found j9.0 $ N

N- _i / 3-methyl-4- (1 ', 1'-difluoro-2 ^1, 2 ^{-dichloräthoxy!)} -Phenyl7-N'-methoxyurea mp I05 -. 106 ⁰ C Calc .: 8.5 ^ N

Found: 8.8 % N

009884/2117 ^

N- ^ 3-methyl-4 (i ·, 1'-difluoro-2 ¹ , 2'-dichloroethoxy) -pheny ^ -N ¹ , N '~ dimethylurea pp. I40 ° C Calc .: 21.7 # Cl 8 , 6 5b N

Found: 21.7 $ Cl B, 7 # N

N- / 3-methyl-4- (i ·, 1'-difluoro-2 ', 2'-dichloroethoxy) -phenyl7-N'-methyl-N · -inethoxyurea f

Mp. 77 - 79 ° C Calc .: 20.7 # Cl # N 8.2 Found .: 20.6 i> Cl 8.2 N #

N - ^ - methyl-4- (1 «, 1» -difluoro-2 ', 2 · -dichloroethoxy) -phenyl7-N', N ' diethylurea mp 114-115 ° C Ber.ι 7.9 #N

Found: 7.9 % N *

N- / 2-Methyl-4- (i ', 1 x ^{2-difluoro-1,} 2'-dichloräthoxy) -phenylJ-N'-raethylharnstoff mp. 159-161 ° C Calc .: 8.9 ^ N

Found: 9.2% N.

-4- (i ', 1 " -difluoro-2 ', 2" -dichloroethoxy) -phenyl7-N ', N ^f diraethylurea Mp. 95-96 ° C Calc .: 21.7 $> Cl 8.6 # N

Found: 21.3 $ Cl 8.7 $ N

N - ^ - methyl-4 ~ (i ·, 1'-difluoro-2 x 2 ^l -dichloräthoxy) -phenyl7-N ^l me thyl-N · -me thoxyharne toff

Mp. 71 ° C- calc .: 8.2 ^ N

Found: 8.2 % N.

N- ^ 3- (1 ', 1'-Difluoro-2', 2 ^l -dichloroethoxy) -4-methyl-phenyl7-N ^l methylurea M.p. 162-163 ° C Ber.J 8.9 # N

Found " 9.3 M.

N - ^ - (I ·, 1 '^ difluoro-2 », Z'-
N- , N-dimethyl urea

r. Mp 117 -. 119 ⁰ C Ber. ι $ 21.7 Cl 8.6 # N

Found " 21.6 56 Cl 8.7 % N

/ 009884/2117 ^BAD ORiOiriu

N- ^ J-Ο ', 1' -Bifluoro-2 ', 2 · -dichloroethoxy) -4-methyl-phenyl7 «N' -methyl-N ¹ -methoxyurea

Pp. 89 - 91 ° C Calc .: 8.2 fo N

Found: 8.5 # N

N- ^ 3-Trifluoromethyl-4- (i ', 1 "-difluoro-2', 2'-dichloroethoxy) -phenyl7-N'-me thyl urine fabric

Mp. 138-14O ° C. Calc .: 7.6 $ N

Found: 7.7 # N
+)

N- / 3-Trifluoromethyl-4- (i ', 1'-difluoro-2 ·, 2 »-dichloroethoxy) -phenyl / -» N ^ -methyl-N · -Methoxyharns tof f

Mp. 6 * O-02 ° C Calc .: 17.9 % Cl 7.1 ^ N 'Found: 17 »6 # Cl 7.3% N

N- / 3-chloro- * f (i ·, 1'-difluoro-2 ^1, 2'-dichloräthoxy) -phenyl7-N · - methylurea mp 137 -. 138 ° C Calc .: 32.0 $, Cl 8, k $> N

Found: 31.7 # Cl 8.3 1> N

N- / 3-chloro-4- (1 ', 1'-difluoro-2', 2'-dichloroethoxy) -phenylJ-N'-

methoxyurea m.p. 118 ° C calc .: 30.4 % Cl 8.0 # N

Found: 29.9 # Cl 8.1 56 N

- ^ - (1 ', 1'-dlfluoro-2', 2'-dichloroethoxy) -phenylJ-N ', N'-dimethylurea M.p. 145 ° C Calc .: 30.6 _t % Cl 8.1 ^ N

Found: 30.2 % Cl 8.2 % N

"- ** - (1 ^f , 1 ^! -Difluoro-2», 2 '-dichloroethoxy) -phenyl7- ^N ' methyl-N '-ine thoxyurea f

M.p. 92-93 ° C calc .: 29.3 ^ Cl 7.7 % N found : 29.2 $ Cl 8.0 # N

N- ^ 2-chloro-4- (1 ', 1'-difluoro-2', 2'-dichloroethoxy) -phenyjJ-N'-methylurea m.p. 156-158 ° C calc .: 32.0 % Cl 8, 4 # N

Found 1 31.8 % Cl 8.6 56 IT _

+) N- / 3 "-TrIfluorraethy 1-4- (1 ', 1' -difluoro-2 ·, 2'-dichloroethoxy) -phenyl /. N ¹ TN'-dimethylurea mp 167-169 ⁰ C Calc .: 7.4 % N found: 7.1 % Tu

009884/2117 bad ordinal

-Jl- (I ^r , 1'-difluoro-2 ·, 2'-dichloroethoxy) -phenyl7-N ', N'-dimethylurea M.p. 92-94 ° C Calc .: 8.1 ^ N

Found: 8.0 # N

/ 2-chloro - ^ - (i ', 1' -difluoro-2 ", 2'-dichloroethoxy) -phenylJ-N'-me thyl-N * -ine thoxy urine

Mp. 5h - 55 ° C. Calc .: 7.7 # N

Found: 7t9 # N

N- / 3- (1 ', 1 »-Difluoro-2', 2'-dichloroethoxy) - ^ - chlorophenylJ-N» - methyl urea m.p. 137-139 ° C. Calc .: 32.0 # Cl 8, ^% N

Found t $ 31.6> Cl 8.6 JiN

N- / 3- (1 ", 1" -Difluoro-2 ", 2'-dichloroethoxy) - ^ - chlorophenylJ-N'.N"

Ber .; 8.1 ^ N Found: 8.2 # N

dimethyl urea mp 115-H7 ° C calc .; 8.1

N- / 3 ~ (1 «, 1 '-nifluoro-2« ^' - diehlorethoxyJ - ^ - chlorophenylJ-N'-me thyl-N'-methoxy urea

Mp. 96 - 98 ⁰ C Calc .: 7.7 # N

Found: 7.8 % N.

N- / 3-O ·, 1'-difluoro-2 ', 2'-dichloroethoxy) -k-chlorophenyl /' - N «, N

diethylurea m.p. 7 ^ - 76 ° C Ber .: 7.5 ^ N

• Found: 7t5 # N

N- / J- (1 ', 1' -Difluor-2 ', 2' -dichloroethoxy) - ^ - Torom-phenylJ-N 'methylurea Mp. 157-158 ° C. Calc .: 21.2 $ Br 7, ^ ^ N

Found: 20.9 ^ Br $ 7.8> N

N- / 3- (i ', 1'-difluoro-2', 2'-dichloroethoxy) - ^ -

Ber .: Found: 7, ^ ^ N

dimethylurate m.p. 112 ° C, calc .: 7.2

N- / 3-O Ι ¹ 'difluoro-2', 2'-dichloräthoxyJ - ^ - me thyl-N'-me thoxyharns toff

009834/2117 ■

Mp . 9k - 97 ° C. Calc .: 6.9 # .N

Found: 7.2 «6 Ν

N- / J- (1 ^f , 1'-difluoro-2 ', 2'-dichloroethoxy) - ^ - bromophenylT-N', N · diethylurea m.p. 105-1O6 ° C calc.s 6.7 ^ N

Found: 6.7 # N

N- / 3 ~ methoxy-4 - '(i ·, 1' -difluoro-2 ¹ ^ '- methylurea m.p. \ k9 ° C Calc .: 8.5 # N

Found: $ 8.8 > N.

N- / 3-methoxy- k- (1 ', 1 ^f- difluoro-2 ", 2" -dlchloroethoxy) -phenylj -N ^f , N'-dimethylurea

M.p. 159 ° C calc .: 8.2 ^ N

Found: 8, ^ $> N

N- / 3-methoxy-4- (i ', 1'-difluoro-2 ¹ , 2'-dichloroethi> xy) -phenyl7-N'. methyl-N'-methoxyurea

M.p. 92-93 ° C. Ber.ι 7.8 % N

Found: 8.0 $ N

^ - (i ', 1'-difluor-2 ^f , 2'-dichloroethoxy) -5-methyl phenyl7-N'-methylureaff

Mp. 168 ° C calc .: 30.7 $> Cl 8 _t 1 ^ N

Found: 31.2 % Cl 8.3 # N

-4- (i ', 1'-difluoro-2 ·, 2'-dichloroethoxy) -5-methyl phenylJ-N ', N'-dimethylurea

M.p. 145-147 ° C calc .: 29.6 % Cl 7.8 # N

Found: 29.4 # Cl 7.6% N

009884/2117

4- (i · _t 1 "difluoro-2 ^1, 2'-dichloräthoxy) -5-methylphenylJ-N-methyl-N'-methoxyurea ·

Pp. 105 ° C calc .: 28.2 $> Cl 7.6 # N

Found: 27.9 % Cl 7.6 fi N

-3,4 (ΐ ', 1'-difluoro-2 ^1, 2 · -dichloräthoxy) -phenyl7-N' - methylurea mp 136 ⁰ C Ber.j 6.3 # N.

Found; 6.6 # N

_} -3,4- (i · 1 · difluoro-2 ^1, 2'-dichloräthoxy) -phenyl7-N ', N'-diraethylharnstoff mp. 128-130 ⁰ C Calc .: 6.1 56 N f

Found: 6.2 $ N

-3 »4- (i ·, 1 · -difluoro-2 · ^ '- dichloroethoxyJ-phenylJ-N'-methyl-N ^f -methoxyharnetoff

Mp. 69 - 70 ° C Calc .: 29.7 $ Cl 5.9% N

Found: 29.3 % Cl 6.0 # N

Ν- ^ Β18-3Λ- (1 ', 1' -difluoro-2 ¹ ^ '- dichlorathoxyJ-phenylJ-N ¹ , Ν · - diethylurea

Mp. 5t - 53 ° C calc .: 5.7 $ N

Found: 5.7 S ^ N

N- ^ T- (2 '-Chlor-3', 3 '1 * ^f , ^ ¹ , 5 *, 5' -hexafluorocyclopentenyl (1) -oxy) -phenyJ ^ -N ^f -methyl urea

Mp. 142 - ikk ° C calc .: 9.5 $ Cl 7.5 # N

Found: 8.9 # Cl 7.3 # N

Ν- / 5Γ- (2'-chloro-3 *, 3 ', *' »* '15', 5 ^f -hexafluorocyclopentenyl (1) oxy)» pheny ^ 7-N ', N · τdimethylurea

Mp. 130-132 ⁰ C. Calc .: 9.2 $ 7.2 Cl # N

Found: 9.4 $> Cl 7.3 # N

bad cr: o: nal 009ÖUA / 2117

15A2889

2? R- (2'-chloro-3 'i3 ^l »^ ^!, ^' T5 ^l iS'-hexafluorocyclopentenylO) -oxy) -phenyl7-N'-methyl-N'-methoxy urea

Mp. 78 - 80 ⁰ C Calc .: 8.8 $> Cl 6.9 N #

Found: 8.7 # Cl 6.9% N

phenyl7-N · methyl urea

1 ° C

Found: 10.6 % Cl $ 8.5> N

Mp. 150-151 ° C bar .: 10.9 # Cl 8.6 $ N

N-2? T- (2-chloro-3 ^f »3 ¹ , 4 ', 4'-tetrafluorocyclobutenylCi) -oxy) phenyl7-N ^f -methyl-N'-methoxy urea

Mp . 9k - 97 ° C calc .: 10.0 $ Cl 7.9 $ N

Cef .: 10.0 # Cl 7.9 % N

example 1

In a cold frame experiment, the preparations were

Nj / 3-chloro-Jf- (1 ·, 1 «-difluoro-S», S'-dichloroethoxyJ-phenylJ-N ¹ -

methyl urea (l)

N- / 3-chloro-4- (i, 1'-difluoro-2 ¹ , 2'-dichloroethoxy) -phenyl7-N ', N ¹ -

dimethylurea (II) and

N- / 3-Qhlor- ^ r (1 ·, 1 · -difluoro-2 · ^ '- dichloroethoxyJ-phenylJ-N ¹ -

ethyl-N'-methoxyurea (ill)

on their herbicidal effectiveness and their gentle action against * tested over a range of crops. For this were Seeds of the weeds

Field mustard Sinapis arvensis

Chickweed Stellaria media

Dog chamomile, Anfchomis arvensis

Ragwort Senecio vulgaris

009884/2117

bath

and the crops

- 11 -

pea

Broad bean broad bean carrot

S omrne rr ο ggen spring barley spring wheat oats
Corn

Rice (mountain rice) and cotton

Pisum sativum Vicia faba
Phaseolvis vulgar is Daucus carota Seeale cereale Hordeum distichum Triticum aestivum Avena sativa Zea mays

Oryza sativa Gossypium sp.

sown boxes filled with humosome, sandy loam; the On the same day, the soil surface was sprayed with aqueous suspensions of the preparations mentioned. After 5 weeks.! the evaluation, whereby the plants were rated in the usual way on the basis of visual inspection. The values obtained thereby were then converted into $ degree of damage. Served as means of comparison

for the cotton

for the vegetables

for the cereals

N-3,4-dichlorophenyl-N, N'-dimethyl urine » substance (diuron, IV)

N-4- (p-chlorophenoxy) -phenyl-N ^f , NA-dimethyl urea (chloroxuron, V) N-4- (chlorophenyl-N'-methyl-N-methoxyurea (monolinuron, Vl)

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

0-09884 / 2117

- 12 table

Expenditure-

lot

Preparation test plant

Degree of damage for kg active ingredient per ha 0.6 kg / ha 1.2 kg / ha 5.0 kg / ha 0.6 kg / 'ra

Test plant

2 kg / ha 5.0 kg / ha

II

III

IV

O ν
O

to VI

Il in

"* IV

VI

Mustard

Dog chamomile

50% 80 % $ 80 80 % 60% £ 75

70 £ 80 # 6o £ 90%

£ 75 £ 80

60 pounds

95 pounds
90
100 80 90

85
95
70
$ 100
85
95

95 100

90 100

90 100

95

100 100 100 100 100

Chickweed 70 %

$ 100

90 %

100 pounds

70 pounds
90 #

Ragwort

80 90 80 100 70 90

85 pounds 100 i>

£ 90 £ 100

80 ^d p £ 100

90 56 £ 100

90. #

100 £ 80 £ 100 #

£ 100 100% £ 100 £ 100 £ 100 £ 100

100 # 100 %

£ 95 £ 100

95 % £ 100

OQ CX) CO

The values given indicate that the inventive Substances I - III in their effect on emerging two cotyledon weeds are approximately in the same range like the known comparison means. The concentration sufficient for normal weed control is in the Usually between 0.6 and 1.2 kg of active ingredient per hectare “But if you compare the results of this test with those that have been tested Cultivated plants, it clearly shows that the gentle Effect of the claimed compounds is better than that of the comparison agent.

009884/2117

On- Test-" 0.6 kg / ha ι 1.2 kg / ha 1.2 - 14 - e 2 Pre 0, test 1.2 k ₍ - / ha 5.0 kg / 6th kg / ha 1.2 kg / ha 5, 36 Test plant: French bean kg / ha 1, 2 l 36 generally 5. Wall- plant 0 56 tab hurry Crops ready plant 0 % 10 36 ■ 36 a 0.6 36 0 lot tree 0 56 effect on I. carrot 30 56 0 * '0 Pre wool ο 56 30 % 0 « kg / ha 5.0 kg / ha II 20 56 40 % 0 56 10 # 0 56 20 I. ready 0 ί : jv 0 0 56 0 f) Ii ^- JCp / Vi yes
IV IVc ^ / Xx C *. I. 10 # 30 < 0 * 20 56 0 56 II 6 $ 0 Test plant: broad bean 0 56 IV Test plant: pea I 0 56 kff / ha Oj 6 kg ^ / ha 0.6 kg / hi 5.0 3 & 40 56 * 0 36 'Hi Pre 0 fa 10 « £ 0 56 O ready ο 56 20 \ 36 20 56 O
ΙΤΊ I. 10 # 40 ⁽ cn II CD V KJ , 0 kg / ha 40 10 40

Pre- test plant: rye Test plant: barley ready 0.6 kg / ha 1.2 kg / ha 5.0 kg / ha 0.6 kg / ha 1.2 kfc / ha 5.0

Tea plant: wheat 0.6 kg / ha 1.2 kg / ha

5.0

I. 0 5 ° 0% 0 36 0 56 0 3 & 20th % 0 56 36 0% 0 96 56 - * II 0 56 0 # 30 56 0 56 20 36 25th 56 0 36 36 ο 56 10 36 56 · cn III 0 56 0 56 30 56 0 96 30 # 40 56 0 56 * ο 56 20th ss VI 30 56 80 56 100 56 30 56 60 36 90 56 40 * 70 56 100 5.0 kg / ha 36 00 Pre Test plant: oats Tea plant : Corn Test plant : Rice 10 CO ready 0.6 kg / ha 1, 0.6 kg / ha 1 , 2 kg / ha 5.0 kg / l ha 0.6 kg / ha 1 , 2 kg / ha 20th I. 0 56 0 56 0 56 0 0 0 56 30th II 0 56 0 56 0 56 10 0 10 56 90 III 0.56 0 36 0 3t 0 * 0 20 % TV IQ $ < -2 £ L ^ 50 _ .., ^ o 50 56 , 2 kg / ha 5.0 kg / ha 0 56 10 56 0 56 10 56 0 56 0 56 So..*. 100 <

Specifically, I and II surpass in cotton, pea, field bean and French bean, II in carrot, and all 3 claimed Compounds I - III on the cereal types clearly represent the comparison agents with regard to their gentle effect. In doing so, lead also significant overconcentrations may lead to less damage.

The clear advantage of the named connections is therefore * in comparison to the respective comparative means, which is perfectly improved, especially on cotton and French beans, as well as rye, wheat, oats, corn and a number of other crops.

Example 2

N- / 3-methyl ~ 4- (1 ', 1'-difluoro-2', S'-dichloroethoxyJ-phenylJ-N ¹ -.

methyl-N »-methoxyurea (VIl)

N- / 3-methyl - ^ - (i ^f , 1'-difluoro-2 ', 2 · -dichlorätlioxy) -phenylJ-N ¹ ,

N'-dimethylurea (VIII)

N-'i-chlorophenyl-N'-methyl-N ¹ -methoxyurea (monolinuron, IX) N - ^ - chlorophonyl-N'-methyl-N'-isobutinylurea (buturon, X) mixed product of 5 # 2-chloro- ' l, 6-bisethylamino-s-triazine (simazine) and 22.5 $ 2-methylmercapto-fc- ± eot> ropylaminO-6-

(3'-methoxy) -propylamino-s-triazine (Xl) The weeds

Field mustard Sinapis arvensis

Chickweed Stellaria media

Dog chamomile, Anthemis arvensis

and White Goosefoot Chenopodium alb \ un

as well as the crops

, Ή ORIGINAL

00983A / 21 17

Spring wheat Triticum aestivum

Spring barley Hordeum distichum

Oats, Avena sativa

Rice (mountain rice) Oryza oativa

Beta vulgaris sugar beet

and broad bean Vacia faba

-were sown in boxes in homosem, sandy loam, on the same day was the soil surface with an aqueous suspension of the preparations h VII and VIII injected. Two urea preparations IX and X, which are frequently used in cereals, as well as a triazine mixed product that can also be used in cereals, served as comparison agents; 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 remained for 6 weeks until the test was evaluated.

The following table gives an overview of the test results j the application rates are given in kg of active ingredient

^ per ha; the rating values determined are converted

"in" Degree of damage in # ".

Degree of damage for active ingredient per hectare of preparation 0.6 kg / ha 1.2 kg / ha 2.5 kg / ha

Weeds * 'VII 5h $> 73 # 100 ^ VIII 76 # 89 # 100 # IX 92 <fo 99 # 100 ^ X '92 # 100 56 loo 5δ XI 90 # 100 # loo 56

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

009 884/21 17 ^{& AD}

Table 3

Effect on crops

Preparation Test plant: wheat Test plant: barley Test plant: oats

0.6 kg / ha 1.2 kg / ha 2.5 kg / ha 0.6 kg / ha 1.2 kg / ha 2.5 kg / ha 0.6 kg / ha 1.2 kg / ha 2, 5 kg / ha

to

VII $ 0 0 * 1.2 kg / ha 0 56 0 # 0 56 0 * 20 56 0% 0 ^ $ 0 2.5 kg / ha VIII $ 10> 10 # 0 56 20 # ■ 0 # 0 # 30 5δ 100 ^ 0 # 0 ^ o 10 # 0 # IX 20 % 50 56 0 # 95 # 20 # 4o i> 50 # 100 5δ 4o 56 $ 80> 100 56, 20 56 X 65 # 80% 95 # -90 56 55 pounds 95 ^ 100 ^ 100 % j5o 56 90 5δ 100 56 A- 80 # XI 84 56 90 pounds 55% 100 56 70 # 90 ^ 100 ^ 100 # 80 5b 85? 6 100? B ¹ J ^ Test plant: rice $ 80> Test plant : Sugar beet Tea plant : Ackerbonne preparation 0.6 kg / ha " 2.5 kg / ha 0.6 kg / ha 1 , 2 kg / ha 2.5 kg / ha 0.6 kg / ha 1 , 2 kg / ha VII 0% 0 $> 0 $> .0 56 0 # 0 # VIII ο 56 0 56 1O0 # 100 # 0 # 10 # IX 80 pounds 100 # 95 56 100 56 $ 50> 60 56 X 40 # $ 70 100 56 100 5δ XI 70 # 90 56 100 56 100%

O!

00 03 CD

. - 18 -

A comparison of the individual preparations showed that the claimed compounds VII and VIII in their weed action hardly inferior to the comparison means; these destroyed all of them at an application rate of 1.2 kg / ha of active ingredient Weeds, while the new compounds in the same dosage consistently caused very severe damage to the weeds and also completely "destroyed" at higher application rates.

At 1.2 kg / ha, the comparison agents severely or very severely damaged all of the cereal types mentioned, those according to the invention On the other hand, substances at 1.2 and 2.5 kg / ha ™ spared wheat, barley, oats and rice completely or almost completely. Likewise, the broad bean was not or hardly damaged by the new substances, while the comparative agent IX damaged this crop very severely. One of the In addition, the claimed substances VII spared the sugar beet at the stated application rates, while all comparative agents almost completely destroyed this plant species.

The advantage of the claimed substances iiogt thus that they are different crops such as wheat, barley, oats, rice, ψ broad bean, partly sugar beet, clearly preserve in Aufwandraengen in which destroyed a number of important arable weeds or ntark damaged while comparative preparations , which are often used in the cultures mentioned, damage them much more severely.

0098 84/2117

Claims (1)

- 19 claim Weedkillers in a further embodiment of the Subject of patent ...., (Patent application P 15 42 874.7 - Fw 5062), characterized by a Content of haloalkyloxy or haloalkenyloxyphenylureas the general formula JR wherein R _{1 is} a haloalkyl or halocycloalkyl or haloalkenyl or halocycloalkenyl radical having 1-5 C atoms, n ₁ = 1 or 2 ' R. halogen, the alkyl, alkoxy or trifluoromethyl radical, n ₂ = 0 - 3, R ₂ = hydrogen or an alkyl radical with 1- k carbon atoms, R "= an alkyl or alkoxy radical with 1-4 carbon atoms in each case, with the proviso that η .. = 2 when n _g = 0 is. ■ ΙΟ Ütrtertajön (Art / s l Alis. 2 No. J Sentence 3 de »Amendment t0ae. Ν. 4,9. U 009884/2117