DE2129418A1 - Sulfamoyl-substituted 1,3,4-thiadiazole urea compounds - Google Patents

Description

concerning

Sulfamoyl-substituted 1,3,4-thiadiazole urea compounds

The invention relates to a new group of 1,3,4-thiadiazole urea compounds, which are substituted with a sulfamoyl group and which have high herbicidal effectiveness have their use as herbicides and herbicidal agents which contain these compounds.

Some herbicidal 1,3,4-thiadiazole urea compounds are known from German Patent 1,901,672. However, these compounds do not have a sulfamoyl group which is responsible for the high activity of the compounds according to the invention is essential.

109852/1943

- 2 - 1A-39

It has been shown that 1, Z- «4- £ hiadiasQlhariaststoffverbindungen, which are substituted in the 5-position on the! Dhiadiazole ring with a sulfamoyl group, have an excellent herbicidal activity for combating weeds.

The compounds according to the invention have the general formula

• ι
in which R is a hydrogen, an alkyl group with up to

3 carbon atoms or an alkeny group with up to 3

9 - 1 carbon atoms, R one of the groups specified for R or an alkoxy group with up to 3 carbon atoms, R a hydrogen atom or an alkyl group with up to 3 carbon atoms, R ^ a hydrogen atom, an alkyl group with up to 6 carbon atoms, an alkenyl group with up to 6 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, R "^ one of the groups specified for .Is * or an alkoxy group with Mb zn 6 carbon atoms, or R and R ^ a R -C (O) - group where R is a hydrogen atom, an alkyl group with up to 6 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms

4. 5 denotes substance atoms and if one of the groups R ^ or R is an RC (O) - * "group, the other can be a metal ion such as a lithium ion or sodium ion. In these compounds, the alkyl groups can either be straight-chain or be branched.

Examples of the connections according to the invention are:

109852/1943

- 3 - 1Δ-39 535

1- (5-sulfamoyl-1,3 * 4-thiadiazol-2-yl) urea; 1- (5- (methylsulfamoyl) -1, 3, 4-thiadiazol-2-yl) -3-methyl urea; 1- (5- (isopropylsulfamoyl) -1,3,4-thiadiazol-2-yl) -3-methyl urea; 1- (5- (H exylsulfamoyl) -1,3,4-thiadiazol-2-yl) -3-methylurea; 1- (5- (hexylsulfamoyl) -1, 3,4-thiadiazol-2-yl) -3-propylurea; 1- (5- (propylsulfamoyl) -1,3,4-thiadiazol-2-yl) -3-propyl urea; 1- (5-Cyclopropylsulfamoyl) -1, 3,4-thiadiazol-2-yl) urea; 1- (5- (Cyclopropylsulfamoyl) -l, 3,4-thiadlazol-2-yl) -3-methyl urine.

1- (5- (Cyclohexylsulfamoyl) -1,3,4-thiadiazol-2-yl) -3-methylurea 1- (5- (t) icyclopropylsulfamoyl) -l, 3i 4-thiad ± azol-2-yl) urea; 1- (5- (JHcyclopropylsulfamoyl) -1,3 * 4-thiadiazol-2-yl) -3-methylurea;

1- (5- (Mlylsulf amoyl) -1, 3,4-thladiazol-2-yl) -3-methylurea; 1- (5- (I.sopropenylsulfamoyl) -l, 3,4-thladiazol-2-yl) -3-Is opropylurea;

1- (5- (2-hexenyl-sulfamoyl) -i., 3,4-thladiazol-2-yl) -3-methylurea; 1- (5- (methylsulfamoyl) -1,3,4-thiadlazol-2-yl) -3-allyiurea; 1-Hetfayl-1- (5-dlmethylsulfamoyl) -1,3 * 4-thiadiazol-2-yl) -3-

methyl urea;
1-iiethyl-1- (5-propylsulfamoyl) -1,3 * 4-thiadiazol-2-yl) -3-methylurea;

1_ (5_ (Aiiyisulfamoyl) -1, 3,4-thladlazol-2-yl) -3-methoxyurea; 1- (5_ (Cyclopropylsulfamoyl) 1,3 * 4-thiadlazol-2-yl) -3-ethox ^ iarnst. 1- (5- (methoxysulfamoyl) -1,3 * 4-thladlazol-2-yl urea; 1- (5- (^ thoxysulf amoyl) -ί, 3 * 4-thladlazol-2-yl) -3-ally * iurea; i- (5-sulfamoyl-1,3,4-thiadlazol-2-yl) -3,3-ethyl urea; 1- (5- (liethylsulfamoyl) -1, 3 * 4-thiadlazol-2-yl) -3,3-dipropy urea 1-propyl-1- (5- (methylsulfamoyl) -1, 3,4-thiadIazol-2-yl) -3,3-dimethylarea f;

1- (5- (Formylsulfamoyl) -1,3 * 4-thiadiazol-2-yl) -3-methyl urea; 1- (5- (acetylsuYamoyl) -1, 3,4-thiadiazol-2-yl) -3-propyl urea; 1- (5- (yexanoylsulfamoy ^ -1, 3, 4-thiadlazol-2-yl) -3-methyl urea; Sodium salt of 1- (5- (acetylsulfamoyl) -l, 3,4-thiadiazol-2-yl) -

3-methy3urea f;
Potassium salt of 1- (5- (propionylsulfamoyl) -1,3 * 4-thiadiazole-

2-yl) -3-methylurea;
Lithium salt of 1-ethyl-1- (5- (acetylsulfamoyl) -1,3 * 4-thiadiazol-2-yl) -3-ethyl urea; · "

109852/1943

- 4 - 1A-39 535

1- (5- (Ethylsulfamoyl) -1,3,4-thiadiazol-2-yl) -I-methyliarub f; i- (5- (N-Sthyl-N-butylsulfamoyl) -l, 3i4-thiadiazol-2-yl) -3-methyl urea;

109852/1943

- 5 - 1A-39

The subgroup appears to have the highest herbicidal effectiveness

to have, in which R is a hydrogen atom or an alkyl

2 group with up to 3 carbon atoms, R is an alkoxy group with up to 3 carbon atoms or an alkyl group with up to 3 carbon atoms, R- ^ a hydrogen atom, R an alkyl group with up to 6 carbon atoms and R ^ is an alkoxy group with up to 6 carbon atoms or an alkyl group with up to 6 carbon atoms. Preferred compounds of these The subgroup includes compounds in which R

ρ an alkyl group having up to 3 carbon atoms, R is an alkoxy group having up to 3 carbon atoms or an alkyl% group having up to 3 carbon atoms, R ^ is a hydrogen atom, R ^ is an alkyl group having up to 3 carbon atoms and R is an alkoxy group having up to 3 carbon atoms or an alkyl group with up to 3 carbon atoms.

Typical examples of this preferred subgroup are:

109852/1943

β - 1Α-39

1- (5-Dlmethylsufamoyl) -1,3 * 4-thiadiazol-2-yl) -3,3-dimethyl urine. 1- (5- (N-Methyl-N-othylsuifamoyl) -l, 3,4-thladiazol-2-yl) 3,3-

dlmethyliarnstof f;

1- (5- (Diethylsufamoyl) -1, 3,4-tM & diazoI ~ 2-yl) -3,3-dimethyl urine. 1- (5- (N-tert-ethyl-N-propylsulfamoyl) -1,3,4 «thiadiazol-2-yl) -3,3-

dimethy! urea; "_"

1- (5-0ipropylsulfaraoyl) -l, 3,4-thiadiazol-2-yl) -3,3-diinethyl-

hari ^ fabric;
1- (5- (i) imethylsulfamoyl) -l, 3,4-thiadiazol-2-yl) -3-methyl-3-

<Hhyliarea;
1- (5- (J) lmethylsulfamoyl) -1, 3, 4-thiadlazol-2-yl) -3-methyl-

3-propyl urea; "

1- (5- (Dlmethylsulfamoyl) -1, 3, 4-thiadlazol-2-yX) -3, 3-dlathy2harn ^ t. 1- (5- (Dlmethylsulfamoyl) -l, 3,4-thiadiazol-2-yl) -3-ethyl-3-

"propyl urea;

1- (5-> (H imethylsulfamoy3) -l, 3,4-thladlazol-2-yl) -3, 3-dipropy2iarnst. 1- (5- (N-klethyl - ^ - QthylsulfamoyI) -l, 3,4-thladlazol-2-yl) -

3-methyl-3-ethyl. urea;
1- (5- (N-methyl-N-isopropylsulfamoyl) -l ^ i ^ -thladlazol ^ -yl) -

3-methyl-3-äthyliärnstof f;

1- (5- (N-tethyl-N-ethylsulfaraoyl) -1, 3, 4-thladlazol-2-yl) -3-methyl-3-isopropyl urea; ". -> ·

109852/1943

1A-39

1- (5- (N-methyl-N-methoxysulfamoyl) -l, 3, M; hiadiazol-2-yl) -

3,3-dimethylurea;
1- (5- (N-methyl-N-thoxysulfamoyl) -1,3,4-thiadiazol-2-yl) -

3,3-dimethylurea;
1- (5_ (N-methyl-N-propoxysulfamoyl) -1,3,4-thiadiazol-2-yl) -

3,3-dimethylurea;
1- (5-N-methyl-N-methoxysulfamoyl) -1,3,4-thladlazol-2-yl) -

3,> -dl <ethylurea f;
1- (5- (N-methyl-N-methoxysulfamoyl) -1,3,4-thladiazol-2-yl) -

3,3-dipropylurea;
1- (5- (N-methyl-N-methoxysulfamoyl) -l, 3 # 4-thiadiazol-2-yl) -

3-methyl-3-propylurea;
1- (5- (N-Methyl-N-üthoxylsulfamoyl) -1,3,4-thladiazol-2-yl) -

3-methyl-3-ethylurea;
l- (5-Pimethylsulfamoyl) -l, 3, ^ - thiadlazol-2-yl) -3-methyl-

3-methoxyurea;
1- (5- (iyiathylsulf amoyl) -1, 3, 4-thiadiazol-2-yl) -3-methyl-

3-f methoxyharnstof;
1- (5- (N-methyl-N-propylsulfamoyl) -1,3,4-thladlazol-2-yl) -

3-ethyl-3-methoxyurea; "

3-propoxyurea;
1- (5- (N-Hethyl-N-propylsulfamoyl) -1,3,4-thiadiazol-2-yl) -

3-ethyl-3-ethoxyurea; "· 1- (5- (N-methyl-N-methoxysulfamoyl) -1,3,4-thiadiazol-2-yl) -

3-methyl-3-methoxyurea;
1- (5- (N-methyl-N-thoxysulfamoyl) -1,3,4-thiadiazol-2-yl) -

3-ethyl-3-methoxyurea;
1- (5- (N-Propyl-N-methoxysulfamoyl) -1, 3,4-thiadiazol-2-yl) -

3-methyl-3-propoxyurea; "

1- (5- (dimethyl sulfamoyl) -1, 3,4-thiadiazol-2-yl) -3-methyl-urea;

1- (5- (N-methyl-N-hexylsulfamoyl) -1,3,4-thiadiazol-2-yl) -

3,3-dimethylurea; "·

1- (5-CDibutylsulfamoyl) -1,3,4-thiadiazol-2-yl) -3,3-dimethy] urinary.

1- (5- (N-tert-ethyl-N-methoxysulfamoyl) -1,3,4-thiadiazol-2-yl) 3-methylene reagent f;

109852/1943

- 8 - 1A-39 535

1- (5- (N-ethyl-N-propoxysulfamoyl) -1, 3, 4-thiadiazol-2-yl) -

3-ethyl urea; 1- (5- (N-methyl-N-pentyloxysulfamoyl) -1, J>, 4-thiadiazol-2-yl) -

3,5-dimethyl urea; '"

1Ό9852 / 19Λ3

- 9 - 11-39 535

The compounds according to the invention are solid at room temperature. They can be formulated for use as herbicidal agents in the form of wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions and pastes. Wettable powders are normally formulated to contain 25, 50 or 75% or more of active ingredient and normally contain, in addition to the solid carrier, 3 to 10 % of a dispersing agent and, if necessary, 0 to 10% stabilizer (s) and / or other additives such as penetrants or tackifiers. However, the dust are normally prepared as dust concentrates with a similar composition to that of the wettable powders, without a dispersant, and is diluted for the application with further solid carrier to give a composition containing typically 0.5 to 10 $> toxin. Granules are normally produced in a particle size of 0.148 to 0.2 mm (10 to 100 mesh) by agglomeration or impregnation processes. Grains normally contain $ 0.5 to $ 25> additives such as stabilizers, slow release modifiers, binders, etc. Emulsifiable concentrates usually contain 2 to 50% (w / v) of active ingredient in addition to the solvent and, if necessary, a second solvent, 2 to 20 i> (wt./vol.) emulsifiers and 0 to 20% of suitable additives, such as stabilizers, penetrants and corrosion inhibitors. Pastes are prepared so as to obtain a stable flowable product and usually contain 10 to 60 $> active ingredient, suitable 2 to 20 $> additives and as carrier, water or an organic liquid in which the active ingredient is substantially insoluble. Unless otherwise stated, percent in this paragraph is always to be understood as percent by weight.

The herbicidal agents according to the invention can be prepared by reacting the substituted 1,3 _f 4-thiadiazole urea of the formula II:

- 10 -

109852/1943

- 10 - 1A-39 535

II

12 3

in which R, R and R have the meanings given above with chlorine in 33 # acetic acid, with the 5-chlorosulfonyl intermediate arises, which is then combined with ammonia or a compound of the formula

4. 5
in which R and R have the meaning given above, except in the cases in which R ^ or R "^ are acyl groups or metal ions, treated, the desired substituted 5-sulfamoyl-1,3,4-thiadiazol-2-yi - Urea is formed. The chlorination is carried out by introducing chlorine gas into an acetic acid suspension of the urea at a temperature of 5 to 10 ° C. The reaction time is approximately 2 to 3 hours. The reaction in which the sulfamoyl is formed is Conveniently carried out in an inert solvent such as water, methylene chloride or tetrahydrofuran at a temperature of 10 to 35 ° C. and a reaction time of 4 to 18 hours

shown amine or amine derivative can be in the free state be added to the reaction mixture or it can be formed in situ from its acid salt by adding a base.

- 11 -

. 109852/1943

- 11 - 1A-39 535

When 5-sulfamoyl-1,3,4-thiadiazol-2-yl-urea compounds are to be prepared which are attached to the nitrogen atom of the sulfamoyl group with acyl groups or metal ions are substituted, it is necessary to first prepare the sulfonamide by the method described above and this then to react with the corresponding acyl halide or the base, the desired acyl derivative or metal salt arises.

The Ihiadiazolharnstoffverbindungen of formula II may be prepared by reaction of 5-mercapto-2-amino-1,3 "4-thiadiazol with either an isocyanate or an acyl halide M, depending on whether a mono- or di-substitution in 3-position of the Urea molecule is desired. They react with the isocyanate is conveniently carried out hours in an anhydrous solvent such as Xther at a temperature of 25 to 100 ⁰ C and a reaction time 3 to 18 The acylation is conveniently carried out in an anhydrous solvent such as ether or tetrahydrofuran and in the presence of a base / Iinem tertiary amine. The reaction temperature should be in the range from 25 to 90 ^° C., the reaction time being 15 minutes to 3 hours

. They compounds of the invention, the process for their preparation and their herbicidal effect is illustrated by the following examples W. Here parts by weight and parts by volume are in the same ratio as kilograms to liters.

example 1

1- (5- (Simethylsulfamoyl) -1,3,4-thiediaEOl-2 -yl) -3-methy! Urea *

- 12 -

109852/1943

- 12 - 1Δ-39 535

CH, O f _t SO

L IlNHCNHCH

13.3 parts by weight of 5-mercapto-2-amino-1,3,4-thiadiazole, which had been prepared by the process described by Guha (J. Am. Chem. Soc. 44 »1510 (1922)). 200 parts by volume of tetrahydrofuran and 5.7 parts by weight of methyl isocyanate were placed in an Erlenmeyer flask. The flask was closed loosely and left at room temperature for 18 hours. During this time, a colorless plague deposited. The resulting solid was collected on a filter, washed well with water and dried. To obtain 17 parts by weight of 1- (5-mercapto-1,3,4-thiadiazole ~ 2-yl) -3-methyl-urea, ZersetzungSr point 245-250 ⁰ G. The structure was confirmed by elemental and infrared spectroscopic analysis.

17 parts by weight of 1- (5-mercapto-1,3,4-thiadiazol-2-yl) -3-methylurea were placed in a flask which contained 300 parts by weight of 33% acetic acid. The resulting suspension was stirred and the temperature was ^{kept at 10 °} C. for 2 h, chlorine being passed into the mixture. After all of the chlorine had been added, the product was filtered off and washed with ice water. The filter cake was then dissolved in methylene chloride and dried with magnesium sulfate. The solvent was then distilled off in vacuo. Decomposition temperature to obtain 15 parts by weight of 1- (5- (chlorosulfonyl) -1,3,4-thiadiazol-2-yl) -3-methyl-urea, 150 ⁰ C.

3.0 parts by weight of 1- (5- (chloro-sulfonyl) -1,3,4-thiadiazol-2-yl) -3-methylurea and 100 parts by weight of methylene chloride were placed in an Erlenmeyer flask. This solution was saturated with dimethylamine and left to stand for 18 h. All products remained in solution. This solution was then made up of 100 parts

- 13 -

109852/1943

1A-39 535

Washed ice water. The methylene chloride portion was evaporated to dryness, leaving no residue. The aqueous portion was acidified with hydrochloric acid, a colorless pesticide separating out. This solid became filtered off and recrystallized from methanol. 15 parts by weight of 1- (5- (dimethylsulfamoyl) -1,3,4-thiadiazol-2-yl) -3-methylurea were obtained as a colorless solid, melting point 216 ° G (decomp.). The structure was determined by elemental and infrared spectral analysis confirmed.

calculated
found

Analysis (wt .- ^)

N_ S_ C_

26.4 24.2 27.2 26.7 24.7 27.2

4.1 4.2

Example 2

methy! urea

-1,3,4-thiadiazol-2-yl) -3-

NHCNHCH, '

3 parts by weight
To a solution of / 1- (5- (chlorosulfonyl) 1,3,4-thiadiazole-

2-yl) -3-methylurea, which was prepared according to Example 1 1.5 parts by weight of cyclopropylamine were added dropwise in 100 parts by volume of methylene chloride.

The reaction was exothermic and the temperature rose to 35 ° C. When the addition was complete, the vessel with the reaction mixture became closed and left to stand at room temperature for 18 h. The reaction mixture was then 100 parts by volume

- 14 -

109852/1943

1A-39 535

Eiswassser extracted and the aqueous extract acidified with hydrochloric acid, whereby a pesticide separated. The solid was filtered off and dried. 3 piles by weight were obtained 1- (5- (Cyclopropylsulfamoyl) 1,3,4-thiadiazol-2-yl) -3-methylurea. Me structure was confirmed by infrared and elemental analysis.

calculated
found

example

Analysis (wt .- ^) ff S H C

25.3 23.1 4.0 30.3

25.0 23.0 4.0 29.7

dimethy! urea

^0Ά Α

25 parts by weight of crude 1- (5- (chlorosulfonyl) -1,3,4-thiadia zol-2-yl) -3, 3-dimethylurea, which had been prepared according to Example 1, were added to a mixture of 200 YoI .-! Parts of 25 ^ -igifi ^r i? Mithylamine and 50 parts by weight of ice were added. The mixture was stirred for 2 hours and left to stand for 14 hours. At the end of this time, the mixture would be acidified with hydrochloric acid, with a pesticide being deposited. The pesticide was filtered off and recrystallized from methanol

colorless sated. 3 parts by weight / 1- (5- (dimethylsulfamoyl) -

i ^^ - thiadiazol-a-yl ^ Pp ³ . ° 86 to 189 ° 0. The structure was confirmed by elemental and infrared spectral analysis.

- 15 -

109 8 52/1943

- 15 - 1A-39 535

Analysis (wt .- ^)

N_ C _- _H_

calculated 25.1 30.1 4.7

found 25.4 29.7. 4.7

Example 4

1- (5- (N-Methyl-N-methoxysulfamoyl) -1,3,4-thiadiazol-2-yl) · 3-methyl-urea

CH, 0

NHCNHCH,

15 parts by weight Ο, Ν-Dimethylhyäroxylaniinhydrochlorid were VoI. parts water were added to a solution of 6 parts by weight of sodium hydroxide in 75, which had been previously cooled immediately to 10 ⁰ C. This solution was obtained by external cooling during the dropwise addition (10 min) of 12.8 parts by weight of 1- (5-chlorosulfonyl) -1,3,4-thiadiazo_l-2-yl) -3methylurea, which had been prepared according to Example 1 was kept ^{at 10 0} C in 50 parts by volume of tetrahydrofuran. The reaction product was stirred for 4 hours, poured into 200 parts by volume of ice water and acidified by adding hydrochloric acid. A colorless pesticide separated out, which after recrystallization from benzene, 8 parts by weight of 1- (5- (N-methyl-N-methoxysulfamoyl) -1,3,4-thiadiazol-2-yl) -3- methyl urea, bp 190-193 ° C. The structure was confirmed by elemental and infrared spectral analysis. ·

- 16 -

109852/1943

-16- 1A-39 555

Analysis (G-ew .- $)

N_ S ^ _ C_ _H_

calculated 24.9 22.8 25.6 3.9

found 24.9 23.2 26.0 4.1

Example 5

In accordance with the procedures given in the preceding examples, those given in the following table were given further compounds according to the invention prepared.

Table 1"

- 17 -

109852/1943

H H H

(D H H

CU

ω ω

co

- 17 -

W. KN ■ ιη ο OJ CU KN -St - = t I. ιη VO ιη VO m O O
CU νο • Η C- CU CO CO
CU η CO 26.4 ι C-
CU ο
KN C-
KN CU
KN νο
KN ι VL
τ:
ί
α
C. ο VO
ιή
OJ ι I. I. I. I. ο
ΙΛ CO CO ιη CO VO tr CU W. 5.0 C-
CU VO
CU ιη
CU τΗ
CU KN
CU eu O CU ι VO σ \ CJN ιη ο O
CU ■ = t ιη ιη ιη ο CO 27.0 I. CU ^ t CO. ^ t ο
KN -P
α m ιη
ιή
OJ C-
CU ο
KN C-
KN CU
KN C-
KN ι C.
α
pc ϋ
©
£ ON I. ι I. ι I. O C-
OJ .St CO σ \ CO ιη
CU CU η * VO
CU tn
CU CU KN
CU CU ο
VO 255 • 210 TTS- OZT- ο
-H
• O
ΟΛ
■ CO
ιη -ZOS ι
00
O
CU ι
VO
■ Η I.
CO C-
CO
• Η

ιη Mr. »!?. ΙΛ
OJ ^ d- ίυ; M ».«. «.» .ο ο ο

ϋ I ΙΛ

CO

CU

«Λ

^ & ^ c c t

OÜOOOÜ

109852 / 19A3

KN
pi www W. -W W W CU
pi . " η » KN KN KN
O ϋ B O O O C

HP.

P ₁

-μ

4) UX U

<a

Nl

- 18 -

- 18 - 1A-39 535

Example 6

Pre-emergence herbicidal activity has been determined for some typical compounds of the invention, by placing weed seeds in soil that was in large test tubes and containing the compound to be examined had been treated in an amount of 1 or 10 mg per test tube. Chicken millet seeds (Echinochloa crusgalli) and cress (Lepidium sativum) were left in treated soil under controlled temperature and light conditions 13-14 Days grow before treatment effectiveness has been determined. After this time, the development was observed and the effect of the treatment was rated according to a 0 (no effect) to 9 (complete kill) scale. · The results are given in Table 2.

The herbicidal effect after emergence was determined by adding dilute solutions of the compound to be examined in a 1: 1 mixture of acetone and water with 0.5 % wetting agent on cinquefoil (Digitaria sanguinalis) and foxtail (Amaranthus sp), which were controlled Conditions had grown in. at a rate of 1.12 and 11.2 kg / ha. After 12 to 13 days, the effect of the treatment was determined on a scale from 0 (no effect) to 9 (complete destruction). The results of these tests are also given in Table 2.

- 19 -

109852/19

Table 2

fs: ο tr φ

CH,

CH,

CH,

CH, CH,

CH, CH, CH,

CH

CH,

CH,

H H H H H

CH OH

CH

R-

CH (CH ₅ ) ₂

^C 6 ^H 13 CH ₅

CH_0 5

CH ₅ CH,

Before the emergence

Chicken millet

1 10

8 8

8 8

7 8 4 6

0 3

8 8 8 8

1 7

8 8

9 9 1 5

cress

9 9 8

9 6

9 9 8 8

After emergence

Cinquefoil

1 10 JL

9 9 9

8 9 9

7 9 9

9 9 9

8 8 6

9 9 9 9 9 9 9 9 9

8 9 9

9 9 9 232

Foxtail 10

9 9 9 9 9 9 9 9 9 9 9

ΓΌ is »

<■ £> ν! * -Ρ ** VO

- * υπ CXD vji

Claims (8)

Patent claims 1, sulfamoyl-substituted 1,3,4-thiadiazole urea ■ Compounds of the general formula in which R is a hydrogen atom, an alkyl group with up to 3 carbon atoms or an alkenyl group with up to 3 2 1 Carbon atoms, R one of the groups specified for R or an alkoxy group with up to 3 carbon atoms, R a hydrogen atom or an alkyl group with up to 3 carbon atoms, R a hydrogen atom, an alkyl group with up to 6 carbon atoms, an alkenyl group with up to 6 carbon atoms or a Cycloalkyl group with 3 to 6 carbon atoms, R- * one of the groups specified for R ^ or an alkoxy group with up to 6 carbon atoms or R ⁴ and R ⁵ an RC (Of group ⁵ each? Where R is a hydrogen atom, an alkyl group with is up to 6 carbon atoms or a cycloalkyl group of 3 to 6 carbon atoms and when R 1 or R ^{5 is} a R -C (O -) group, the other can be a metal ion such as a lithium, potassium or sodium atom. - 21 - 109852/1 943 - 21 - 1A-39 535 2. Compounds according to claim 1, characterized in that R is a hydrogen atom or a ρ alkyl group with up to 3 carbon atoms, R an alkoxy group with up to 3 carbon atoms or an alkyl group with up to 3 carbon atoms, R · ^ a hydrogen atom, R an alkyl group of up to 6 carbon atoms and R ^ one Denotes an alkoxy group of up to 6 carbon atoms or an alkyl group of up to 6 carbon atoms. 3. Compounds according to claim 2, characterized in that R is a methyl or ethyl group, R a methyl, ethyl, methoxy or ethoxy group, R a Hydrogen atom, R a methyl or ethyl group and R mean a methyl, ethyl, methoxy or ethoxy group. 4. Compounds according to claim 3 »thereby g e k e η η - 1 2 4. 5 draws that R, R, R ^ and R ^ are each one Mean methyl group. 5. Compounds according to claim .3 »thereby g e k e η η - 14 5 draws that R, R ^ and R are each a methyl 2
group and R is a methoxy group. 6. Compounds according to claim 3 »thereby g e k e η η Λ O A indicates that R, R and R each represent a methyl group and R ^ represent a methoxy group. 7. Compounds according to claim 3 »thereby g e k e η η - • indicates that R and R ^ "are each a methyl group 2 5
and R and R each represent a methoxy group. 8. Use of the compounds according to Claims 1 to 4 as herbicidal agents. 109852/1943