CH630234A5 - Herbicidal composition and process for its preparation - Google Patents

Description

The invention relates to a herbicidal composition and a process for its preparation.

1- (1,4-Thiadiazol-2-yl) urea derivatives with herbicidal activity are already known (DE-OS 1 816 696, DE-OS 1 901 672, DE-OS 2118 520). However, these have an insufficient effect against undesired plant growth in cultivated plants.

The object of the present invention is therefore the sheep!

(-)

fungicidal agent which has an excellent action against weeds and a broad selectivity spectrum against crop plants.

i5 The herbicidal composition according to the invention is characterized by a content of at least one new 2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id salt of the general formula I

R-C v C = N-C0-N <

.CH

'CH.

B

(+)

I,

in which R is an aliphatic hydrocarbon radical and B® is a monovalent metal equivalent, as at least one active component.

The process according to the invention for the preparation of the herbicidal composition mentioned above is characterized in that a) dimethylcarbamoyl chloride of the formula II

H_C.

3LC '

J4-CO-C1

TT

with l, 3,4-thiadiazol-2-amines of the general formula III

v N

R- ° \ s / c

-NE.

III

CH / 3

-N-

CO ïst / \

CH.

R-C C.

V

.CH.

N-CO-N ^

IV

where R has the above meaning

\

CH.

30th

and this with metal compounds of the general formula V

B®Ye V

where B® is a monovalent metal equivalent, and Y® is hydrogen, hydroxyl, lower alkoxy or the amino group,

splits,

or that 1- (1,3,4-thiadiazol-2-yl) -3,3-dimethylurea derivatives of the general formula VI

40

N-

■ N

/ »3

R-C

45

^ -NH-CO-N ^

VI

CH.

wherein R is an aliphatic hydrocarbon radical, in the presence of acid-binding agents to 2- (dimethyl-carbamoylimino) -l, 3,4-thiadiazoline-3-carboxylic acid dimethyl amide derivatives of the general formula IV

50

55

where R has the above meaning,

Metal compounds of the general formula V

B®Y® V

in which B® and Y® have the above meanings,

can act and then new 2- (dimethylcarbamoylimino) -1, 3,4-thiadiazolin-3-id salts of the general formula I thus obtained

R-Cv C = 2x'-C0-K <

SX

, CH_

'CE.

, (+)

I,

where R and B® have the above meanings, mixed with formulation auxiliaries.

The labeled compounds are characterized, for example, by a broad soil and leaf herbicidal activity.

630234

4th

kung out. They can be used to control mono- and dicotyledon weeds.

The compounds are preferably pre-emergence and post-emergence arable weeds, such as Sinapis ssp., Stellaria media, Senecio vulgaris, Matricaria chamomilla, Ipomoea purpurea, Chrysanthemum segetum, Lamium amplexicaule, Centaurea cyanus, Amaranthus retroflexuro, alides crusus, myides crusus, also alopecurus myopus , Setaria italica, Sorghum halepense, Lo-lium perenne and other weeds.

To control seed weeds, application rates of 0.5 kg of active ingredient / ha to 5 kg of active ingredient / ha are generally used. In general, the labeled active ingredients prove to be selective in crops such as bush bean, peanut, potato, pea, rice, sorghum and soy.

At higher application rates, the compounds are also suitable, for example, as total herbicides for the destruction or suppression of a wasteland flora during a growing season.

The active compounds can be used either alone, in a mixture with one another or with other active compounds.

Depending on the desired purpose, there are, for example, the following herbicidal active substances which, if appropriate, can also be added to the active new compounds only immediately before use: substituted anilines,

substituted aryloxycarboxylic acids and their salts, esters and amides,

substituted ether,

substituted arsonic acids and their salts, esters and amides,

substituted benzimidazoles,

substituted benzisothiazoles,

substituted benzthiadiazinone dioxides,

substituted benzoxazines,

substituted benzoxazinones,

substituted benzothiazoles,

substituted benzthiadiazoles,

substituted biurets,

substituted quinolines,

substituted carbamates,

substituted aliphatic carboxylic acids and their salts,

Esters and amides,

substituted aromatic carboxylic acids and their salts,

Esters and amides,

substituted carbamoylalkyl thio- or dithiophosphates, substituted quinazolines,

substituted cycloalkylamidocarbonthiol acids and their

Salts, esters and amides,

substituted cycloalkylcarbonamidothiazoles,

substituted dicarboxylic acids and their salts, esters and amides,

substituted dihydrobenzofuranyl sulfonates,

substituted disulfides,

substituted dipyridylium salts,

substituted dithiocarbamates,

substituted dithiophosphoric acids and their salts, esters and amides,

substituted ureas,

substituted hexahydro-lH-carbothioates,

substituted hydrogen ions,

substituted hydrazides,

substituted hydrazone salts,

substituted isoxazole pyrimidones,

substituted imidazoles,

substituted isothiazole pyrimidones,

substituted ketones,

substituted naphthoquinones,

substituted aliphatic nitriles,

substituted aromatic nitriles,

substituted oxadiazoles,

substituted oxadiazinones,

substituted oxadiazolidinediones,

substituted oxadiazinediones,

substituted phenols and their salts and esters, substituted phosphonic acids and their salts, esters and amides,

substituted phosphonium chlorides,

substituted phosphonalkylglycins,

substituted phosphites,

substituted phosphoric acids and their salts, esters and

Amides,

substituted piperidines,

substituted pyrazoles,

substituted pyrazole alkyl carboxylic acids and their salts,

Esters and amides,

substituted pyrazolium salts,

substituted pyrazolium alkyl sulfates,

substituted pyridazines,

substituted pyrimidines,

substituted pyrrolidones,

substituted pyridazones,

substituted pyridinecarboxylic acids and their salts, esters and amides,

substituted pyridines,

substituted pyridine carboxylates,

substituted pyridinones,

substituted pyrimidones,

substituted pyrrolidine carboxylic acids and their salts,

Esters and amides,

substituted pyrrolidines,

substituted arylsulfonic acids and their salts, esters and

Amides,

substituted styrenes,

substituted tetrahydro-oxadiazinediones,

substituted tetrahydromethanoindenes,

substituted T etrahy drr-diazol-thione,

substituted tetrahydro-thiadiazine-thione,

substituted tetrahydro-thiadiazole diones,

substituted thiadiazoles,

substituted aromatic thiocarboxamides, substituted thiocarboxylic acids and their salts, esters and amides,

substituted thiol carbamates,

substituted thiophosphoric acids and their salts, esters and amides,

substituted triazines,

substituted triazoles,

substituted tetrahydro-oxadiazole diones,

substituted thioureas,

substituted uracils and substituted uretidinediones.

In addition, other additives can also be used, for example non-phytotoxic additives which give herbicides a synergistic increase in activity, such as wetting agents, emulsifiers, solvents and oily additives.

The labeled active ingredients or their mixtures are in the form of preparations, such as powders, sprinkling agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and, if appropriate, wetting agents, adhesives, emulsifiers and / or dispersing aids applied.

s

10th

15

20th

25th

30th

35

40

45

50

55

60

65

5

Suitable liquid carriers are e.g. Water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide and mineral oil fractions.

As a rule, mineral earths are suitable as solid carriers, e.g. Tonsil, silica gel, talc, kaolin, Attaclay, limestone, silica and vegetable products, e.g. Flour.

Examples of surface-active substances are: calcium lignin sulfonate, polyoxyethylene alkylphenyl ether, naphthalene sulfonic acids and their salts, phenol sulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.

The proportion of the active ingredient (s) in the various preparations can vary within wide limits. For example, the agents contain about 10 to 80 percent by weight of active ingredients, about 90 to 20 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active agents.

R-

R-

R-

For the sake of simplicity, not all limit formulas have been taken into account in general formula I.

The reaction of the reactants in the preparation of the herbicidal composition can take place between 0 and 100.degree. C., but generally at room temperature.

The reactants are usually used in approximately equimolar amounts for the synthesis of the new active compounds. Suitable reaction media are, for example, polar organic solvents, alone or in a mixture with 50 water. Your choice depends on the use of the B®Ye metal compounds, for example, according to generally known criteria. Examples of solvents or suspending agents which may be mentioned are: acid amides such as dimethylformamide, acid nitriles such as acetonitrile, alcohols 55 such as methanol or ethanol, ethers such as tetrahydrofuran and many others.

To synthesize the compounds of the general formula IV, all customary acid-binding agents can be used as acid binders, such as organic bases, expediently 60 tert-amines, for example triethylamine, N, N-dimethylaniline or pyridine derivatives, or inorganic bases , for example oxides, hydroxides, carbonates and alkane acid salts or alkali and alkaline earth metals, where liquid acid binders can simultaneously serve as solvents. 6s

Finally, the active new compounds formed are generally isolated by distilling off the solvents used at normal or reduced temperatures

The agents can be applied in a customary manner, for example using water as a carrier in spray liquor amounts of about 100 to 1000 liters / ha. Application of the agents in the so-called “low-volume” and “ultra-low-volume method” is generally possible, as is their application in the form of so-called microgranules.

Of the labeled compounds, those according to the invention can in particular be used which correspond to the general formula I in which R is a Q-Q-alkyl radical and B is an alkali metal atom, preferably a lithium, sodium or potassium atom.

Suitable alkyl radicals for this are, for example, straight-chain and branched alkyl radicals, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1-methylbutyl, 1-ethyl-propyl, n-hexyl, isohexyl, 1,1-dimethylbutyl and others.

The active new compounds are salts which are ionogenic, corresponding to the following polar limit formulas, pressure or by precipitation with less polar organic solvents, for example with ketones such as acetone or ethers such as diisopropyl ether and others.

The following examples can illustrate the preparation of the new active compounds.

example 1

27.1 g of 5-ethyl-2- (dimethylcarbamoylimino) -l, 3,4-thia-diazoline-3-carboxylic acid dimethylamide, mp 100 ° C., are suspended in 150 ml of methanol. A solution of 4 g of sodium hydroxide in 100 ml of methanol is added dropwise at room temperature with stirring. After 3 hours, a clear solution is obtained, from which the methanol is then distilled off in vacuo. The remaining residue is digested with acetonitrile, suctioned off from the detergent and dried at 80 ° C. in vacuo.

Yield: 15.5 g (69.8% of theory) of 5-ethyl-2- (dimethyldarbamoylimino) -1,3,4-thiadiazolin-3-id, sodium salt, mp:> 250 ° C.

C7H11N4NaOs MG: 222.26 analysis

Calculated: C 37.83 H 4.99 N 25.21 Na 10.34% Found: C 37.70 H 5.05 N 24.95 Na 10.76%

Example 2

8.1 g (l- (5-tert-butyl-l, 3,4-thiadiazol-2-yl) -3,3-dimethylurea, mp. 121 ° C., together with 0.853 g of Li

.51

(-)

Η / CIS

L J = N-CO-N <B (+ as

\

R-

CH "

V

/ CH3

-N-CO-N

/

\

ch "

| 0 | (_) CH_ -N = C-N <^

CH.,

(+)

B, or in general terms

N N (-) 0

»1 1

-s / VC- <

CH-

CH.

B ^ + \ are present.

630234

thium hydroxide dissolved in 70 ml of methanol. The solution is then concentrated in vacuo, the residue is triturated with a diisopropyl ether-isopropanol mixture, suction filtered and washed with diethyl ether. After drying in vacuo at 120 ° C., 7.8 g (93.8% of theory) of 5-tert-butyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id, lithium salt, with a melting point> 250 ° C.

C9H15LiN4OS

Analysis Calculated: Found:

MG: 234.26

C 46.15 C 46.04

N 6.45 H 6.33

N 23.92 N 23.73

Li 2.96% Li 2.68%

The following active compounds can be prepared in an analogous manner.

Name of the connection

Physical constant

2- (dimethylcarbamoylimino) -5-isopropyl- mp: 288 ° C l, 3,4-thiadiazolin-3-id, sodium salt (decomposition)

5-tert-butyl-2- (dimethylcarbamoylimino) - mp .: 306 ° C. l, 3,4-thiadiazolin-3-id, sodium salt (decomposition)

5-ethyl-2- (dimethylcarbamoylimino) - mp .:> 250 ° C

1,3,4-thiadiazolin-3-id, potassium salt 5-ethyl-2- (dimethylcarbamoylimino) - mp:> 250 ° C

l, 3,4-thiadiazolin-3-id, lithium salt 2- (dimethylcarbamoylimino) -5-propyl- mp .:> 250 ° C 1,3,4-thiadiazolin-3-id, sodium salt 5-isobutyl-2- ( dimethylcarbamoylimino) - mp .:> 250 ° C 1,3,4-thiadiaziolin-3-id, sodium salt 2- (dimethylcarbamoylimino) -5-isopropyl- mp:> 250 ° C l, 3,4-thiadiazolin-3- id, lithium salt

2- (dimethylcarbamoylimino) -5-methyl mp:> 250 ° C 1,3,4-thiadiazolin-3-id, sodium salt 5- (l, l-dimethylbutyl) -2- (dimethyl mp:> 250 ° C carbamoylimino) -1,3,4-thiadiazoline-

3-id, lithium salt

5-butyl-2- (dimethylcarbamoylimino) - mp:> 250 ° C

l, 3,4-thiadiazolin-3-id, sodium salt 5-butyl-2- (dimethylcarbamoylimino) - mp:> 250 ° C

1,3,4-thiadiazolin-3-id, lithium salt

The active compounds are normally colorless and odorless crystalline bodies which are excellently soluble in water, readily soluble in polar organic solvents such as carboxamides, for example dimethylformamide, sulfoxides, for example dimethyl sulfoxide, lower alcohols, for example methanol and ethanol Carbonitriles, for example acetonitrile, and are insoluble in hydrocarbons, halogenated hydrocarbons, ethers and ketones.

The following exemplary embodiments can be used to explain the mode of action of the new active 2- (dimethylcarbamoylimino) -! , 3,4-thiadiazolin-3-id derivatives are used.

Example 3

40 In the greenhouse, the active compounds listed in the table were applied at 5 kg of active ingredient / ha, dissolved in 5001 water / ha, to Sinapis sp. and Solanum sp. sprayed as test plants in the pre- and post-emergence process. 3 weeks after the treatment, the 45 treatment result was rated, whereby

0 = no effect and 4 = destruction of plants. As can be seen from the table, the test plants were generally destroyed in this way.

Active connection pre-emergence post-emergence

Sinapis Solanum Sinapis Solanum

2- (dimethylcarbamoylimino) -5-isopropyl-

l, 3,4-thiadiazolin-3-id, sodium salt 4 4 4 4

5-tert-butyl-2- (dimethylcarbamoylimino) -

1,3; 4-thiadiazolin-3-id, sodium salt 4 4 4 4

5-ethyl-2- (dimethylcarbamoylimino) -

1,3,4-thiadiazolin-3-id, sodium salt 4 4 4 4

5-ethyl-2- (dimethylcarbamoylimino) -

l, 3,4-thiadiazolin-3-id, potassium salt 4 4 4 4

5-ethyl-2- (dimethylcarbamoylimino) -

l, 3,4-thiadiazolin-3-id, lithium salt 4 4 4 4

2- (dimethylcarbamoylimino) -4-propyl-

l, 3,4-thiadiazolin-3-id, sodium salt 4444

7

630 234

Active connection

Pre-emergence of Sinapis Solanum

Post-emergence Sinapis Solanum

6-isobutyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id, sodium salt 4

2- (dimethylcarbamoylimino) -5-isopropyl-l, 3,4-thiadiazolin-3-id, lithium salt 4

5-tert-butyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id, lithium salt 4

2- (dimethylcarbamoylimino) -5-methyl-l, 3,4-thiadiazolin-3-id, sodium salt 4

5- (1,1-dimethylbutyl) -2- (dimethylcarbamoyl-imino) -l, 3,4-thiadiazolin-3-id, lithium salt 4 5-butyl-2- (dimethylcarbamoylimino) -l, 3,4-thjiadiazoline- 3-id, sodium salt 4

5-butyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id, lithium salt 3

4 4 4 4 4 4 4

4 4 4 4 4 4 4

4 4 4 4 4 4 4

Example 4

In the greenhouse, the plants listed were applied uniformly to the soil before the crop / ha with 500 liters of water / ha on the soil using the agents in the soil indicated. The results show that the invention

wall quantity treated. For this purpose, the agents were more effective than the known Mitais aqueous solution in an application amount of 1 kg of agent.

Pre-emergence process

Active connection

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2- (dimethylcarbamoylimino) -5-iso-propyl-1,3,4-thiadiazolin-3-id,

Sodium salt 1

5-tert-butyl-2- (dimethylcarbamoyl-imino) -1,3,4-thiadiazolin-3-id,

Sodium salt 1

5-ethyl-2- (dimethylcarbamoyl-imino) -l, 3,4-thiadiazolin-3-id,

Sodium salt 1

5-ethyl-2- (dimethylcarbamoyl-imino) -1,3,4-thiadiazolin-3-id,

Potassium salt 1

5-ethyl-2- (dimethylcarbamoyl-imino) -l, 3,4-thiadiazolin-3-id,

Lithium salt 1

2- (dimethylcarbamoylimino) -5-propyl-l, 3,4-thiadiazolin-3-id,

Sodium salt 1

5-isobutyl-2- (dimethylcarbamoyl-imino) -l, 3,4-thiadiazolin-3-id,

Sodium salt 1

Comparative means (according to DE-OS 1 901 672)

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

3,3-dimethyl-urea 1 1 10 10 9 10 6 10 500 260 4006

0-00-0 3 0 0 -

10 10 8 10 10 10 0 0 0 0 0 0 3 0 0 0 10 10 10 10 10 9 1 0 0 0 3 0 - 0 0 -

Example 5

The plants listed were sprayed afterwards in the greenhouse. Here, too, 3 weeks after the treatment, when treated with the agents listed in an agent according to the invention, treated with a high selectivity with an applied amount of 1 kg of active ingredient / ha. The agent was effective against weeds. The comparative

were evenly distributed over the plants for this purpose did not show the good effect.

630 234

Follow-up procedure

Active connection

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2- (dimethylcarbamoylimino) -

5-isopropyl-1,3,4-thiadiazolin-3-id,

Sodium salt

7

- 0

0

0

0

0

0

0

0

0

0

5-tert-butyl-2- (dimethylcarbamoyl-

imino) -1,3,4-thiadiazolin-3-id,

-

Sodium salt

8th

0

0

0

0

0

0

0

0

0

0

5-ethyl-2- (dimethylcarbamoyl-

imino) -l, 3,4-thiadiazolin-3-id,

Sodium salt

- 10th

7

10th

10th

10th

9 0

0

2nd

1

-

0

0

0

0

3rd

5-ethyl-2- (dimethylcarbamoyl-

imino) -l, 3,4-thiadiazolin-3-id,

Potassium salt

- 10th

-

9

8th

7

8 0

0

3rd

1

0

0

0

0

1

3rd

5-ethyl-2- (dimethylcarbamoyl-

imino) -1,3,4-thiadiazolin-3-id,

Lithium salt

- 10th

7

9

10th

10th

8 0

0

0

0

-

0

3rd

0

1

3rd

2- (dimethylcarbamoylimino) -

5-propyl-l, 3,4-thiadiazolin-3-id,

Sodium salt

- 8th

9

9

10th

8 0

0

0

0

2nd

0

1

0

0

1

5-isobutyl-2- (dimethylcarbamoyl-

imino) -1,3,4-thiadiazolin-3-id,

Sodium salt

9

7

9

7

9 0

0

4th

0

0

0

0

0

4th

2- (dimethylcarbamoylimino) -

5-isopropyl) -1,3,4-thiadiazolin-3-id,

Lithium salt

8th

- 0

0

0

0

0

0

0

0

0

0

5-tert-butyl-2- (dimethylcarbamoyl-

imino) -l, 3,4-thiadiazolin-3-id,

Lithium salt

- 0

0

0

0

0

0

0

0

0

0

Comparative means (according to DE-OS 1 901 672)

1 - (5-ethyl-1,3,4-thiadiazole-

2-yl) -3,3-dimethyl-urea

8 10

10th

10th

10th

10th

10 1

4th

8th

2nd

8th

8th

10th

1

5

10th

S

Claims (18)

630234 2- (dimethylcarbamoylimino) -5-methyl-l, 3,4-thiadiazoline- 2- (dimethylcarbamoylimino) -5-propyl-l, 3,4-thiadiazoline- 2- (DimethyIcarbamoylimino) -5-isopropyl-l, 3,4-thiadia-zolin-3-id, sodium salt contains. 2. Herbicidal composition according to claim 1, characterized in that in the salts of the general formula I the radical R is a Cj-Cg-alkyl radical and B is an alkali metal atom. 2nd PATENT CLAIMS 1. Herbicidal agent, characterized by a content of at least one new 2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id salt of the general formula I in'-' R "C \ .C = N-CO-N < , CH. CH. B (+) I., in the R an aliphatic hydrocarbon residue, and B® mean a monovalent metal equivalent as at least one active component. Contains 3-id, sodium salt. Contains 3-id, sodium salt. 3-id, contains potassium salt. 3. Herbicidal composition according to one of claims 1 to 2, characterized in that the metal equivalent means a lithium, sodium or potassium atom. 4. Herbicidal composition according to claim 1, characterized in that it contains as at least one active compound the 5-ethyl-2- (dimethylcarbamoylimino) -1,3,4-thiadiazolin-3-id, sodium salt. Contains 5-butyl-2- (dimethylcarbamoylimino) -1,3,4-thiadiazolin-3-id, sodium salt. 5. Herbicidal composition according to claim 1, characterized in that it contains 5-tert-butyl-2- (dimethylcarbamoylimino) -1,3,4-thiadia-zolin-3-id, lithium salt as at least one active compound. 6. Herbicidal composition according to claim 1, characterized in that it is at least one active compound 7. Herbicidal composition according to claim 1, characterized in that it contains 5-tert-butyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadia-zolin-3-id, sodium salt as at least one active compound. 8. Herbicidal composition according to claim 1, characterized in that it contains at least one active compound 5-ethyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadiazoline- 9. Herbicidal composition according to claim 1, characterized in that it contains as at least one active compound the 5-ethyl-2- (dimethylcarbamoylimino) -1,3,4-thiadiazolin-3-id, lithium salt. 10th H3C \ ^ N-CO-Cl II 10. Herbicidal composition according to claim 1, characterized in that it is at least one active compound 11. Herbicidal composition according to claim 1, characterized in that it contains 5-isobutyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id, sodium salt as at least one active compound. 12. Herbicidal composition according to claim 1, characterized in that it contains the 2- (dimethylcarbamoylimino) -5-isopropyl-l, 3,4-thiadia-zolin-3-id, lithium salt as at least one active compound. 13. Herbicidal composition according to claim 1, characterized in that it is at least one active compound 14. Herbicidal composition according to claim 1, characterized in that it contains the 5- (l, 1-dimethylbutyl) -2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id, lithium salt as at least one active compound. 15 H, C ' With 20th l, 3,4-thiadiazol-2-amines of the general formula III -N II H-C x C-Mz III 25 wherein R is an aliphatic hydrocarbon radical, in the presence of acid-binding agents to give 2- (dimethyl-carbamoylimino) -l, 3,4-thiadiazoline-3-carboxylic acid dimethyl amide derivatives of the general formula IV 30th ch / 3 co-n -n- / \ ch, r-c 40 : c / CH- V \ N-co-N / ' ^ • CH. iv 45 where R has the above meaning, implemented and this with metal compounds of the general formula V B®Y® V wherein B® is a monovalent metal equivalent and Y® is hydrogen, hydroxyl, lower alkoxy or the amino group, 50 splits, or that b) l- (l, 3,4-thiadiazol-2-yl) -3,3-dimethylurea derivatives of the general formula VI 55 60 n- • n ch. r-c x-nh-co-nC \ s7 ch. vi in which R has the above meaning, Metal compounds of the general formula V B®y © V 65 in which B® and Ye have the above meanings, can act and then new 2- (dimethylcarbamoylimino) -1, 3,4-thiadiazolin-3-id salts of the general formula I thus obtained nI ^ R-C s. C = N-CO-N I, 630234 where R and B® have the above meanings, mixed with formulation auxiliaries. 15. Herbicidal composition according to claim 1, characterized in that it is at least one active compound 16. Herbicidal composition according to claim 1, characterized in that it contains as at least one active compound the 5-butyl-2- (dimethylcarbamoylimino) -l, 3,4-thiadiazolin-3-id, lithium salt. 17. A process for the preparation of the herbicidal composition according to claim 1, characterized in that a) dimethylcarbamoyl chloride of the formula II 18. The method according to claim 17, characterized in that the reaction according to variant b) is carried out using a solvent.