DE2341816A1 - HERBICIDES 1,3,4-THIADIAZOL-2-YL URBAN MATERIAL - Google Patents

Description

Thiadiazolylureas with herbicidal action are already known (German Offenlegungsschriften Nos. I.816.696 and No. 2,044,492). However, these funds are not sufficient Effect against grass weeds and dicotyledon weeds and are also unsatisfactory in their selectivity. when used in agricultural crops.

The object of the present invention is therefore to create an agent effective against grass weeds and dicotyledonous plants Plants and properties selective towards agricultural crops.

According to the invention, this object is achieved by a means ^:. ' which is characterized by a content of at least one compound of the general formula

Ν— Ν

509809/1 181

SCHERINGAG

ß 1 R patent department

O IO August 10, 1973

in the

R is an aliphatic hydrocarbon radical with 4 to 8 Carbon atoms,

Rp is hydrogen or - in the case that η = O - methyl and η represent the numbers 0, 1 or 2, The invention therefore relates to compounds of the general formula (I), processes for their preparation and herbicidal Agents containing these compounds.

The radical R denoted in the general formula I are to be understood as aliphatic hydrocarbon radicals e.g. η-butyl, isobutyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, tert. Butyl, isopentyl, neopentyl, methylpropyl, 1-methylbutyl, 1,3-dimethylbutyl, 1,2-dimethylpropyl, l-ethylpropyl, Ethylpentyl and ethylbutyl.

The compounds according to the invention are distinguished by a broad soil and leaf herbicidal action and can be used for ' Control of monocotyledon and dicotyledon weeds used in agricultural crops.

Agricultural crops of this type are, for example, susceptible to cereals, potatoes, maize, rice, seed sorghum, seed tomatoes, peanuts, peas and other legumes, woody plants and plantations.

509809/1181

SCHERINGAG Q 1 β patent department

b I O ^. August 1973

• a »

Weeds that can be controlled are e.g. Stellaria media, Senecio vulgaris, Matricaria chamomilla, Lamium arnplexicaule, Centaurea cyanus, Amarantus retroflexus, Galiurn aparine, Chrysanthemum, segetum, Ipomea sp., Sinapis sp., Solarium sp., Chenopodaceae, Allium sp., Avena fatua, Alopecurus myosuroides, -Echinochloa crus galli, Setaria italica, Setaria faberi, Poa annua and Lolium perenne.

Depending on the compound and field of application, application rates of about 0.55 are generally used to control seed weeds kg of active ingredient / ha required, whereby the application can take place in the pre-emergence as well as in the post-emergence method.

The active ingredients can be used either alone or as a mixture of several active ingredients. If necessary, can other pesticides or pesticides, e.g. fungicides, nematicides or other agents, depending on the desired purpose can be added. An addition of fertilizers is also possible, for example.

If a broadening of the spectrum of activity or destruction other herbicides can also be added. For example, are suitable active ingredients from the group of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxylic acids and halocarboxylic acids, halogenated

509809/1181

. _v . SCHERINGAG

OO / Λ Q 1 R Pt «nlabt« i! Ung

^ O k IO IO August 10, 1975

te benzoic acids, carbamic acid and thiocarbamic acid esters, Urea, 2, j5j6-Trichlorobenzyloxypropanol. ·. and rhodanic agents and others. Among other accessories are e.g. also non-phytotoxic additives to be understood, which in the case of herbicides have a synergistic increase in effectiveness result, such as wetting agents, emulsifiers, solvents and oily additives.

The active ingredients are expedient in the form of preparations such as powders, scattering agents, granules, solutions, emulsions or suspensions with the addition of liquid and / or solid carriers or diluents and optionally of wetting agents, adhesives, emulsifying agents and / or dispersing agents.

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

Mineral earths are suitable as solid carriers, e.g. Tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid and vegetable products such as flours.

The following surface-active substances should be mentioned: e.g. calcium lignosulfonate, Polyoxyethylene octylphenol ether, naphthalene

509809/1 18Ί

, SCHERINGAG

Stand-by department

2341816 ίο. August 1973

sulfonic acids, phenolsulfonic acids, formaldehyde condensates, Fatty alcohol sulfates and fatty acid alkali and alkaline earth salts.

The proportion of the active ingredient (s) on average can be in vary widely. For example, the agents contain about 20 to 80 percent by weight of active ingredients, for example 80 to 20 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active substances Fabrics.

The previously unknown compounds of the formula (I)

can be established, for example, by making connections

the general formula

N-N

R ₁ - ^s (o) _n J \ !! - ν - η (H),

a) if Rp is hydrogen, with methyl isocyanate the formula

CH ₅ - N * C »0. (III)

can react dissolved in an organic solvent or, if R _{2 is} methyl,

b) with carbamoy halides of the general formula

Shark - CO - N <^ (IV). -6-

CH ₅

509809/1181

SCHERINGAG

*) 3 L 1 8 1 R flattening

August 10, 1973

in the presence of acid-binding agents, dissolved in inert Solvents, reacts or

c) with carbonic acid ester halides, preferably carbonic acid phenyl ester chloride or thiocarbonic acid S-phenyl ester chloride, or with phosgene in the presence of an acid-binding agent, dissolved in inert solvents, and then the reaction product with dimethylamine of the formula _Cf j

HN <(V)

brings to implementation and the process products obtained optionally with oxidizing agents, preferably organic hydroperoxides, peracids or inorganic oxidizing agents treated, where R, and η have the above meaning and Hai represents a halogen atom.

For the preparation of the compounds of formula (I) can, if η = 1 means, as the oxidizing agent, preferably organic hydroperoxides, such as tert-buty! hydroperoxide, or peracids, such as m-chloroperbenzoic acid and others, or N-halo acid amides, such as N-bromosuccinimide, or inorganic compounds such as hydrogen peroxide, sodium meta-periodate and others will. It is advantageous to use two oxidation equiva-

509809/1181

SCHERINGAG

August 10, 1973 * τ
lente of the oxidizing agent or a small excess

to a mol of the sulfur compounds at temperatures of about 0 to 60 ⁰ C a.

For the preparation of compounds of the formula (I) with η meaning 2, in addition to those already mentioned Oxidizing agents inorganic agents such as chlorine or potassium permanganate, Use chromic acid or its salts or nitric acid in the temperature range from about 0 to 120 C.

For this purpose, it is expedient to use one mole of thio compound four oxidation equivalents or - if desired - an excess of this used, i.e. at least twice as much as for the sulfoxidation described above to produce the compounds marked with η = 1.

The reaction media can expediently be organic Solvents such as carboxylic acids, e.g. acetic acid, ethers, e.g. dioxane, ketones, e.g. acetone, acid amides, e.g. dimethylformamide, Use nitriles, e.g. acetonitrile, or others, either alone or in a mixture with water.

The carbonic acid ester halides used are preferably carbonic acid phenyl ester chloride and thiocarbonic acid-S-phenyl ester chloride and thus obtain e.g. N- (5-alkylsulfonyl-1,5,4-thiadiazol-2-yl) -thiocarbamic acid-S-phenyl ester, which are then reacted with dimethylamine.

In processes in which hydrohalic acid is formed, sets

509809/1181

SCHERINGAG

_w ß ^ August 10, 1973 organic bases such as tertiary amines, e.g.

Triethylamine, or dimethylaniline, pyridine bases or suitable ones inorganic bases, such as oxides and hydroxides of the alkali and alkaline earth metals.

The reaction with carbonic acid chlorides is carried out between about -10 ⁰ C and 15O ⁰ C, the subsequent reaction with dimethylamine of the formula (V) is between about -10 C and 100 C, but generally at room temperature.

Solvents which are inert towards the reactants are used as reaction media. These include the following: aliphatic and aromatic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, chlorinated ethylene, ketones, ethereal Compounds, N, N-diakylated amides and nitriles, etc. The starting materials for carrying out the processes described are known per se, or can be prepared by processes known per se.

The following examples illustrate the preparation of the inventive Links.

l _J 3-Dimethyl-1- (5- * isobutylthio-l _J 3 _J 4-thiadia? _J Ql-2-yl) urea 162.5 g of 2-isobutylthio-5-methylamino-1,3,4-thiadiazole are dissolved in 200 ml of tetrahydrofuran. To this, ^ 5> 5 g of methyl isocyanate are added dropwise with stirring. After standing overnight, it is poured onto 1.5 l of ice water, and the precipitated substance is filtered off with suction and recrystallized from acetonitrile. One obtains 187 g (9Q ^ of theory).

509809/1 18Ί

SCHERINGAG

August 10, 1975

Pp .: 106 ° C.

20 2-Isobutylthio-5-methylamino-1,3,4-thiadiazole (η

1.5782) as the starting product is obtained by reacting Isobutyl bromide with 2-methylamino-1,2,4-thiadiazoline-5-thione.

1,3-Dimethyl-l ^ (5-isobutylsulfin.Yl-l _t 3,4-thiadiazol-2 "yl) urea

A solution of 52 g of 3-dimethyl-1- (5-isobutylthio-l, 3,4-thiadiazol-2-yl) urea in 160 ml of glacial acetic acid is added dropwise and with stirring with 22.6 g of 50% perhydrol. offset. After standing for 6 days, the solution is concentrated in vacuo. The solid residue is recrystallized from methanol. 55 g (96? ° of theory).

Pp .: 128 ° C.

- ^ - Tr

always off

In a mixture of 27.5 g of 3-dimethyl-1- (5-isopentylthiol, 3,4-thiadiazol-2-yl) urea, 200 ml of glacial acetic acid and 60 ml of water v / earth between 45 and 85 slowly 22, 4 g of finely powdered potassium permanganate added with stirring. To terminate the reaction, the mixture is stirred for 50 minutes, cooled at 80, mixed with 300 ml of ice water and the precipitated manganese dioxide is reduced with 19 S sodium metabisulphite, dissolved in 70 ml v / water, until it becomes discolored. The precipitated reaction product is filtered off with suction, washed with water and removed

-10-

509809/1181

SCHERINGAG

• 40. August 10, 1975

Recrystallized acetonitrile: 23 g (75% of theory). Fp .: 136 ⁰ C.

l «> ^ imethyl-1- (5-isope n tylthio-1,3,4-thiadiazol- 2-yl) - urea

From isoamyl bromide and 2-methylamino-1,3,4-thiadiazoline-5-thione, 2-isopentylthio-5-methylamino-1,3,4-thiadiazole of ^{p. 92 °} C. (boiling point 0.1 Torr-187 ⁰ C), which reacts with methyl isocyanate to give 1,3-dimethyl-1- (5-isopentylthiol, 3,4-thiadiazol-2-yl) urea with a melting point of 75 ° C.

The following table shows further compounds according to the invention listed.

N a me of the compound Physical constant ___,

1,3-dimethyl-l- (5-isobutylsulfonyl-

1,3,4-thladiazol-2-yl) urea pp .: '145 C 1,3-dimethyl-l- (5-butylsulfinyl-

1 * 3 * 4-thiadiazol-2-yl) urea P. 94 C

1,3-dimethyl-1- (5-pentylsulfinyl- _o

1,3,4-thiadiazol-2-yl) urea M.p .: 83 C

1,3-Dimethyl-1- (5-isopentylsulfinyll, 3,4-thiadiaaol-2-yl) urea Pp .: 9ITC

l, 3- ^D imethyl-l- (5- ' ^? nethylpropylsulfinyl-

1,3,4-thiadiazol-2-yl) urea M.p .: 102 C

1- (5-butylthio-1,3,4-thiadiazol-2-yl) -1,3-dimethyl urea M.p .: 87 C.

l- (5-ethylpentylsulfonyl-IV3 _i , 4-

thiadiazol-2-y1) -1,3-dimethy1-

urea m.p .: 98 ^° C

-11-

509809/1181

SCHERINGAG

2 3 A 1 8 1 6 Patient removal

. ^ _β August 10, 1975

Name of the connection. Physical constant

1- (5-Ethylbutylsulfinyl-1,3,4-thiadiazol-2-yl) _{-1,3-dimethyl pn} urea n ^ = 1,56ll

1- (5-Ethylpentylsulfinyl-1,3,4-thiadiazol-2-yl) _{-1,3-dimethyl-20 urea n D} = 1.5,562

1- (5-Ethylbutylsulfonyl-1,3,4-thiadiazol-2-yl) -1, 3-diinethylurea M.p .: 90 C.

1,3-Dimethyl-1- (5-methylpropylsulfinyll, 3,4-thiadiasol-2-yl) urea M.p .: 175 C.

1- (5-Butylthio-1,3,4-thiadiazol-2-yl) - " _n 1,3,3-trimethyl-urea η ^ ^υ = 1.5726 ·

1- (5-pentylthio-1,3,4-thiadiazol-2-yl) j5 _O 1,3,3-trimethylurea n ^ = 1.5638

1- (5-hexylthio-1,3,4-thiadiazol-2-yl) -20

1,3,3-trimethy1-urea n _ß = 1,556l

1- (5-0ctylthio-1,3,4-thiadiazol-2-yl) -l * 3 * 3-trimethyl urea M.p .: 54 C.

l- (5-heptylthio-l, 3,4-thiadiazol-2-yl) S0 l> 3,3-trimethyl-urea 'ώ ^ = 1.5475

l- (5-isobutylthio-l, 3,4-thiadiazol-2-yAA-

1,3,3-trimettiB.-urea n ^ = 1.5630

1- (5_Methylpropylthio-l, 3,4-thiadiazol2o 2-yl) -l, 3,3-trimethyl-urea n _ß = 1.5501

2o

The compounds according to the invention are colorless and odorless, oily or crystalline substances, which are only slightly in water, but good in organic solvents, such as acetone, methylene chloride, tetrahydrofuran, dimethylformamide, cyclohexanone and isophorone are soluble.

-12-

509809/1 18.1

SCHERiNGAG

2 3 A 1 8 1 6 Patent Department

August 10, 1973

The following examples illustrate the herbicidal and selective ones Properties of the compounds according to the invention in Comparison of known active ingredients

Example 1

In a greenhouse experiment, the plants listed were pre-emerged with the agents in one application rate of 1 kg active ingredient / ha treated. The agents were used for this purpose as aqueous suspensions with 50 ° liters of water / ha evenly sprayed over the ground. The results summarized in the table below 3 weeks after treatment show that the agents according to the invention with good Action against the weeds for the crops listed were compatible. In contrast, the comparison agents caused damage the cultures.

-13-

509809/1181

SCHERINGAG

Patent department

August 10, 1975

• ds

• ds

• expoiu "ex

oxoousg

Θχη-BoxxaxdwB

-P P. <y ω ■ Ρ ο ^: 1 W. ο (D > to rH "P ₁ Cj • Ρ ο O • Η ■ Ρ Il Il O O rH

• Ρ 4-5

ε
ω

to

• Η

γΗ

= t V)

• ν CtJ

ι .Η, α

LA I I

· Η I

H «η CM

PWO J) HN £ 1 ί >> «5 • Η -P · Η« ^ S TJ Xi ei

! ■ · ~ \ O · Η

O O

O O

O O

O O

O O O

rH
I.

CM

O

rH

H rHCM

ε -ρ cj

* rH ί-ϊ γΗ

Q O T)

D, Cj

(Λ O ν \

· «Ώ XJ ι ~) τ! JJ

O O

O O

O O

O O

O O

CM

■ Ρ

■ -I
I.

-P
• Η

rH
γ-!

• Η
H

γ-Ι

O I

O O

O O

CM ΚΛ

H i> j

Χ1

• Η

rH

O -P

· »Cj

ΚΛΧί

I rH

}>, I «CM -H I

<Η O 0 ti

η ei

-P PJ · Η

ο .ti

r-i

r-l

Xi • Ρ

ω ρ

■ = t V)

γΗ ^ ~ ^

O I

AROUND

r ~ \ I Ti <Η

ω ο

τ- \ NP

, η Cj

O · Η

W XJ

• rl -P

80 9/11 8.1

Means according to the invention

•H W. CD η CD 3 CD ε ω to Q) CD W. CD • • CD Sh •H O <D • Η α> ^ 3 3 H • Η ■ Η ft <D. pH •H -P rH Sh χ. S. 3 I j Γ ¹ TS W. W. ο CD rH •H CD O 3 O CU CD CD • Η CD Q) Century CD ti CD O «Η ft ω H O ε to ε ο Ξ CD 4-5 • Η Century O •H ο H 3 ο •H 3 CD C ^ W. O ε 3 CD CD • Η CD I. W. 4-5 ft U CD O) CD • Η O - I W. -H CD CD O O CD .it H £ _, • Η γΗ 3 Century Ui •Pi |> ft CD 3 Ph ft "ο O CD Ό «A; ο CD CD CD Q) ε Sh 3 ε • Η rH O 3 CD rH ε Q) CD CD CD ϋ H CD ω •H Q) ο to • Η O O Ω CD CO co ^ s S3 ft ■ Ρ 3 G ε pH • 4-5 3 CD Ph 3 H ω 3 CD O CO .P c CD 4-> O • Η ο CO •H O O {!} egg ε ■ Η CD bO O UD CD CD Century •H a Century Sh l-H CD Q O rH CD CD O rH O O Ξ Ξ Ph Ph

thiadiazol-2-yl) urea

1,3,3-Trimethyl-1- (iGcbutylthio-1,3 j ² I -thiadiazol-2-yl) urea

v, l: I-diazol-2-yl) urea f

py, 5i thiadiazol-2-yl) urea 0--0 12 0100 000000 1 0 0 - - 0 - 000 0 0-000 0 00 0 -'10 20 00 0 0 000 00 0 0 0 0-23 12 0000 00000 0 01

pm

d I a thy 1-heir nc toff 2 320 00 010 0 00010 0 00

ο co οο σ

Means according to the invention

•H M. CD W. CD ε CD ε W. W. Φ CD Ui CD • • CD SU •H O φ 3 Φ 3 3 3 H H • Η • Η a a 4-3 Q) rH •H 4 ^> • Η S3 3 rH JLi Ό O CD rH • Η CD rH 3. φ Φ CD CD • Η CD Φ SU CD CD O O a rH ! ⁵ ^ ο ε to ε ο ε CD • Η +3 C ₁ -I Q) ς_ι ο • Η ο rH hO 3 ο 3 •H ; 3 a • Η 3 O ε 3 CD CD • Η CD W. φ x: a CD φ κ! • Η ο »—I W. •H CD O ε +3 φ H U • Η rH 3 SU CD •H CD CD 3 Φ • a ο O CD • Ö ο CD r_, ε a φ ε JL ₁ 3 S. • Η rH Φ 3 -P CD CD ε φ CD CD CD O rH CD φ CD W. rH ο Cj W. 4-3 • Η Φ φ P. CO •H Φ a 4-3 3 C. E. SU £ öS SU co ! U £ H φ 3 CD Φ CO 3 CD 3 3 CD 4Y O • Η ο CO O Ö CQ • Η •H φ O J> 3 CD CD SU. CD hO EiO j., 4-3 •H O ^^ CD CD CD Q rH rH O O O CM Cm

1,3-dimethyl-l- (5-rne ethylpr opylsulfynyl-1,3ί 4— thiadiazol-2-yl) urea

1,3-Dimethyl-1- (5-methylpropylsulf onyl-1, J, 4-thiadiazol-2-yl) urea

i- (5-Ethylpentylsulfinyl-1,3,4-thiadiazol-2-yl) -1,3-dimethylurea

l- (5-Äthylbutylsulfinyl-l, 3,4-thiadiazole ^1-2-yl) -l, 3-dimethylurea

1,3 * 3-triraethyl-l- (5-

; r, ethylpropylthio) -l, 3,4-

thiadiazol-2-yl) urea O 11 O- 20 1,000 OO O O O O O 0 01 00 00 1 0 00 00 00 00 0 - _- -0 0 1 -100 00 00

0 -0 0000 00 00 -0 0

022232000000000000

W. • r) H

Means according to the invention

co 3

CD

ed O

•8th

5-1

03

+3

cd -H

• H cd Sh cd

• η cd

03 Cu

rs

• rl O

cd 03 O O

CD

•H

Λ -P cd a cd

•H

CD

-P

3 ο ω

CD · Η CQ P

hO -P O CO rH (I) CO

H> O <P-I

03

O

CD rH

5h

Q) O

Cd 03 Sh

CD -P

Sh Q) 03

Qi -P c!

OP

cd cd C!

ω ω cd

§ h b

O Sh cd

M Ü <

CD

Q) H H

CD

S Ή

cd X

W • H Sh cd

(OE ¹ H

ω cd Sh

CD

• H Q)

ε a

to cd

CD

•H

co cd

CD

O -H • H

a) ö

co

CD

co εο

O

U fcO

cd cd ε

H ο

rH Ή Ή

CD Ό H

+3 CO H

CD

• Ρ

ft cd

03 3

<

1- (5-Ethylpentylsulfonyl, 3 ^ -thiadiazol-2-yl) -1,>. dimethy1 urea

1- (5- (ethylbutylsulphonyl-1,3ί4-thiadiazol-2-yl) -l, 3-dimethyl urea

- »Untreated It

33 -2 001 - 00 00 0010

00 -3300 0 0000 000 10 10 101010 101010 10 10 10 10 1010 1010

Comparison means

1,3-Dimethyl-1- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) urea

11 10 000 0 00 00 0000

1- (5-Ethylsulfonyl-1,3,4-thiadiazol-2-yl) -1, 3-dimethylurea 0

-0 00 000 0 02 00 0000

• CJ

I / 8U / 60860S

M. M. te M M O M M O M M M M M. M. I. M. M. I. M. W. PYYYYY VM PYYYYY I. VjJVM M. PYYYYY VjJVM VMVM V> 4 et VM H) I. <· I M.
O «· I I. * I * I te H- M. te tr i H- (-3 -t = -ö I. I. -J = TO _ £ r 3 I. H- Ü a I. I H- I. I H- I. I H- I H- I. φ • —s P. H- p. Ct H- et 3 et 3 et 3 ct3 Ct Ct Ui p, 3 V 3 I. V Φ I. tr ro tr φ V tr I. H- Φ W. H- φ H- et M. H- et M. H- et H-ct H- p. «; H- P. et P. Ct P V O P tr O P V P V P. H- cn tsi V cn ρ, V p. << J VO I. Ρ · ** « & << P. O O CK) H- H- M I. H- M H- M H- M N M. M. φ P. M. P I I. P I O
I. P I P I O Φ I. 1 N I. N M I. N M N M N M I-ι ro M. pi O M. O I I. O I I. O I O I I. Ct I. I. ED M. I. I— ¹ ** "** I - ******* I— '** - ^ φ I. I ul O I ul O I ul I ul I. l-i M. Ul ro H- ro ι ro ι ro ι ro ι cn I. I. cn I H- I H- ι he M. c; I. H- O «<! cn · < Cn «<Ί φ M. rr cn ^. f-i he M O M O M 3 M et I. H) P. O et V - ^ ΰ ^ he ^ - ^ ct O ■ he Φ I. Ct I Φ ι C ι ^^ 1 M. P. 3 c; Ι — ι tr «<5 kick ό * Μ tr cn M. cn et P. M. P et P cn P C 3 Ct t «3 Ct • ~ i * ^ * ~ i Ι — ι J- ^ J I cn O M. tr 3 M. 3 cn 3 M. 3 H) Ct H> cn cn H- cn cn cn C cn Ha cn H- O H) C. Ct O Etc; ctM CtH- et 3 H) M. O I. O M O H) O 3 o * <! H) Hi H) H) H) H) O H) ^ HM O H- H) H) H- ¹ ^ «^ HM
I. HI I. y_j O I. M. M.
I. I. I. I. I. O O O I. I. Sinapis sp. O I. 1 M.
O M. cotton I. I. ¹ , O tomato I. OO I. M. I. pea I. I. . I. O M. Soybean M. M. , O Peanut O O I. M. M. , _, CO OO O O
■ rice O M. M. I.
I. Corn M. VO O O
■ I. O M. ■
I. potatoes M.
O O O
I. I. O barley co I. wheat CO
M. I. O Seed Sorghum O O ro M. nViAnnnnrl-i a s

OVONiHBHOS

• ir

SCHERINGAG

Patent department

August 10, 1975

^l ds

lunqSog-

ds

•H

:CD

• Η

Sh W

OK

O I. O rH Xi CD H I. O t I. I. ■ Ρ W. I. I. I. O 4Y I. I. I. O I. 1 O H O H r "S •H H rH ι I 1 r- \ I. rH N I. ,H H rH O rH •H I. <ΰ XJ. O I. £> j i-H = * rH Cj • l I ί> 5 r * 3 tsJ ¹ X! ¹ OJ E. CJ I. OJ ft r *> >, I. P. •H ¹ K> ■ XJ OO XJ CD I. I. -P I. I. ' -H I. Cj I. O I. KN I. O I. T) KN I. CjO •H I. rH H Q - = »■ •H OJ • ν CU CD • I rH O O (D T5 O O O O KNKN TJ O Q, rH O •H rH O I. E. rH E. CD rH rH 4 ^> rH N CD rH i-H rH I. rH D ₁₁ -H in xj I. r-i rH I. • rl Cj H •H X? O rH rH rH H Ό O H O O ω σ \ •H XJ G"\ 4-5 N if I. I. I. ti I. rH > ^ * P rH rH +5 CD CD ς * XJ rH CJ; · Γ ^ KN I. I. I. E. • Η • Η
r. I. 4Y I. O I. ¹ H. • ι O in O ^{1 1} I. 1 ti
KNrH ω i-H r-l rH H rH S X • t r-i I. I. I. CD • ι I. E. I. p ¹ I. O I. KN O I. I. K> I. • Η H I. XJ cn , W. • ->. H rH H in xj 4-3 r-i iH O I. rH I. I. ON i-H I. ! Ο) I. *> 3 rH rH I. I. 1 H I. CO ί » <■ - ^ I. 1 I. O I. rH I. • rl I. CJ CU O XJ O ¹ I. •H ¹ I. I. Q I. Q) ! I. rH -P •H I. O O XJ O i-H O O rH O
r-i CD· XJ I. <H U 4Y • I H , O O E. O <H U rf H N •H rH I. O O ί> 5 I · \ x; Cj U ί> 5 O -P -P ω ■ P •H EH O ■ Η W. W. 1 * H E. Ό I. Century X! £ j pq • rH * I
1 Γ \ • Η KN -P Century r ^ O O U ΐ XJ KN rH rj CD U \ I. [> j Xi X! ω r-i H 4 ^ I. H α p $ CV- * U rH O Cj O ί> 5 ω XJ ω I. • Η > ι • Η OJ ir-) ι I. in ■ ί> 5 m rH XJ ■ - * O I. ι N rH GJ rH CD I. E. I. •H rH • Η O rH Ό Ti 4-3 X? CD I. W. 4Y •H ι KN ζ I fj Φ XJ • ι ς_ | ^ H £ -1 E. 4Y rH O O Cj ■ Η I " I. 4Y O XJ Q ■ =! · eg W. P. r » KN KN U Sh , I. • ι CD CD H H XJ XJ CD XJ ftOJ

509809/1181

SCHERINGAG

Patent department

August 10, 1973

- gnupjcg amjoq-epog

ds

iH Φ • Ρ ■ Ρ

E Φ

• Η W

rH

O O

I.

• H KN ■ HrH

rH rH

P (Ii WJ-H

ι χ} in ö

O ΐ-ί

O H

O rH

rH

rH

* ι

• ιΐΗ

rH -P H E

& 3

& 3

ο ι

γΗ · »

? JrH

ω I

ι Λ

rH -P

rH rH

■ Ρ cd K-H-P

ι · ο ω in cd q

rHPXi C- O

cd - < ο

H

ο ö ο

τ-ί «Η

whether S

rH

; ^f : S

O O H

I.

^ J- H

• ν-P H Φ

rH -H OKN

rlH
{>>} >>

-P I

XJ I rH rH

ί >> οςΗ

Xl N (M

JJ cd O

in

H-P

cd ö

X!

rH 43

-P rH

Φ Ό

CU X!

Xi C.

-IJ ■ Ρ • Η

• Η Φ

rH ti

CVl

CVJ O

in
in
ο ι ο

O O

X! -P

-ρ ω

Φ C
G

rH I

-P I CV]

in ι

> - 'rH O

rH N CD

■ ΡΉ

E4 •HI

CVl CVl

O N ti •H

CD

X5iI -P O I -P

■ = * ■ S

Vf

rHrH

<m φ

rH E

to ti

rH I

pH rH

X?

JJrH

in «H

509809/1 18.1

-20-

_1ft1R SCHERINGAG

IO ID patent department

August 10, 1975

Example 2

In a greenhouse experiment, the plant species listed below were post-emergence with the agents in the Treated specified application rates. The agents were used for this purpose as aqueous suspensions with 500 liters of water / ha sprayed evenly over the plants. The "J weeks after the Treatment results show that the agents according to the invention even with 8 kg of active ingredient / ha the potatoes did not damage, while the weeds already with 5 kg of active ingredient / ha was completely destroyed. In contrast to this, the comparison agents already caused 5 kg of active ingredient / ha Damage to crops.

-21-

509809/1181

W.
• Η U

rf W)

Φ -P

ε approx

H Φ

Means according to the invention

Ö SU C3 <η
rf · Η PO
■> · - F · ι · »
.ί "^ - RP Ό SU SU rf

• Ό Φ

rf H

Φ P.

§ O Ή

W)

• Η O Φ

CQ

rf

+ Φ

φ rf χα φ

Φ.

H ϋ. rf rf ft

■ η Γ-ι ε rf w

rf Φ 3

φ SU G -P

SUrH

rf · Η

ϋ ε

• Η O

SU ε

• Η

rf φ

3 rf rf o 3

• HP SU SU · Η
Ö rfP

CQ

rf ο

rf Φ

> * ε

JU O

rfÄ ft

ε ο

ο si

Top

ιΗ ft
O rf

rf

O H

O O

rf O ■ Η

rf -P • Η

approx

• Η Η rf O rf Φ

• Η rf SU · • Η rf SU -P rf

• Η

rf

rf • Η U rf P Φ

rf

rf O

CQ Φ SO ^ τΗ 3 O O SU Φ 3

a cc ο ο

<ε

1,5-Dimethy1-1- (5-isobuty1-

sulfinyl-1.5, ^2! thiadiazol-2-yl)

_m -urea 3 IO IO OOOOOOOOOOO 00001

^ 1,3-dimethyl-l- (5-isopentyl-

S sulfonyl-1,3,4-thiadiazol-2-jl) 3 10 10 OOOOOOOOOOO 00000

to -urea 8-10 ----------- -----

- * 1,3-dimethyl-l- (5-butyl-

- * sulfinyl-1,3 * ^ - thiadiazol-2-SL) 3 10 10 OOOOOOOOOOO 00001

-urea 8-Ί0 ----------- -

1,3-dimethyl-l- (5-pentyl-

sulfinyl-1,3,4-thiadiazol-2-yl) 5 10 10 OOOOOOOOOOO 01000 j -urea g- 10 ----------- -

(O l, 3-dimethyl-l- (5-isobutyl-

) sulfonyl-1,3,4-thiadiazol-2-yl) 3 10 10 OOOOOOOOOOO 00101 -urea. 8-10 -----------

Og 9, ι-τΊ

c 1 * m

02

O +5

CQ

CtJ Ή
• Η U

τ) cd
φ to

Means according to the invention

Φ Ή

SOH
Ö -PH
¹ O U Φ

cd cd

• Η H
PhH
O cd-Η

CD

■ Ρ

φ
ω

-ρ ö ε

3 Ή

• Η H

H H

O Cj

• Η H

• Η

CD
φ

O Ή
Φ Ph
C! -P

• Η -P

ε ö

-P

CD
D <

ta

rf
(D

3
CD

CD
α, rf

H cd O

CO

• Η

ϋ Ή H

O tp-H

■ Ρ H · Η

O O

CD

fcO Ö Ph -P ί> 3 · Η Cd · Η

Ph Φ

ω &

CD

cd <η

■ Η

U cd cd · Η

ΟΟ

CD
3

CD
ο

lj3-Dimethyl-l- (5-isopentyl-Oi sulfinyl-l, 3i ⁱⁱ --thiadiazole-

ο 2-yl) -harnst off co

g l- (5-ethylpentyl-sulfinyl-

^ dimethyl urea

^ l- (5-A "thylbutylsulfinyl-

- * dimethyl urea

1- (5-ethylpentyl-sulfonyl-J 1,3,4-thiadiazol-2-yl) -1,3-rJ dimethyl urea

l- (5-fithylbutylsulfonyl- ' 1,3,4-thiadiasol-2-yl) 1,3-dimethyl urea (/ 3 O

• Η 0

ca ο

ο φ

O t-1

10 10 OO O 00 0 00 0 000 000 0

10 10 00 0 00 0 00 0 000 000 0

ίο ίο Όο ο οο ο οο ο ooo 330 3

10 10 00 0 000 00 0 000 -00 -

- 10 - - -i

10 10 00 0 00 0 00 0 000 000 0

§ In the

VO

■ Srf in improper connections

. 3 Ή W

CtJ W · Η r- {Vl O

H 3 H ιΗ · Η 'Ο

Ή O Χ O CtJ γΗ Ή

• Η H O ζ-ι hO CtJ O

S 3 H «η β SU

WOcJW <H, UW -η 3

ctJ cö Ή E ο 3 O cd -P 3 ctJ 3 w

..G Ή SU CtJ Ή G SU Φ OCtSSUObO-H O

'S τι liÄ X ö ρ öS su a 5 -h ^ Iu g,

G> <l-i οωο (ϋ!?> Θ · Η3 3 · ctJ i-lccJci) E.

ö'id 8H ^ t-loSU! M8 ft ri (j d μ ί

GO C 3rta CtJG) SU Ο4-5 rf W

G.P ιΗ ^> ΗεοΐΟ AX! 3Sr-H-H ctJ <MCtJ3

εw O. Ή SUctJcüSctJ-P a3x! · Η 3SU

rdii <i-4SUOctJ SUJJ ΰ ε GoctJSUcJG3

G? U <3 «h ^ Ήοε 3 G εκ53 ctJ O O. · Η cö -HG ο rf-ngOHO'HSctJctipW-POtOGSU-PSUCvjQ) 55: G-PHC) SU-H-PSU-H> sQ8!>) - HctJ-Hc3 a

<tl ¹ O fl ü C-PE; β (liriJiöOrlilPfci) +) (l! O

l-CS-Butylthlo-1,3, ^ - thiadiazole- 3 - 10 0 00 0 0 00-00004 - - 0

2-yl) -l, 3,3-trimethylurea 'J.

cn '. OO

σ l- (5-pentylthio-l, 5,4-thiadiazole-3 -10 000000-00000 4 2 '->.

co 2-yl) -l, 5,3-trimethyl urea. σ>

1- (5-hexylthio-1,3,4-thiadiazole- 5 'τ 10 O 0000 0- 2 00 1 04 -

2-yl) -l, j5,3-trimethyl urea

1- (5-Octylthio-1,3,4-thiadiazole- 3 9 10 4 130-3 3-22 ------ PS "

2-yl) -l, 3,3-trimethyl urea> g

l- (5-heptylthio-1,3,4-thiadiazol-3 -10 000 000-1-020-4 Z ^

2-yl) -l, 3,3-trimethyl urea

Packing aids

1- (5-ethylsulfonyl-1,3,4- ' ~ ^

thiadiazol-2-yl) -l, 3-diraethyl- 3 7 5 0 0 0 0 0 00 0 00 0 00 00 0 (J)

urea 8 - 2- ---- - - - - - - - -

18U / 60860S

£ 26T

VH M. <ί I. I. (D (D ■ fr tr Ct I. M. Jy (D ο 4th Η · H O O tr Ό ^ P. P. ! T 3
t L ί3 G (U
3 Γ *
Ct
Ct P. Ct (D O (D Η> V ν! H 1 3 Ct (D Ct tr ο

0OVjJ

Application rate kg active ingredient / ha

I. O Peanut Ι— ¹
O O potatoes Η- »
O fOV » O Stellaria media M.
O I. O Senecio vulgaris ί- · I. O Matrioaria chamomilla O
Ö O Lamium amplexicaule H
* -Ν I. O Centaurea eyanus V_J I. O Amarantus retroflexus ^ - \ I. O Galium aparine I. O Chrysanthemum segetum O I. O Ipomea purpurea Η ¹
O I. M. Polygonum lapathifolium H
** ■ * I. O Echinochloa crus galli O
M. I. 1 Setaria italica O
Ö _t I. Digitaria sanguinalis ρ , H Setaria faberi O I. Poa annua H
O I. Alopecurus myosuroides I.

ÖVQNiaSHOS

SCHERINGAG

Patent Department \ _ August 10, 1975

Example 3

In the greenhouse, the plants listed were after Emergence treated with the agents according to the invention at an application rate of 1 kg active ingredient / ha. The means were used for this purpose as aqueous suspensions with 500 Liters of water / ha evenly sprayed over the plants. As can be seen from the table, a better selectivity than was achieved with the agents according to the invention with the comparison means.

-26-

509809/1181

OO CD CO

Means according to the invention

-P W.
U

φ
ο

fcsO

"δ

Ö CO

O) I.

N -P CQ

• Η rf

rf

W 03

£ 2 Ή

Sh Q)

W K

C9

CO

rf O • Η H

rf

rf Ή

• Η H O

• Η

■ Ρ rf rf Φ ft Sh

rf 2

rH ft

ft

• Ρ

φ
to
φ

.. rf ö ö

Ö -H O rf rf

rf Sn & 0 Φ CO

rf>, ε> i

rf -p rH O Sn

ο φ o a jzj

Oh CO Ph HO

rf
φ Ή

C -d

• Η Φ

rf ft rf

rf · Η

S rf H • Η Η

rf

rf

• Η

rf ϋ • Η U -P

α)

rf O • Η

K!

C P

rf Φ

! >> U
υ

rf 3

Φ Λ

U P.

I rf ^G ■ Η P

Φ ■ Η
ft

rf

rf P rf
O CO S

rf

Ö Q) Ü

rf
Century

rf

IO • H Sh rf bO

• H ft 3

ω> co ο

• Η · Η ft O

rf φ C Ö

• Η φ

CO CO

1,3-Dimethyl-1- (5-isobutylsulfinyl-1,5,4-thiadiazol-2-yl) urea

1,3-Dimethyl-1- (5-isopentylsulfonyl-1,5,4-thiadiazol-2-yl) urea

1,3-Dimethyl-l- (5-butyl-.sulfinyl-1,5,4-thiadiazol-2-yl) -ureas

1,3-Dimethyl-1- (5-pentylsulfinyl-1,3,4-thiadiazol-2-yl) urea

1,3-Dimethyl-1- (5-isotylsulfonyl-1, J, 4-thiadiazol-2-yl) urea IfO CO

- 8- 10 10 10 1100 1 1 010 10 O.

_ 9 10 10 -OO O 0 - 000 00 0 0

«- · - 10-- 10 10 -000 O - 000 OO O O ΡΙΟ

«Gf m

-_ - 10-10 10 -000 O 2,000 OO O O cf ^

.. io- -000 0 0 0.0 0 00 0 0

ίο · α η »

OVjJ

Ö } -> Η V ι 3 P 01 (D C Ct

Ct H- Η »

Hj ¹ Q Η · Hj HI '■ "^

H ¹ VJl

ViJ3 W (D

A3

tr η «

Η 1
P.
P.
HP
N
O

ff

ζ, -

(Oil I.

181L / 60860S

Ct I

OMP
Hj "Ct

Η ·
P..ct

η- tr

H- Φ O et I

*

et fT H-P P.

H-

P. N O H" I.

ι H- 3

D * ctH
P trw

H-VjJ

I.
I.

CtH
O"·
HjVjJ H) * et

4 = -tr

^ et H ¹

tr ι

H-VJl P I N H-O oil HO TJ

ro ro
.ι. α

Ct

I.

H"
O I. VO H·
O H>
O I. H"
O VO H ¹
O H ¹ O O O
O
O O
O
O O
O
O O O O O O O O O O O O O O O O O O H· O O O O O O

tr ctH P tr *

H-VjJ POI Ol I Ö CtHH-O "3 H) VjJO H) * et • tr ΟΙ « i et H

ir i

P I

P, / - »« H-VJl P I N H-O Ol

V8

roq

et

I. I. I. 00

O O O O O

ro

O O

ro

O O

et H- H

tr οι w

HOV) I.

ρ tr *

P-CVjJ H-ct I P ^ t-3 N HI

0 et H-HtT

t H- (D

ro o et

1 previous year

tr * ι

P -Js - ^ - N 4 I VJl

Ct

Hj Hj

00

t-J O

H "O

1- · O

HO

O O O O

O O

O O

0VDNIH3H0S

«<I 01 H

HC *

wHVjJ

I Hj I

tr h-u pa η-

4 ^ 3 3 H (D 01 I et CtHO "HjVjI

I I

tr GT

HI

P H-P. 0) HO P * O N Φ

o a

rs

raw

I I

I I

VO

VO

H «O

t- ¹

O O

O O

O O

Barley seed sorghum Corn Pea Rice Peanut Potato Poa annua_ Setaria italica Polygonum lapathifolium Ipomea purpurea Chrysanthemum segetum Galium aparine Stellaria media Matricaria chamomilla Lamium amplexicaule Centaurea cyanus Amaranthus retroflexus Sinapis sp.

Senecio vulgaris

18 1 L / 60860S

M M -J I. M. M M M. * M. et p. M. Previous year I. P.M M. . M.
Q t » et tJ
ti 4 M. M) te te co * -> te * I * I. JTH-th te k3 Η · «· I. M.
O Ct H-O te H· PYYYYY M.
O Ui VjI PYYYYY I. H-3 P. et VjJ "1
H· 3PYY M.
O P Ό
Ρ «VJ VjI a I «· M.
O 1 <* Ui I. Ct ui P Φ Η ff Φ «· GT -:
M.
ο M. Η · Μ I. C. 10 10 P. -r = · ι P. ff I. pj VJ Ct Ct-JST .1 M.
O
M. 01 ρ η O HI M. Ct H- ι> t Η · P. N M
m3 tr > t C. ν c;
O M α 3 et O 3 ctct 3 P. Ct ι Ά ν; VJ et Ct M. M M) G Φ φ ff
et H- M. Φ Φ P * 5 Vi M M. MtJ "
I Η · M. M) ^ § Ct 3 ff P O G" P M hyl M. Mead I. ff P M. ° H· 1 ^ c ρ: * A P et M. 23 ι O CJ * ^ sff M. ρ ρ. «
4 Η-Φ 1-1 QJ VJ M M. I? Vp * M. * s P 3 M. Ct I H- I. ρ ρ ; - * = f — 1 M I I. M.
O M. J3 * N «Ι P. I. ff O CtO • Μ I. M. H? P O O CO P. Ο Vj M. P% - Ul O M ^C M I * I. Ct • "J M I. pi M M £ J I. M. ^ I I. ¹ I. tr previous year Ct
φ Office M. IN THE D) W ι ι
t / 5 te Μι ro . _Γ ι p> te Ul M. Ct I ο M) O roc: Cf I— · et VjJ I. ^: · Γο I. O <<! O O Ct IN THE I. M) O * 'ι i ^f B. M) M O O VJ M » M) I- !. M) -F ^ M.
»^ ^C M Ct I. M. M O M> I ^C M O Ct barley Km /
O I. I V} M. I. (—I M) Previous year wheat O M. I. I. te ^c o Μι M. Seed Sorghum O I. M.
O Previous year
I. ^c to ι 1 Corn M.
O ι pea
rice VO -J I.
M.
O co IS peanut VO M.
O M. 1 M.
O M.
O O I.
I. potato M.
O VO
M.
O M. VO Poa annua M.
O
vo M. O M. O O M.
O Setaria italica O Η " O O Pplygonum lapathifoliura O O Ipomea purpurea O ro O O Chrysanthemum segetum I. Previous year O O Galium aparine O O I. O Stellaria media O M. O O Matricaria chamomilla O ro O O Lamium amplexicaule Previous year I. O Centaurea cyanus I. O O O Amaranthus retroflexus O Previous year O O Siriapis sp. O ro O O Senecio vulgaris O M. O O O O O O O O O O O

L8U / 60860S

ίίβτ

re-

a P. ci H • I * ι H- ts * I. I CD ti 3 Η · y ^. I 4 co ίο Ul CR σ ¹ Ct P. I. Η · 5 « CD co P. Ct Η · H IS) O • O tr P. H CQ O) ti 4th (Ο
4th Η » Η ·
Ct
Ci- P < Ct \ -> O CD CD O
Hj ι M. M. H) M.
W. Ι- · et Previous year
I. M.
ι · VW
I * -Fr O Previous year barley H
O Ul wheat M.
O Previous year Seed Sorghum O Ul Corn H I. pea O I- ¹
ο rice M. - <ι Peanut O H
O potato M. I. Poa annua O ο Setaria italica O
M. I. Polygonum lapathifolium O
^^ O Ipomea purpurea :. O
H ¹ O Chrysanthemum segetum O
t =; O Galium aparine U
H ¹ ο Stellaria media O
ε O Matricaria chamomilla O ο Lamium amplexicaule l -
O O Centaurea cyanus M. Amaranthus O retroflexus Η · '
O O Sinapis sp. H
O O Senecio vulgaris

918

Claims (10)

Claims R is an aliphatic hydrocarbon radical with 4 to 8 Carbon atoms, Rp hydrogen or - in the event that η = 0 is - methyl and η represent the numbers 0,1 or 2. 2. 1,3-Dimethyl-1- (5-isobutylsulfonyl-1,3,4-thiadiazol-2-yl) urea. 3.1,3-Dimethy1-1- (5-isobutylsulfiny1-1,3,4-thiadiazol-2-yl) urea. 4.1,3-Dimethyl-1- (5-isopentylsulfony1-1,3,4-thiadiazol-2-yl) urea. 5. 1,3-Dimethyl-1- (5-butylsulfinyl-1,3,4-thiadiazol-2-y1) urea. 6. 1,3-Dimethyl-1- (5-penty-sulfynyl-1,3,4-thiadiazol-2-y1) '- urea. 7. 1,3-Dimethyl-1- (5-isopentylsulfinyl-1,3-4-thiadiazol-2-yl) urea. 8. 1,3-Dimethyl-1- (5-methylpropylsulfonyl-1,3,4-thiadiazol-2-yl) urea. 9. 1,3-Dimethyl-1- (5-methylpropylsulfinyl-1,3,4-thiadiazol-2-yl) ■ urea. -31- 509809/1181 Z O * »IO IQ patent department ν. August 10, 1975 3Π 10. l ^ -yC
.2-yl) urea. 11. 1,3-Dimethyl-1- (5-isopentylthio-1,3,4-thiadiazol-2-yl) urea. 12. 1- (5-Butylthio-1,3,4-thiadiazol-2-yl) -1, 3-dimethylurea. 15. Ir (5-ethylpentylsulfony1-1,3,4-thiadiazol-2-yl) -1,3-dimethy1-urea. 14. It (5-ethylbutylsulfinyl-1,3,4-thiadiazol-2-y1) -1,5-dimethyl urea. 15. Ir (5-ethylpentylsulfynyl-1, I, 4-thiadiazol-2-yl) -1, 3-dimethyl urea. 16.l- (5-Ethylbutylsulfonyl-l, 3,4-thiadiazol-2-yl) -l, 3- -dimethy1-urea. 17. 1- (5-Butylthio-1,3,4-thiadiazol-2-yl) -1,3,3-trimethylurea. 18. 1- (5-Pentylthio-1,3,4-thiadiazol-2-yl) -1,3,3-triraethylurea. 19. 1- (5-Hexylthio-1,3,4-thiadiazol-2-yl) -1,3,3-trimethylurea. 20. 1- (5-0ctylthio-1,3,4-thiadiazol-2-yl) -1,3,3-trimethylurea. 21. 1- (5-Heptylthio-1,3,4-thiadiazol-2-yl) -1,3,3-trimethylurea. 22. i- (5-Isobutylthio-1,3,4-thiadiazol-2-yl) -1,3,3-trimethylurea. 23. l- (5-Methylpropylthio-1,3, -4-thiadiazol-2-yl) -l, 3,3-triraethyl-urea 24. Process for the preparation of 1,3,4-thiadiazol-2-yl-ureas the general formula -52-509809 / 1181 SCHERINGAG _godfather ubteilung 10 August 1975 N- N R-S (O) Il | i __N - CO - ^{1 η} - \ 8 ^^ "^^ ΟΗ in the R is an aliphatic hydrocarbon radical with 4 to 8 carbon atoms,
Rp hydrogen or - in the event that
η = 0 is - methyl and η represent the numbers 0, 1 or 2, characterized in that compounds of the general formula N N - II ■ CH. - S (O) Ji Il N - H (II), a) if PU is hydrogen, with methyl isocyanate of the formula CH - N = C = 0 (III) can react dissolved in an organic solvent or, if R _{2 is} methyl, b) with carbamoy halides of the general formula CH Shark - CO - N <^ (IV) N ₃ H ₅ "33. 509809/1181 " _{/ 1ft1ß} SCHERINGAG I 6 k I Ö I b Pat.nt.bt.uung August 10, 1975 ■ in the presence of acid-binding agents, dissolved in inert solvents, lets react or c) with carbonic acid ester halides, preferably carbonic acid phenyl ester chloride or thiocarbonic acid-S-phenyl ester chloride, or with phosgene in the presence of an acid-binding agent, dissolved in inert solvents, and then the Reaction product with dimethylamine of the formula HN <"(V) ^CH 5 ^: brings to implementation and the resulting process products optionally with oxidizing agents, preferably organic Hydroperoxides, peracids or inorganic oxidizing agents, treated in solvents, where R, and η have the above meaning and Hai represents a halogen atom. 25. Selective herbicidal agents, characterized by a content on at least one compound of the general formula N N R R ₁ - S (O) _n J "/ N -CO-N ^ (I), CH -34- 509809/1 1 8-1 Patent department August 10, 1975 in the R, an aliphatic hydrocarbon radical with 4 to 8 Carbon atoms, R _{2 is} hydrogen or - in the case that η = O - methyl and η represent the numbers o, 1 or 2, in a mixture with carriers or auxiliaries. 509809/1 181