DE2124037A1 - Meta bifunctional benzenes and herbicidal preparations containing them - Google Patents

Description

DR. BERG DIPL ..- ING. STAPF

PATENT LAWYERS ? 1 9 £ Π ^ 7

8 MUNICH 8O. MAUERKIRCHERSTR. 48 Δ Ι Δ Hl) ό I

Dr. Berg Dipl.-Ing. Stapf, 8 Munich 80, Mauerkirch8rstro6e 45

R. May 1971

your mark your letter our mark * date

Attorney file 21 003

Monsanto Company, St. Louis, Missouri

(UNITED STATES)

Me ta-bi funk ti one He Benzoles and herbicides containing them

Preparations

The invention relates to new, meta-bifunctionally substituted benzenes; it also relates to herbicidal preparations and herbicides Application method using the novel meta-bifunctionally substituted benzenes.

In the case of the new, meta-bifunctionally substituted ones according to the invention Benzene is a compound of the formula

R ¹ No. ¹ I. Ii N - -C

6-21-0766 Ifa / eehr ^ "__« _ _R 2 109849/2026

(0811) 48 82 72 <98 82 72) 48 70 43 <98 7otj> 48 3310 (98 3310) telegrams ι BERGSTAPFrATENT Munich TELEX 05 24 5 «BERG d Bank! Bayejhch Vereinibank MOndwit 453100 Poitsdiedci Manchen 653 43 A.

INSPECTED

where mean:

Z oxygen or sulfur; R. I) a hydrogen atom,

II) a radical of the formula R - / B / - in which B is the carbonyl group or an oxygen atom, R is an alkyl group with a maximum of 12 carbon atoms, an alkenyl group with a maximum of 7 carbon atoms or an alkynyl group with at least 3 and a maximum of 6 carbon atoms, and an integer of 0 to 1 mean ₉ or

III) a group of the formula R ⁰ O- ^ R ⁵ Oj.-R ⁴ - where R "'is an alkylene group with not more than 4

Carbon atoms ₉ R ^{3 with} an alkylene group ©

no more than 4 carbon atoms, r © ine An alkyl or alkenyl group with not more than 6 carbon atoms and m is an integer of Represent 0 to 1;

R I) a hydrogen atom,

II) a hydrocarbon radical from the group of alkyl groups with a maximum of 12 carbon atoms the alkenyl groups with a maximum of 8 carbon atoms, the alkynyl groups with a maximum of 6 carbon atoms " Substance atoms and the haloalkyl groups with a maximum of 6 carbon atoms and a maximum of 3 Ilalogen-

109349/2026

atoms,

III) a group of the formula R ⁶ O- / ~ R ⁵ O 7 -R ⁴ - in which R ^, R, R and m are as defined above,

IV) a cycloalkyl or alkylcycloalkyl group
with 3 to 7 ring carbon atoms and a maximum
4 chain carbon atoms,

V) a phenyl or substituted phenyl group
with a maximum of 2 substituents, with
the substituents are halogen, alkyl with a maximum of 4 carbon atoms or -COOH, or

VI) an aralkyl group of the formula

wherein R is a hydrogen atom, an alkyl group
with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms or a haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 halogen atoms, R ° a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms or a haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 halo

G
genatomen, R is independently an alkyl group

1098A9 / 2Ü26

with a maximum of 4 carbon atoms, an alkoxy group with a maximum of 2 carbon atoms, -COOH or a halogen atom, ρ an integer between 0 and 2 and q an integer between 0 and 2 mean; and

a group of the formula

- N - C - Z ⁶ R ²¹

U fs

wherein Z and Z are each independently

2Ω

Oxygen or sulfur atom, R a hydrogen atom, an alkyl group with a maximum of 6 carbon atoms or an alkenyl group with a maximum of 6 carbon atoms

21
Substance atoms and R is an alkyl group with a maximum of 8 carbon atoms, an alkenyl group with a maximum of 6 carbon atoms, a cycloalkyl group with 3 to 7 ring carbon atoms, a cyclohexenyl group, a phenyl group, a substituted phenyl group with a maximum of 2 substituents, the substituents i «a being halogen atoms, Nitro or alkyl groups with a maximum of 4 carbon atoms is a group of the formula

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or the formula

- C

13th

12th

12 I ^
wherein R and R each independently represent a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms, a chloroalkyl group with a maximum of 3 carbon atoms and a maximum of 3 halogen atoms, a chloralkenyl group with a maximum of 3 carbon atoms and 3 halogen atoms, with the proviso that only

12 11
one of the radicals R and R is an alkenyl group or

can be a chioralkenyl group, R * a halogen atom, an alkyl group with a maximum of 4 carbon atoms, a nitro group, an alkoxy group with a maximum of 3 carbon atoms, R ' ⁵ an alkyl group or an alkenyl group, each of which has a maximum of 4 carbon atoms, with the proviso that R one

means other than an alkenyl group if

12 1 ^
neither R or R is an alkenyl group, and

r is an integer from 0 to two. 109849V2026

The new compounds according to the invention have herbicidal activity. The term "plant ¹¹ " as used here includes dormant seeds (seeds), germinating seeds, germinable seeds, emerging (emerging) seed plants (seedlings) and the finished wood and herbaceous vegetation including the roots and the above-ground parts.

The term "control" used here includes the following effects: 1) Killing, 2) inhibiting growth, reproduction or development, and 3) eliminating, destroying or otherwise reduce the occurrence and activity of plants and it is due to each of the mentioned effects or applicable to any combination thereof.

Under the terms "alkyl", "alkenyl", "Alkynyl", "alkylene" and the like are to be understood as meaning both straight-chain and branched-chain radicals.

In the above formula, R - / " ^B -7 _{n can} mean, for example, methyl, ethyl, n-propyl, isopropyl, η-butyl, sec-butyl, isobutyl, tert-butyl, amyl, hexyl, heptyl, octyl , Nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl and the various homologues and isomers of alkyl with 1 to 12 carbon atoms, alkenyl, such as vinyl, allyl, n-butenyl-1, n-butenyl-2, n -Pentenyl-2, n-hexenyl-2, 2,3-dimethylbutenyl-2, n-heptenyl, n-decenyl, n-dodecenyl and

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the various homologues and isomers of alkenyl with 2 to 12 carbon atoms, alkynyl, such as ζ. B. propargyl, n-butynyl-2, n-Pentynyl-3 and the various homologues and isomers of alkynyl with 3 to 12 carbon atoms, alkoxy, such as ζ. B. methoxy, Ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, hexoxy, heptoxy, dodecoxy and the various homologues and isomers of alkoxy with 1 to 12 carbon atoms, Alkenoxy such as B. allyloxy, n-butenoxy, n-pentenoxy, n-hexenoxy, 2,3-dimethylbutenoxy, n-heptenoxy, n-dodecenoxy and the various homologues and isomers of alkenoxy having 2 to 12 carbon atoms, alkynoxy, such as e.g. B. propargoxy, n-butynoxy and the various homologues and isomers of alkynoxy of 3 to 12 carbon atoms, acyl, such as ζ. Β. Methyl carbonyl, Ethyl carbonyl, isopropyl carbonyl, sec-butyl carbonyl, tert-butyl carbonyl, Heptylcarbonyl, decylcarbonyl, hexadecylcarbonyl, allylcarbonyl, n-butenylcarbonyl, n-pentenylcarbonyl, 2,3-dimethylbutenylcarbonyl, n-decenyl carbonyl, propargyl carbonyl, n-butynyl carbonyl and the various homologues and isomers of acyl with no more than 12 carbon atoms «

In the above formula, R O - / "RO _- J -R- can mean: alkoxyalkyl, alkenoxyalkyl, alkoxyalkoxyalky1, alkenoxyalkoxyalkyl, dialkoxyalkyl, alkenoxy (alkoxy) alkyl", alkenoxyalkoxy (alkoxy) alkyl and alkoxyalkoxy (alkoxy) alkyl, such as ζ. Β. 2-methoxyethyl, 4-ethoxy, 2-methylbutyl, 2-ethoxyethyl, 3-propoxypropyl, 4-methoxybutyl, 4-methoxy-2-ethylbutyl, 4-butoxybutyl, 2-allyloxyethyl, 2-butenoxyethyl, 4-butenoxybutyl, 2- (2-

109849/2 "'

2124Q37

Methoxyethoxy) ethyl, 2- (2-butoxyethoxy) ethyl, 4- (3-methoxypropoxy) butyl, 2- (3-allyloxypropoxy) ethyl, 2- (2-butenoxyethoxy) ethyl, 4,4-dimethoxybutyl, 2,2-diethoxyethyl, 2,4-dimethoxybutyl, 4,4-diethoxybutyl, 2-methoxy-4-allyroxybutyl, 2-ethoxy-2-propenoxyethyl, 4- (2-allyloxyethoxy) -2-methoxybutyl, 2- (4-methoxybutoxy) -2-methoxyethyl, 4- (2-methoxyethoxy) -4-butoxybutyl and the same.

2 In the above formula, R can be hydrogen, alkyl,

Alkenyl and alkynyl, as listed above for R ^m i ~% _m 7- , alkoxyalkyl and alkenoxyalkyl, such as. B, methoxyethyl, ethoxyethyl, propoxypropyl, methoxybutyl, butoxybutyl, allyloxyethyl, butenoxyethyl, butenoxybutyl, ethoxyoctyl, butoxydecyl, butenoxyoctyl and the like., Cycloalkyl, alkylcycloalkyl, cycloalkenyl and alkylcycloalkenyl. B. cyclopentyl, 3-methoxycyclopentyl, 5-methylcyclopentyl, 3,4-dimethylcyclopentyl, 2,5-dimethylcyclopentyl, 3,4-dimethylcyclopentyl, 5- (tert-butyl) -cyclopentyl, I-cyclohexyl, S-methylcyclohexyl, 3 , 4-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 3-methylcyclohexyl, 4-butylcyclohexyl, 2,6-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 6- (tert-butyl) -cyclohexyl, cycloheptyl, 3-methylcycloheptyl, 3, _4-t Dimethylcycloheptyl 7-methylcycloheptyl, 4,5-Dimethylcycloheptyl, 6-methylcycloheptyl, 7-methylcycloheptyl, 7- (tert, butyl) -cycloheptyl, 4-Isopropylcycloheptyl and the like., and aryl, alkaryl, aralkyl and aralkenyl such, for example, phenyl, tolyl, ethylphenyl »butylphenyl, xylyl, t-butylphenyl, diethylphenyl, diphenylmethyl,

Benzyl, phenylethyl and the like

1098 ^ 9/2026

The meta-bifunctional compounds according to the invention can can be produced by a process represented by the following syntheses:

NH

R ² CX or (R ² C) ₂ O

R ¹ 0

N-C-R '

1 7

wherein Y a NO, X ^s chlorine or bromine and R and R are as defined above.

When Y is a nitro group, a production mode of the desired Compounds are represented by the following synthesis:

R ¹ 0

N - C - R ^Z

NO,

R ¹ 0

I I

N —C -

R ² + R ²⁰ X

NILE

NH,

NiI

R ¹ Ό

I H

R ¹ 0

I Il

N - C

-R '

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or (4)

- R ²

+ XC- Z ⁶ - R ²¹

H- CZ ⁶ - R ²¹

wherein R ¹ _f R ^2, R ^2Ot, R ^21, Z ^5, Z ⁶ and X are as defined above.

The above reactions are representative equations for ways of making the desired compounds. It can also andae species are applied as they are in the literature and are listed in the following examples.

In the reaction (1) it is desired to obtain a maximum yield, that the amine is present in at least equimolar amount with respect to the acyl halide or anhydride, and preferably the halide or anhydride for. the relative cost of the reagents in excess. The reaction is expediently carried out at a temperature of from about 0 to about 15.degree. However, higher or lower temperatures can also be used, since the temperature is not critical. For example, generally employed temperatures of greater than about 40 ° C when no acid acceptor is used and often is the temperature employed is within the range of about 80 to 150 ⁰ C.

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With an acyl halide, reaction (1) is preferably carried out in the presence of an acid acceptor and an inert organic one Medium · If reactive acyl halides are used, the reaction is carried out in an aqueous medium. It can also be an aqueous organic medium, such as. B. aqueous ethyl acetate can be used. The acid acceptor lies generally in at least equimolar amounts, based on the amount of hydrogen halide formed in the reaction. Suitable acid acceptors, e.g. B. alkaline or basic materials, which the acid formed in the reaction can bind, the tertiary amines, such as. B. trimethylarain, Triethylamine, pyridine, quaternary ammonium hydroxides, N-ethylmorpholine and the like., inorganic bases, such as. B. Sodium hydroxide and potassium hydroxide, sodium and potassium carbonate, bicarbonate and the like. An excess of the amine reactant also serves as an acid acceptor. With an anhydride the implementation (1) preferably carried out in the presence of an aqueous medium.

The separation of the reaction product obtained, usually is in the form of crystalline solids, from the reaction mixture (1) can be easily obtained. For example the salt, e.g. B. a during the reaction due to the presence of a tertiary amine compound as an acid acceptor formed tertiary amine hydrochloride salt of the the product

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ORIGINAL INSPECTED

containing reaction mixture in a simple manner, for example 'separated by filtration and the solvent is removed from the filtrate obtained by stripping or distillation, preferably by distillation in vacuo at low temperature. The product can be used in a known manner be purified, for example by fractional distillation under reduced pressure, selective extraction, fractional Distillation using a carrier gas or any suitable combination of these methods. Normally the product is sufficiently pure that no recrystallization is required. If desired, the product can be a Film distillation (thin film distillation), a recrystallization or a combination of both methods for further To be subjected to cleaning. The m-nitroanilines used as the starting material in Reaction Schemes (2) to (4) are commercially available or can be easily manufactured.

The hydrogenation of the nitro group can be carried out by one of the known processes, for example by catalytic ones Hydrogenation, by a metal-acid combination, e.g. B. an iron-acid combination, through a metal-alcohol combination, z. R- zinc dust or aluminum amalgams and aqueous. Alcohol, lithium aluminum hydride and the like.

The procedure used depends on what is already on the ring Groups off. These methods are known per se. That

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preferred method is using catalytic hydrogenation .of 5% palladium on activated carbon.

In the preparation of the product of Reaction Scheme (4) can the multitude of methods shown below and the various order of addition or. Formation of groups occur.

N - COR ²

R ² COCl

N-COR '

N - COR '

1 ^H 2 J

HCOR ²¹ NHC-OR ²¹ M

^NH 2 R ² COCl

NHCOOR 109849/2026 2

-03

- 14 -

The m-nitroaniline used as starting material can be implemented are formed with the formation of either the amido group, an isocyanate or a carbanilate. The nitro group then becomes the Minogroup reduced and further implemented to form the required amido or carbanilate group.

The above reaction schemes show the mutual relationship W between the four groups of compounds. The reactions, the starting compounds, the intermediates and / or the reactants to form each group are common to the groups

It will be explained below that this mutual relationship between the four groups extends to their herbicidal activity. The following examples are intended to explain the invention in more detail without, however, restricting it thereto. In the examples as well as the rest of the description and in the claims, parts and percent, unless otherwise specified, are on based on weight.

example 1

This example describes the preparation of methyl m-aminocarbanilate.

In a suitable reaction vessel _s which was cooled in an ice bath, were 500 parts of m-nitroaniline, 315 parts of potassium carbonate, 800 parts of water, 800 parts ice and 900 parts of ethyl acetate mono-

ο led. About 15 GÜüer were added to this mixture at below

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380 parts of methyl chloroformate were added over a period of about 2 hours with stirring. 330 parts of η-hexane were added to the mixture obtained, and the mixture was stirred ^{at a temperature in the vicinity of the range from 25 to 30 ° C. for a further 2 hours.} The mixture was filtered and the product was washed with a 50/50 n-hexane / ethyl acetate solution and water and dried in the air, mp 148-15O ⁰ C.

The solid thus obtained was placed in a shaking autoclave and 9 parts of 5% palladium on activated carbon and 1236 parts of dioxane were added. The autoclave was flushed and with

Hydrogen to a pressure of 56.2 kg / cm (800 psi). On shaking, the reaction ^{temperature increased to about 80 °} C., while the pressure decreased. If necessary, the autoclave was repressurized up to 35.2 kg / cm (500 psi) until the pressure remained essentially constant ^{at about 60 ° C.} The mixture was filtered and the filtrate was vacuum distilled to a pot temperature of 80 ⁰ C at 0.2 mm pressure. The residue, an oil, crystallized on standing overnight. It was crystallized from aqueous methanol and then an ethyl acetate / toluene / methylcyclohexane solution, mp 71-71.5 ° C.

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Example 2

This example describes the preparation of methyl m- (2-methylvaleramido) carbanilate. 16.6 parts of methyl m-aminocarbanilate, 18 parts of potassium carbonate, 100 parts of water, 300 parts of ice and 89 parts of ethyl propionate were placed in a suitable reaction vessel. To this mixture was added a benzene solution of 2-methylvaleroyl chloride (20.2 parts of 2-methylvaleroyl chloride in 52.8 parts of benzene) over a period of 10 minutes with stirring. The mixture was heated to about 75 ° C then allowed to stand overnight. Crystals separated on standing. The crystals were removed by filtration, washed with water and an ethyl acetate / hexane solution, and air-dried. F. 110-112 ⁰ C.

Example 3

This example describes the preparation of methyl m-propionamidothionocarbanilate.

M-Propionamidophenylisothiocyanat were placed in a suitable reaction vessel (made from m-aminopropionanilide and thiophosgene), 80 parts of methanol and 7.3 parts of triethylamine and the mixture was refluxed for about 14 hours * Then the mixture was cooled and evaporated in vacuo, leaving a solid residue. The solid

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was dissolved in 73 parts of methanol, the mixture was filtered and the Eiltrat was heated to about 6O ⁰ C, there were about 50 parts of water is added, seeded and cooled. The product obtained was separated and dried, mp 150-152 ⁰ C.

Example 4

This example describes the preparation of methyl m-propionamidothiolcarbanilate.

16.4 parts of 3'-aminopropionanilide, 14 parts of potassium carbonate, 100 parts of water, 100 parts of ice and 90 parts of ethyl acetate were placed in a suitable reaction vessel. To this mixture, 13 parts of methyl chlorothioformate were added over a period of 5 minutes with stirring. Then 66 parts of η-hexane were added to this mixture and the mixture was filtered. The desired product, a solid, was mixed with a hexane / ethyl acetate (3/2) mixture, then washed with water and air dried, mp 167-168 ⁰ C.

By practically the same procedure as above, the following were made Amidocarbanilate Manufactured · The sulfur analogues of the carbanilate group are represented by the following formulas;

I «

-N-C-OR carbanilate

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I Il

-N-C-SR thiol carbanilate

-NC-OR Thionocarbanilat ι ^s

I ti

-N-C-S-R dithiocarbanilate

The nomenclature of the thioamido group and the nitrogen atom
the amido group is the same as described above. The Sticks to fiäom of the Ca rb anilate group is designated with ¹¹ N " ¹

n-propyl-m- (acetamido) thi & carbanilate n-propyl-m- (propionamido) thiolcarbanilate Phenyl m- (propionamido) thiol carbanilate Methyl m- (acetamido) thiol carbanilate Ethyl-m- (acetamido) thiolcarbanilate n-Propyl-m- (acetamido) thionocarbanilate Allyl m- (propionamido) dithiocarbanilate Methyl m- (2-methylpropionamido) dithiocarbanilate Methyl m- (2,2-dimethylpropionamido) dithiocarbanilate Isopropyl m- (acetamido) thionocarbanilate Methyl m- (butyramido) dithiocarbanilate phenyl m- (acetamido) thiolcarbanilate

2,4-dichlorobenzyl-m- (2-methylpropionamido) dithiocarbanilate

2,4-dichlorobenzyl-m- (butyramido) dithiocarbanilate

2,6-dichlorobenzyl-m- (2-methylpropionamido) dithiocarbanilate

n-propyl-m- (butyramido) dithiocarbanilate

10984 9/2 026

n-butyl-m- (butyramido) dithiocarbanilate Ethyl m- (butyramido) dithiocarbanilate allyl m- (propionamido) carbanilate Allyl-m- (acetamido) dithiocarbanilate

2-Cyclohexenyl-m- (2-methylpropionamido) dithiocarbanilate

Methyl m- (2,2-diraethylvaleramido) fliolcarbanilate Ethyl m- (2,2-dimethylvaleramido) thiolcarbanilate n-propyl m- (2,2-dimethylvaleramido) thiolcarbanilate Phenyl m- (2,2-dimethylvaleramido) thiolcarbanilate Ethyl m- (2,2-dimethylpropionamido) thiolcarbanilate Ethyl m- (2-methylvaleramido) thiolcarbanilate Ethyl m- (2-methylvaleramido) thionocarbanilate i-propyl m- (2-methylvaleramido) thionocarbanilate methyl m- (2-methylvaleramido) carbanilate Methyl m- (2,2-dimethylvaleramido) carbanilate Methyl m- (2,2,4-trimethylvaleramido) carbanilate Methyl m- (2-methylpropionamido) thiol carbanilate i-propyl m- (2-methylpropionamido) carbanilate Methyl m- (2-methylpropionamido) carbanilate n-propyl-m- (propionamido) thionocarbanilate i-propyl-m- (propionamido) carbanilate Methyl m- (2-methylvaleramido) thiolcarbanilate methyl m- (propionamidojthionocarbanilate Ethyl-m- (propionamido) thiolcarbanilate Ethyl-m- (2-methylpropionamido) thiolcarbanilate Methyl m- (cyclopropylcarboxamido) thiolcarbanilate Ethyl m- (cyclopropylcarboxamido) thiolcarbanilate

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ORIGINAL INSPECTED

Phenyl-m- (cyclopropylcarboxamido) thiolcarbanilate i-propyl-m- ^ ~ N- (i-propyl) -2-chloroacetamido7carbanilate Methyl m- (2-IIιethyl-2-n-propyl-4-pentenamido) carbanilate Methyl m- (2,2-dimethyl-3-phenyl-4-pentenamido) carbanilate Methyl m- (2,2-dimethyl-4-pentenamido) carbanilate n-propyl m- (benzamido) thiol carbanilate Methyl m- (benzamido) dithiocarbanilate

W methyl m- (2-carboxybenzamido) carbanilate

i-Propyl-m- (2-methylpropionthioamido) -N ^I - (ethyl) dithiocarbanilate n-Pentyl-m- (butyrthioamido) -N '- (methyl) carbanilate, allyl-m-C-butyrthioamido) carbanilate

Cyclohexyl-Tn- ^ K- (raethoxy) butyrthioamido7dithiocarbanilate Allyl-ra - ^ "N- (n-hexoxy) -2-methylpropionamido7carbanilate 1,2-Dimethylhexyl-m - ^ - (decoxy) butyramido7carbanilate Methyl m- ^ ft- (1-ethyloctoxy) propionamido7carbanilate 2-butenyl-m- ^ N- (dodecoxy) -2-methylvaleralnido7carbanilate

^, Cyclopentyl-m- ^ N- (1,2,7-trimethyloctoxy) acetamido7carbanilate

1,2-Dimethylbutyl-m- / K- (2-heptenoxy) -3,3-dichloropropionthioamido7carbanilate

Cyclopopy l-m- ^ i5- (allyloxy) -3,4,4-trichlorobutyrthioamido7-carbanilate

Methyl m- / 15- (2-propynoxy) benzainido 7-N '- (methyl) carbanilate Cyclopopy l-m- / M- (2-pentynoxy) -2-phenylacetalnido7carbanilate

Methyl m- / R- (4-methyl-2-pentynoxy) -2-methyllylbutyralnido7-N '- (ethyl) carbanilate

Methyl -m- / f} - (acetyl) -2,4-dichlorobenzamido7carbanilate Methyl m- ^ N- (2,2-dimethylcaproyl) -3-pent ± namido7carbanilate

109849/202 6

1,1-Dimethylbutyl-m - / ^ - (2,2,4-trimethyldecoyl) -4-methyl-3-hexynamido7carbanilate

Methyl m- / N- (methacryl) acetamido7carbanilate

n-Propyl-m- / fJ- (crotonoyl) -2-methyl-4-t-butylbenzamido-7-carbanilate

Methyl m- ^ N- (4-methyl-2-pentenoyl) propionamido 7carbanilate Ethyl m- ^ N- (2-methyl-2-heptenoyl) acetamide-7carbanilate n-propyl-m- ^ fi- (2-butinoyl) acetamido7carbanilate Methyl m- / f3- (4-methyl-2-hexinoyl) butyramido7carbanilate Phenyl m- (3,4-cyclopentylcarboxamido) carbanilate Benzyl-m- ^ N- (ethyl) propionthioamide-carbanilate

4-methyl-2-pentenyl-m- ^ N- (isopropyl) acetamido7-N '- (allyl) carbaiylate

Methyl m- (2, o-diethylcyclohexylcarboxamido) -N '- (t-butyl) -carbanilate

4-nitrophenyl-m- / R- (methyl) propionthioamido7thionocarbanilate

Ethyl ra- (cyclopropylcarboxthioamido) -N ^l - (3-methyl-2-butenyl) -carbanilate

Methyl m- (cyclohexylcarboxthioamido) carbanilate Allyl-m- / N- (allyl) acetamido7carbanilate

Methyl m- / 2-t-butyl-4- (4-methylphenyl) butyramido7thiolcarbanilate Methyl m- / R- (methallyl) propionamido 7carbanilate

2,4-Dimethylphenyl-m- (2-ethoxypropionamido) -N • - (4-methyl-2-pentenyl) carbanilate

Isopropyl-m- / 5- (ethoxymethoxy) caproamido7carbanilate ^^ Bi! ^! ^?! ^^^^^ -! ^ / ?? - (methyl) -3-me thoxy-4-ethoxybutyramido / dithiocarbanilate

t-butyl-m- (3-allyloxypropionamido) carbanilate

1,1-Dimethyl-2-phenyl-3-butenyl-m- / ft- (2-n-propoxyethyl) -propionamido7-N ^l - (1,1-dimethyloutyl) carbanilate

Cycloheptyl-m- / fi- (3- (2-methoxyethoxy) propyl) acetamide 27carbanilmt

109 84 9/2026

n-Butyl-m- ^ N- (2- (n-butoxymethoxy) ethyl) propionthioamido7-thiolcarbanilate

1,1-dimethyl-2- (2,4-dimethylphenyl) ethyl-m- ^ N- (allyloxymethyl) valeramido7-N- (η-propyl) carbanilate

Ethyl m- / ft- (4- (2-allyloxyethoxy) butyl) acetamido7carbanilate

1,1-Dimethyl-2- (2-methyl-4-t-butyl) ethyl-m- / N- (methyl) -2- (2-carboxyphenyl) thioacetamido 7-N '- (methyl) thionocarbanilate

Methyl m- (2,2-di-chloromethyl-2-phenylpropionami do) carbanilate

3,4-dichlorophenyl-m- ^ N- (ethyl) -2- (4-methoxyphenyl) acetamido7 ~ dithiocarbanilate

Although the compounds according to the invention are valuable fungicides, nematocides, bactericides, bacteriostats and fungistats, Their most outstanding property is the regulation of plant growth. According to the invention was founded that the growth of dormant seeds, germinating seeds, germinable seeds (seeds), emerging seed plants (emerging Seedlings), wood and herbaceous vegetation that has already grown, and aquatic plants can be modified by removing the seeds xiaf (the seed), the rising seed plants or the Roots or aerial parts of established vegetation or aquatic plants are exposed to an effective amount of the exposing compounds according to the invention. The compounds can be used as individual compounds, as mixtures of two or more Compounds or in admixture with an adjuvant. These compounds are effective as general plant

109849/2026

growth regulators, including as phytotoxic agents after emergence (emergence) and before emergence, however, their most salient utility is as selective pre-emergence and post-emergence phytotoxic agent; d. H. for selective control of the growth of a or more monocotyledon species and / or one or more dicotyledon species in the presence of other monocotyledons and / or dicotyledons. In addition, these compounds are characterized by a broad spectrum of activity, i. H. modify them the growth of a large number of different plants, including ferns, conifers (pine, fir and the like), aquatic plants, monocotyledons and dicotyledons, but without being limited to it.

For the sake of brevity and simplicity, the expression “more active” is used below for the amidocarbanilates according to the invention Component "is used.

The plant growth regulating preparations according to the invention contain at least one active ingredient and an adjuvant in liquid or solid form. The preparations are made by mixing the active ingredient with an adjuvant, e.g. B. diluents, extenders, carriers and conditioned agents to make preparations in the form of finely divided particulate solids, granules, pellets, solutions, To create dispersions or emulsions. So can he

109849/2026

active ingredient with an adjuvant such as B. a finely divided Solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or any other combination thereof can be used. As used herein, "plant growth regulation · preparation "does not include, only preparations in one for application suitable form, but also concentrated preparations made with a suitable amount of a liquid. or solid Adjuvana must be diluted or stretched prior to application. The pre-emergence (before emergence) plant growth regulating effect of the compounds of the present invention will be as definitely follows:

A good quality topsoil is placed in aluminum pans and tamped to a depth of 0.952 to 1.27 cm from the top of each pan. A predetermined number of Seeds from each of the various plant species are placed on top of the soil in each pan. The plant growth regulating preparations are applied to the topsoil by two methods:

1) They are applied to the surface of the top layer of the earth and

2) they are mixed with or incorporated into the top layer of soil.

109849/2026

In the surface application method, the seeds are covered with a 0.952 cm thick layer of prepared soil and the pan is made. The vegetable wax turns regulating, preparation is made by spraying on the surface of the top layer of the soil before soaking the seeds of a solution, that of a sufficient amount of the active ingredient to provide the desired amount per acre of soil surface contains, applied.

In the method of incorporation into the ground, it is used to cover of the seeds required soil weighed and mixed with a plant growth regulating preparation, the one contains known amount of active ingredient. The pans are then filled with the mixture and made level. The watering will carried out in such a way that the soil in the pans absorb moisture through the bottom openings of the pans leaves. The pans containing the seeds are placed on a wet sandbank and placed under ordinary sunlight for about 14 days. and watering conditions maintained. After about 14 days, the plants are examined and the results obtained are recorded.

The phy'totoxic activity of the active ingredients before Emergence (before emergence) is determined by the average percentage control (regulation) of each seed sample.

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The average percent control is shown in relative terms in the examples for brevity and simplicity converted to numerical scale. The pre-emergence phytotoxic activity index used in the tables is as follows Are defined:

Average control
in % Numerical scale O - 25 0 26-50 1 51-75 2 76-100 3

The phytotoxic activity of some of the 3 ¹ -amidocarbanilates according to the invention before emergence is recorded in Table I below for various application amounts of the active constituents, both according to the surface method and according to the incorporation method.

109849/2026

Table I.

link Amount in activities U Beard grass Ryegrass the various amidocarbanilates Fox swan Fingergrass Goosefoot Soybean izen tomato Sorghum cotton Corn wheat to the Accruing Cockelbur white geese chicory Semolina root Chicken millet I. kg / acre wild harbor 3 0 1 3 3 0 (U
I = S 3 2 _ _ _ _ _ _ (lbs / acre) 0 wild book O
to II 2.27 (5) Morning glory 0 - radish sugar beet - 0 3 0 2 - - 0 0 0 rice Water pepper 2 0 0 0 ¹ p OO III 3 0 1 1 2 3 2 2 3 0 2 0 - - - _ _ - - - - _ I co IV 0.454 (1) + 1 1 - - 0 2 1 - - - 1 0 0 0 2 0 0 1 V 4.54 (10) - 1 0 _ - 2 3 3 0 1 - 1 2 0 1 1 - 3 2 "2 1 O
to 0.454 (1) + 2 2 2 2 - - - cn 0.454 (1) + - - 1 - 0 1 - 1 2 2

Worked into the ground,

Compound I Compound II Compound III Compound IV Compound V

* Methyl 3 ¹ - (2,2-dimethyl-4-pentenamido) carbanilate

- methyl 3 '- (2-methylvaleramido) thiolcarbanilate

β methyl 3 • - (2-methylvaleramido) carbanilate

= n-propyl-3 ¹ - (2,2-dimethylvaleramido) thiolcarbanilate

a methyl 3 '- (2,2-dimethylvaleramido) carbanilate

ro

CD GJ

The plant growth regulating activity of the various compounds of the invention after emergence (after the Rising) is determined as follows:

The active ingredients are in the form of a spray on 14 day old samples of many of the same plant species as they are in the pre-emergence tests described above were applied. The spray, an aqueous-organic solvent, which contains the active ingredient comes in different pan sets with different amounts of the active ingredient applied to the plants per morning. The treated plants are placed in a greenhouse and after about 14 Days the effects are examined and recorded.

The phytotoxic activity index used in Table II below after emergence (after emergence) is determined by the average percentage control (regulation) every plant species and is defined as follows :;

Phytotoxicity Numerical scale no 0 weak 1 moderate = 2 strong 3 fatal 4th

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Table II

* to m «
I. J i I. !
4th
S.

link

II

III

IV

Concentration in *

Q ₁ OS 0.05 0.05 0.05 0.05

Phytotoxic QJ a activity (Η W) ¹ p of the various , Q
γΗ H 0) cu (U Amidocarbanilates CJ do after this . iH O Accruing (U •H m 0) (U • Η m to CD tH
O , α N 4Y V (U r ^ O H CD H H CD «Rl oi 4π υ Pj ι— » ς * W. > H tso O) '! -> (U 2 PS Μ * Ί ο !CD υ eg H ■ Ö cu rQ O 1 ad OJ υ C3 • Η (U (U CU bo 5P CD co 1 0 4η 4th ISI • Η ti (0 W. 2 1 3 4th S * 1 (U 4th H CD
U •H O 1 1 1 1 4th υ 1 03 2 U • Η Bra 0 1 3 4th W. 4th • Η 2 1 Se + J K 2 U 0 2 •H O 4th U) 0 (U 3 1 1 H 1 1 3 1 0 CD 4th J * * 1 1 1 0 1 2 tM 0 4th 2 1 1 2 4th 3 4th 2 0 2 1 3 2 3 1 3 4th 1 1 0 4th 0 4th 4th 2 4th 1 4th 4th 2 1 0 4th 0

Compound I. Compound II Compound III Compound IV Compound V

Methyl 3 ^l -C2-methylpropionamido) thiolcarbanilate; 3ithyl 3'- (2-meth.ylvaleramido) thiol carbanilate ethyl 3 '- (2,2-dimethylvaleraraido) thiol carbanilate methyl 3 ¹ - (2,2-dimethylvaleramido) thiol carbanilate isopropyl 3' - (propionamido) carbanilate

As previously mentioned, the plant growth regulating preparations of the present invention comprise an active ingredient and one or more adjuvants which include solid or liquid extenders, carriers, diluents, conditioning agents and the like. could be. Preferred plant growth regulating formulations containing the active ingredients of the present invention have been developed so that the active ingredients can be used to the greatest advantage in modifying plant growth. Preferred preparations include wettable powders, aqueous suspensions, dust formulations, granules, emulsifiable oils and solutions in solvents. In general, these preferred preparations all contain one or more surface-active agents. The surfactants that can be used in the novel phytotoxic compositions are described for example in the US patents 2,426,417, 2,655,447, 2,412,510 and 2,139,276. A detailed list of these agents is also in "Soap and Chemical Specialties", November 1947, page 8011 ff., Under the title "Synthetic Detergents", in "Detergents and Emulsifiers Up To Date" (1960) by JW McCutcheon, Inc., and reported in "Bulletin E-607 of the Bureau of Entomology and Plant Quarantine of the USDA". Generally, there will be less than 50 parts by weight of the surfactant in 100 parts by weight of the plant growth regulating formulation.

101149/2026

Wettable powders are water-dispersible preparations that contain one or more active ingredients, an inert solid Extenders and one or more wetting and dispersing agents contain. The inert solid extenders are usually of mineral origin, e.g. B. natural clays, diatomaceous earth and synthetic minerals derived from silica and the like. Examples of such extenders are kaolinite, attapulgite clay and synthetic magnesium silicate.

Preferred wetting agents are alkylbenzene and alkylnaphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long-chain Esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum sulfonates (Petroleum sulfonates), sulfonated vegetable oils, di-tert-acetylene glycols, polyoxyethylene derivatives of alkylphenols (especially isooctylphenol and nonylphenol) and | polyoxyethylene derivatives the monoester of hexitol anhydrides (e.g. sorbitan) with higher fatty acids. Preferred dispersants are Methyl cellulose, polyvinyl alcohol, sodium lignosulfonate, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bis-naphthalene sulfonate, and sodium N-methyl-N- (long-chain Acid) taurate.

109849/2026

Contain the wettable powder formulations of the invention . usually about 5 to about 95 parts by weight of the active ingredient, about 0.25 to 25 parts by weight of wetting agent, about 0.25 to 25 parts by weight dispersant and 4.5 to about 94.5 parts by weight of the inert solid expanding agent, all parts by weight of the total preparation. If necessary, about 0.1 to 2.0 parts by weight of the solid inert stretch " by means of a corrosion inhibitor or an antifoam agent or both.

The aqueous suspensions can be prepared by making an aqueous slurry of the water-insoluble active The ingredient in the presence of the dispersant mixes and grinds to form a concentrated slurry of very fine distributed particles. The concentrated aqueous suspension obtained is exceptional due to its extremely small particle size ^ characterized so that it is very even when thinned and sprayed on.

The dusts are dense, finely divided particulate preparations, which are intended for application to the ground in dry form. The dusts are characterized by that they flow freely and settle quickly so that they are not easily carried by the wind to areas where they are without Benefits are. The dusts primarily contain an active one

109849/2026

Ingredient and a dense, free flowing, finely divided particulate extender. However, their effect sometimes becomes assisted by the inclusion of a wetting agent, such as, for example, above under wettable powder formulations and convenience of manufacture often requires the inclusion of an inert, absorbent grinding aid. by means of. Suitable classes of grinding aids are natural clays, diatomic stoves, and synthetic minerals, those of silica or silicate derived. Preferred grinding aids are attapulgite clay, diatomaceous silica, synthetic fine silica and synthetic calcium and magnesium silicates.

The inert, finely divided solid extenders used for the dusts can either be vegetable or mineral Be of origin. The solid extenders are characterized by having a relatively small surface area and absorb liquid poorly. Suitable inert solid extenders for plant growth regulating dusts are a.B. micaceous talc, pyrophyllite, dense kaolin clays, ground Calcium phosphate stone and tobacco dust. The dusts usually contain about 0.5 to 95 parts of the active ingredient, 0 to 50 parts grinding aid (grinding aid), 0 to 50 parts Wetting agent and 5 to 99.5 parts of the dense solid extender, all parts being based on the weight and in particular on the total weight of the dust. The ones described above wettable powders can also be used to produce dusts

109849/2026

be used. Although such wettable powders could also be used directly in dust form, it is more advantageous to dilute them by mixing them with the dense dust thinner. In this way, dispersants and corrosion inhibitors can also be used and anti-foaming agents may be contained as components in a dust.

The emulsifiable oils are usually solutions of the active ingredient in water immiscible ones or partially water immiscible solvents together with a surfactant. Suitable solvents for the active ingredient according to the invention are e.g. Hydrocarbons and ethers, esters or ketones that are immiscible with water. Suitable surfactants are e.g. B. at = ionic, cationic and non-ionic surface-active agents, for example alkylaryl polyethoxy alcohols, polyethylene sorbitol or sorbitan fatty acid esters, polyethylene glycol fatty acid esters, fatty alkyllolamide condensates, amine salts of fatty alcohol sulfates together with long-chain alcohols and oil-soluble petroleum sulfonates or mixtures thereof. The emulsifiable oil preparations generally contain about 5 to 95 parts of the active ingredient, about 1 to 50 parts of the surfactant Means and about 4 to 94 parts of solvent, all parts by weight and especially by total weight of the emulsifiable oil.

109849/2028

The granules (granules) are physically stable particulate preparations that contain the active ingredient which adheres to a basic matrix of an inert, finely divided, particulate extender or distributed within it. In order to facilitate the leaching of the active ingredient therefrom, in the preparation a surface-active agent, for example as enumerated above under wettable powders, is present be. Examples of usable classes of particulate mineral extenders are natural clays, pyrophyllites, Illite and vermiculite. Preferred extenders are the porous, absorbent, preformed particles, such as. B. preformed and sieved attapulgite particles or foamed in the heat (Stretched) particulate vermiculite and the finely divided clays, such as. B. kaolin clays that hydrate attapulgite or Bentonite clays. These extenders are sprayed onto or mixed with the active ingredient to form of phytotoxic granules.

The mineral particles that are present in the granular Plant growth regulating preparations are used are usually within the range of 2.0 to 0.15 mm (10-100 mesh), but this is preferred so that the vast majority of the particles have a size of

1098A9 / 2026

1.4-0.25mm (14-60 mesh) with an optimal size of 0.84 . up to 0,44 mm (20-40 mesh). A clay in which virtually all of the particles are between 1.4 and 0.18 mm (14-80 mesh) and in which at least about 80% is between 0.84 and 0.44 mm (20-40 mesh) is for use in the invention granular preparation is particularly preferred. The values given here in "mesh" relate to the US) Sieve rows.

The granular plant growth regulating preparations of the invention generally contain from about 5 to about 30 parts by weight of the active ingredient per 100 parts by weight of clay and 0 to about 5 parts by weight of the surfactant per 100 parts by weight particulate! Volume. The preferred particulate. Plant growth regulating preparations contain about 10 to about 25 parts by weight of the active ingredient per 100 parts by weight of clay. The plant growth regulating preparations according to the invention may also contain other additives, for example fertilizers, phytotoxic agents, other plant growth regulators, Pesticides and the like, used as an adjuvant or in combination with any of the adjuvants described above be used. Chemicals suitable for combination with the active ingredient of the invention include triazines, Ureas, carbamates, acetamides, acetanilides, uracils, acetic acids, Phenols, thiocarbamates, triazoles, benzoic acids, nitriles and the like, such as. B .:

1098 4 9/2026

3-amino-2,5-dichlorobenzoic acid 3-amino-1,2,4-triazole 2-methoxy-4-ethylamino-6-isopropylamino-s-triazine 2-chloro-4-ethylamino-6-isopropylamino-s-triazine 2-chloro-N, N-diallylacetamide 2-chloroallyl diethyldithiocarbamate N ^l - (4-chlorophenoxy) -phenyl-N, N-dimethylhafnsto £ f isopropyl-M- (3-chlorophenyl) carbamate 2,2-dichloropropionic acid S-2 , 3-dichloroallyl-N, N-diisopropylthiolcarbamate 2-methoxy-3,6-dichlorobenzoic acid 2,6-dichlorobenzonitrile 6,7-dihydrodipyrido- (1, 2-a: 2 ', 1 ^! -C) -pyrazidinium salt 3- ( 3,4-dichlorophenyl) -1,1-dimethylurea 4,6-dinitro-o-sec-butylphenol 2-methyl-4,6-dinitrophenol ethyl N, N-dipropylthiol carbamate 2,3,6-trichlorophenylacetic acid S-bromine -S-isopropyl-o-methyluracil 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea £ 2-methyl-4-chlorophenoxyacetic acid (S-Cp-chlorophenyl) - !, 1-dimethylurea 1-butyl-3 - (3,4-diclilorphenyl) -1-methylurea £ N-1-naphthylphthalamic acid 1,1 ^l -Dimethyl-4,4 ^l -bipyridinium salt 2-chloro-4,6-bis (isopropylamino) -s-triazine

109849/2026

2-chloro-4,6-bis (ethylamino) -s-triazine 2,4-dichlorophenyl-4-nitrophenyl ether, a-Trifluoro-Zjo-dinitro-1, N-dipropyl-p-toluidine . S-propyl dipropyl thiol carbamate 2,4-dichlorophenoxyacetic acid, Z'jö'-diethyl-N-methoxymethyl-Z-culoroacetanilide.

Fertilizers which can be used in combination with the active ingredients according to the invention are e.g. B. ammonium nitrate, urea, Potash and superphosphate. Other suitable additives are substances in which the plant organisms take root and / grow, such as B. compost, manure, humus, sand and the like.

In operating the present invention, effective amounts of the active ingredient are in or on the ground or dispersed in the plant growth media and / or applied to the aerial parts of the plants or to any suitable Way incorporated into aqueous media. Application to the ground or to growth media can be carried out by simple mixing with the soil, by applying to the surface of the soil and then drawing in or Digging into the ground to the desired depth or using a liquid vehicle to achieve penetration and the impregnation are applied. The application

109849/2026

- - 39 -

of liquid and particulate solid plant growth regulating preparations on the surface of the ground or on the parts of the plants above ground can be done according to conventional methods take place, for example, by means of powder atomization devices, by means of paint and hand sprays and spray atomizers. the Because of their effectiveness at low dosages, preparations can also be taken from airplanes in the form of a dust or a Sprays are applied. According to a further method, the distribution of the active ingredients in the soil can thereby can be achieved that they can be used to sprinkle the ground the water used. In such processes, the amount of water can vary depending on the porosity and water retention capacity of the soil can be varied to the desired depth of distribution of plant growth regulators. The application of plant growth regulating preparations to aquatic plants usually takes place in such a way that the preparations are added to the aqueous media in the areas in which the control of the aquatic plants is desired. The application of an effective amount of the 3 '- (carboxamido) -carbanilate according to the invention on the soil or on growth media and / or on the plant is essential and critical to the practical Carrying out an embodiment of the invention. The exact amount of active ingredient to be used depends on the desired reaction in the plant as well as other factors such as e.g. B. the plant species and their stage of development, the specific soil and the depth at which the active

109849/2028

Ingredients are distributed in the soil and the amount of precipitation depends on the specific active used Component. In treating the leaves to modify plant growth, the active ingredients are used in quantities from about 0.454 to about 22.7 kg / acre or more (1-50 pounds / acre). When applied to the ground for the Modification of the growth of germinating seeds, viable seeds, emerging seed plants and established vegetation the active ingredients would be applied in amounts from about 0.000454 to about 11.3 kg / acre or more (0.001-25 pounds / acre). In these types of soil application, it is desirable that the active ingredients be to a depth of at least 0.508 cm (0.2 inches). With selective For pre-emergence phytotoxic applications, the active ingredients will usually be used in amounts from about 0.0454 to 9.07 kg / acre (0.1-20 pounds / acre) applied. When used to increase the rate of maturation (aging rate) of the plants including increasing the sugar content of the plants, e.g. B. from sugar cane, and to facilitate defoliation of plants, ζ. B. of cotton and soybeans, the active ingredients are used in amounts of at least 0.0454 kg / Morning (0.1 pound / acre) applied. When used to stimulate the growth of the plant to achieve better Yields of plant products will have the active ingredients in amounts of at least 0.0454 kg / acre (0.1 pounds / acre).

109849/2026

brought. When used to control aquatic plants, the active ingredients are used in amounts from about 0.01 to about 1000 ppm, based on the aqueous medium, applied. So the effective amount for each effect (reaction) can through the type of response must be specified, e.g. B. a plant growth regulating amount for general modification, a phytotoxic amount for total control or selective Control, a sprout-forming amount for the ■ .spot formation, an amount sufficient to increase the rate of ripening (Aging rate) for responding to, for example, defoliation, increased sugar content and the like. And a desiccating amount for desiccation. It is believed that those skilled in the art would, based on the foregoing, inclusive the examples can easily determine the approximate amount of application for any situation.

The terms "soil" and "growth medium" used here are to be understood in their broadest sense and include all common "floors" as used in Webster's New International Dictionary, Second Edition, Unabridged (1961). The term includes and includes any substance or medium in which plants can take root and grow not only soil, but also compost, manure, peat soil, humus, sand and the like that help maintain plant growth are suitable.

109 849/20 26

Although the invention has been described above with reference to specific embodiments, it is not limited to the specified details are limited.

109849/2026

Claims (1)

Claims II) a radical of the formula R "I'BJJ - in which B is a carbonyl group or an oxygen atom, R is an alkyl group with a maximum of 12 carbon atoms, an alkeny group with a maximum of 7 carbon atoms or an alkynyl group with at least 3 and a maximum of 6 carbon atoms and η a whole Number from 0 to 1, or III) a radical of the formula R ⁶ O- ^ ^- R ⁵ O _- ? -R ⁴ - where R is an allylene group with not more than A carbon atoms, R is an alkylene group with not 109849/2026 212A037 more than 4 carbon atoms, R is an alkyl or alkenyl group having not more than 6 carbon atoms and m an integer of 0 to 1; R I) a hydrogen atom, II) a hydrocarbon radical from the group of _k alkyl groups with a maximum of 12 carbon atoms, the alkenyl groups with a maximum of 8 carbon atoms, the alkynyl groups with a maximum of 6 carbon atoms and the haloalkyl groups with a maximum of 6 carbon atoms and a maximum of 3 halogen atoms, III) a radical of the formula R ⁶ O- ^ ~ R ⁵ O_7 -R ⁴ - in which R, R, R and m have the meanings given above, IV) a cycloalkyl or alkylcycloalkyl group with) 3 to 7 ring carbon atoms and a maximum of 4 Chain carbon atoms, V) a phenyl group or a substituted phenyl group with a maximum of 2 substituents, with it the substituent is an analogue atom, an alkyl group with a maximum of 4 carbon atoms or-COOH can act, or 109849 / 2Q26 VI) an aralkyl radical of the formula: wherein R is a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms or a haloalkyl group with a maximum of 4 carbons substance atoms and a maximum of 3 halogen atoms, R a hydrogen atom, an alkyl group with a maximum 4 carbon atoms or a haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 halogen atoms, R independently of this is an alkyl group with a maximum of 4 carbon atoms, an alkoxy group with a maximum of 2 carbon atoms, -COOH or a halogen atom, ρ an integer from 0 to 2 and q is an integer from 0 to 2; and A is a remainder of the formula: - N - C - Z ⁶ - R ²¹ R ^ Z 109849/2028 wherein Z and Z are independently of one another 20 oxygen or sulfur atom, R a carbon atom, an alkyl group with a maximum of 6 carbon atoms or an alkenyl group with inaxi- 21 times 6 carbon atoms and R is an alkyl group with a maximum of 8 carbon atoms, an alkenyl group with a maximum of 6 carbon atoms, a cycloalkyl group with 3 to 7 ring carbon atoms, a cyclohexenyl group, a phenyl group, a substituted phenyl group with a maximum of 2 substituents, with the Substituents around a halogen atom, a nitro group or an alkyl group with a maximum of 4 carbon atoms can act a remainder of the formula: or the formula 109849/2026 12 13
mean where R and R are each independently each other is a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms, a chloroalkyl group with a maximum of 3 carbon atoms and a maximum of 3 halogen atoms, a chloralkenyl group with a maximum of 3 carbon atoms and 3 halogen atoms, with the proviso that · that only 1 ? 13th
one of the radicals R and R is an alkenyl or Can be chloralkenyl group, R ^ a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, a nitro group, an alkoxy group with a maximum of 3 carbon atoms, R is an alkyl group or an alkenyl group with a maximum of 4 carbon atoms, with the proviso that R is a different Group as an alkenyl group means when ent- 12 13
neither R or R is an alkenyl group, and r is an integer from 0 to .2. 2 »Connection according to claim 1, characterized in that in the Formula mean: R is a hydrogen atom, an alkoxy group with a maximum of 6 oil atoms, an alkyl group with a maximum of 6 carbon atoms or an alkenyl group with a maximum of 6 carbon atoms , 2
R is an alkyl group with a maximum of 12 carbon atoms, one 103849/2026 Alkenyl group with a maximum of 10 carbon atoms, a haloalkyl group with a maximum of 6 carbon atoms and a maximum of 4 chlorine atoms, a cycloalkyl group with 3 to 7 ring carbon atoms and a maximum of 4 chain carbon atoms, a phenyl group, a substituted phenyl group with a maximum of 2 substituents, the substituents being a halogen atom, an alkyl group with can be a maximum of 4 carbon atoms or -COOH, or a residue of the formula 8 '7 R ⁸ - CR ⁷ (CH ₀ \ 2 wherein R is a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms or a haloalkyl group with. a maximum of 4 carbon atoms and a maximum of 3 halogen atoms, R ⁸ a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms or a haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 halogen atoms, R is independently an alkyl group with a maximum of 4 carbon atoms, an alkoxy group with a maximum of 2 carbon 109849/2026 s to ff atoms -COOII or a halogen atom and ρ a whole Number from 0 to 2 mean. 3. A compound according to claim 2, characterized by the formula methyl m- (2,2-dimethylpentanamido) thiolcarbanilate. 4. A compound according to claim 2, characterized by the formula methyl m- (cyclopropylcarboxamido) thiolcarbanilate. 5. A compound according to claim 2, characterized by the formula methyl m- (2-methylvaleramido) thiol carbamate. 6. Compound | according to claim 2, characterized by the formula Methyl m- (2,2-dimethylpropionamido) dithiocarbanilate. 7. A compound according to claim 2, characterized by the formula Methyl m- (2,2-dimethyl-3,3-dicilorpropionamido) carbanilate. 8. A compound according to claim 2, characterized by the formula I.iethyl-m- (2,2-dimethylvaleramido) carbanilate. 9. Phytotoxic preparation, characterized in that it contains a phytotoxically effective amount of a compound of the formula contains 109849/2026 R ^{1 line 1} I I NCR ² where mean: Z a. Oxygen atom or a sulfur atom; R I) a hydrogen atom, II) a radical of the formula R - / ~ B 7 ~ wherein B is a ^u - η Carbonyl group or an oxygen atom, R is an alkyl group with a maximum of 12 carbon atoms, an alkenyl group with a maximum of 7 carbon atoms and an alkynyl group with at least 3 and a maximum of 6 carbon atoms and η is an integer from 1 to 1, or
III) a radical of the formula R ⁶ O- ^ ~ R ⁵ O_7 -R ⁴ - wherein R is an alkylene radical with not more than 4 carbon atoms, R is an alkylene radical with not more than 4 carbon atoms, R is an alkyl radical or an alkenyl radical with not more than 6 carbon atoms and m is an integer from 0 to 1; R I) a hydrogen atom, II) a hydrocarbon radical from the group of Alkyl groups with a maximum of 12 carbon atoms, 109849/2026 the alkenyl groups with a maximum of 8 carbon atoms, the alkynyl groups with a maximum of 6 carbon atoms and the haloalkyl groups with a maximum of 6 carbon atoms and a maximum of 3 halogen atoms,
III) a radical of the formula R ⁶ 0 - ^ "k ⁵ 0_7 _m -R ⁴ - wherein R ⁴ , R, R and m have the meanings given above, IV) a cycloalkyl or alkylcycloalkyl group with 3 to 7 ring carbon atoms and a maximum of 4 Chain carbon atoms, V) a phenyl group or a substituted phenyl group with a maximum of 2 substituents, the substituents being a halogen atom ,, a Alkyl group with a maximum of 4 carbon atoms or -COOH can act, or VI) an aralkyl radical of the formula 8th
R ⁸ 109849/2026 wherein R is a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms or one Haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 halogen atoms, R a hydrogen atom, an alkyl group with a maximum of 4 Carbon atoms or a haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 Halogen atoms, R is independently an alkyl group with a maximum of 4 carbon atoms, a Alkoxy group with a maximum of 2 carbon atoms, -COOH or a halogen atom, ρ an integer from 0 to 2 and q is an integer from 0 to 2; and A is a remainder of the formula - N - C - Z ⁶ - R ²¹ R ^{20 line 5} wherein Z and Z are each independently of one another 20 is an oxygen or sulfur atom, R is a water hydrogen atom, an alkyl group with a maximum of 6 Carbon atoms or an alkenyl group with 21st a maximum of 6 carbon atoms and R is an alkyl group with a maximum of 8 carbon atoms, one 109849/2026 Alkenyl group with a maximum of 6 carbon atoms, a cycloalkyl group with 3 to 7 ring carbon atoms, a cyclohexenyl group, a phenyl group, a substituted phenyl group with a maximum 2 substituents, with the substituents a halogen atom, a nitro group or an alkyl group with a maximum of 4 carbon atoms can act a remainder of the formula or the formula R ¹² R ¹⁵ 12 13
where R and R each independently represent a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms, a chloroalkyl group with a maximum of 3 carbon atoms and a maximum of 3 halogen atoms, a chlorine 109849/2026 2124Q37 alkenyl group with a maximum of 3 carbon atoms and 3 halogen atoms, with the proviso that only 12 13
one of the radicals R and R is an alkenyl or Can be a chloralkenyl group, R a halogen atom, an alkyl group with a maximum of 4 carbon atoms, a nitro group, an alkoxy group with a maximum of 3 carbon atoms, R is an alkyl or alkenyl group with a maximum of 4 carbon atoms each, with the proviso that R is a different 1 means group as an alkenyl group when R 1 3
or R is an alkenyl group and r is a an integer from 0 to 2. 10. Phytotoxic method, characterized in that a plant with a phytotoxic. effective amount of a compound the formula is brought into contact, R ^{1 line 1} - C - R ² 109849/2026 where mean: Z is an oxygen atom or a sulfur atom; R 'I) is a hydrogen atom, II) a radical of the formula R - ^ "B_7 ~ where B is a Carbonyl group or an oxygen atom, R "an alkyl group with a maximum of 12 carbon atoms, an alkenyl group with a maximum of 7 carbon atoms or an alkynyl group with at least 3 and a maximum of 6 carbon atoms and η is an integer from 0 to 1, or III) a radical of the formula R ⁶ O - / "R ⁵ O 7 -R ⁴ - wherein * ■ - m R is an alkylene group with no more than 4 carbon atoms, R is an alkylene group with not more than 4 carbon atoms, .R is an alkyl or Alkenyl group having not more than 6 carbon atoms and m is an integer from 0 to 1 ; 2
RI) a hydrogen atom, II) a hydrocarbon radical from the group of Alkyl groups with a maximum of 12 carbon atoms, the alkenyl groups with a maximum of 8 carbon atoms, the alkynyl groups with a maximum of 6 carbon atoms and the haloalkyl groups with a maximum 6 carbon atoms and a maximum of 3 halogen atoms, 109849/2026 III) a radical of the formula R ⁶ O- / ~ R ⁵ O 7 "-R ⁴ - in which R, R, R and m have the meanings given above, IV) a cycloalkyl or alkylcycloalkyl group with 3 to 7 ring carbon atoms and a maximum of 4 Chain carbon atoms, V) a phenyl group or a substituted phenyl group with a maximum of 2 substituents, the substituents being a halogen atom, a Alkyl group with a maximum of 4 carbon atoms or -COOH can act, or VI) an aralkyl radical of the formula wherein R is a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms or one Haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 halogen atoms, R is a hydrogen atom, an alkyl group with a maximum of 4 carbon 109849/2026 stoffatoraen or a haloalkyl group with a maximum of 4 carbon atoms and a maximum of 3 9
Halogen atoms, R independently of this is an alkyl group with a maximum of 4 carbon atoms, an alkoxy group with a maximum of 2 carbon atoms, -COOH or a halogen atom, ρ is an integer from 0 to 2 and q is an integer from 0 to 2 ; and a radical of the formula - N - CZ ⁶ - R ²¹ R ^{20 line 5} wherein Z and Z are each independently of one another 20 is an oxygen or sulfur atom, R is a An alkyl group with a maximum of 6 carbon atoms j or an alkenyl group with a maximum of 6 carbon atoms and R 'an alkyl group with a maximum of 8 carbon atoms, an alkenyl group with a maximum of 6 carbon atoms, a cycloalkyl group with 3 to 7 ring carbon atoms, a cyclohexenyl group, a phenyl group, a substituted phenyl group with a maximum of 2 substituents, the substituents being 109849/2026 ORIGINAL INSPECTED a halogen atom, a nitro group or an alkyl group with a maximum of 4 carbon atoms can act a remainder of the formula or the formula k ¹ * R ¹⁵ 12 13
where R and R are each independently a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms, an alkenyl group with a maximum of 3 carbon atoms, a chloroalkyl group with a maximum of 3 carbon atoms and a maximum of 3 halogen atoms, a chloralkenyl group with a maximum of 3 carbon atoms and 3 halogen atoms, with the proviso that only one the radicals R ¹² and R ^{13 are} an alkenyl or chlorine 14th
can be alkenyl group, R a halogen atom, an alkyl group with a maximum of 4 carbon atoms, a nitru ^ ri: 3 'ii--? klkar.nruiyo? - At. ..oiivml. 109849/2026 INSPECTED 3 carbon atoms, R is an alkyl or alkenyl group with a maximum of 4 carbon atoms each, with the proviso that R is a group other than an alkenyl group, 12 13
when R or R is an alkenyl group and r is an integer from 0 to 2. 1 09849/2026