DE2921002A1 - CYCLOHEXEN-1,2-DICARBONIC ACID DIAMIDE, METHOD OF PRODUCING IT AND USING IT FOR WEED CONTROL - Google Patents

Description

Certain derivatives of cyclohexene-1,2-dicarboxylic acid with herbicidal effects are already known. For example, in Japanese laid-open specification 96722/1973 cyclohexene-1,2-dicarboxylic acid diamides the general formula

5 [■■■■ · - ■ - : <.

COJSHR

described, in which H and R 'optionally by halogen atoms, lower alkyl radicals, haloalkyl radicals, lower alkoxy radicals, lower alkylthio radicals, hydroxyl groups or Acyl radicals mean substituted phenyl groups. In US Pat. No. 4,006,926 there are compounds of the general formula

described, in which X is a fluorine, chlorine or bromine atom, X is a hydrogen or fluorine atom, with 20th

with the proviso that X represents a fluorine atom when Y is Fluorine atom means, R a hydrogen atom or a lithium, Sodium, potassium, calcium, magnesium, zinc, manganese or barium cation or a cation of the general formula

»2

represents, where R., R "and R_ are identical or different and are hydrogen atoms, alkyl radicals having 1 to 4 carbon atoms or hydroxyalkyl radicals having 2 to 4 carbon atoms and R ^ is a hydrogen atom, an alkyl radical with 1 to Ί2 carbon atoms, a benzyl group or a Represents group of the general formula URcRg, where Rc a hydrogen atom or an alkyl radical having 1 to 4 · carbon atoms and Rg is a hydrogen atom or denotes an alkyl radical having 1 to 4 carbon atoms.

909848/0868

ORIGINAL INSPECTED

-6-

In the Japanese published 25191/1967 and the Japanese Offenlegungsschrift 44425/1973 are Δ '-letrahydrophthalamic acids the general formula

• CONH

* COOH χ

described, in which X is a hydrogen or halogen atom, a lower alkyl group, a lower alkoxy group, a Denotes nitro, isothiocyanato or trifluoromethyl group. For this compound is a herbicidal or plant growth regulating Effect indicated.

Although there are numerous herbicidal compounds, undesired plant growth can be prevented with these compounds not completely suppress, so that useful plants by the emergence of undesirable weeds in their development be harmed. There is therefore a need for herbicidal compounds with which undesired plants can be controlled without damaging crops.

The invention is therefore based on the object of providing new cyclohexene-1,2-dicarboxylic acid diamides to create that are characterized by a selective herbicidal effect. This task is achieved by the invention. The invention thus relates to the subject matter characterized in the patent claims.

The halogen atoms R and r "are preferably fluorine, Chlorine or bromine atoms. As lower alkyl radicals R and R residues with 1 to 4 carbon atoms are possible. Specific examples are the methyl, ethyl, propyl, isopropyl, Butyl, sec-butyl and isobutyl groups. The alkenyl radicals are radicals with 3 or 4 carbon atoms Question. · The allyl and butenyl groups are preferred. Specific Examples of the cycloalkyl radicals are radicals with 5 to 7 carbon atoms, such as the cyclopentyl, cyclohexyl and cycloheptyl groups. Specific examples of araltyl radicals are radicals with 7 or 8 carbon atoms, such as

909848/0868

ORIGINAL INSPECTED

'the benzyl and phenethyl groups. As alkylamino and Dialkylamino radicals are amino groups which are replaced by one or two alkyl radicals each having 1 to 4 carbon atoms are substituted. The alkenyloxy radicals are radicals with 3 or 4 carbon atoms. Is preferred Allyloxy group. The alkoxycarbonylamino group can be 2 to 4 Contain carbon atoms. Specific examples are the methoxycarbonylamino, ithoxycarbonylamino and propoxycarbonylamino groups. The alkoxycarbonylmethyl group can contain 3 to 5 carbon atoms in the molecule. Specific Examples are the methoxycarbonylmethyl and ithoxycarbonylmethyl groups.

Specific examples of 5- and 6-membered heterocyclic

saturated radicals NR ³ R ⁴ _s i _n d the pyrrolidino, piperi-

n dino and morpholino groups. The alkyl radical R can be a radical

with 1 to 4 carbon atoms.

Because of their higher herbicidal properties and their lighter weight Preparability are compounds of the general formula I preferred in which R is a hydrogen or fluorine

atom, R is a chlorine or bromine atom or a group of all-

3 4

represents, R and R the same

or are different and hydrogen atoms, alkyl radicals with 1 to 4 carbon atoms, amino groups, allyl, allyloxy, alkoxycarbonylmethyl groups with 5 or 4 carbon atoms, Dialky! Amino groups with 2 to 4 carbon atoms or alkoxy mean carbonylamino groups with 2 or 3 carbon atoms in the alkyl part.

Compounds of the general formula I in which R * ^{1 is} a hydrogen or fluorine atom and R is a chlorine or bromine atom are particularly preferred. One of the radicals R 1 or R is a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms or an ethoxycarbonylmethyl group and the other radical is a hydrogen atom.

909848/0868

common formula -OCH ₂ -V 7-R ⁷

The compounds of the invention can be prepared in a number of ways.

Wäg) A

Tetrahydrophthalisoimide be reacted with amines in a Lörsungsmittel at temperatures from -80 to 5O ° C, preferably from -40 to 3O ⁰ C according to the following reaction equation:

CONH-ZvWr ²

cn

Λ O 7. l \.

R, R, R and ι R have the meaning given in claim 1.

Way B

A Tetrahydrophthalamidsäure säureester is reacted with a chloroformate in a solvent in the presence of a base at temperatures from -80 to 50 ⁰ C, preferably -40 to ⁰ C JO. The intermediate obtained is then reacted with an amine in a solvent at temperatures from -80 to 50 ⁰ C, preferably -40 to 3O ⁰ C. This reaction is illustrated by the following reaction scheme:

ClCOOR Base

R ^J

909848/0868

• (2)

ORlGfNAL INSPECTED

R means a lower alkyl radical, R, R, R and R have the meaning given in claim 1.

Examples of solvents which can be used in the reactions described above are ethers, such as diethyl ether and Diisopropyl ether, cyclic ethers such as tetrahydrofuran and dioxane, esters such as ethyl acetate and methyl acetate, ketones, such as acetone and methyl ethyl ketone, aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide, alcohol Ie, such as methanol and ethanol, as well as water.

Examples of chloroformic acid esters which can be used are methyl and ethyl chloroformate. Examples of usable Bases in route B are organic bases such as triethylamine, N, N-diethy! Aniline, pyridine, N-methylmorpholine and N-MethyIpiperidin, as well as inorganic bases such as sodium hydroxide, Potassium hydroxide, sodium carbonate, potassium carbonate, barium hydroxide and calcium hydroxide.

The reactions are generally within 24 hours completed. The reaction time depends on the reaction conditions such as the temperature, the starting materials and the Reagents.

After the reaction has ended, the cyclohexene-1,2-dicarboxylic acid diamides obtained can be used can be purified by chromatography.

The examples illustrate the preparation of compounds of the invention.

example 1

A solution of 2.80 g of N- (4-chlorophenyl) "3" 4-, 5,6-tetrahydro · phthalamsäure and 1.01 g of triethylamine in 16 ml of tetrahydrofuran at 0 ⁰ C under stirring with 1.10 g Chlorameisensäureäthyl ester added »After 10 minutes, the

909848/0868

crystallized triethylamine hydrochloride filtered off. A solution of 0.99 g of cyclohexylamine in 4 ml of tetrahydrofuran is added to the ^{filtrate at 0} ° C. and the mixture is left to stand for 15 to 1 hours. The crystals formed are filtered off and then washed with water and tetrahydrofuran. 1.73 S N- (4-chlorophenyl) -li ^l -cyclohexyl-cyclohexene-1,2-dicarboxylic acid diamide are obtained. The compound is listed in Table I as Compound No. 6. Similarly, Compound No. 2 of Table I is obtained. The melting points and the values for the elemental analyzes of the compounds are also given in Table I.

Example 2 In a solution of 1 g of N- (4-chlorophenyl) -3,4,5,6-tetrahydrophthalisoimide gaseous ammonia is passed into 20 ml of diethyl ether at room temperature. The resulting white precipitate is filtered off and washed with diethyl ether. There are 1.02 g of N- (4-chlorophenyl) cyclohexene-1,2-dicarboxylic acid diamide obtain. The connection is in table

20 ie ι given under No. 1.

Similarly, compounds Nos. 10, 17 and 20 made.

²⁵ example?

A solution of 5.23 g of N- (A-chlorophenyl) -3,4,5,6-tetrahydrophthalisoimide in 80 ml of diethyl ether is stirred at room temperature with 1.55 g of a 70% aqueous ethylamine solution offset. After 20 minutes, the resulting white crystals are filtered off and washed with diethyl ether. There are 5 »50 g of N- (4-chlorophenyl) -N'-ethyl-cyclohexene-1,2-dicarboxylic acid diamide obtain. The compound is listed in Table I under No. 2.

Similarly, compounds No. 3, 4, 5, 7, 8, 9, 11 to 16, 22, 23, 25, 26, 27, 29 Iris 36.

903848/0868

1 example 4 '

A solution of 3.67 g of N- ^ 4 "- (4-chlorobenzyloxy) -phenyl7-3j4,5,6-tetrahydrophthalisoimide in 40 ml of tetrahydrofuran is slowly stirred with 28 percent at room temperature aqueous ammonia solution added. After a few minutes, the white crystals formed are filtered off and washed with diethyl ether. It will be 2.50 g N- ^ F- (4-chlorobenzyloxy) -phenyl-7-cyclohexene-1,2-dicarboxylic acid diamide obtain. The connection is in Table I.

10 listed under Kr. 24.

Compound No. 19 is made in a similar manner.

Example 5

A suspension of 3.51 g of N-Z4- (4-methylbenzyloxy) ~ phenyl7-3,4,5,6-tetrahydrophthalisoimide in 50 ml of diethyl ether is admixed with 1.3 g of piperidine while stirring. The mixture is then stirred at room temperature for 12 hours. The crystals formed are then filtered off and washed with diethyl ether. 4.17 S d. ^ei> i ^Q Table I under No. 21 given compound obtained.

Similarly, compounds # 18 and # 28

manufactured.
25th

The melting points and the values for the elemental analyzes of the compounds listed above are given in Table I. specified.

in Table I are the calculated values for the elemental analysis in the top row and the values found in the bottom row.

The structure of the compounds is indicated by the IR absorption spectrum and confirmed the NMR spectrum.

9 09848/0868

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9038 4 8/0868

ORIGINAL INSPECTED

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909848/0868

ORIGINAL INSPECTED

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9098 4 8/0868

/ NSPECTED

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909848/0868

ORIGINAL INSPECTED

to σ co co

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22nd

23

Structural formula.

CO ΝΗ ⁰⁰

O ONH- (O) -O OH ₂ - (OV

0 OMH,

GONHCH.

P.,. ⁰ G-

2/6 ~ 2U

■. Elementary analysis.

σ OO

ff-, 97

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909848/0868

ORIGINAL INSPECTED

909848/0868

O t Γ U O * » - ■ 'ta . ¹ p. • W * ■ «Ο O _Q - * - · C. «3 O> cf.
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90 9 8 A 8/0868

INSPECTED

The compounds of general formula I are valuable herbicides, which are suitable for controlling weeds in crops. For this purpose, the connections of the Invention can be used immediately. In general, however, they are formulated into herbicidal compositions, for example emulsions, dusts, wettable powders or granules. Inert liquid or solid carriers or diluents, if appropriate, are used to produce these agents surface-active compounds and other auxiliaries used. Furthermore, the compounds of the invention can be used together with other active ingredients, such as fungicides, insecticides, Nematocides, fertilizers, synergists, other herbicides or plant growth regulators are used.

Examples of usable liquid carriers are various Solvents, for example hydrocarbons, such as Kerosene, benzene and xylene, halogenated hydrocarbons such as chlorobenzene and dichloroethylene, lower aliphatic alcohols, such as ethanol, and ketones such as acetone. Examples of solid carriers that can be used are bentonite, kaolin, clay, Talc, activated clay, diatomaceous earth, quartz sand and calcium carbonate.

Examples of usable surface-active compounds (surfactants) are alkylbenzenesulfonates, ligninsulfonates, sulfuric acid esters higher alcohols or aliphatic esters of polyglycols, polyoxyethylene sorbitan esters, dialkylsulfobern

stinic acid esters and alkyltrimethylammonium chlorides.

The amount of the compounds of the invention to be taken up depends on the desired, herbicidal effect. In general, the Compounds used in an amount of 5 to 40 g per 100 m From the next trial results it can be seen that that herbicidal agents of the invention have an excellent effect in foliar treatment or soil foshandling Grasses tma leaflet tears from the time of germination

9848/0863

^Γ ■ -21-

to show advanced growth. With the herbicidal compositions of the invention, young weeds can be destroyed because they are absorbed by the buds of the young plants. The herbicidal compositions of the invention also show significantly prolonged activity. Finally, the herbicidal compositions of the invention are poor. Phytotoxicity to rice plants under submerged conditions. They can also be applied to rice plants that are being transplanted.
10

Formulations for the preparation of herbicidal compositions and the herbicidal effects are given below. The grief the compound used corresponds to that listed in Table I. Grief. Parts and percentages relate to weight, unless stated otherwise.

Making an emulsion

30 parts of the compound Mr. 1 are in a mixture of Dissolved 35 parts of xylene and 30 parts of dimethylformamide. the Solution is made with 5 parts of polyoxyethylene naphthyl ether sulfonate offset. An emulsion with 30% active ingredient is obtained.

Manufacture of a wettable powder

50 parts of compound no. 1, 10 parts of diatomaceous earth, 35 Parts of kaolin and 5 parts of matrium dodecylbenzenesulfonate evenly mixed and ground together. A wettable powder with 50% active ingredient content is obtained.

Production of a granulate

A mixture of 5 parts of the compound ETr ^ 1 and 27 parts Diatomaceous earth, 66 parts of bentonite and 2 parts of a surface-active compound (Aerol GT-1) is mixed with water kneaded and granulated, »The granules obtained are 2 hours dried at 60 ° C. A granulate with 5% active

35 substance content obtained.

909848/0868

1 attempt 1; Use as a soil herbicide

Rice, soybeans and corn are found at a depth of 2 to J cm sown in plastic flower pots. The earth has been mixed with fertilizer beforehand. Furthermore, the

5 surface of the earth sown seeds of blood millet and rootwort. An aqueous dilution of a herbicidal agent in the form of a wettable powder is then applied over the soil surface with a spray gun in an application rate of

2
Sprayed on 10 g, 20 g and 30 g per 100 m. For comparison, the experiment with the known herbicide 3- (3 ', 4 -'-dichlorophenyl) -1,1-dimethylurea (DCMiJ) is repeated. 25 days after spraying, the herbicidal effect on the weeds and the phytotoxicity on the useful plants

certainly. The results are summarized in Table II. 15th

The herbicidal activity and phytotoxicity are assessed as follows:
Herbicidal activity

Evaluation number A *

20 ο 0 to 10

1 11 to 30

2 31 to 50

3 51 to 70 4- 71 to 95

25 5 96 to 100

/ Fresh weight of the weeds in the treated \

* A (%) = (1- del th area \ _{1 (χ)}

\ Fresh weight of weeds in the uncultivated /

acted area
30th

Phytotoxicity

Phytotoxicity rating number

0 no trace

1 track

2 low
^dö 3 moderate

u strong

5 completely

^L 9098 4 8/0868 '. ^J

20th 25th 30th 35

Tabel II - 23 ■ . .-.-, 2921002 Rice· ¹ BB Soybean ϊ corn Connect
manure
No. expenditure
lot,_:
g / 100 m ² Herbicides
Activity ~
* - - ^: .-ζ '_τ. - ' Phytotoxicity O . ■ 0 "- 0 10 5 0 0 .0 1 20th 5 0 0 0 - 30th 5 - - - ο · 0 ο 10 5 0 0 0 2 20th 5 0. / Q 0 30th 5 0 0 .0 10 '5 0. 0 0 3 20th 5 0 0 O 30th . 5 0 O 0 10 4th 0 0 0 4th 20th 5 0 ό 0 30th 5 0 0 0 10 5 0 0 0 5, . 20th 5 0 O 0 30th 5 0 0. . 0 • 10 1 0 O 0 6th 20th 3 0 0 • 0 30th 5. 0 0 0 . . ■ - 10 5 0 . 0 0 7th 20th 5 ' 0 0 0 30th . 5 ■ ο ■ ■ 0 . ο • 10 4th 0 O 0 S. 20th 5 0 0 0 30th 5 0 0 0 10 4th 0 Θ 0 - "9 20th 5 0 0 "0
. • 30. . '5 ■ ii - ■ 309848/08

ORIGINAL INSPECTED

- . 15th expenditure
lot, .:
g / 100 m ² Herbicides
activity 2921002 rice Soybean Corn Connect
dung _v
Mp, 10 VJt. Phytotoxicfitäf. 0 O O . 20th VJt 1 - O "* '■ · "°, • 10 ■ 24 30th vji . 1 0 ' 0 10 VJt 0 0 O 20th 5 . 0 ■; .. 0 0 11 25th 30th 5 1 O O 10 5 0 O 0 20th VJt 0 0 O 12th BCMXS 30th VJt 1 ό O 10 5 O O O uabehan = '
clelt 20th 5 0 O O 13th 30th Vjt O O 0 10 VJt 0 O 0. 20th 5 0 O O 14th . 30th 5 1 0 O 10 5 0 0 O 20th 5 0 0 0 ■ 30 . 5 0 0 O 10 2 . 0 O .0 . ■ 20 4th 0 - · 0 ► 0 30 - 5 0 * O 0 10 - 2 . 0 O 0 20th 4th 0. ^; 0 0 30th 4th 0 0 ■ 0 ■ 10 4th 0 0 0 20th - 5th 1 1 ·. . 0 30th 5 3 2 1 = · O 0 0 0

909848/0868

INSPECTF ₁

Γ -1

1 Versucli 2; Application in the rice field

The seeds of chicken millet, Rotala indica and sea corn (Scirpus o'uncoides) are sown in 1/50 m ^{2 flower pots filled with rice field soil.} Furthermore, rice plants are planted in the 2.7 leaf stage. The water depth in the flower pot is set to 3 cm. After 3 days, an aqueous dilution of a wettable powder of the invention is applied evenly to the surface of the water at an application rate of 10 g, 20 g and 30 g per 100 m. The herbicidal activity and phytotoxicity are determined 25 days after spraying.

For comparison, the test is carried out with the known herbicide 2,4,6-trichlorophenyl-4 ^l -nitrophenyl ether (CHP). The herbicidal activity and phytotoxicity are assessed according to Experiment 1. The results are summarized in Table III.

909848/0868

Tatelle III

.Connect. 16 -. 18th • 20th expenditure Phytotoxicity Herbicidal activity. , Hotala ledge ^Λ manure - ■ "- amount ρ
g / iöo before HtüiTretr- ' indica-- 3 No. 0 hirser, · * ■■ "4 .3 17th 19th 21st 10 0 3 5 · "5 ■; ■ 20th 0 4th 5 3 30th 0 5 5 4th 22nd . 10 0 4th 5 • 5.;. 20th 0 4th 5 2 30th ο 5 4th 4th 23 10 0 3 4th : 4. 20th 0 4th 5 4th 30th 0; 5 5 4th 24 10 0 5 5 5 20th 0 5 5 3 30th 0 5 4th 3 10 Q- 4th 5 4th 20th 0 Ui. 5 3 30th 0 5 4th 3 10 0 3 4th . 4th 20th 0 4th 5 3. 30th 0 5 5 * ^4th 10 0 3 5 ■ - 5 ·· 20th 0 5 . 5 3 30th 0 5 5 4th 10 0 3 5. 4th . 20th 0 5 5 4th 30th ¹ 0 5 5 . 5 10 0 5 5 • 5 20th 0 5 5 30th 5

909848/0868

ORIGINAL INSPECTED

20th 25th 30th

Connect
manure
No.. ...' ■ 26th expenditure
quantity ^
g / 100 m ² Phytotoxicity Herbicides. Activity- Sotala
indicä '"' ■ Lake-
text '* " 10 0 Chicken-
millet-. 5 4th .25 20 .. 0 5 .- 5 5 27 30th 0 5 - 5th 5 10. 0 5 '-: 5 4th 20th .0 4 ._ "■ '. 5 4 " 28 30th 0 5 5 5 ' • - 10 0 5 - 5 4th 20th 0 5 5 5 29 30th 0 5 5 ■ 5 10 0 5 4th 2 20th 0 2 4th "2 30th 30th 0 4th 5 4th 10 0 5 5 4th 20th 0 4th 5 4th 31 30th 0 . 5 5 5 10 0 5 4th - 0 . 20th 0 2 5 ■ 3 32 30th 0 4th 5 4th 10 0 5 4th 2 20th 0 .3 5. 4th - 33 30th 0 4th - 5 ■. 4th 10 0 5 4th -3 20th 0 4th 5 " 4th 34 30th 0 4th '5 * - ■ "* 10 0 ' 5 4th . 3 20th 0 • 3 - '5. 3 30th 0 : 5 ■ 5 - 5th . 10 0 ■ · 5 ' 4th - 3 20 .. 0 ■ 3 . 4th 3 30th 0 . 4th ■ '5 '4 90 9848/086 5 ■ - ■

10

15th

- 28 -

expenditure
lot ._-. Phy t ο t ο xiz i t ät 292 ' 002 Eotala
indica Lake-
ledges. Connect
dung -, -. g / 100 m ² O Herbicidal activity: - • 3. O No... IO O Hüliner
millet - •. 4th ; ^; ι • * · 20th O 1 5 4th . 35 .30 O 4th 2 P. 10 O 4th 4th 1 20th O 2 5 3 36 30th O 3 O 10 O 4th 4th . 1 20th 1 3 5 4th . CNP 30th O 4th O O - ■ 5 - untreated
delt ":" O

20th 25th 30th

0 8 8 4 8/0868

Attempt. 3; Leaf treatment

Polyethylene flower pots are filled with fertilizer Earth filled. The seeds of barnacle millet, blood millet and radish are then sown in the flower pots. After emergence of the plants, emulsions of the compounds of the invention in the indicated concentration, on the leaves

sprayed with a spray gun in an amount of 10 liters per 100 m. In the case of chicken millet and blood millet the herbicide is sprayed in the two- to three-leaf stage, in the case of radish in the first real leaf stage. The herbicidal activity is determined after 15 days. the Results are summarized in Table IV.

For comparison, the test is also carried out with the known herbicide 3,4- dichloropropionanilide (Propanil).

^L 909848/0868

Table IT 3 - 4th • * 7th concentration Herbicides: ■ Activity Blood ■
millet "■■ radish Connecting 4th 5 0.125 Chicken-'
millet - 5 ■ manure
No. ■ ·· - ■. 5 8th 0.25 4th V "5 5. 0.5 5 - 5th 5 · ": Ι - - ■. 0.125 5 ■ 5 5 ■ 6th 9 ' 0.25 5 '■ 5 ". 5 • 0.5 Ut. 5 5 2 0.125 5 5 5 0.25 4th 5 5 0.5 5 4th 3 0.125 '5 5 . 5 0.25 4th 5 5 0.5 5 5. 5 O.I25 5 - 5 5 O.25 5 5 5 O.5 5 4 · 4th O.I25 5 4th 5 O.25 3 5 5 O.5. 4th . 4th 5 O.I25 5 5 5 * O.25 4th 5 5 O.5 5 4th 4th O.125 5 5 5 O.25 4th 5 5 O.5 5 5 5 O.125 Ut 5 ". 5 0.25 4th 5 O.5 5 5 -

9098 4 8/0868

concentration
.. "I *) · Herbicidal activity blood
millet- Bed i- Connect
manure "*"
Mr. • 0.125
0.25
0.5 Chicken
millet ' Ui Ui Ui . ■ ■ 5 ■
5
/ 5 ' 10 0.125
0.25
0.5 Ui Ul Ui
• Ui Ut Ut Ui Ui Ui 11 0.125
0.25
0.5 4th
5; ■
5 5
5
5 Ul Ut Ui ■ '■■ 12 0.125
0.25
0.5 Ui Ui Ui 5
5
5 5
5
5 ! 3 0.125
0.25
0.5 = Ui Ui Ui 4th
5
5 5
■ 5 -
.5 14th 0.125
0.25
0.5 4th
5
5 Ui Ut Ui Ut Ut Ui ■. ■; «■ - ' 0.125
0.25
0.5 Ul Ui Ut 3
4th
• 5 3
"5
5 * 24 0.125
0.25
0.5 2
4th
5 · 3
4th
5 4th
4th
5- · 25th 0.125
0.25
0.5 1 .
4th
5. 4th
5
5 3 _s
4th
- Λ " PxOpanil 3
4th
'5 O. ο ■ ' untreated ---- "
delt O '

909848/0 86

Claims (15)

VOSSIUS · VOSSIUS · HILTL · TAUChNER · HEUNEMANN SIEBERTSTRASSE 4- · SOOO MÖNCHEN 86 - PHONE: (Ο89) 474Ο75 CABLE: BENZOLPATENT MDNCHEN -TELEX 5-29 4-5 3 VOPAT D u.Z. : P 189 (Vo / H) May 23, 1979 Case: 2333 MITSUBISHI CHEMICAL INDUSTRIES LIMITED Tokyo, Japan "Cyclohexene-1,2-dicarboxylic acid diamides, process for their preparation and their use for weed control" Priority: May 25, 1978, Japan, No. 62586/1978: Claims 1. Ipyclohexene-1,2-dicarboxylic acid diamide of the general formula I. ■ ■. · (Ι) in which H represents a hydrogen or fluorine atom, ■ Z / J. R and R are identical or different and are hydrogen atoms, lower alkyl radicals, lower alkenyl radicals, cycloalkyl radicals, aralkyl radicals, amino groups, alkylamino groups, dialky / amino groups, lower alkoxy radicals, lower alkenyloxy radicals, lower alkoxycarbonylamino or lower alkoxycarbonylamino or lower alkoxycarbonylmethyl groups with the or R and R together to which they are bound, form a 5- or 6-membered saturated hydrocyclic radical which can also contain an oxygen atom in the ring, R is a halogen atom or a group of the general formula 909848/0868 represents, wherein R- ⁷ and R are the same or different η and hydrogen atoms or methyl groups mean and R ^{L represents} a hydrogen or halogen atom or a lower alkyl radical. 2. Compounds according to claim 1 of the general formula I, in which R ^ is a hydrogen atom, R is a chlorine or bromine . and-χ 4 atom, / «- 'and R, which are identical or different, denote hydrogen atoms or alkyl radicals with Λ to 4 · carbon atoms.
15th 3. Compounds according to claim 1 of the general formula I, i 2 in which R is a fluorine atom, R is a chlorine or bromine atom and Έ? and R, which are identical or different, represent hydrogen atoms or alkyl radicals having 1 to 4 carbon atoms. 4. Compounds according to claim 1 of the general formula I, Ί 2 in which R is a hydrogen atom, R is a group of the general formula -OQH ₂ -fi ~ \ - _R 7
' \ - ■ / where R ^ represents a chlorine atom or an alkyl radical having 1 to 4 carbon atoms, and Ή / and R are identical or different and represent hydrogen atoms or alkyl radicals having 1 to 4 carbon atoms. 30th 5. Compounds according to claim 1 and 2 of the general formula I, in which R ^{1 is} a hydrogen atom, R is a chlorine atom and either R * or R is a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms and the other ³⁵ radical means a hydrogen atom. 9 0 9848/0868 Γ. 6. Compounds according to claim 1 of the general formula I, in which r '' is a hydrogen or fluorine atom, R is a chlorine or bromine atom, one of the radicals R ^ or R is an allyl, Allyloxy, alkoxycarbonylmethyl group with 3 to 4 carbon atoms, a dialkylamino group having 2 to 4 carbon atoms or an alkoxycarbonylamino group Mean 2 to 3 carbon atoms. 7 Compounds according to Claim 1 of the general formula I, 1 2 in which R is a hydrogen atom, R is the group of the formula -OCH ₂ and one of the radicals R * or R ^ a what and the other is an allyl group. 8. N- (4-chlorophenyl) -cyclohexene-1,2-dicarboxylic acid ediamide. 9 · N- (4-chlorophenyl) -li ^l -ethyl-cyclohexene-1,2-dicarboxylic acid diamide. 10. N- (4-chlorophenyl) -N '-ethoxycarbonylmethyl-cyclohexene-1,2-dicarboxylic acid diamide. 11. N- (2-] iTuor-4- chlorophenyl) -cyclohexene-1,2-dicarboxylic acid diamide. 12. lf- (2-fluoro-4-chlorophenyl) -N ^l -n-butyl-cyclohexene-1,2-dicarboxylic acid diamide. 13. N- (2-fluoro-A-bromophenyl) -N * -methy 1-cyclohexene-1,2-dicarboxylic acid diamide. 14. Process for the preparation of the compounds according to claim 1, characterized in that either a) a compound of the general formula II 909848/086 in which R and R have the meaning given in claim 1 have, with an amine of the general formula III 3 ■ · In the Έ? and R have the meaning given in claim 1, brings or b) a compound of the general formula IV COOH 1 2
in which R and R have the meaning given in claim 1, initially reacted with a chloroformic acid ester and then the compound obtained with an amine of the general formula III in which R ³ and R have the meaning given in claim Λ , brings about implementation. 15. Use of the compounds according to Claims Λ to I3 for combating weeds. 909848/0868