DE2601447B2 - CYCLOHEXENONE DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND HERBICIDAL AGENTS CONTAINING THEM - Google Patents

Description

The invention relates to new cyclohexenone derivatives, processes for their preparation and herbicidal agents containing them.
The compounds according to the invention have the general formula

NO-CH ₁ -CH = CH ₂

NO-CH ₁ -CH = CH

H ₃ C CH ₃ H ₃ C CH ₃

in which R _{1 is} an ethyl or propyl group, R _{2 is} a hydrogen atom or the —COOCHj group and R is the res

~ ^co ~ 0 ^c ° -

means.

The following are particularly effective herbicides:

—CO— (CH ₂ );, - CO-

or —CO— (CH ₂ ) ₄ —CO—

Bis- [2- (N-allyloxybutyrimidoyl) -5,5-dimethyl-3-oxo-1-cyclohexen-1-yl] -teiephthalate,

Bis- [2- (N-allyloxybutyrirnidoyl) -5,5-dimethy 1-3-oxo-1 -cyclohexen- i -yH-isophthalate,

Bis- [2- (N-allyloxybutyrimidoyl) -4-methoxycarbonyl-5,5-dimethyl-3-oxo-1-cyclohexen-1 -yl] -tercphthalate

and

Bis- [2- (N-allyloxybutyrimidoy 1) -5,5-dimethyl-3-oxo-1-cyclohexen-1-yl] adipate.

The compounds according to the invention can be prepared according to the following equation:

NO-CH ₂ -CH = CH ₂

NH-O-CH ₂ -CH = CH ₂ R,

+ R (CI) ₂

H ₃ C CH ₃

(H) (HD

R ₁ and R ₂ therein have the meaning given above.

26 Ol

5 I. 6th

The initial subscription II can be established using the following equations:

OR ₁

NH ₁ O-CH ₁ -CH

R. NH-O-CH ₁ CH-CH,

O = T

H, C CH.,

(II)

O = /

HON R ₁

NH-O-CH ₁ -CH-CH

HONH, HCi ο = - 'From ch = ch-ch, x o = f - = o

R ₁ -

R ₁ - \ 1 or HONHSO ₁ Na R ₁ -

H., C CH,

(VI)

H., C CH,

(VIl)

H ₁ C

(ID

where M is a hydrogen or alkali atom (preferably sodium) and X is a halogen atom. The connection of formula I! can be in the following two tautomic formulas.

NH-O-CH ₁ -CH = CH ₁ R

F = O

(H)

(VIII)

NO-CH ₁ -CH = CH,

H., C Cl

In the practical implementation, the alkali salt of the starting compound II is first prepared, by treating the compound with sodium or potassium hydroxide in an organic Solvent.

This alkali salt is, as it is obtained, with the compound of the general formula III in one inert solvent reacted or after it has been separated from the reaction mixture. The compound II can also with the compound III in the presence of sodium or potassium hydroxide implemented.

Acetone, ether, alcohol, benzene, toluene, chloroform, ethyl acetate can be used as the inert solvent etc. can be applied.

usually grazing temperatures ranging from - 2O ^r C to the boiling point of the solvent, preferably to temperatures below room temperature, applied. The reaction is complete within about 15 minutes to 3 hours. After the reaction has ended, the solvent used is replaced by another solvent, if necessary, and the reaction mixture is then washed with an alkaline solution and water and dried. The solvent is then evaporated off under reduced pressure and the crude product is obtained in the form of crystals or as a liquid.

The crude product can be purified by recrystallization or column chromatography.

The structure of the purified compound obtained can be determined with the help of elemental analysis, the NMR spectrum or the IR spectrum, etc. identified

do or be confirmed.

Acid chlorides of the formula III which can be used as starting substances are, for. B. the Suitable for chlorides of the following acids:

a) succinic acid, adipic acid,
'■ * b) terephthalic acid, isophthalic acid, phthalic acid.

The invention is illustrated in more detail by the following examples.

f ,

26 Ol

Ii cis ρ ic II
CIL NO CU, CH- CII, CMI, N 0-CH ₁ CH-CM,

C C

ν oco- <o; - coo

H., C CH,

(Connection I)

5 g of 2- (1-allyloxyaminopropylidane) -5,5-dimethyleydoxy-1,3-dione were dissolved in 50 ml of acetone and 2 ml of an aqueous solution containing 0.9 g of sodium hydroxide contained, admitted. The resulting solution was stirred at room temperature for 1.5 hours. Man obtained the sodium salt of 2- (l-allyloxyaminopropyliden1-S.S-dimethylcyclohexane-1,3-dione.

After the resulting solution had cooled down, 1.6 g of terephthalic acid dichloride were added to a Temperature of 0 to 5 "C added to a solution and this 30 minutes at 0 to 5" C and more stirred for two hours at room temperature.

CW,

After completion of the reaction, the precipitated sodium chloride was removed, the acetone was distilled off, the residue is poured into 100 ml of water and extracted with chloroform.

The obtained chloroform layer was washed with an aqueous solution containing 5% sodium hydroxide. and washed with water. The chloroform layer was dried over sodium sulfate and the chloroform distilled off. When the residue obtained was recrystallized from acetone, 4.3 g of des were obtained desired product, m.p. 122 to 125 ° C.

Example O CH ₂ CH-CH, C ₂ H,

NO "CH ₁ CH-CH,

OCO-CH ₁ CH, COO

1I., C CH,

(Connection 2)

5 g of 2- (1-allyloxyaminorropylidcn) -5,5-dimethylcyclohexane-1,3-dione twist dissolved in 50 ml of acetone and 2 ml of an aqueous solution containing 0.9 g of sodium hydroxide contained, admitted. The resulting solution was stirred for 1 hour at room temperature, whereby the sodium salt of 2- (l-allyloxyaminopropylidene) -5,5-dimethylcyeloxane-1,3-dione originated. After the solution was cooled, 1.5 g of succinic acid dichloride was slowly added to the solution. The mixture was stirred for 30 minutes at 0 to 5 "C and a further 2 hours at room temperature. After Ab-CH,

At the end of the reaction, the precipitated sodium chloride was removed, the acetone was distilled off and the Pour residue into K) O ml of water and extract with chloroform.

The resulting chloroform layer was washed with an aqueous solution containing 5% sodium hydroxide, and washed with water. The chloroform layer was dried over sodium sulfate and the chloroform distilled off. When the residue obtained was recrystallized from n-hexane, 2.5 g were obtained of the desired product, m.p. 71 to 74 C.

C, I

example N O CILCH CIL CIU

OCO

COO N O CII, CII CII,

H ₁ C CH,

(Connection 31

5 g of 2- (l-allyloxyaminopropylidene) -5.5-dimethylcyclohexane-l.3-dione were dissolved in 40 ml of acetone and treated with 2 ml of an aqueous solution containing O, S μ sodium

CH,

hydroxide contained, versel / .l. The resulting solution was genihil for 1 hour at room temperature. wöbe the sodium salt of 2- (l-allyloxyaminopri.> pylideiil

26 Ol

ίο

5,5-dimethylcyclohexane-1,3-dione was formed. Upon concentration, the acetone and the water distilled Reaction solution, and an additional 40 ml of acetone was added to the remaining material.

While cooling in ice water, 1.5 g of adipic acid chloride were added dropwise to the acetone solution and Stirred for 1 hour at room temperature. After the acetone had been distilled off, the reaction mixture was poured into ice water and twice with a Mixture of n-hexane and ether (1: 1) extract the organic layer with an aqueous Solution containing 10% by weight sodium hydroxide and then washed twice with water and dried over magnesium sulfate.

When the organic solvent was distilled off under reduced pressure, 3.7 g of de were obtained desired product, m.p. 52 to 54 "C.

Ii C ι: S ρ i C 1

C ₁ H ₇ N --Ο CH ₂ CH CH ₂ C ₁ H ₇ NO - CH ₂ CH CH,

O ^ / V- C) - CC) ~ < O> - CO - O - '

CH _-1 OCO -}

H
H ₁ C CH _- ,

(Compound 9)

10 g of 2- (l-N-allyloxyaminobutylidene) -4-methoxycarbonyl-S.S-dimethylcyclohexane-l ^ -dione were dissolved in 80 ml of acetone, and there were 8 ml of an aqueous solution containing 1.23 g of sodium hydroxide, admitted. While cooling the resulting solution, 3.14 μterephthalic acid dichloride were added in 30 ml Acetone was added dropwise. After stirring for one hour at room temperature, the precipitate was filtered off and the acetone is distilled off.

The residue was extracted with chloroform, the chloroform layer with an aqueous solution,

Table I.

which contained 5 wt .-% sodium hydroxide, and then washed with water.

After the chloroform layer has dried, practice

Sodium sulfate, the chloroform was distilled off. This gave 8.4 g of the desired product al;

oily substance with a refractive index in ³ = 1.5215 Examples of compounds according to the invention

are including those already described in the table below specified.

Before Sirukuir-l'ornicl

dun ^ s-

Chemical name

N O ΙΊΙ / ΊΙ CH; C., 11, NO ('11, CII CH,

C C

I O

OCO < O> COO

O COCH, CU, C (H) bis [2-N-iillylo. \ Ypr «pioniini (loyl) - l-'p I22liis 5,5-1IiIDeIIIyIvV ₁ ) Xi) -I-CyCIoIIeXCn- 12.5 C l-yl- l-lcrcphlhiiliH

11., C ^- CH, M ₁ C CH,

C ₁ II, NO ('11, CII ClI, C _-1 II., NO CII _-1 CH Cl

C C

His | 2-lN-iillyl () \ jpri) piopiiniiili) yl | - Ip. 71 7-1 C .S.S-ilinKMliyl-.Vnvo-l-cvdiilicxcM-

1 -> ■ 1 l-MICCMIill

H ₁ C CII, ||, C CII,

C..II, NO CH ₁ CII CII _- , C _-1 II ₁ , NO CII _-1 CII CIl,

C C

OCO

COO His | 2-N-iillyliixypi'i> pli) iiiini (li) \ l | - η ',!' ls

O-cliiiH'lhyM-uMi-l-cvclohcxiMi-

1 -y] | -isophthuhu

H ₁ C CII ₁

H ₁ C CII ₁

26 Ol

brtsel / .ung

he Slnikuir-I'onnel
in-

IHlJiS-

Chemical name

C ₂ H, NO CH ₂ CII CIl, C, ll _s NO CIU'II CH,

OCO

COO f VO

H., C

! 1, C CH, Dis [2- (N-allyloxypropionimidoyI) - »i? 1.5292 5,5-dimethyl-i-nxo-1-cycIohcxcnl-yll-phlhalal

C ₁ H ₇ N OCH ₁ CIi = QI, C ₁ H ₇ NO (11, (11 CII,

C C

5 O- ■■ - (

■ <ο V- coo / '' Vo

Bis | 2- (N-allyloxybulyrimidoyl) - l-p.9K -KK) "C 5,5-dimethyl-3-i) xo-1 -cyclohcxcn l-yl] -lercphlhalal

H ₁ C CH ₁ \\, ν CHj

C ₁ H, NO CH ₂ CH = CH, C ₁ II ₇ N -C) CH ₂ CIl CH,

C V

(i C) ■■■ - · / "V --- OCO t'qV COO

His (2- (N-allyloxybutyrimidoyl) - «, ';' 1,5243 5, .S-dimethyl-.voxo-1-cyclohexenl-yl] isophthalal

\\ _S C CII ₁ H ₁ C CH ₁

C ₁ II _x NO CH ₂ CH CH, C ₁ II ₇ NO CII ₂ CH CH ₂

7 O

O CO (CH ₂ I ₄ - CO-O

C) Uis | 2- | N-allyloxybulyrimid (iyl) -S.S-dimethyl-i-oxo-1 -cyclohcxcn-

\ l, C CHj HjC VW,

C ₂ IU NO CII ₂ CH CH ₂ C _: \ U NO ('11 ..CH " CIi ₂

O [■ 'ι C) CO ICII ₂ I ₄ CO - () ■ -

A. Bis | 2- | N-allyloxyprnpii) niniiiloyl) - I'p. 52 54 "C SS-ilimclhyl-.Vmo-1-cyclohcxcnl] li

CH ₁ H ₁ C CII,

C ₁ II ₇ NO CH.Cll CU, C ₁ II ₇ NO CII ₂ CIl CH ₂

■■ - ,, '* \ ■ ·' ■■

O C. O O C. ■ ο ■ O. · ( O O ' 1 C.
[ 1., CII CII CII ₁ OCO CII ₁ OCO I _x COCK "ι ⁽⁾ \ H L ('(»κ CII, HjC CII ₁ 11th H η N O CH ₂ C Il CII CIk N OC CII ₁ H ₁ C H ₁ C CJI, O C. () ■ (ι ■ C. () O CII ₁ H ₁ C

His | 2- (N-allyl () xybiilyrimiduyl) - iii, '1.5215 • l-inellioxyeMilinnvl-5,5-diim: lhyl-Voxo-l-cyilohcNCM-l-yll-luieplillialal

llis | 2 (N-IiIIv Ii ixyprnpii hi imidoyl) - n \, ' Ι,. "2Κ2>l-nii'llio \ yi'iiilionyl-5,5-iliiiii; lhyl- \ -o \ ii-iytliilk'xen-1 -yl l-lereplilhiilal

In the following, the compounds are designated by the number given in Table I.

As previously mentioned, lit.

26 Ol

possess herbicidal activity. The use of the compounds according to the invention is explained in more detail below.

The compounds according to the invention are particularly effective for controlling grass weeds, such as annual bluegrass (Poa annua L.), water fox tail (Alopccurus aequalis Sobol), cinquefoil (Digitaria adscendens Henr.), Green millet (Sctaria viridis Bcauv), wild oats (Avcna fatua L) etc. and hardly damage broad-leaved crops such as adzuki beans (Phascolusangiilaris W. F '. Wight) and soybeans (Glycine max Merrill) and sugar beet (Beta vulgaris L.) the most particularly are sensitive. The connections found thus represent selectively acting herbicides.

Ice is known that ^ Acctoxy-ö-mclhyl-a-pyron-Dervatc with (N-alkoxy or -alknyloxyl-acetimidoyl groups have herbicidal properties (DT-OS 22 52 818).

However, in order to completely destroy the aforesaid grass weeds, there is a large amount of them Herbicides required, which is a major disadvantage.

If, on the other hand, the invent
genes used as herbicides
than a quarter of the Mcnj
Connections required
protection and extermination
achieved, ie, the invention
are about four times as w
Links.

At the Blattbchandliing

Ings according to connections, will be done with less ic required for the known si, a full vcrdcs of weed growth Good connections as effective as the known ones

using the crfindungsrt the same amount that

appropriate connections
leads to a complete destruction of red deer and other grass-like weeds , to no damage to leafy plants such as radish (Raphanus sativus L.), soybeans, garden peas (Pisum sativum L.), spinach (Spinacia olcracea L.), sugar beets and carrots ( Daucus earota L.) and when treating the soil before germination, the amount which will result in complete prevention of germination of barnyardgrass will not damage brcitblällrigcii plants.

As mentioned above, the phytotoxicity is safe against broad-leaved crops extraordinarily large, and in this way the applicability of the connections according to the d. H. In other words, the application line, the application location and the application concentration in one very wide range variable, and the connections can be generally applied.

P. in another advantage of the connection-compliant connections consists in the fact that the residual toxicity in the soil or the plants as well as the acute toxicity for warm-blooded animals and fish not too lüieliien isl, there the compounds in its low concentration can be applied.

The original connections can be made directly to be applied to the ground for pre-emergence treatment or post-emergence treatment Emergence on the leaves of the plants, or they can mixed with the testicle! will emerge for treatment. You can aiii ilen soil or the leaves of the plants in quantities of S (I to K) OOg per K) Ar. preferably .SO to 200 μ per 10 Λι and especially applied in an amount of approximately K) (1 g per K) Ar will.

The F.rliiiiiliing be! Riff! also liquid or solid

('S herbicidal agents which contain at least one of the compounds according to the invention together with a customary carrier and / or surface-active agent. These agents can be prepared by mixing the active ingredient according to the invention with suitable carriers in a form which is customarily used, for example as wettable powders, emulsifiable concentrates, dusts, granulates, water-soluble powders and aerosols are produced. Solid carriers include bentonil, dialomene crude, apatite, gypsum, talc, pyrophyllite, vermiculite, clay and other applied liquid carriers. Kerosene, mineral oil, petroleum, Solvent naphtha, benzene, xylene, cyclohexane, cyclohexanone, dimethylformamide, alcohol or acetone in question. Surfactants can be added in order to obtain a homogeneous, stable preparation.

The compounds according to the invention can also mixed with other substances used in agriculture and horticulture and which are compatible with the respective compounds, can be used together. SoIcIn Chemicals can e.g. B. Substance.cn be, as sii as a plant nutrient. Fertilizer. Insecticides, aka rizidc. Fungicides. Herbicides and nematocides hekainv are.

As with known herbicides, it is beneficial to use dii Compounds according to the invention in a mixture with a herbicidal compound of the following group to apply:

N- (3-chloro-4-methoxyphynyl) -

N ', N'-dimethyl urinates off.

N-I.M-Dichlorophynyn-N'.N'-dimclhylharrisloff.

N-I. ^ - Dichlorphcny I) -N'-met hoxy-N'-met hylliarnstoff,

1,3-Dimcthyi- (3-bcnzothiazol-2-yl) urine,

1.3-Dimethyl-3- (S-methylbeii / olhia / ol-2-yl | -

urea,

1,3-Dimethyl-3 - (. S-i-buiy! benzene hiazoT-2-yl) -

harnsloff,

l, l, 3-trimethyl-3- (5-methylbenzothiazol-2-yl) urine,

U, 3-trimethyl-3- (S-ethylbenzothiazol-2-yl) -

notification,
1.3-dimethyl-3- (5.7-dimethylbenzothiazol-2-yl) urea,
l, l, 3-trinictliyl-3- (S, 7-ilimethylben / olhiazole

2-yl) urine slolT,

2-chloro-4,6-diethylamino-1,3,5-iriazine.

2-chloro-4-ätliylamino-6-isopropylamino-

1,3,5-triazine,

2-Clilor-4.i) -cliisopropylamino-1.3.? - tria7in,

2-Mi: ethylmercaplo-4-ethylaniino-fi-isopropylamiiio-1,3,5-iriazine.
2-methylmcrcaplo-4, (vdiisopropylamino-

1,3,5-lriazine,
3-methoxycarbonyl; iiiinophynyl-N- (3'-niclhylplienyl-carbanial.

Methyl-Nf.M-diclilor-phciiyll-carbamal,
isopropy | -N- (3-chlo! "phcnyl ^l -carbaiual,
S- | 4-Chion) bciizyl) -NN-iiiä! Hylthiolcarbainat, 4'-Nilro-2,4-dichli) r-diphynyl-ether,
'l-Nilro ^ .ld-lricliloro-iliphenyl-ällier.
2-McI hy I-4-CIiIOrO-PlKiIiOXyCSSIgSa ure.
2.4-dichloro-phenoxyacetic acid.
3-isopropyl-2,3-bcn / olhiadiazini ⁱ -4-oiKv

2,2-dioxide and

26 Ol

The concentration of the active ingredients in the inventive ingredients varies according to the type of preparation i.nd is z. B. in the range from 5 to 50% by weight, preferably 10 to 60% by weight, with wettable powders. 5 to 70. preferably 20 to 60% by weight. in the case of emulsifiable concentrates and 0.5 to 30, preferably 1 to 10% by weight Stiiubemitln.

So becomes a wettable powder or an emulgicrbarcs Concentrate diluted with water to a specific concentration and in the form of a liquid Suspension or liquid emulsion used to treat the soil or leaves.

A dust millel is used directly to treat the soil or leaves.

The following are examples of founding dimensions herbicidal agents indicated.

B e i s ρ i c 1 11

Benelzbarcs powder

Parts by weight

Compound No. 2 50

Dialomeencrdc 21 _{: 5}

Sodium alkyl sulfate K

Talc ... "21

These substances were mixed homogeneously and ground to a fine powder. One received -, ο a wettable powder containing 50% active ingredient. In practical use it was with water diluted to a certain concentration and sprayed as a suspension.

Example 12
Emulsifiable concentrate

Weight lc

Connection No. 1 40

Xylene 35

Dimethylformamide 15

Polyoxyethylene-phcnyläthcr IO

The substances were mixed and dissolved. An emulsifying concentrate with 40% by weight was obtained. Active ingredient. In practical use, it was diluted to a certain concentration with water and sprayed as an emusion.

45

example 1
granules

Connection No. 3.

talc

Bentonite

volume

Sodium alkyl sulfal

Parts by weight

. . 38
.. 10

The superior herbicidal effective wedge of the invention Connections emerge from the following experiments.

Attempt 1

Treatment before emergence

(Treatment of the soil under greenhouse conditions)

About 60 seeds of chicken millet were sown in a pot with a surface area of 60 cm ² and lightly covered with soil. Water was poured into the pot until the surface was wet.

10 ml of an aqueous emulsion obtained by diluting an emulsifiable concentrate with water had been made on a specific concentration, were sprayed on the pot. The pots were kept in the greenhouse and watered daily to maintain the water level. Three weeks after spraying, the degree of destruction of the plants was observed and on a 0 to 5 scale rated according to their respective importance.

r \

V; -

1 ₌

2 ₌

3 =

4 =

5 ₌

no effect.

Parts of the plants easily damaged.

Plants easily damaged.

Plants moderately damaged.

Plants badly damaged.

Plants completely unsoldered or none

Germination.

The results given in Table 2 were obtained.

Tabel

Connection no.

Aulbringmcnuc (g / 10 Ar)

40

2 3 4 5 6 7 9 Comparison connection
O —CO-CH,

125

5 5 5 5 5 5 5 5

W)

5 5 5 5 5 5 5 5

fiO

NOC ₂ H ₅ *)

These substances were mixed homogeneously and ground into a fine powder. From the powder a granulate with a particle size in the range of (V5 to 1.0 mm with the help of: a Granulalors (> s manufactured. Granules with 7% active ingredient were obtained. These granules were used in practical Application applied directly.

*) Disclosure letter 22 52 SIK.

26 Ol 447

Attempt 2

Treatment na:! I the emergence

(Treatment of the leaves
under greenhouse conditions)

About 50 seeds of chicken millet were in sown a pot with a surface of 60 cm and lightly covered with earth. The pot was in a Height of about 3 cm above the surface of the earth Lulled with water after the plants hold a leaf.

E:, an aqueous solution that is obtained by diluting an emulsifiable concentrate with water to a A certain concentration had been established, was sprayed onto the pot. The pots were im Kept greenhouse. Water was added daily to keep the water land constant. Two weeks after the spraying, the degree of destruction of the test plants was observed and rated according to the 0 to 5 scale given above. Those in Table 3 below were obtained aiiüCücbenen results.

Table 3

Connection no.

Aiifbringmeime
(g / 10 Ar)

250

5
5
5
5
5
5

125

5
5
5
5
5
5

M)

3 5 5 5 5

Comparison connection
O — CO — CH,

NOC ₂ H ₅

Table 4

Wrbmiluhi! No.

Comparison connection
O- COCH,

Ig / ΙΟ Ar) W) .11 250 125 5 3 5 5 4th 3 5 5 5 4th 5 5 4th 3 5 5 5 5 5 5 5 5 5 5 5 5 5 5

STILL.

CH.,

Not treated

Attempt 4

Not treated

Post-emergence treatment (treatment of leaves)

Cinquefoil seeds were sown in a pot with an area of 100 cm ² . After the plants reached 2 to 4 leaves, an aqueous emulsion prepared by diluting an emulsifiable concentrate with water to a certain concentration was sprayed on the leaves of the test plants in an amount of 100 1/10 ares. The plants were kept in the greenhouse.

21 days after the spraying, the degree of destruction of the test plants was observed and rated according to the 0 to 5 scale given above. Those given in Table 5 were obtained Results:

Table 5

Attempt 3
Treatment before emergence

Cinquefoil seeds were placed in a pot with an area of 100 cm ² . An aqueous emulsion prepared by diluting an emulsifiable concentrate with water to a certain concentration was sprayed on the surface of the soil before emergence. The pots were kept in the greenhouse. 21 days after spraying, the degree of destruction of the test plants was observed and rated according to the 0 to 5 scale given above.

The results given in Table 4 below were obtained:

Connection no.

Aiifbringiiicngc (g / 10 Ar)

200 100 50

/ ft

* 19th

Ol 447

Connection no.

Comparison connection via —COCH,

NOC ₂ H

"5

Aiifhrinjimcngc (μ / ΙΙΙΛΠ

2 (H) ΙΟΙ) 50

H ₃ C ° O

Not treated

Claims (7)

26 OI 447 Claims: I. Cyclohexenone derivatives of the general formula NO-CH ₁ -CH = CH, R Ν -Ο -CH ₁ -CH = C II ₃ C CU., H ₁ C CH, in which R _{1 is} an ethyl or propyl group, R is a hydrogen atom or the —COOCHj group and R is the remainder ) - - CO— (CH ₂ ), - CO— or —CO— (CH,) ₄ —CO— means. 2. A compound according to claim ί, characterized by the formula C ₃ H ₁ NO-CH ₁ CH = CH ₁ C ₃ H ₇ NO-CH ₂ CH = CH, O '. · ■ —CO- = o H ₃ C CH, HjC CHj 3. A compound according to claim 1, characterized by the formula NO-CH ₂ CH = CH ₂ C ₃ H ₇ NO-CH ₂ CH = CH ₂ O CO— (~ Λ —CO — O H ₃ C CH ₃ H _; , C CH ₃ 4. A compound according to claim 1, characterized by the formula C ₃ H ₇ NO-CH ₂ CH = CH ₂ C ₃ H ₇ NO-CH ₂ CH = CH ₂ C C o — co— <ο> - co — ο -COOCH ₃ HH ₃ C CH ₃ H ₃ C CH ₃ 5. A compound according to claim 1, characterized by the formula N-O-CH ₇ CH = CH ₁ C ₃ H ₇ NO-CH ₂ CH = CH ₂ O - CO - (CH ₂ ) ₄ - CO - O - f > = O H ₃ C CH ₃ 26 Ol 447 6. Process for the preparation of the compounds according to Claim I to 5, characterized in that one 2 moles of a compound of the formula H
R ₁ NO-CH ₁ -CH = CH, in which R ₁ and R _{2 have} the meaning given above, is reacted in a manner known per se in the presence of alkali with a compound of the formula R (Cl) ₂ . 7. Herbicidal agents containing at least one compound according to Claims 1 to 5, optionally together with a conventional inert carrier and / or surfactant.