DE3521934A1 - HYDROXYPROP-2-YL-4- (5- (2,4-DISUBST.-PHENOXY) -2-SUBST.-PHENOXY) CROTONATE DERIVATIVES, HERBICIDES CONTAINING THEM AND THEIR USE - Google Patents

Description

The invention relates to hydroxyprop-2-y1-4-f5- (2,4-disubstituted-phenoxy) -2-substituted-phenoxy] crotonate and the use of such compounds as herbicides. In lower doses you can these compounds are used as plant growth regulators.

A large number of diphenoxy-type herbicides are described in various publications. For example, U.S. Patent 4,163,661 describes herbicidal alkyl esters of 4-methyl-4- [4- (4-trifluoromethylphenoxy) phenoxy] crotonic acid. U.S. Patent No. 4,093,446 describes herbicidal 4-Trilfuormethyl-4 -nitrodiphenyl ^1-2'-alkoxy ether and the US-PS 4,134,753 herbicidal 4-halo-4-nitro-3'-· alkanoyloxydiphenylether. Other diphenoxyether herbicides are described in US Pat. No. 4,221,581 and DE-OS 2,905,458. U.S. Patent 4,419,123 relates to multisubstituted diphenoxyether herbicides and describes extensive testing of various substituents which may be meta to the phenoxy linkage.

US Pat. No. 4,414,017 and British Pat. No. 2,079,271 disclose herbicidal esters and salts of 4- [5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrophenoxy] crotonic acid described. In EP 34 120 are similar compounds and their

25 2-chlorophenoxy analogs are described.

The present invention relates to herbicidal compounds having both pre- and post-emergence activity against both grassy weeds as well as broad-leaved plants. The compounds show a particularly excellent one Pre-emergence activity against broad-leaved plants and have sufficient selectivity so that they are effective

10

15th

- 5 ~

a safer and safer way to control broadleaf weeds in certain grassy crops,
in particular rice, can be used.

The compounds according to the invention can be represented by the general formula:

(I)

O-CH-C = CHCOCH-Ch ₂ OH

wherein

1 2
R and R independently of one another represent hydrogen or

Lower alkyl with 1 to 4 carbon atoms,
X is halogen,

Y is halogen or trifluoromethyl and
Z denotes nitro or halogen.

25 30

Compatible salts of the above-mentioned compound
also fall within the scope of the invention.

The compounds have an asymmetric carbon atom and can exist as optical isomers. The connections can also exist as geometric isomers with respect to the double bond. The above formula includes that respective individual isomers and mixtures thereof and the respective isomers and mixtures thereof fall within the scope of the invention.

According to a further feature, the invention provides a herbicidal composition of an acceptable carrier and a herbicidally effective amounts of compounds of the formula (I) or compatible salts thereof or of mixtures thereof

■ * ■■ ο ■■ "

made available.

The present invention also relates to a method for preventing growth or for controlling Growth of undesirable vegetation and consists in the fact that growth media and / or the leaves of such Vegetation with a herbicidally effective amount of one or to treat several compounds of the formula (I) and / or compatible salts thereof.

According to another feature, the invention provides a plant growth regulating agent from a compatible one Carrier and a plant growth-regulating amount of a compound of the formula (I), compatible salts of formula (I) or mixtures thereof, which are able to change the normal growth pattern of such plants, made available.

The present invention also relates to a method for regulating plant growth, which consists in that the growth medium and / or the leaves of such vegetation with a plant growth regulating Amount of one or more compounds of the formula (I) and / or compatible salts thereof which form the normal Able to change the growth pattern of such plants, treat.

The invention also relates to chemical intermediates and processes for the preparation of the compounds of the formula (I).

The invention is explained in more detail below.

Typical compounds of the formula (I) are described in Examples 1 and 2 below. What the Substi-

As regards tuenten, the preferred compounds are those in which Y is trifluoromethyl, X is chlorine means, Z nitro or chlorine, especially nitro, meaning

1 2

image light. R and R are independently hydrogen, methyl or ethyl. In particular, one of the sub-

1 ?

substituent R or R is hydrogen and the other is hydrogen or methyl. In a particularly preferred manner

1 2

R is methyl and R is hydrogen. The preferred compounds have at least one preferred substituent and in particular have a combination of two or more preferred substituents.

The compounds according to the invention can be used in an expedient manner Wise prepared by reacting the corresponding di (phenoxy) crotonic acid analogs with propylene oxide. This reaction can be represented schematically by the following overall reaction equation:

It

0-CHC = CHCOH

+ H ₂ C-

-CHCH-

(B)

·> I.

1 2

wherein R, R, X, Y and Z have the meanings given above own.

0 This production can be achieved by making the connection (A) with the compound (B) (propylene oxide) under reactive conditions, preferably in an inert organic Solvent, is contacted. It has also been found that good results are obtained when the 5 Reaction also carried out in the presence of a trimethylsulfoxonium halide (for example trimethylsulfoxonium iodide)

to be led. In this way, it is believed that the reaction is improved by forming the alkyl ester of compound (A) and releasing hydrogen halide, since the alkyl ester is more easily converted to an alcohol than the acid. In addition, hydrogen halides catalyze the conversion to the alcohol. Typically, this process is carried out at temperatures between about 20 and 150 ⁰ C and preferably 78 to 105 ⁰ C for about 1 to 48 hours and preferably 8 to 24 hours, with about 1 to 25 moles and preferably 1 to 10 moles of propylene oxide per Mol of the compound (A) are used. When a trimethylsulfoxonium halide is used, about 0.10 to 1 mole, and preferably 0.15 to 0.50 mole, is typically used per mole of the compound (A). Trimethylsulfoxonium iodide or bromide is typically used. Suitable inert organic solvents which can be used are, for example, ethanol, dichloromethane, toluene, 1,2-dimethoxyethane or the like, as well as compatible mixtures thereof.

The starting materials of the formula (A) are generally known compounds and can be prepared by known methods or obvious modifications thereof through the use of suitable solvents and appropriately substituted ones Manufacture raw materials. The compounds of formula A in which Z is nitro are, for example in U.S. Patent 4,414,017. The connections of the formula A, in which Z represents chlorine, are described in EP 34,120.

The compatible salts of the formula (I) can be prepared by conventional methods. For example, can the salts are prepared by treating the compound of formula (I) with a suitable base which is the desired Has cation, such as n-butyllithium, sodium hydride, potassium hydride or the like. To the corresponding

Salt to get. Further changes in the salt cation can also be achieved via an ion exchange with a Effect ion exchange resin with the desired cation.

The general process conditions are described below.

In general, in practicing the methods described above, it is preferable to use the respective products separate before proceeding to the next stage in the sequence of reactions, unless it is is an in situ stage or is otherwise indicated. These products can be made from their respective reaction product mixtures be recovered by any suitable separation and purification method, for example by recrystallization and chromatography. Suitable separation and purification methods are, for example explained in the following examples.

In general, the reactions described above are carried out as a liquid phase reaction, so that the Pressure in general is not important unless it affects temperature (boiling point) in the reactions be carried out under reflux. Therefore, these reactions will generally occur at pressures of about 300 carried out up to 3,000 mmHg and carried out in an expedient manner at atmospheric pressure or ambient pressure.

It should also be noted that if typical or preferred process conditions (e.g. reaction temperatures, times, molar ratios of the reactants, solvents, etc.) are given, other process conditions can also be selected. Optimal reaction conditions (For example, temperature, reaction time, molar ratios, solvent, etc.) can be used with the Reagents or organic solvents vary

They can be determined by routine optimization methods.

If optical isomer mixtures are obtained, then the respective optical isomers can be obtained by conventional separation methods. Geometric isomers can be used according to conventional separation methods can be obtained from differences in physical properties between depend on the geometric isomers. 10

The following terms have the meanings given below, unless otherwise stated:

The term "lower alkyl" applies to both straight chain as well as branched alkyl groups with a total of 1 to 4 carbon atoms, for example primary, secondary and tertiary alkyl groups. Typical lower alkyl groups are, for example, methyl, ethyl, n-propyl, isopropyl,

η-butyl, t-butyl. 20th

The term "halogen" or "halogen atom" or "halide"

affects fluorine, chlorine, bromine and iodine.

The term "compatible salts" or "compatible cations" refers to salts that do not significantly affect the herbicidal properties of the parent compound. Suitable salts are cation salts, such as, for example, cation salts of lithium, sodium, potassium, alkaline earth metals, ammonia, quaternary ammonium salts or the like.
30th

The term "room temperature" or "ambient temperature" refers to a temperature of about 20-25 ° C.

The compounds of the formula (I) show both a herbicidal pre-emergence and post-emergence activity and a special one good herbicidal activity against broad-leaved

Plants.

In general, the herbicides are used for post-emergence purposes Compounds applied directly to the leaves or other parts of the plant. Can be used for pre-emergence purposes the herbicidal compounds applied to the growth medium or any growth medium of the plant. The optimal one The amount of the herbicidal compound or herbicidal agent varies depending on the particular one Plant species and the extent of plant growth, if any, and the particular part of the plant, who is contacted and the extent of the contact. The optimal dosage may also depend on the location or the environment, for example, depending on whether the surfaces are shielded such as greenhouses or exposed areas such as fields, as well as the type and extent of the desired Combat. In general, both pre-emergence and post-emergence control are those according to the invention Compounds in amounts of about 0.02 to 60 kg / ha and preferably about 0.02 to 10 kg / ha upset.

Although the compounds can theoretically be applied in undiluted form, in practice they will generally as a preparation or formulation of an effective amount of the compound (s) and an acceptable one Applied carrier. An acceptable or compatible carrier (agriculturally acceptable carrier) 0 is one that does not noticeably have the desired biological effect achieved by the active ingredients, affects, but only causes a dilution. Typically a formulation will contain about 0.05 to 95 % By weight of the compound of the formula (I) or of mixtures thereof. Concentrates with high concentrations can also

if prepared, designed to be diluted prior to application. The carrier can be solid, liquid or be an aerosol. The actual composition can consist of granules, powders, foams, solvents, Emulsions, slurries, aerosols or the like. Exist.

Suitable solid carriers that can be used are, for example, natural clays such as kaolin, attapulgite, Montmorillonite etc., talc, pyrophyllite, diatomaceous silica, synthetic fine silica, calcium aluminosilicate, Tricalcium phosphate or the like. Furthermore, organic materials such as walnut shell flour, Cottonseed pods, wheat flour, wood flour, wood bark flour or the like. Can be used as a carrier. Suitable liquid diluents are, for example, water, organic solvents such as hydrocarbons, z. B. benzene, toluene, dimethyl sulfoxide, kerosene, diesel fuel, Fuel oil, petroleum naphtha etc., or the like. Suitable aerosol carriers are conventional aerosol carriers,

20 like halogenated alkanes, etc.

The agent can also have various promoters and surfactants Contain agents that increase the rate of transport of the active ingredient into the plant tissue, such as organic solvents, wetting agents and oils. In the case of preparations intended for pre-emergence applications are suitable, agents can be used which reduce the leachability of the compounds or otherwise increase soil stability.

The agent can also contain various compatible adjuvants, stabilizers, conditioning agents, Contain insecticides, fungicides and optionally other herbicidally active compounds.

5 At reduced dosages, the inventive

Compounds used to alter the normal growth pattern of plants.

The compounds of the formula (I) can be used as plant growth regulators are used in pure form, but, as in the case of herbicidal application, in Used in combination with a carrier. The same types of carriers as described above in connection with herbicides Means explained can also be used. Depending on the desired application the plant growth regulating agent can also contain other compatible ingredients, such as drying agents, Defoliants, surfactants, adjuvants, fungicides and insecticides, or in combination be applied with it. Typically, the plant growth regulating agent contains approximately a total of 0.005 to 90% by weight of the compound (s) of the formula (I), depending on whether the compound is applied directly or is diluted first.

The invention is illustrated by the following preparation examples and examples. Unless otherwise stated, refer to all temperatures refer to the same system, while the term "ambient temperature" or "room temperature" means one

Temperature from 20 to 25 ° C included. The term "percent" or "%" refers to percent by weight and the term "mole" refers to gramsol. The term "equivalent" refers to an amount of the Reagent, expressed in moles, being the number of moles of the preceding or following reactant given in the example is equivalent with respect to finite moles or a finite weight or volume. The proton magnetic Resonance spectrum (PMR or NMR) is determined at 60 mHz, the signals are doubled as singlets (s), broad singlets (bs), doublets (d), double doublets (dd), triplets (t) Triplets (dt), quartets (q) and multiplets (m) an-

given, cps relates to vibrations per second. If necessary, examples were repeated in order to have additional starting material available for subsequent examples.
5

Examples example 1

3-hydroxyprop-2-yl-4- [5- (2-chloro-4-trifluoromethylphenoxy) ~ 2-nitrophenoxy] -4-methylcrotonate

To carry out this example, a mixture containing 10.9 g of 4- [5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrophenoxy] -4-methylcrotonic acid, Contains 10 g propylene oxide and 1 g trimethylsulfoxonium iodide in 150 ml ethanol, refluxed for 24 h and then filtered. The filtrate is evaporated and the residue is redissolved in ethyl ether dissolved, whereupon it is evaporated again. The residue is chromatographed over silica gel, using mixtures is eluted from ethyl ether and petroleum ether in order to arrive at the desired compound in the form of an oil. Elemental analysis: carbon: calculated 51.49%, found 51.66%, hydrogen: calculated 3.92%, found 4.32%, nitrogen: calculated 2.86%, found 2.86%.

Similarly, applying the above methods to the appropriate crotonic acid analogs, the following Connections are made:

3-hydroxyprop-2-yl 4- [5- (2-fluoro -4-trifluoro-methylphenoxy) -2-nitrophenoxy] -4-methylcrotonate / 3-hydroxyprop-2-yl 4- [5- (2-broin -4-trifluoro-methyl-

phenoxy) -2-nitrophenoxy] -4-methylcrotonate _/

3-Hydroxyprop-2-yl 4- [5- (2-iodo-4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -4-methylcrotonate , 3-hydroxyprop-2-yl 4- [5- (2- chloro-4-fluoro-phenoxy) -2-nitrophenoxy] -4-methylene crotonate,

3-hydroxyprop-2-yl 4- [5- (2-j od-4-chlorophenoxy) -2-nitrophenoxy] -4-methyl crotonate;

3-Hydroxyprop-2-yl 4- [5- (2-fluoro-4-bromo-rphenoxy) -2-nitrophenoxy] -4-methyl crotonate _t

3-hydroxyprop-2-yl 4- [5- (2 _# 4-dichlorophenoxy ) -2-

nitrophenoxy] -4-methylcrotonate,

3-hydroxyprop-2-yl 4- [5- (2 , 4-difluorophenoxy) -2-nitrophenoxy] -4-methylcrotonate /

3-% droxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methylphenoxy) -2-nitrophenoxy] crotonate,

3-% droxyprop-2-yl 4- [5- (2-iod. -4-trifluoromethylphenoxy) -2-nitrophenoxy] crotonate,

3-hydroxyprop-2-yl 4- [5- (2-iodo-4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] crotonate /

3-hydroxyprop-2-yl 4- [5- (2-chloro-4-fluoro-phenoxy) -2-

nitrophenoxyJ-crotonate /

3-Hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -3-methylcrotonate _/ , 3-hydroxyprop-2-y1 4- [5- (2nd -bromo-4-iodo-phenoxy) -2-nitrophenoxyl-S-methylcrotonate /

3-hydroxyprop-2-yl 4- [5- (2-chloro -4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -4-ethyl crotonate _/

3-hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -3-ethyl crotonate / 3-hydroxyprop-2-y1 4- [5- (2-chloro -4-trifluoro-methy1-

phenoxy) -2-nitrophenoxy] -4-propyl crotonate /

3-hydroxyprop-2-y1 4- [5- (2-chloro -4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -3-butyl crotonate / 3-hydroxyprop-2-yl 4- [5- (2-chloro - 4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -4-isopropyl crotonate /

3-hydroxyprop-2-yl 4- [5- (2-chloro -4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -3-t-butyl crotonate /

3-hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -3,4-dimethyl crotonate /

3-hydroxyprop-2-yl 4- [5- (2-chloro -4-trifluoro-methy1-phenoxy) -2-nitrophenoxy] -3,4-dibutyl crotonate / 3-hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy1-phenoxy ) -2-nitrophenoxy] -S-ethyl ^ propyl crotonate,

Hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy 1-phenoxy) -2-chlorophenoxy] -4-methylcrotonate ,.

3-Hydroxyprop-2-yl 4- [5- (2-bromo- 4-trifluoromethyl 1-phenoxy) -2-chlorophenoxy] -4-methylcrotonate /

3-hydroxyprop-2-yl 4- [5- (2- iodo-4-trifluoro-methy 1-phenoxy)) - 2-chlorophenoxy] -4-methylcrotonate,

3_Hydroxyprop-2-yl 4- [5- (2-chloro -4-fluorophenoxy) -2-chlorophenoxy] -4-methylcrotonate /

^ 3-Hydroxyprop-2-yl 4- [5- (2-iodo-4-chlorophenoxy) -2-chlorophenoxy] -4-methylcrotonate /

3-hydroxyprop-2-yl 4- [5- (2-fluoro-4-bromophenoxy) -2-chlorophenoxy] -4-methylcrotonate /

3-hydroxyprop-2-yl 4- [5- (2,4-dichlorophenoxy) -2-chlorophenoxy] -4-methylcrotonate /

3-hydroxyprop-2-yl4- [5- (2,4-difluorophenoxy) -2-chloro- «Phenoxy] -4-methylcrotonate /

3-Hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoromethyl 1-phenoxy) -2-chloro-phenoxy] -crotonate ,

3-hydroxyprop-2-yl 4- [5- (2-iodo-4-trifluoro- .iiethy 1-phenoxy) -2-chlorophenoxy] crotonate /

3-hydroxyprop-2-yl 4- [5- (2-iodo-4-trifluoro-methylphenoxy) -2-chlorophenoxy] crotonate _/

3-hydroxyprop-2-yl 4- [5- (2-chloro-4-fluoro-phenoxy) -2-

chloro »phenoxy] crotonate / 30 vj.,

3-Hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy1-phenoxy) -2-chloro-phenoxy] -3-methylcrotonate /

3-hydroxyprop-2-yl 4- [5- (2-bromo -4-iodo-phenoxy) -2-chloro phenoxy] -3-methylcrotonate /

3-hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy1-phenoxy) -2-chloro-phenoxy] -4-ethylcrotonate /,

3-Hydroxyprop-2-yl 4- [5- (2-chloro -'4-trifluoro-methy 1-phenoxy) -2-chloro-phenoxy] -3-ethyl crotonate /

3-Hydroxyprop-2-yl4- [5- (2-chloro-4-trifluoro-methy 1-phenoxy) -2-chloro-phenoxy] -4-propyl crotonate /

3-Hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluor "--methylphenoxy) -2-chloro- ^ phenoxy] -3-butyl crotonate _/ 3-hydroxyprop-2-yl 4- [ 5- (2-chloro-4-trifluoro-methyl-

phenoxy) -2-chloro-phenoxy] -4-isopropyl crotonate,

3-hydroxyprop-2-yl 4- [5- (2-chloro- 4-trifluoro-methylphenoxy) -2-chloro-> phenoxy] -3-t-butyl crotonate,

3-Hydroxyprop-2-yl 4- [5- (2-chloro - ^ - 4-trifluoro-methyl-1Q phenoxy) -2-chloro-phenoxy] -3,4-dimethyl crotonate /

3-hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methylphenoxy) -2-chloro-phenoxy] -3 _f 4-dibutyl crotonate /

3-Hydroxyprop-2-yl 4- [5- (2-chloro-4-trifluoro-methy1-phenoxy) -2-chloro-phenoxy] -3-ethyl-4-propyl crotonate "

Example 2

Sodium salt of 3-hydroxyprop-2-yl-4- [5- (2-chloro-4- trifluoromethylphenoxy) -2-nitrophenoxy] -2-methylcrotonate

The connection you are looking for can be established using the following method.

0.54 g of sodium hydride (50%) are added in portions to one added stirred solution containing 5.5 g (0.0112 mol) of 3-hydroxyprop-2-yl-4- [5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrophenoxy] -2-methyl crotonate in 100 ml of anhydrous ethyl ether at room temperature under a nitrogen atmosphere contains. After the release of hydrogen has ceased, two drops of ethanol are added to

destroy unreacted sodium hydride. The reaction mixture is filtered through magnesium sulfate. The filtrate is then evaporated in vacuo to give the sought compound as a residue. 35

Similarly, using the above method on the compounds given in Example 1, one can prepare the corresponding salts.

Example 3

In this example, the compound of Example 1 is compared to its pre-emergence and post-emergence activity a variety of grasses and broad-leaved plants including a corn plant and a broad-leaved plant Crop tested using the methods described below.

15 Herbicidal Pre-emergence Test

Pre-emergence herbicidal activity is determined in the following way:

A test solution of the compound is made as follows:

355.5 mg of the test compound is dissolved in 15 ml of acetone. 2 ml of acetone containing 110 mg of a nonionic surfactant Means included are added to the solution. 12 ml of this starting solution then becomes 47.7 ml Added water, which is the same nonionic surfactant Contains agent at a concentration of 625 mg / 1.

Seeds of the test vegetation are planted in a pot filled with soil, and the test solution becomes uniform on the surface of the earth at a dose of 27.5 micrograms / cm ^ sprayed on. The pot is poured and placed in a greenhouse. The pot is poured at intervals and on the emergence of the seedlings, on the health of the

emerging seedlings were observed for a period of 3 weeks. At the end of this period of time the herbicidal effectiveness of the compound is assessed on the basis of physiological observations. It will be one of A scale ranging from 0 to 100 is used, with O indicating no phytotoxicity means, while 100 reflects a complete kill. The results of these tests are in the Table I summarized.

10 herbicidal post-emergence test

The test compound is described in the same manner as described above in connection with the pre-emergence test formulated. This formulation is divided equally into two

similar pots are sprayed containing 50 to 75 mm tall plants (with the exception of wild oats, soybeans and watergrass which are 75 to 100 mm tall) with approximately 15 to 25 plants growing per pot. The spray is applied at a dose of 27.5 micrograms / cm ² . After the plants have dried, they are placed in a greenhouse and then watered at intervals as needed. The plants are periodically observed for phytotoxic effects and physiological and morphological responses to the treatment. After 3 weeks, the herbicidal effects of the compound are evaluated based on these observations. A scale from 0 to 100 is used, with 0 indicating no phytotoxicity while 100 indicating complete kill. The results are shown in Table II.

Table I Herbicidal pre-emergence activity

Application rate: 27.5 micrograms / cm, unless otherwise stated

Broad-leaved plants

Grasses

Connection no.

% Phytotoxicity

% Phytotoxicity

White goosefoot

Mustard Foxtail Soybeans Watergrass Fingergrass Wild Oat Rice

100

100

100

100

93

93

95

to
ο

Tables Herbicidal Preemergence Activity

Application rate: 27.5 microgranuns / cm, unless otherwise stated

Broad-leaved plants

Grasses

Connection no.

% Phytotoxicity

% Phytotoxicity

White goosefoot

Mustard Foxtail Soybeans Watergrass Fingergrass Wild Oat Rice

100

100

100

50

35

50

40

to

Claims (18)

European Patent Attorneys Dr. Mdller-Bore and Partner · POB 26 02 47 · D-8000 Manchen 26 German patent attorneys Dr. W. MüUer-ΒθΓέ * Dr. Paul Deufel DipL-Chem., Dipl.-Wirtscfa.-Ing. Dr. Alfred Schön DipL-Chem. Werner Hertel Dipl.-Phys. Dietrich Lewald Dipl.-Ing. Dr.-Ing. Dieter Otto Dipl.-Ing. Brit. Chartered Patent Agent B. David P. Wetters MA (Oxon) Ch. Chem. MRSC C 3547 S / sm Chevron Research Company 555 Market Street San Francisco, CA 94105-2870 / USA Hydroxyprop-2-y1-4- [5 - ( 2,4-di sub st.-phenoxy) -2-sub st.-phenoxy] crotonate derivatives, herbicidal compositions containing them and their use claims 1. Compound of formula O CH- O-CH-C = CHCO-CHCh ₂ OH R ¹ R ² 10 wherein 1 2
R and R independently of one another represent hydrogen or Toloonnior Tnfntof RAC \ n R TfileX Stand lower alkyl,
X is halogen, Y is halogen or trifluoromethyl and
Z is nitro or halogen, as well as compatible salts thereof. 2. A compound according to claim 1, characterized in that Y stands for trifluoromethyl. 3. A compound according to claim 1, characterized in that X is chlorine. 4. A compound according to claim 1, characterized in that 1 2
one of the substituents R or R is hydrogen and the other is hydrogen, methyl or ethyl. 5. A compound according to claim 4, characterized in that 2
, R is hydrogen. 0 6. A compound according to claim 5, characterized in that R ^{1 is} methyl or ethyl. 7. A compound according to claim 6, characterized in that R ^{1 is} methyl. 25th 8. A compound according to claim 7, characterized in that Y is trifluoromethyl. 9. A compound according to claim 8, characterized in that X is chlorine and Z is nitro. 10. A compound according to claim 8, characterized in that X is chlorine and Z is chlorine. 11. A compound according to claim 1, characterized in that Z stands for nitro. 12. A compound according to claim 1, characterized in that Z stands for chlorine. 13. Herbicidal agent, characterized by a herbicide effective amount of a compound according to claim 1 or a mixture thereof and an acceptable carrier. 14. Herbicidal agent, characterized by a herbicidally effective amount of a compound according to claim 9 or a mixture thereof and a compatible carrier. 15. A method for preventing the growth of plants or for the destruction of plants, characterized in that that a herbicidally effective amount of a compound according to claim 1 or mixtures thereof is applied to the leaves or the possible growth medium of the plants is applied. 16. A method for preventing the growth of plants or for the destruction of plants, characterized in that that a herbicidally effective amount of a compound according to claim 9 or mixtures thereof is applied to the leaves or is applied to the possible growth medium of the plants. 17. Plant growth regulating agent, characterized by such an amount of a compound according to claim 1 or mixtures thereof, which is able to change the growth pattern of plants. 18. A method for regulating the growth of plants, characterized in that on the leaves of the plants or such an amount of a compound as claimed in claim 1 or mixtures thereof on its growth medium is brought, which is able to change the growth pattern of such plants.