DD239515A5 - PLANT GROWTH-REGULATING MEDIUM - Google Patents

Abstract

The novel derivatives of 1-phenylimidazole-5-carboxylic acids substituted in the phenyl ring are described by the general formula (I) in which the symbols have the following meaning: R 1, R 2 independently of one another (C 1 -C 4) alkyl; R 3 (C 1 -C 4) ) Alkyl, (C 1 -C 4) alkoxy or halogen, where in n1 the substituents may also be different n0, 1, 2 or 3; andX is a cyano, ester, thiolester, amide, thioester, amidoxime, alkoxymethyl, hydroxymethyl, aldehyde, keto, oxime, acetal, ketal, thioacetal or thioketal group or a heterocyclic substituent (e.g. B. B. tetrazolyl). The novel compounds have plant growth regulating activity. In a process for preparing these compounds, the free carboxylic acid (XCOOH), its amide (XCONH2), its lower alkyl esters (XCOO (C 1 -C 4) alkyl) or activated derivatives such as acid halides are assumed and then derivatized. The compounds also include the salts and quaternization products of the basic imidazole ring. Formula I

Description

The invention relates to plant growth regulators containing l-phenyl-imidazole-S-carboxylic acid derivatives such as nitriles (cyano compounds), amides or thiol esters, a process for the preparation of these derivatives and their use as growth regulators.

Characteristic of the known technical solutions

In the phenyl ring substituted l-phenyl-iraidazol-S-carboxylic acids, -carbonsäureamide, -carboxylic esters or -carbonsäurethiolester or salts of these carboxylic acids and their use as growth regulators are known from DE-A 3 217 094. These compounds are described by the following general formula

R "

(R) _{n R} ". wherein the symbols have the following meaning: XO, S or N-R ';

R 'is H, phenyl, (C ₂ -C ₆ ) alkenyl, (C ₁ -C ₁₂ ) unsubstituted or substituted up to three times by (C ₁ -C ₆ ) alkoxy, di (C ₁ -C ₃ ) alkylamino or halogen , where at

X = N-R * two identical or different radicals R 'are attached to the N; or a metal or ammonium cation at X-R * with X = O ^ or S ^;

R ", R" independently of one another (C ₁ -C ₄ ) Alkyl; R "" (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or halogen,

where η 1, the substituents may also be different; and

η O, 1, 2 or 3.

Although some of the known compounds already have a sufficient effect as growth regulators, in their use, however, often relatively large amounts must be used, so that occasionally unwanted side effects can occur «

Object of the invention

The aim of the invention is the provision of new agents with strong plant growth regulating action «

Explanation of the essence of the invention

It is an object of the present invention to synthesize novel effective derivatives of 1-phenylimidazole-5-carboxylic acids which can also be used as growth regulators in smaller quantities.

The subject of the present invention is therefore the connection

239 5f5

of the formula (I) R ¹

(I)

wherein

R ¹ . R ²

independently of one another (C ₁ -C ₄ ) alkyl;

(C ₁ -C ₄ ) AllCyI, (C ₁ -C ₄ ) alkoxy or halogen, where at η 1, the substituents may also be different;

O, l, 2 or 3 ··

2 39 51 p

O '0

-CN, -COOR ⁴ , -COSR ⁵ , -CNR ⁶ , -CN = C = S,

S .Ν-Ν

-N (-R ⁶ ) ₂ , -C

10 β

γ- ^/

¹⁵ ·

N o

ON, NH ₂

^ ¹⁶

, -CH ₂ -OR ¹⁶ , -C; or

⁶

25 Y ο. ZR ¹⁸ · -CZR ¹⁸ ; R ⁶ , S or NR ⁶ ; 30 Z 0 R ⁴ or S; substituted

C ¹ -C _2, C ¹ -C 4 alkyl, preferably (C ¹ -C 8) alkyl, which is up to three times, preferably just monosubstituted, by hydroxy,

(C _λ -O 1 ₁ ) alkoxy- (C ₁ -C ₄ ) alkoxy, CyCl (C ₁ -C 4) alkyl, benzyloxy, benzyloxyethoxy, phenyl, halogen

- sis

phenyl, methylphenyl, cyano, carbamoyl, üxlranyl, mono (C _n -Cg) alkylamino, (C ₁ -C 4) alkylthio, trimethylsillyl, (C ₁ -C 4) alkanoyl, (C ₁ -C 4) alkoxycarbonyl, phenoxy, phenylthio, -ON = C (-CH_-) ₂ »triazolyl, imidazolyl, carboxyl or carboxylate

with an ammonium or metal cation, preferably from the group of alkali or alkaline earth metal cations, or with an organic ammonium, phosphonium, sulfonium or sulfoxonium cation;

Halo (C ^ -CG) alkenyl; unsubstituted or (C ₁ -C ₄ ) alkyl-substituted cyclo (C ₁ -C ₄ ) alkyl; unsubstituted or halogen or methyl substituted cyclo (C 1 -C 8) alkenyl; (C ₆ -C ₆ ) alkynyl; l, 2-epoxy-prop-3-yl;

substituted phenyl which is mono- or disubstituted by halogen, nitro, cyano, (C.-C.) alkyl, (C ₁ -C.) alkoxycarbonyl or (C -C.) alkoxy; -N = CR ¹ R ¹¹ , -NR ⁶ R ¹²

²⁰

°, ~ NI, - N Π -N

(C ₁ -C 6) alkyl) carbonyl, phenylcarbonyl, the

may be substituted by halogen, nitro, cyano or (C ₁ -C ₄ ) -alkyl, or a radical of the formula

30

35

R- * substituted (C.-C.g) alkyl, preferably

(C ₁ -C 6 -alkyl) which is up to twice, preferably monosubstituted, by (C ₁ -C ₄ ) alkoxyethoxy, cyclo (C ₁ -C ₆ ) alkyl, benzyloxy, phenyl, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₂₁ ) alkoxycarbonyl, phen

oxy, carboxyl or carboxylate with an ammonium or metal cation, preferably from the group of alkali or alkaline earth metal cations, or with an organic ammonium, phosphonium, sulfonium or sulfoxonium cation;

or cyclo (C ~ -Cg) alkyl;

R ^{6 is} H or (C ₁ -C ₄ ) alkyl;

15 R 'substituted (C.-C ₁₂ ) alkyl, preferably

(C ₂ -C ₆ ) -alkyl which is up to twice, preferably monosubstituted, by (C ₄ -C ₄ ) -alkoxyethoxy, hydroxyl, cyclo (C 1 -C ₆ ) -alkyl, benzyloxy, phenyl, cyano, carbamoyl, carboxyl,

20 (C ₁ -C ₁ ) alkoxycarbonyl, formyl or phenoxy;

Cyclo (C -C -alkyl); up to two times halogen substituted by halogen, nitro, cyano, (C -C ^) alkyl or (C ₁ -C ₄ ) alkoxy-substituted phenyl; -NR ⁶ R ¹³ , -OR ¹ **, -NH-CO-NH ₂ , -NH-CS-NH ₂

25 or -SO R ¹⁵ ;

6 7 or R and R form - together with the

Nitrogen atom to which they are attached - a saturated or unsaturated, optionally benzo-fused three to seven-membered

Ring containing up to three heteroatoms from the group 0, N and S and which is unsubstitulert or substituted by (C ^ -C ^ alkyl or halogen and may contain an oxo group;

, Halogen, (C, alkyl, nitro or cyano;

R independently of one another H, halogen, (Cj-C ₁ ) -

R ° H, (C, -Cg) alkyl or phenyl, or in the case of thiocarboxylates an alkali metal or alkaline earth metal cation

tion, ammonium or organic ammonium cation;

R, R are independently H, unsubstituted or by triazolyl or imidazolyl

substituted (C ₁ -Cg) AlCl yI; CyCl (C ₃ -Cg) -alkyl, (C ₃ -Cg) alkenyl, phenyl or benzyl;

or together with the carbon atom to which they are attached form an unsubstituted

substituted or methyl or halogen substituted cyclo (C ₅ -C ") alkyl;

R ^{12 is} (C ₁ -C ₁₊ ) alkyl, phenyl, (C ₁ -Cg) alkylcarbonyl, benzyl, benzoyl, halobenzyl, halobenzobenzene

or methylbenzoyl;

R ^{13 is} H, (C ₁ -C ₄ ) alkyl, pormyl, (C ₁ -Cg) alkylcarbonyl, benzoyl, halobenzobenzene, methylbenzoyl or trihaloacetyl;

R ¹¹ * H, (C ₁ -Cj ₁ ) AlCl yI or benzyl;

R ¹ - ⁵ (C ₁ -C ₁ ) alkyl, phenyl, chlorophenyl or methylphenyl,.

R is H, unsubstituted or (C ₁ -C 4) -alkyl-substituted (C ₁ -C ₁₂ ) -alkyl; (C ₁ -C 6 alkylcarbonyl, halo (C ₁ -C 9) alkylcarbonyl, N- (C ₁ -CG) alkylcarbamoyl, Ben

zoyl, halobenzobenzene or methylbenzoyl;

R ¹ ^ O (including the bisulfide adducts) or = NOR ¹⁶ ; and

 Q

R. independently of each other unsubstituted or

5 by phenyl, cyclo (C ₁ -C 4) alkyl, (C ₁ -C

(C ₁ -C ₄ ) alkylthio or halogen substituted (C ₁ -C ₆ ) alkyl;

or both radicals R form, together with Z and the carbon atom to which they are bonded, an unsubstituted or by

(C ₁ -C ₄ ) AlCliI, hydroxy (C ₁ -C ₄ ) alkyl, HaloGCn (C ₁ -C ₄ ) alkyl or phenyl substituted 5- or 6-membered ring

mean as well as their usable for agriculture salts or quaternization.

In this case, the alkyl, alkenyl and alkynyl radicals occurring in the definition of the general formula (I) can be both straight-chain and branched; halogen is understood as meaning P, Cl, Br or J, in particular F, Cl or Br.

The salt formation or quaternization takes place on the basic imidazole ring of the compounds of formula I. However, this derivatization is not possible in the case of R, R 1 or R 1 = a cation. In the event that in the listed Substltuenten - in addition to the imidazole ring - more basic nitrogen atoms occur, a multiple salt formation or quaternization is possible.

Preferred among the compounds of formula I are those in which

35 R » R independently of one another (C ₁ -Co) alkyl, r 3 is methyl or halogen,

η 0 or 1,

0 .N N

X -COOR ⁴ , -CNR ⁶ , - <f ",

η *

/ N .1 0 Γ V ty IN c; or ^ R ⁶

U *

R (C ₁ -C 6) -alkyl which is monosubstituted by hydroxy, (C ₁ -C ₁₁ ) -alkylthio, cyclo (C ₃ -C 6) -alkyl, C ₁ -C 4 -alkynyl, a radical of the formulas -N = CR R ¹¹ or _n ^R -j I '/ ^ - v V - ^^ η

R ^{6 is} H or methyl,

R ^ (Cj-Cz-i-alkyl which is monosubstituted by hydroxy, cyano, carboxy, (C - C.) Alkoxycarbonyl, a radical of the formulas -NR R, -0R or -SO ₀ R;

R and R, together with the nitrogen atom, form on the

they are bonded to a heterocyclic ring of the formulas

Λ-Ν

Ar ^ T f ι - ivi ιm '. "- I

R ⁹ (C ₁ -Cg) -alkyl,

R ¹⁰ , R ¹¹ methyl,

R ¹³ , R ¹⁴ H, 5 R chlorophenyl and

R ¹⁷ O (including the bisulfide adducts)

and their salts and quaternization products. 10

The invention furthermore relates to processes for the preparation of the compounds of the general formula (I):

The cyano compound (X = -CN) is obtained by reacting the carboxylic acid amide known per se (X = -CONHp, see DE-A

32 17 094) dehydrated. As agents for this purpose, for example, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, phosphorus pentoxide and acetic anhydride infräge. The reaction temperature depends strongly on the choice of dehydrating agent and is generally between 20 and 120 ⁰ C. Optionally, inert organic solvents may also be added.

Ii c The esters, thiolesters or amide derivatives (X = -COOR, -COSR,

f \ 1

25 -CONR R) can be prepared from the carboxylic acids (see DE-A

32 17 094) or the activated compounds obtainable therefrom, such as acid halides or mixed carbonic anhydrides, by reaction with the corresponding alcohols, thiols or amine compounds. In addition, esters and thiol esters can also be obtained by alkylation of the carboxylic acids with haloalkyl compounds in the presence of bases.

The tetrazoles can be obtained by reacting the nitriles (X = -CN) with azides in organic solvents such as DMSO or DMP at temperatures from 20 ⁰ C to 15O ⁰ C. The other heterocyclic compounds of the formula (I) where X =

The tetrazoles are prepared by reacting the nitriles (X * = - CN) with azides in organic solvents such as DMF or DMSO obtained at temperatures of 2O ⁰ C to 15O ⁰ C. The other heterocyclic compounds of the formula (I) with X

N v /

-of

/ N

(R ⁸ )

/ N O

10 Ν- ^ Λ

and

are by implementing the ent

speaking carboxylic acids (see DE-A 32 17 09 ^ 4) or their activated representatives such as their acid chlorides with bifunctional compounds such as diamines, amino alcohols, aminothiols or Amidoxlmen according to known methods accessible (see, for example, JP-A 57/175 177 and 57 / 175 179).

Q Q

The thioesters (X = -CSOR, -CSSR) can be obtained from the corresponding oxygen compounds (esters) by reaction with phosphorus pentasulfide, advantageously in the presence of bases, in organic solvents such as dimethylformamide, acetonitrile, toluene or xylene.

The amidoximes / X = -C

become from the nitriles

NH,

(X "-CN) obtained by reaction with hydroxylamine and can be converted by reaction with alkylating agents in the other derivatives with R * H.

-CH ₂ -OR ¹⁶ with R ¹⁶ «H) can be

The alcohols (X are prepared by reduction from the known acids and esters (see DE-A 32 17 09 ² O. For example, the reduction of the lower alkyl esters with complex proved to be advantageous

- n - 239 5t S

Hydrides such as lithium aluminum hydride in tetrahydrofuran or diethyl ether. The hydroxyl group can then be converted by conventional methods such as alkylation, acylation or carbamoylation in the other compounds with X * -CH - OR and R ¹⁶ * H.

, R ¹⁷

The aldehyde derivatives (X- -C "with R ⁶ = H, R ¹⁷ = 0)

are due to selective oxidation of the alcohols

(X = -CHp-OR ¹⁶ with R ¹⁶ = H) accessible. As the oxidizing agent, for example, dimethylsulfoxide in the presence of oxalyl chloride or acetic anhydride are suitable. The ketone derivatives

(C 1 -C ₁₊ ) alkyl, R ¹⁷ - θ]

χ. _c with R ⁶ = (C -C 1 ₊ ) alkyl, R ¹⁷ - [theta] are by

Reaction of suitable Dlalkylamide of the carboxylic acids with Grignard reagents obtained (see Synthesis ( 1984 ), p 228 f). The further derivatizations to the oxime derivatives

¹⁷

U = tf with R ¹⁷ = -NOR ¹⁶ J

vates IX = C with R '= "NOR) or the acetal

^R 6

Ketal, thioacetal or thioketal compounds

(X = -cZR ¹ ) are according to common methods such as

25 R

Reaction with Hydroxylamlnhydrochlorid in the presence of. inorganic or organic bases and optionally subsequent alkylation, acylation or carbamoylation, or reaction with alcohols or thiols with dehydration possible.

As already defined above, compounds which can be used according to the invention are also the salts of the compounds of the formula (I) and the quaternization products of the compounds of the formula (I).

- 12 - ^{239 51S}

For the preparation of the salts of the compounds of the formula (I), the following acids are suitable: hydrohalic acids such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, Salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid. The acid addition salts of the compounds of formula (I) can be readily prepared by conventional salt formation techniques, e.g. by dissolving a compound of formula (I) in a suitable organic solvent and adding the acid and in known catfish, e.g. by filtration, isolated and optionally purified by washing with an inert organic solvent.

For the preparation of quaternization are alkyl, alkylthioalkyl, alkoxyalkyl, in particular (C -Cg) alkyl and optionally substituted in the phenyl radical, in particular halogenated Phenacylhalogenide. The preparation of these derivatives is carried out according to the commonly used methods.

With the compounds of the invention typical growth-regulating effects can be achieved, which - compared to the compounds known from DE-A 32 17 094 - in some cases can already use at lower dosages. They regulate the plant's metabolism and can thus be used to specifically influence plant ingredients and to facilitate harvesting, as well as triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesired vegetative growth.

- ι ³ - 239 5? 5

turn without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented. Particularly noteworthy is the growth-regulatory activity of the compounds as growth inhibitors in cereals, corn, soybeans, tobacco, cotton, field bean, oilseed rape, rice, turf and their capabilities, the content of desirable ingredients such as carbohydrates (eg in sugar raw millet cultures) and protein in crops increase. Finally, the compounds show a very good improvement in fruit abscission, especially in citrus fruits.

Another solution to the problem is the plant growth regulating agents, which are characterized by an effective content of at least one of the compounds of the invention. The application rate of the compounds according to the invention is generally 0.02 to 2.5 kg of active substance per ha, preferably 0.05 to 1.5 kg / ha. If appropriate, the compounds according to the invention may also advantageously be combined with known growth regulators or natural or plant hormones in their practical use.

The compounds according to the invention can, if appropriate in admixture with further active components, be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts, mordants, dispersions, granules or microgranules in the customary formulations.

Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance (s), may also contain wetting agents, such as polyoxethylated fatty alcohols, alkyl or alkylphenylsulfonates and / or dispersing aids, such as ligninsulfonate, optionally diluent or inert.

- n -. 239 5!

acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleoylmethyltaurine acid. The preparation is carried out in the usual way, e.g. by grinding and mixing the components.

Emulsifiable concentrates may e.g. by dissolving the active ingredient (s) in an inert organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or aliphatic or cycloaliphatic hydrocarbons with the addition of one or more emulsifiers. In the case of liquid active substances, the proportion of solvent can also be omitted in whole or in part. Examples of emulsifiers which may be used are alkyl-arylsulfonic acid calcium salts such as cadodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, fatty alcohol-propylene oxide condensation products, alkyl polyglycol ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusts may be obtained by grinding the active ingredient (s) with finely divided solid materials, e.g. Talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomaceous earth obtained. Granules can be prepared either by atomizing the active ingredient (s) on adsorptive, granulated inert material or by applying drug concentrations by means of binders, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.

In wettable powders, the active ingredient concentration is about 90 Gow .-%, the remainder to 100 wt .-% consists of conventional formulation components. In emulsifiable concentrates, the active substance concentration can be about 10 to 80 wt _# - amount%. Dust-like formulations usually contain 5 to 20 wt .-% of active substance (s) _# sprayable solutions about 2 to 20 wt -.%, The case of granules, the active ingredient content depends partly on whether the active compound is liquid or solid and which granulation auxiliaries, Fillers, etc. are used. In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, solvents, fillers or excipients,

For use, the present in commercial form concentrates are optionally diluted in a conventional manner, z, B * in wettable powders, emulsifiable concentrates, dispersions and partially also in microgranules by means of water, dust-like and granular preparations and ver sprayable solutions are usually no longer with before use diluted with other inert substances.

Also mixtures or mixed formulations with other active ingredients such as insecticides, acaricides, herbicides, fertilizers or fungicides may be possible,

embodiment

The invention will be described in more detail below with reference to some examples

explained.

In the following examples, parts by weight behave

(GT) to parts by volume (VT) such as kg to dm ³ (1) and% data are given unless otherwise specified

the weight,

239 51 p

Formulation facings Example 1

A dust is obtained by mixing a) IO GT active ingredient (s) and 90 GT talc or another inert material and comminuting in a hammer mill, or by mixing

b) 60 GT of active ingredient, 35 GT of talc and 5 GT of adhesive (e.g.

(R) a polysaccharide such as' Rhodopol of Rhone-Poulenc S.A.)

10 homogenized in the same catfish. Example 2

A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active ingredient (s), 64 parts by weight of quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting and dispersing aid and to mill in a pin mill. A formulation with 5 % active ingredient content may be composed as follows: 5 % active ingredient (s), 6 % one

C R) sulfonated Napthallnformaldehydkondensats (eg Dispersogen A HOECHST AG), 2 % of a sodium salt of an alkylnapthalene sulfonic acid (eg ^iR) Leonil DB of HOECHST AG), 5 % of a mixture of polypropylene glycol and SIO «(eg

^; Acrotin 3 ^ 1 by Hoechst AG), 25% of a SiO ₂ .b _(eg.

Cr)

Sipernat of Degussa AG) and 57 % kaolin type 1777 ·

Example 3

A dispersible concentrate readily dispersible in water is obtained by adding 20 parts by weight of active compound (s) with 6 OT of a

(R) Alkylphenolpolyglykolethers (eg Triton X 207 from Rohm and Haas Co.), 3 GT Isotridecanolpolyglykolether (8 ethylene oxide units) and 71 GT paraffinic mineral oil (boiling range about 255 to about 377 ⁰ C) mixed and in a Relbkugelraühle to a fineness of less than 5 um .

example

An emulsifiable concentrate is obtained from 15 parts by weight of active substance (s), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol (10 ethylene oxide units) as emulsifier.

Chemical Examples 10 Example 1 5-Cyano-1- (2,6-diethylphenyl) -imidazole

36.3 g (0.15 mol) of 1- (2,6-diethyl-phenyl) -imidazole-5-carboxamide are added portionwise at room temperature to 110% of phosphorus oxychloride. After 2 hours at 8O ⁰ C is evaporated in vacuo, the residue placed on ice, neutralized with sodium hydroxide solution, and extracted twice with toluene. After drying over sodium sulfate, the organic phase is evaporated and distilled in vacuo. This gives 27.2 g (81 % of theory) of 5-cyano-l- (2,6-diethylphenyl) imidazole boiling point (bp) 133-5 ° C / 0.01 mbar.

Example 2

Pthallmido-l- (2,6-diethylphenyl) -imidazole-5-carboxylate

6,0 GT (0.020 mol) of l- (2,6-diethylphenyl) -imidazole-5-carbonyl chloride hydrochloride (prepared from l- (2,6-diethylphenyl) -imidazole-5-carboxylic acid and thionyl chloride at 8O ⁰ C ) and 3.7 parts by weight (0.0023 mol) of N-hydroxy-phthalimide in 50 parts by weight of absolute acetonitrile, 4.1 g (0.029 mol) of KpCO are added in portions. The mixture is heated for 1 h at 60 ° C, allowed to cool *, poured into water and filtered off with suction. This gives 6.9 g (88 % of theory) of Phthallmido-1- (2,6-diethylphenyl) -imidazole-5-carboxylate, a colorless pesticide of melting point (Pp) 179-8O ⁰ C.

- ^ιε - 23? 515

Example 3

N- (2-hydroxyethyl) -1- (2, or-diethylphenyl) -imidazole-5-carboxyamide

To 25.0 pbw (0.083 mol) of 1- (2,6-diethylphenyl) -imidazole-5-carbonyl chloride hydrochloride (see Example 2) in 50% acetonitrile is added dropwise at room temperature a mixture of 5.5 pbw (0.091 mol) Aminoethanol and 18.4 GT (0.18 mol) of triethylamine. After 1 h is added to water / toluene, the organic phase dried over sodium sulfate and evaporated. This gives 16.1 GT (67.5% of th.) Of N- (2-hydroxyethyl) -l- (2,6-diethylphenyl) -imidazole-5-carboxamld, a solid, mp. 165-8 ⁰ C ,

15 Example 4

Methylthiomethyl-l- (2,6-diethylphenyl) -imldazol'-5-pcarboxylat

20.0 g (0.082 mol) of 1- (2,6-diethylphenyl) -imidazole-5-carboxylic acid, 7.9 g (0.082 mol) of chlorodimethylsulfide and 14.7 g (0.11 mol) of potassium carbonate become absolute in 100 parts by vol Acetonitrile heated for 1 h under reflux. Allow to cool, pour into 200 parts of water and extract the product twice with 100 parts of toluene per liter. After drying and evaporation, 20.1 g (80.1 % of theory) of methylthiomethyl-1- (2,6-diethylphenyl) -imidazole-5-carboxylate, a pale yellow oil, are obtained. The identification is carried out by ¹ H NMR spectroscopy.

Example 5

l- (2,6-diethylphenyl) -5- (5-tetrazolyl) imidazole

10.0 pbw (0.044 mol) of 5-cyano-1- (2,6-diethylphenyl) -imidazole (see Example 1), 2.4 pbw (0.44 mol) of ammonium chloride

and 2.9 pbw (0.044 mol) of sodium azide are stirred for 24 h at 100 ^° C in 50 v / v absolute dimethylformamide. After cooling, water is added to 200 μl, acidified to pH 5 with glacial acetic acid and the precipitate is filtered off with suction. (Theory 48% d.) To give 5.7 GT of l- (2,6-diethylphenyl) -5- (imidazol-tetrazolyD, a pale yellow solid of melting point 109-13 ⁰ C.

Example 6 10

1- (2,6-diethylphenyl) -5- (4, -dimethyl) -oxazole in-2-yl) -imidazole

To 19.5 g (0.062 mol) of N-2- (1-hydroxy-2-methyl-propyl) -1- (2,6-diethylphenyl) -imidazole-5-carboxamide in 60 parts by weight of absolute methylene chloride is added dropwise at room temperature 44 GT (0.37 mol) of thionyl chloride. After 1 h, it is evaporated in vacuo, the residue is taken up in 100 g of water, the mixture is neutralized with sodium bicarbonate, extracted with toluene and, after drying (Na ₂ SCv) and evaporation, chromatographed on a silica gel column (eluent: petroleum ether / acetic acid 7: 3). , This gives 13.3 g (72 % of theory) of 1- (2,6-diethylphenyl) -5- (4,4-dimethyl-2-oxazolin-2-yl) -imidazole, a colorless oil. The identification is carried out by H-NMR spectroscopy.

Example 7

1- (2,6-diethylphenyl) -5- (3-methyl-l, 2,4-oxadiazol-5-yl) imidazole

To 5.1 GT (0.047 mol) of acetamide oxime hydrochloride in 50 VT Pyridln are added at 0 to 1O ⁰ C 10.0 GT (0.033 · mol) of 1- (2,6-DiethylphenylJ-imidazol-S-carbonyl-hydro- Chloride in portions, followed by two hours of stirring

_ 20 _

Room temperature is added to water and filtered off with suction. This gives 6.6 g (50 % of theory) of 1- (2,6-diethylphenyl) -5- (3-methyl-l, 2,4-oxadiazol-5-yl) imidazole, mp

Example 8 1- (2,6-Diethylphenyl) -imidazole-5-carboxamidoxime

18.6 g (0.083 mol) of 5-cyano-1- (2,6-diethyl-phenyl) -imidazole are dissolved in 50 part of ethanol, at room temperature a solution of 6.9 g (0.99 mol) of hydroxylammonium chloride and 9 GT (0.05 ml) of potassium carbonate in 10 VT of water was added dropwise. The mixture is stirred for 2 h at 80 ° C, allowed to cool, taken up in 300 parts of toluene VT, washed twice with water, dried and evaporated. This gives 19.7 GT (92 t d. Theory) of l- (2,6-diethylphenyl) -imidazole-5-carboxamide oxime, a slightly pale yellow solid of melting point 107-12 ⁰ C.

Example 9 20

1- (2,6-Dimethylphenyl) -5- (5-methyl-1,2,3-oxadiazol-3-yl) -imidazole

15.0 GT (0.045 mol) of 0-chloroacetyl-l- (2,6-diethylphenyl) -imidazole-5-carboxamide oxime are stirred for 2 h in 50 VT glacial acetic acid at 100 ⁰ C. It is allowed to cool, taken up in 200 parts by volume of water / 200 parts by volume of toluene, neutralized with sodium bicarbonate and the organic phase is separated off. After drying, evaporation and chromatography (silica gel, eluent: petroleum ether / ethyl acetate 1: 1), 7.3 % of theory (61 % of theory) of 1- (2,6-diethylphenyl) -5- (5-methyll, 2,4-oxadiazol-3-yl) -imidazole, a colorless oil. The identification is carried out by H-NMR spectroscopy. ·

Example 10

N-methylsulfonyl-l ^ jo-diethylphenylJ-imidazole-S-carbox-

amide

To a mixture of 13.6 GT (0.14 mol) of methanesulfonamide, 24 GT (0.24 mol) of triethylamine and 100 VT of absolute acetonitrile are added at room temperature 25 GT (0.08 mol) of 1- (2,6-diethylphenyl ) imidazole-5-carbonyl chloride hydrochloride in portions. After 2 h is added to water, acidified to pH 4 and filtered with suction. This gives 21.1 GT (79% of th.) Of N-methylsulfonyl-l- (2,6-diethylphenyl) -imidazole-5-carboxamide, a solid, mp 240-2 ⁰ C.

Example 11 5- (2-Benzimidazolyl) -1- (2,6-diethylphenyl) -imidazole

15.0 pbw (0.045 mol) of N- (2-aminophenyl) -1- (2,6-dimethylphenyl) -imidazole-5-carboxamide are heated with 0.5 pbw of p-toluenesulfonic acid in 100 ppw xylene on a water separator. It is allowed to cool, washed twice with water, dried and evaporated. 13.7 g (96 % of theory) of 5- (2-benzimidazolyl) -1- (2,6-diethylphenyl) imidazole are obtained.

Example 12

1- (2,6-diethylphenyl) -5-hydroxymethyl-imldazol

54.8 pbw (0.20 mol) of ethyl 1- (2,6-diethylphenyl) -imidazole-5-carboxylate are added dropwise at room temperature to 7.60 pbw (0.20 mol) of lithium alanate in 150 pbw of absolute tetrahydrofuran to. After 1 h, carefully 7.6 parts by weight of water, 7.6 parts by weight of a 15% strength aqueous NaOH solution and 22.8 parts by weight of water are added dropwise.

After aspiration of the inorganic salt, the organic

²³⁹

concentrated niche phase and to obtain 45.5 T (99 % of theory) of 1- (2,6-diethylphenyl) -5-hydroxymethyl-iinidazol, colorless needles of Pp 79-82 ⁰ C.

5 Example 13

l- (2,6-diethylphenyl) -5-imidazol-forrayl

To 500 VT of absolute methylene chloride and 32.5 GT (0.26 mol) of oxalyl chloride is added dropwise at -78 ⁰ C 26.4 GT (0.33 mol) of absolute dimethyl sulfoxide in 50 VT of absolute methylene chloride. After 1/2 h at -78 ⁰ C a solution of 39.0 g (0.17 mol) of l- (2,6-diethylphenyl) -5-hydroxymethyl-is added dropwise in 50 iraidazol VT absolute methylene chloride. After 2 h at -7O ⁰ C 85 GT (0.85 mol) of triethylamine are added dropwise. After warming to room temperature, the organic phase is washed twice with water, dried (Na ₂ SO ₁₁ ) and evaporated. 38.5 g (98 % of theory) of 1- (2,6-diethylphenyl) -5-formyl-imidazole, a pale yellow oil, are obtained. The identification is ¹ H

example 1

l- (2,6-diethylphenyl) -5-hydroxlminomethyl-imldazol

To 16.8 parts by weight (0.074 mol) of 1- (2,6-diethylphenyl) -5-formyl-imidazole 7.7 parts by weight (0.11 mol) of hydroxylammonium chloride are added in portions at room temperature in 30 parts of pyridyl is poured onto 500 VT of water and the succinic substance is sucked off, giving 13.0 g (73 % of theory) of 1- (2-diethylphenyl) -5-hydroxirinomethyl-1-imidazole, mp 80 ° -80 ° C.

Example 15

5 ~ acetyl-l- (2.6 ~ diethylphenyl) imidazole

To a methylmagnesium bromide solution prepared from 5.9 g (0.042 mol) of methyl iodide and 1.0 g (0.042 mol) of magnesium in 100 part of absolute tetrahydrofuran is added dropwise at room temperature a solution of 8.7 part by weight (0.032 mol) of N, N-dimethyl- l- (2,6-diethylphenyl) -imidazole-5-carboxamide in 50VT of absolute tetrahydrofuran. After 1.5 h, pour on ammonium chloride solution and extract the product twice with ether. After drying (Na 2 SO 4) is evaporated, giving 7.1 parts by weight (91 % of theory) of 5-acetyl-1- (2,6-dimethylphenid-imidazole, a colorless oil.

15 annealing is carried out by H-NMR spectroscopy.

Further examples are listed in Table 1.

Table 1

Imidazole derivatives of formula 0)

Ex. R ¹ No. 16 CH ₃ 17 tt 15 19 η 20 η 21 ft 22 ft 23 tt 24 ft 25 ft 26 C ₂ H ₅ · 27 tt 28 tt 29 tt

(I) η = O or 1

-X Mp

made according to example

CH ₃

dt tt

C ₂ H

₂ H ₅

tt η η tt

tf

1) 1)

3-CH ₃

1)

I)

COO-cyclohexyl

-COO-CHj-CCI = CH ₂

-COO- (A-Cl-phenyl)

-C (NHz) = NOCH ₃

-COO-CH ₂ -CH ₂ -cyclohexyl

-Ci = S) OC ₂ H ₅

-Ci = S) SC ₂ H ₅

-C = S) NfCH ₃₎

-CONH-NH-CO-phenyl

-CONH-NH-COCH ₃

-CONH-OCH ₃

-COO-NH-COCH ₃

-COO (-CH ₂ ) 2-O (-CH ₂ J ₇ -O-CH ₃

-COO-CHi-phenyl OeI

2 4 2 8

2 - 2)

~ 2)

2 3 3 3 2 2 2

Continuation Table 1

Ex. R ¹ R * R ³ -X Fp. [ ⁰ Cj manufactured No. to example 3G C ₂ H ₅ C ₂ H ₅ -COO-CH (CH ₃ ) CN 2 31 tf ti - -COOCH ₂ -CONH ₂ 4 32 ft tt - -COO-CH ₂ -CO-CH (CHj) ₂ 4 33 ti -COO-CH ₂ -COOCHj 60-3 4 34 tf tt - -COO-CH (CH _{3) 3} -C00CH Oei 4 35 ff If - -COO-CH ₂ -TrIaZOl 4 35 tf tf - COO-cyclohexyl Oei 2 37 ff " - -COO-CH ₂ -C =CH ti 4 33 tt tf -COO-CH ₂ - (2-methylphenyl) resin 4 39 tt It - -COO -7 "j Oei 4 40 It If - -COO-N = C (CHj) ₂ η 2 41 42 tt tf ft ff - ^ CH ₃ -COO-N = C ^ C ₂ H ₅ ^ CH ₃ -COO-N = C - N) N)

Continuation Table 1

Ex. R ¹ ' R * R ³ -X Mp [° C] manufactured No. nadh example 43 C ₁ H, C, H ₅ - -COO-NC (C ₂ H ₈ ), Oei 2 44 If it - / CH, -COO-NC ^ CH ₂ -CH (CH,), η 2 45 Il W - / CH ₃ -COO-NC ^ cyclopropyl Oei 2 46 n η , - CH, -COO-N-C, CH-CH, N 2 47 If ff - / CH, -COO-N-C "* cyclohexyl Il 2 43 n j H- - / CH, -COO-N- ( ^x CH (CH- (CH ₃ ) ζ ) -triazole ff 2 "9 ti If - / CH, -COO-N-C ^ phenyl fl 2 50 N ff - -COO-N-C I resin 2

Continuation Table 1

Ex. R ¹ - It R ² R ³ -X COO N- (T ~ \ Mp [ ⁰ C] manufactured No. It -COO-N (C ₂ H ₅ ) Z to COS-CHz-COOH example 51 CzH ₅ W CzH ₅ - -COS-CH ₂ -COOCzH ₅ resin 2 52 η η It - -C0NH-C (CH ₃₎ z-CHz-0H 2 53 ti n Il - -CONH-CHz-phenyl 2 54 It ti W - -CONH-CH ₂ -CN Oei 2 55 It Il - CH ₃ 3 56 It It - -CNH-C-CH (CH ₃ ) z 3 57 It Il - -C0NH-C (CH ₃₎ -C0NHz 128-34 3 CH (CH ₃ ) z 58 It - -CONH-CHz-COOH resin 3 59 It - -CONH-CHz-COOCH ₃ 3 -CONH-CHz-COOCzH ₅ 60 M - -CONH-CH ₂ -CHO 210-4 - 3) 61 W - 155-9 3 62 N - 140-1 3 63 H - · 115-21

Continuation Table 1

Ex. R ¹ R ¹ R ³ -X Mp [° C] manufactured No. to example 64 C, H, C ₁ H ₉ -CONH- (3,4-dJ-Cl-phenyl) 220 (Zers.) 3 65 η η - CONH-NH, 145-7 3 66 If , - -CONH-N (CH ₃ ), 123-8 3 67 H Il - CONH-NH CHO resin 3 68 Ν If - -CONH-OH resin 3 69 If η - -CONH-O-CH ₁ -phenyl 143-5 3 70 If N - -CONH-NH-CONH ₂ Oei 3 71 If ti - -CONH-NH-CSNH ₁ 148 (Zers.) 3 72 If If - -CONH-SO ₂ - (4-methylphenyl) 143-7 3 73 ti R - ^co U Oei 3 - ^c ° O *, ... ^ 74 W If - -CON O V f resin 3 75 If If - Oei 3 - ^co vj 76 ti If If 3

continuation Table 1 Example no. R ¹ R ² R ³ -X- Mp [ ⁰ C] made according to example 77 78 C ₂ H ₅ C ₂ H ₅ η - ^ NH ₂ CH ₃ / N- {- CH (-CH ₃ J ₂ NnhJ 3 11 79 m η - VIHJ 11 30 η η - VOJ 6 81 ff If - \ sJ 6 82 Il n - 11 83 η η i - ^ SCH ₃ I - ²⁾ I

Continuation Table 1

Ex. R ¹ - R * - -X Mp [ ⁰ C] manufactured 5) No. CH (CH ₃ ), - to - 5) η example - 5) 84 C ₁ H ₅ η CH (CH ₃ ), - -CONH-cyclohexyl 3  - 5) 85 η R - -CON YY O 2 2 η - -C (-S) SH 2 86 η η - θ®-Ci-S) SNa 87 η - θ · -Ci-S) SNH * 88 η θ β -C (SS) S-NH, iCHj), 89 η COO-N-C ^ s ^ 90 n -COO-CH ₂ -COO ⁰ NH * 91 N

Continuation Table 1

Ex. R ¹ R ² R ³ -X -CH J Mp ["C] manufactured No. after example 92 C ₂ H ₅ C ₂ H ₅ -CH ₂ -O-COCH ₃ Oei 93 It - -CH ₂ -O-CONHCH ₃ 113-5 94 ti Il - -CHJ-0-CO-phenyl Oei Q / j. \ 95 ti It - -CH ₂ -O-CH ₂ - (2-methylphenyl) η _ 6) 96 Il It -CH J - ⁷⁾ 97 η It - -CH ₂ -O-C0-CH (4-chlorophenyl) Oei _ 6) CH (CH ₃ ) ₂ 98 η - _ 7)

continuation R ¹ Table 1 Example no. C ₂ H ₅ R ² 99 η C ₂ H ₅ 100 η η 101 η η 102 tf η 103 η It 104 η W 105

mfd. η. Example no.

107 N η 108 η η 109 η η 110 If η 111 η It 112 η CH ₁ 113 η η 114 Il Il

-Ci = S) OC ₂ H ₅ -CO ₂ -CH ₂ -C <= O) -CH ₃ -COO-CH ₂ -CH (OH) -CH ₃ -CONH-SO ₂ - (4-CH ₃ ) -phenyl -CONH-SO ₂ - (2-Cl) -phenyl-COO-CH ₂ -COOH • Ν (-CH ₂ -CH ₂ -OH) ₃ -COO-N = C (CH ₃ ) -C ₃ H _s (sulphate )

/ S-] -CH

\ sJ

-CH (SC ₂ Hb) ₂

-C (CH ₃ ) = NOH

-C (CH ₃ J = NOCOCH ₃

-C (NH ₂ J = N-OCH ₃

-C (NH ₂ ) = N-0C ₂ H,

-CH ₂ OH

CHO

-CH = NOH OeI

Oei

2)

Il 10 I 143-7 10 IO J) 88-90 _10) resin

J)

86-9 J) Ni O) 143-6 14 vO 91-5 _ ⁶ > cn Oei _ ⁶ > cn If _ ⁶ > 61-3 12 Oei 13 168-74 14

Continued table

Ex. R ¹ R ² R ³ No. Fp [ ⁰ C] mfd.

n. Ex. no.

115 C ₂ H ₅ C ₂ H.

0 ti H -COCC (CH ₃ )

0

120-8

117-20

resin

12)

Footnotes to Table 1

1) the other two radicals R ³ are hydrogen

2) prepared by reacting the ester / thioester with P * S, <

3) prepared by alkaline saponification of the ester in Example 61

4) prepared by acid cleavage of the dimethyl acetal following amide formation

^N 5) prepared from the aldehyde by reaction with ammonium sulfide and optionally subsequent salt formation

6) prepared by alkylation, acylation or carbamylation of the OH compound

7) prepared by acetalization of the aldehyde

8) prepared by sodium borohydride reduction of the ketone

Example 100

9) Prepared by a) hydrogenation of the benzyl ester to the acid, b) salt formation with the amine

10) prepared by reacting the imidazole with sulfuric acid

11) prepared by reacting the corresponding acid chlorides with the sodium salt X = COONa

12) prepared by reacting the corresponding acid chloride with lead rhodanide

Biological examples

1. Growth inhibition on cereals

In shell experiments in the greenhouse young cereal plants (wheat, barley, rye) in the 3-leaf stage with compounds of the invention in different concentrations of active ingredient (kg / ha) are sprayed dripping wet.

After the untreated control plants have reached a stature height of about 55 cm, the growth is measured in all plants and the stalk inhibition in % of the growth of the control plants is calculated. In addition, the phytotoxic effect of the compound is observed. The growth inhibition is determined as a percentage, with 100% meaning the stoppage of growth and 0% a growth corresponding to the untreated control plants. It turns out that the compounds have very good growth-regulating properties, see Table I.

Table I

Compound application growth inhibition in % at Phytotox. after concentrate. effect

25 Game No (Kg / ha) wheat barley rye none 2 2.5 23 37 27 damage 1.25 12 18 21 none 3 2.5 22 35 26 damage 30 1.25 13 17 20 none H 2.5 21 34 26 damage 1.25 14 17 20 none 5 ² > ⁵ 18 30 21 damage 1.25 9 13 9 none 35 6 2.5 17 25 17 damage 1.25 8th 13 9

Table I ₁ cont.

Compound application after adj.

Growth inhibition in % at Phytotox.

effect

Game No (Kg / ha) wheat barley rye none 7 2.5 24 39 28 damage 1.25 15 19 21 none 8th 2.5 22 34 25 damage 1.25 12 18 17 none 12 2.5 23 33 24 damage 1.25 11 17 17 none 13 2.5 24 37 27 damage 1.25 15 19 19 none 14 2.5 19 32 24 damage 1.25 11 ' 16 13 none 36 2.5 19 33 23 damage 1.25 10 17 13 none 37 2.5 15 25 19 damage 1.25 8th 12 7 none 40 2.5 25 38 27 damage 1.25 16 19 21 none 42 2.5 21 31 19 damage 1.25 12 16 14 none 45 2.5 19 32 22 damage 1.25 11 15 15 none 48 2.5 22 34 26 damage 1.25 13 17 20 none 51 2.5 25 37 27 damage 1.25 16 18 20 none 54 2.5 22 33 24 damage 1.25 13 19 18 none 57 2.5 23 31 23 damage 1.25 12 18 17 none 60 2.5 23 32 24 damage 1.25 13 19 17 none 61 2.5 23 31 25 " damage 1.25 13 19 18

239 SiS

Table I

Compound application growth inhibition in % for phytotox, according to Bei-Konzentr. effect

Game No (Kg / ha) wheat barley rye none 65 2.5 21 29 24 damage 1.25 14 19 18 none 66 2.5 22 31 25 damage 1.25 14 19 18 none 68 2.5 24 34 27 damage 1.25 20 21 21 none 70 2.5 22 27 25 .Schäden 1.25 12 18 21 none 73 2.5 21 28 24 damage 1.25 12 17 16 none 76 2.5 21 27 23 damage 1.25 13 17 15 none 95 2.5 19 25 22 damage 1.25 14 17 15 none 103 2.5 23 29 27 damage 1.25 16 19 16 none 105 2.5 19 25 25 damage 1.25 15 18 16 none 115 2.5 24 38 31 damage 1.25 14 19 24 none A 2.5 27 8th 10 damage 1.2S 23 0 0

A = 2-chloroethyltriethylammonium chloride 2. Growth inhibition in water rice

Rice plants are grown in small plots (2 m χ 2m) and treated in the stage of maximum tillering with compounds of the invention. The substances are applied both by spraying and in the water.

3 weeks after the treatment, the growth is measured in all plants and the growth inhibition in % of the growth of the control plants is calculated. In addition, attention is paid to a possible phytotoxic effect of the compounds.

The growth inhibition is determined as a percentage value, where 100 / den means the stoppage of growth and 0J {a growth corresponding to that of the untreated control plants. It shows the very good growth inhibition of the compounds, see Table II.

Table II ro VJl 6 35 Ik application Grew shemmung 22 Phytotox. connection concentr. {%) 25 effect 15 after at 7 (Kg / ha) 21 Game No 1.25 16 none I CVJ 30 8 0.62 21 damage 1.25 16 none 20 3 12 0.62 19 damage 1.25 11 none k 13 0.62 18 damage 1.25 11 none VJL 0.62 2k damage 1.25 15 none 0.62 22 damage 1.25 12 none .0,62 21 damage 1.25 13 none 0.62 2k damage 1.25 16 none 0.62 21 damage 1.25 - 13 none 0.62 damage 1.25 none 0.62 damage

Table II, Ports.

Connection after example no.

application

concentr.

(kg / ha) grew shemmung

Phytotox. effect

36 37 HO 1 * 2 45 48

51 54 57 60 61 65 66 68 70 73

1.25 0.62 1.25 0.62

1.25 0.62

1.25 0.62 1.25 0.62

1.25 0.62

1.25 0.62 1.25 0.62

1.25 0.62 1.25 0.62 1.25 0.62

1.25 0.62

1.25 0.62 1.25 0.62

1.25 0.62 1.25 0.62 21 14 19 11 25 18 19 14 19 13 19 14 26 19 21 14 20 13 21 13 20 13 21

21 12 25 18 21 14 22 14

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

-UO-

Table II, Ports

connection 0 103 application growth inhibition 19 Phytotox. after ßei- concentr. (*) IU effect 5 game no. 105 (Kg / ha) 18 76 1.25 14 none 5 115 0.62 21 damage 95 1.25 15 none 0.62 20 damage 1.25 14 none 0.62 28 damage 1.25 19 none 0.62 damage 1.25 none 0.62 damage 3. Growth inhibition on soybeans

About 10 cm large soybeans are sprayed dripping wet with the active ingredient preparations. After 3 weeks is scored.

The growth inhibition is determined as a percentage value, with 100 / S meaning the stoppage of growth and 0% a growth corresponding to that of the untreated control plants. It turns out that the compounds have very good growth-regulating properties, see Table III.

Table III Application concentr. (Kg / ha) Wushhem inhibition Phytotox. effect Connection according to example no. 2.5 20 no damages 2

Table III, Ports.

connection application growth inhibition Phytotox. after at concentr. (Ji) effect Game No (KR / ha) 3 2.5 21 none damage U 2.5 21 none damage 5 2.5 18 none damage 6 2.5 19 none damage 7 2.5 26 none damage 8th 2.5 21 none damage 12 2.5 21 none damage 13 2.5 25 none damage 14 2.5 20 none damage 36 2.5 19 none damage 37 2.5 17 none damage UO 2.5 26 none damage 42 2.5 19 none damage 45 2.5 18 none damage 48 2.5 17 none damage

Table III , Ports.

Compound application after adj. 5 game No. (kg / ha)

growth inhibition

Phytotox, effect

51 2.5 5k 2.5 57 2.5 60 2.5 61 2.5 65 2.5 66 2.5 68 2.5 70 2.5 73 2.5 76 2.5 95 2.5 103 2.5 105 2.5 115 2.5

2k 19 18 21 17 17 18 26 19 19 21 20 22 18 15

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

none

damage

Claims (3)

Erfindunqsanspruch 1 2 R ₁ R independently of one another R (C ₁ -C ₄ ) Alkyl, (C ₁ -C ₄ ) alkoxy or halogen, where the substituents may also be different at η 1; η 0,1,2 or 3; -CN, -COOR ⁴ , -COSR ⁵ , -CNR ⁶ , -CN = C = S,   Ν 7 ο R -C, -CHp-OR ¹⁶ , -C ^/ or ^ s-r9 ⁿ r ⁶ ZR ¹⁸
-CZR ¹⁸ 15 Y is 0, S or NR ⁶ ; Z 0 or S; R ^ substituted (C-pC- ^ iAlkyl, preferably (C ^ -C ^) alkyl, up to three times, preferably as is monosubstituted by hydroxy (C ₁ -C _it) alkoxy (C ₁ -C) alkoxy, CyCIo (C ^ -Cy) alkyl, benzyloxy, benzyloxyethoxy, phenyl, halophenyl, methylphenyl, cyano, carbamoyl, oxiranyl , MonoCC ^ -CgJ-alkylamino, (C ₁ -Cj) alkylthio, trimethylsilyl, (C ₁ -C ₁ ) -alkanoyl, (C ₁ -C) -alkoxycarbonyl, phenoxy,
Phenylthio, -O-N = C (-CH ₃ ) ₂ , triazolyl, imidazolyl, carboxyl or carboxylate with an ammonium or metal cation, preferably from the group of alkali or alkaline earth metal cations, or with an organic ammonium, phosphonium, sulfonium or
SuIfoxoniumkation; Halogen (Cg-Cg) alkenyl; unsubstituted or by halogen or (C ₁ -C _i ,) alkyl-substituted CyClo (Cg-Cg) alkyl; unsubstituted or by halogen or methyl-substituted cyclo (C 1 -C 6) -alkenyl; (Co-Cg) -alkynyl; l, 2-Epoxyprop-3-yl; substituted phenyl, which is a
or monosubstituted by halo, nitro, cyano, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₂₄ ) alkoxycarbonyl or (C ₁ -C ¹⁰ R ¹¹ -N = CR ¹⁰ R -NR ⁶ R ¹² -N fl -Ν (C ₁ -Cj) alkyl) carbonyl, phenylcarbonyl, which may be substituted by halogen, nitro, cyano or (C ₁ -CJj) alkyl, or a
Remainder of the formula substituted (C 1 -C 4) alkyl, preferably
(C ₁ -Cg) alkyl which is up to twice, preferably monosubstituted by (C ₁ -C ₁ J) alkoxyethoxy, cyclo (Cg-Cg) alkyl, benzyloxy, phenyl, (C ₁ -C ₄ -alkylthio, (C ₁ -CiJ) alkoxycarbonyl, phenoxy, carboxyl or carboxylate with a
Ammonium or metal cation, preferably from the group of the alkali metal or alkaline earth metal cations, or with an organic ammonium, phosphonium, sulfonium or sulfoxonium cation; or cyclo (C ₃ -C 6) alkyl; R ⁶ H or R 1 is substituted (C ₁ -C ₁₂ ) AlCl 3, preferably (C ₁ -Cr) AlCl y, which is up to twice, preferably monosubstituted by (C ₁ -CJj) alkoxyethoxy, hydroxyl, cyclo (Cg-Cg) alkyl, benzyloxy , Phenyl, cyano, carbamoyl, carboxyl, (C ₁ -CiJ) alkoxycarbonyl, #formyl or phenoxy; Cyclo (co-Cg) alkyl; up to two times by halogen, nitro, cyano, (C ₁ -C ₄ ) alkyl or (C ₁ -Cj ₄ ) - Alkoxy-substituted phenyl; -NR ⁶ R ¹³ , -OR ¹⁴ , -NH-CO-NH ₂ , -NH-CS-NH ₂ • or -SO ₂ R ¹⁵ ; X5 or R and R 'form - together with the Nitrogen atom to which they are attached - a saturated or unsaturated, optionally benzo-fused three- to seven-membered ring containing up to three heteroatoms from the group 0, N and S and which is unsubstituted or is substituted by (C ₁ -C 4) alkyl or halogen and may contain an oxo group; R ° independently of one another are H, halogen, (C ₁ -Cj) -alkyl, nitro or cyano; R ^ H, (C ^ CgjAlkyl or phenyl, or in Thiocarboxylaten an alkali or Erdalkalimetallka- tion, ammonium or organic ammonium cation; R ¹⁰ , R ¹¹ are each independently H, unsubstituted or triazolyl or imidazolyl substituted (C 1 -C 4 alkyl, cyclo (Co-Cg) alkyl, (C 1 -C 4) alkenyl, phenyl or benzyl; or together with the carbon atom to which they are bound form an unsubstituted substituted or methyl or halogen substituted CyClO (C ₅ -C ₇ ) alkyl; R ^{12 is} (C ₁ -C ₄ ) alkyl, phenyl, (C ₁ -C ₆ ) alkylcarbonyl, benzyl, benzoyl, halobenzyl, halobenzoyl or methylbenzoyl; R ^{1 is} H, (C ₁ -C ₄ ) alkyl, formyl, (C ₁ -C ₆ ) alkylcarbonyl, benzoyl, halobenzoyl, methylbenzoyl or trihaloacetyl; R ^{14 is} H, (C ₁ -C ₄ ) alkyl or benzyl; R ^{15 is} (C ₁ -C ₄ ) alkyl, phenyl, chlorophenyl or methylphenyl, R 1 is H, unsubstituted or substituted by phenyl or (C ₁ -C ₄ ) alkylphenyl, (C ₁ -C ₄ -alkyl, (C ₁ -C ₆ ) -alkylcarbonyl, halogen (C ₁ -C ₆ ) -alkylcarbonyl, N- (C ₁ -C ₆ ) alkylcarbamoyl, benzoyl, halobenzoyl or methylbenzoyl; R ¹⁷ O (including the Bisulfidaddukte) or ⁶ y and 18 independently of one another unsubstituted or (C ₁ -C ₆ ) -alkyl substituted by phenyl, CyCl (C ₅ -C ₇ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkyl or halogen;
or both radicals R ¹⁸ form, together with Z and the carbon atom to which they are attached, a 5- or 6-unsubstituted or substituted by (C ₁ -C ₄ ) alkyl, hydroxy (C ₁ -C ₄ ) alkyl, haloGo n- (C ₃ -C ₄ ) alkyl or phenyl -membered ring and their salts or quaternization products which can be used for agriculture in addition to customary carriers, diluents and / or wetting agents. 1. Plant growth regulators characterized as having an effective content of at least
a compound of general formula (I) worxn Use of compounds according to item 1, characterized in that they are used as growth regulators for plants * 3. A method for growth regulation of plants, characterized in that applied to the plants or the acreage an effective amount of at least one compound according to item 1 ·