CH639957A5 - IMIDAZOLINYLBENZOATE. - Google Patents

Description

The invention relates to imidazolinyl benzoates of the formula I:

, coofu

(I)

30th

35

40

45

50

Ri

Ri

R

R

55

wherein

X is hydrogen, Ci-C3-alkyl, halogen or nitro, is C1-c4-alkyl,

represents Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl, halophenyl or benzyl, or the substituents and R2 together with the carbon atom to which they are attached mean Cj-Q-cycloalkyl, which optionally substituted by methyl,

Hydrogen, Ci-Ci2-alkyl, which is optionally substituted with a QC-alkoxy group or a C3-C6-cycloalkyl group or a phenyl group or a furyl group or 1 to 3 halogen substituents, preferably chlorine, c3-c5-alkenyl, which is optionally substituted with 1 or 2C] -C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, is substituted,

65

C3-C5-alkynyl, which is optionally substituted with 1 to 2 C1-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, benzyl, cyclohexenylmethyl, ethynylcyclohexyl, ethynylalkyl, pentadienyl or C3-C6-cycloalkyl, which is optionally substituted with 1 or 2 Ci-C3-alkyl groups, or denotes a salt-forming cation of alkali metals, ammonium or aliphatic ammonium,

and, if the substituents Rt and R2 are not the same, the optical isomers thereof and the acid addition salts of these compounds, if the substituent R3 is not a salt-forming cation.

The invention further relates to a herbicidal composition for controlling undesirable plant species which contains a herbicidally effective amount of an imidazolinyl benzoate of the formula I given above as active ingredient.

Such a herbicidal composition can either be applied to the foliage of undesirable plant species or to the soil which contains seeds, seedlings or reproductive organs of such undesirable plant species.

For use as herbicidal agents, those imidazolinylbenzoates of the formula I mentioned at the outset are preferred, in which X is hydrogen, Q-C3-alkyl or halogen, Rj is C1-C3-alkyl, R2 is QQ-alkyl or cyclohexyl, or the substituents R 1 and R 2 together with the carbon atom to which they are attached mean cyclohexyl or methylcy-clohexyl, R 3 is hydrogen, Q-Cn-alkyl, which may be replaced by a Ci-C3-alkoxy group or a C3-C6-cyclo-alkyl group or a Phenyl group or a furyl group or

1 to 3 halogen substituents, preferably chlorine, is substituted, c3-c5-alkenyl, which is optionally substituted by 1 or 2 QQ-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, C3-C5-alkynyl, which is optionally substituted by 1 up to 2 Ci-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, is substituted, benzyl, cyclohexenylmethyl, ethynylcyclohexyl, ethynylalkyl, pentadienyl or C3-C6-cycloalkyl, which is optionally substituted by 1 or 2 C1-C3-alkyl groups or is a salt-forming cation of alkali metals, ammonium or aliphatic ammonium, and, if the substituents Rj and R2 are not the same, the optical isomers and isomer mixtures thereof and the acid addition salts of these compounds if the substituent R3 is not a salt-forming cation.

Compounds of the formula I in which R 1 is methyl and R 2 is isopropyl are more preferred, and the following subgroups also result:

a. Compounds in which X is hydrogen or chlorine and R3 is hydrogen, and the alkali metal salts and the ammonium salts thereof, the optical isomers thereof and the isomer mixtures thereof,

b. Compounds in which X is hydrogen, methyl or chlorine and R3 is Ci-Ci2-alkyl, which is optionally substituted with a QQ-alkoxy group or a QQ-cycloalkyl group or a phenyl group or a furyl group or 1 to 3 halogen substituents, preferably chlorine, stands, the optical isomers thereof, the isomer mixtures thereof and the acid addition salts thereof,

c. Compounds in which X is hydrogen, methyl or chlorine and R3 is c3-c5-alkenyl which is optionally substituted by 1 or 2 Ci-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine,

stands, the optical isomers thereof, the isomer mixtures thereof and the acid addition salts thereof,

d. Compounds in which X is hydrogen, methyl or chlorine and R3 is c3-c5-alkynyl, optionally with 1 or

2 Ci-C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, preferably chlorine, is substituted,

639 957

stands, the optical isomers thereof, the isomer mixtures thereof and the acid addition salts thereof.

Those imidazolinylbenzoates of the formula I in which R3 is not hydrogen are prepared according to the invention by reacting an imidazoisoindoldione of the formula II given later with a corresponding alcohol in the presence of an alkali metal or an alkali metal hydride at 20 to 50 ° C. The reaction is preferably carried out under inert gas protection. Generally, an alkali metal or an alkali metal hydride is first mixed with a corresponding one

Alcohol and then mixes the mixture obtained thereafter with the respective imidazoisoindoldione of the formula II.

In the above process, nitrogen, 5 argon or helium can be used as inert gases, nitrogen being preferred.

Examples of alkali metals or alkali metal hydrides which can be used are sodium, sodium hydride, potassium, potassium hydride, lithium or lithium hydride.

The above implementations can be explained as follows:

(II)

R30-

ALKALI metal

(III)

(/ ^ v ^ C00R3

H

Herein, X, Rj, R2 and R3 have the meanings given above.

In the above reactions, the alcohol acts both as a reactant and as a solvent. There is therefore no need for a second solvent. However, if an expensive alcohol is used in the reaction and a large excess of alcohol is required to achieve optimal reaction conditions, then it is advisable to add a cheaper second solvent to the reaction mixture, such as dioxane, tetrahydrofuran or another non-protic solvent. The amount of non-protic solvent to be added to the reaction mixture can be varied quite widely, but in general it does not exceed a multiple of the amount

25th

30th

35

alcohol used. The ratio of second solvent and alcohol, which can be used according to the invention, is therefore between 0.0: 1 and 4.0: 1.

Those compounds of formula I in which R3 is hydrogen are prepared by reacting an imidazoisoindoldione of formula II with an excess of hydrochloric acid, preferably in the presence of a water-miscible solvent, such as tetrahydrofuran or dioxane. This reaction leads to a lactone hydrochloride of the formula IV mentioned below, from which the corresponding acid is obtained by treatment with an equivalent base, such as sodium hydroxide, potassium hydroxide or sodium carbonate. The implementation proceeds formally as follows:

(II)

(IV)

^ T ^ COOH H

60

NaOH

The imidazolinylbenzoic acid obtained in the above manner can then be converted in the customary manner into the alkali metal salt, ammonium salt or aliphatic ammonium salt desired in each case.

To form an alkali metal salt, the respective acid can be treated with a concentrated aqueous solution of the respective alkali metal hydroxide and then the water can be removed from the reaction mixture in a conventional manner, preferably by

65

(I)

azeotropic distillation with an organic solvent such as dioxane.

The ammonium salts or the aliphatic ammonium salts can be prepared in a similar manner, but, in deviation from this, the respective acid of the formula I is partially dissolved in a lower alcohol, such as methanol, ethanol or isopropanol, and the solution thus obtained is then dissolved in ammonia or the corresponding aliphatic Amine treated. In the arrival

639 957

finally, the reaction mixture obtained can be concentrated, the remaining solid can be treated with hexane and the material can finally be dried, whereby an ammonium salt or an aliphatic ammonium salt of the formula I is obtained.

Suitable aliphatic ammonium are: monoalkylammonium, dialkylammonium, trialkylammonium, monoalkenylammonium, dialkenylammonium, trialkenylammonium, monoalkynylammonium, dialkinylammonium, monoalkanolammonium, or trialkanolammonium contains 1

The aliphatic ammonium salts according to the invention can be prepared from organic amines with a molecular weight of less than about 300. Examples of such amines are methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, s-butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine , Tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octa-decylamine, methylethylamine, methylisopropylamine, methylhe-

10th

15

20th

xylamine, methylnonylamine, methylpentadecylamine, methyloc-tadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-amylamine, diptylamine, diptylamine, diisoaminamine Trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-s-butylamine, tri-n-amylamine, ethanolamine, n-propanolamine, isopropanolamine, diethanolamine, N, N-diethylethanolamine, N-ethylpropanola-min, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl- 2-amine, and propylenediamine.

The compounds of formula I above can be mixtures of two positional isomers if X has a meaning other than hydrogen, since the imidazoisoindoldiones of formula II used as intermediates are also mixtures of isomers if X is not hydrogen. The starting products of formula II can be prepared by cyclizing an appropriate phthalimidocarboxamide. The cyclization can occur on one of the two imide carbonyl groups, which results in a mixture of isomers if X has a meaning other than hydrogen:

A

c - conh-j I *

or

oh or h

, 4 "

and

The substituents Rj, R2 and X have the meanings given above, with the exception that X cannot stand for hydrogen.

The imidazolinyl benzoates of formula I above can also be tautomeric. They are through goor for simplicity.

x-

45

The substituents X, Rj, R2 and R3 have the meanings given above. Formula I is therefore also understood to mean both isomeric forms of imidazolinyl benzoates.

The connections are amphoteric. They dissolve in both acidic and basic aqueous solutions, the acid addition salts of the imidazolinylbenzoates of the formula I being formed on treatment with strong acids, in particular strong mineral acid, such as hydrochloric acid, sulfuric acid or bromohydric acid.

If the substituents R 1 and R 2 in the imidazolinyl benzoates of the formula I mean different groups, then that is

60

denotes a single structure with the formula I, but can occur in one of the following two isomeric forms:

Carbon atom to which these groups are attached is an asymmetric carbon atom. Such compounds therefore (as well as their intermediates) occur in d and 1 forms as well as in dl forms.

To prepare the respective d- or 1-form, the respective optically active d- or 1-imidazoisoindoldione of the formula II is reacted with the corresponding alcohol of the formula III, which gives the corresponding d- or 1-imidazolinylbenzoate 65 of the formula I.

The imidazoisoindoldiones of the formula II are intermediates for the preparation of the imidazolinylbenzoates according to the invention and are described in US Pat. No. 4,017,510.

639 957

The compounds according to the invention are extremely effective herbicidal compositions for controlling monocotyledonous plants, sedge grasses (Cyperacae) and dicotyledonous plants. They can be used to control the emergence of undesirable plant species by treating the foliage of such plants with a herbicidally active amount of such compounds, or they can also be used to control the emergence of undesirable plants by applying to the soil, seeds, seedlings or reproductive organs contains unwanted plants, applies a herbicidally effective amount of the respective active ingredient. Since the imidazolinylbenzoates of the formula I according to the invention have very limited solubility in water, they are generally formulated as wettable powders, emulsifiable concentrates or free-flowing liquids, which are then normally dispersed in water or another cheap liquid diluent for spraying. The compounds according to the invention can also be formulated as granules which generally contain about 10 to 15% by weight of active ingredient.

To produce a wettable powder, for example, 25 to 80% by weight of the respective imidazolinylbenzoate, 2 to 5% by weight of a surface-active agent, such as sodium N-methyl-N-oleyltautrate, alkylphenoxypolyoxyethylene ethanol or sodium alkylnaphthalenesulfonate, 5 to 10% by weight are mixed. % of a dispersant, such as highly purified sodium lignosulfonate, and 25 to 63% by weight of a finely divided carrier, such as kaolin, attapulgite or diatomaceous earth, with one another.

A typical formulation produced in the above way is composed as follows:

50% by weight of 2-propynyl-o- (5-isopropyl-5-methyl-4-oxo-2-imi-dazolin-2-yl) benzoate, 3% by weight of sodium N-methyl-N- oleoyl tautrate, 10% by weight sodium lignosulfonate and 37% by weight kaolin.

Flowable liquid formulations can be prepared by mixing about 40 to 60% by weight of an imidazolinyl benzoate of the formula 1.2 to 3% by weight of the sodium salt of condensed naphthalenesulfonic acid, 2 to 3% by weight of a clay formed, 2% by weight. -% propylene glycol and 54 to 32 wt .-% water ground together.

To produce a corresponding granulate, the respective active ingredient can be dissolved or dispersed in a solvent and the active ingredient can then be applied to a sorptive or non-sorptive carrier, such as attapulgite, corncob groats, pumice stone or talc.

As indicated above, the imidazolinyl compounds of the formula I are effective pre-emergence herbicides. They are suitable for controlling broad-leaved weeds and grasses if the soil, seeds, seedlings or reproductive organs of broad-leaved weeds, sedge grasses or grass plants are treated with active compound amounts of 0.07 to 11.2 kg / ha.

The compounds according to the invention are also suitable for controlling broad-leaved weeds, sedge grasses and grass plants if the foliage of such plants is treated with active compound amounts of about 0.28 to 11.2 kg / ha.

A wide variety of plant species can be effectively combated with the compounds according to the invention, but they differ from the known herbicides in that they are particularly good at combating certain cyperaceans, in particular reed grasses, at relatively low levels

Allow application concentrations to be used. In practice, the compounds of the formula I have therefore proven to be particularly effective agents for combating reed grasses 5 in pre-emergence treatments in amounts of active ingredient from 0.14 to 11.2 kg / ha. To control reed grasses and other annual plants, it is of course also possible to use higher amounts of the compounds of the formula I if the stock of cyperaceas or annual plants is particularly strong.

10 Under such conditions, the imidazolinyl benzoates of the formula I can be used for pre-emergence treatment or for post-emergence treatment in amounts of up to 25 kg / ha.

Cyperacaen that can be controlled with the imidazoline derivatives according to the invention include purple cypergrass 15 (Cyperus rotundus L.), yellow cypergrass (Cyperus esulentus L.), false cypergrass (Cyperus strigosus) and the flat sedge, umbrella plants and Kyllinga.

The invention is further illustrated by the following examples.

20th

example 1

2-propionyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -

benzoate

25th

12.5 ml of propargyl alcohol are added to 0.1 g of a 50% suspension of sodium hydride in mineral oil. The addition is carried out under nitrogen protection, the reaction mixture being stirred and kept at 20 to 25 ° C. by external cooling. After about 1 to 2 30 hours, the formation of the sodium salt of propargyl alcohol has ended. The solution is then mixed with 5.0 g of 3-isopropyl-3-methyl-5H-imidazo [2, l-a] isoindole-2 (3H), 5-dione and the reaction mixture is stirred overnight under nitrogen protection at room temperature. A subsequent thin-layer chromatography study shows that the reaction is incomplete and the reaction mixture is therefore mixed with a further 50 mg of a 50% suspension of sodium hydride in mineral oil. The reaction mixture is stirred overnight, whereupon it is cooled to 5 ° C. and mixed with 0.7 ml of 3 normal hydrochloric acid. The reaction mixture is then diluted with methylene chloride, the whole is washed with water, the organic layer is dried and concentrated in vacuo. The resulting crystalline residue is transferred to a filter funnel with hexane and air-dried, yielding 6.02 g of 2-propynyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazoline-2- yl) benzoate reaches, which melts at 131 to 144 ° C. By recrystallizing this material from acetone-hexane, a pure product is obtained which melts at 145 to 147 ° C.

40

50

Example 2

Preparation of Imidazolinylbenzoates The imidazolinylbenzoates given below are prepared by the process described in Example 1, 55 by using the alcohol indicated in each case instead of propargyl alcohol and instead of 3-isopropyl-3-methyl-5H-imida-zo [2, la] - isoindol-2 (3H) -5-dione uses the respective imidazoisoindoldione. The implementation proceeds formally as follows:

60

+ FUOR

! _ •

IN d.i.

COOR.

639 957

8th

r,

r2

ch,

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3),

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3>

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3),

ch3

ch (ch3) 2

ch3

ch, ch2ch3 / \

ch3

- (ch2) 5-

-ch (ch3) ch2ch2ch2ch2-

ch3

-ch (ch3) 2

ch3

-ch (ch3) 2

ch3

-ch (ch3) 2

ch3

-ch (ch3) 2

ch3

-ch (ch3) 2

ch3

-ch (ch3),

ch3

-CH (ch3) o ch (ch3>

-ch (ch3) 2

- (ch2) 5-

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3),

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) -,

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3) 2

ch3

ch (ch3),

ch3

ch (ch3),

R3

X

Melting point, ° C

-ch, ch, ch3

-ch22c6h5

- (ch2) 7ch3 - (ch2) uch3

-ch2ch = ch,

-ch3

-c (ch3> ch = ch2 -c (ch3) o = ch -ch (ch3),

-c (ch3) 3

-ch2ch3

-ch (ch3) c = ch -ch2c (c1) = ch2

-ch2ch2c = ch

-ch (ch3) ch = ch2 -c (ch3) 2ch = ch2

-c (ch3) 2ch = ch2 -c (ch3) 2ch = ch,

-ch2c = ch

- ^ ch (ch3) -c (ch3) = ch,

-ch2ch = chch3

-ch2c (ch3) = ch2 -ch2ch = c (ch3) 2

-CH.

<i>

-CH (CH = CH2) 2 -CH (CH3) -CH = CHCH3

-ch3 -ch3

-CH2C (CH3) 3

-C18H37-n

-CH2CH2OCH3

-ch2- ^

-C6H13-n ch3 I

-c-c2h5 ch3

-ch, ch, oc2h5 -ch2ch = ch-c6h5 -ch2-c = c-c6h5 -ch2-c = c-ch3

- ch- <!

ch3

-CHi-C = C-C7hi5-n

-ch2cci3

-C (C, HS) 2CH = CH2

qh (ch3) 2

-O

"CH3

ce ck

Cl

-ch2-c = ch2 -ch3

-ch2-c = ch

H H H H H H H H H H H

H H H H H

H H H H H H H H

H

H H H H H H H

H H

H

H H H H

H

H H H

H

H

120-121.5 (decomposition) 110-113 (decomposition)

73-75 (decomposition) 62.5-64.5 (decomposition) 109-111.5 (decomposition) 117-118 115.5-117.5 115-116

121-122.5 139.5-141 123-124.5

97-104

114-116 127-128

94-98 (decomposition) 103.5-107 (decomposition)

115-120 (decomposition) 133.5-134.5 (decomposition) 168-171 (decomposition)

85-94 (decomposition) 101-112 (decomposition) 91-102 (decomposition) 107-111

100-106 (decomposition)

78-87 (decomposition) 89-107 (decomposition)

146-147 164-165

147-148

79-81.5 87.5-92.5

122-125 84-86

87-89

99-100 120-125 134.5-138 125-128

4 (5) CH3 4 (5) CH3 4 (5) CH3

95.98

94-96.5 143-145 111.5-115.5

74-78

168-169

128-130 143-151 154-159

9

639 957

Ri

R2

R3

X

Melting point, ° C

ch3

ch (ch3) 2

ch (ch3) 2

-c-ch = ch2

H

153-157.5

ch3 ch3 ch3

ch3 ch3 ch3 ch3 ch3

ch (ch3) 2

(+) - Isomer ch (ch3) 2

(-) - Isomer ch (ch3) 2

(+) - Isomer ch (ch3> ch (ch3), ch (ch3) 2 ch (ch3), ch (ch3) 2

ch (ch3) 2

-c2h5

-ch2c = ch -ch2-c = ch2

ci

-ch (ch3) ch = chch3

-ch3

-ch2-c = ch

-ch2-c = c-ch2oh

-ch2-c = ch2

H H H

4 (5) CH3 3 (6) Cl 3 (6) Cl H

3 (6) Cl

106-108 134-135 120-122

95-111 162-166 164-166 132-134 154-160

ch3 ch3 ch3 ch3 ch3 ch3

ch (ch3) 2 ch (ch3) 2 ch (ch3) 2

c, h5

c2h5

c2h5

CI

-ch2-ch2

-ch (ch3) ch = ch-ch3

-c2h5 -ch3

-ch2-c = ch -ch2-c = ch2

H

3 (6) Cl 3 (6) N02 H H H

166-169 161-163 156-157 135-136 137-139 125-126

ch3

ch (ch3) 2

CI

-ch2-c = chc1

H

107-114

ch3 ch3

c, h5

ch (ch3) 2

ci

-ch (ch3) ch = chch3

-ch2-c = ch2

1

H

3 (6) N02

119-121 161-162

ch3

ch (ch3) 2

CI

ch3

-c-ch = ch2

H

73-79

ch3

c2h5

1

c2h5 ch3

-c-ch = ch,

1

H

127-128

ch3

ch (ch3) 2

ch3

ch (ch3) 2 -c-ch = ch

H

122-122.5

ch3 c2h5

GH, C2H5

ch (ch3), ch (ch3) 2 ch (ch3) o ch (ch3) 2

ch (ch3),

-c2h5 -ch3

-ch2-c = ch -ch2-c = ch2

4 (5) Cl H H H

112-138 139-140 147-149 134-135

ch3

ch,

ch3

ch (ch3), ch (ch3), ch (ch3) 2

ci

-chi-c = c = ch -ch (ch3) ch = chch3 -ch, -c = ch,

" 1

4 (5) Cl 4 (5) Cl 4 (5) Cl

177-187

01

01

ch3

ch (ch3) 2

1

CI

CH = cht 1

H

01

ch3

ch (ch3) 2

-ch-c = ch ch3

-c-CH = cht

1

ch3

4 (5) Cl

01

639 957

10th

r>

R:

r3

X

Melting point, ° C

CH,

CH (CH3) 2

H

4 (5) Cl

177-179

CH,

C, H,

H

H

195-197

C, H,

CH (CH,) 2

H

H

179-180

CH,

CH (CH3h

H

3 (6) Cl

154-156

CH,

CH (CH3>

C2H5

4 (5) CH3

CHj

CH (CH3) 2

C3Ht-ii

4 (5) CH3 (4 or 5)

CH,

CH (CH3) 2

C3Hr-n

4 (5) CH3 (4 or 5)

ch3

CH (CH3) 2

C3Hr-n

4 (5) CH3 (4 or 5)

CHJ

CH (CH3) 2

CH (CH3) 2

4 (5) CH3

15

Example 3

1, l-Dimethylallyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate hydrochloride

.cooc (ch3) 2ch = ch2

N-

\ <»CH3

^ ch (ch3) 2

0

t:

HCl

, COOC (CH3) 2CH = CH2

■ HCl

ChT (CH) ^ 0

A solution of 164 mg of 1, l-dimethylallyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate (0.5 mM) in 5 ml of methylene chloride and 5 ml of absolute ethanol 0.5 ml of 1.0 normal hydrochloric acid is added. The reaction mixture is concentrated under vacuum, whereupon the residue is treated with ether and the crystalline product obtained is filtered off with

35

Ether washes and air dries. In this way, 170 mg of the hydrochloride specified in the title are obtained, which melts at 259 to 262 ° C. with decomposition. The melting point of this salt and other salts depends on the rate of heating.

Example 4

o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid

Oh OH

Nil • HCl

A solution of 5 g of 3-isopropyl-3-methyl-5H-imidazo [2, la] isoindole-2 (3H), 5-dione in 15 ml of dioxane is stirred with a mixture of 10 ml of concentrated hydrochloric acid and 10 ml Water added. The reaction mixture is heated to boiling, whereupon it is allowed to cool to room temperature. The resulting crystalline solid is filtered off,

u

639 957

washed with water and acetone and air dried. The filtrate is concentrated in vacuo, whereupon the solid obtained is washed with acetone and air-dried. In this way a total of 4.5 g of the lactone hydrochloride of structure A given above is obtained, which melts at 265 ° C with decomposition.

A partial solution of the above hydrochloride (4.5 g) in 30 ml of water is mixed with a solution of 0.6 g of sodium hydroxide in 10 ml of water. A complete solution is formed within a few minutes and a solid separates from the solution after about 15 minutes. This solid is filtered off. The filtrate is concentrated in vacuo, whereupon the solid obtained is filtered off, combined with the first solid, washed with water and air-dried. This gives 3.8 g of o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid, which melts at 162 to 163 ° C.

An analytically pure sample has a melting point of 163 to 165 ° C.

Example 5

10th

mical Industries) and contain such an amount of active ingredient that when the corresponding active ingredient-containing dispersions are applied to the respective plants by means of a spray nozzle operated at a pressure of 2.8 kg / cm 2 for a predetermined time, an active ingredient amount of about 0.07 to 11.2 kg per ha. After spraying, the plants are placed on greenhouse tables and kept in the usual manner. 2 weeks after the treatment, the seedling plants, with the exception of the wind oat seedling plants, which are only assessed after 5 weeks, are tested accordingly and rated on the following assessment scale. The data obtained here are shown in Table I below.

15 rating scale

25th

20th

o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid

To prepare the corresponding sodium salt, 9.9 ml of 1-normal sodium hydroxide are added to a partial solution of 2.58 g of imidazolinyl acid in 10 ml of water with stirring. After 1.5 hours, the solution is concentrated in vacuo and the remaining water is then removed azeotropically with dioxane, giving the hygroscopic sodium salt, which melts at 184 to 188 ° C.

The corresponding amine salts are simply prepared by reaction in methanol. For this purpose, a partial solution of 5.0 g imidazolinyl acid in 15 ml methanol is stirred with 3.17 ml triethylamine. A clear solution is obtained after 0.75 hours. The solution is concentrated and the remaining slurry is diluted with hexane, filtered and dried. This leads to the triethylamine salt, which melts at 54 to 55 ° C. The isopropylamine salt, which has a melting point of 92 to 98 ° C., is also prepared in a similar manner.

40

Example 6

Efficacy as post-emergence herbicides The efficacy of the compounds according to the invention as post-emergence herbicides is shown by the following tests, in which a number of monocotyledonous plants, cyperaceas and dicotyledonous plants are treated with the corresponding active compounds, which are dispersed in mixtures of water and acetone. For the investigations, seedlings of the respective plants are grown in separate beakers for about 2 weeks. The active compounds to be investigated are dispersed in mixtures of 50 parts of acetone and 50 parts of water, each of which contains 0.5% surface-active agent based on polyoxyethylene sorbitan monolaurate (TWEEN 20 from Atlas Che45

50

55

Percentage difference in growth over control *

0 - no effect 0

1 - possible effects 1-10

2 - light effect 11-25

3 - medium effect 26-40

5 - clear injury 41-60

6 - herbicidal activity 61-75

7 - good herbicidal activity 76-90

8 - near complete kill 91-99

9 - complete kill 100

35

4-Abnormal growth, namely a clear physical malformation, but the overall effect on the assessment scale is less than 5.

* Based on a visual determination of the position, size, strength, chlorosis, growth deformity and overall appearance of the plant.

Abbreviations of plants:

PN - Purple Cypergrass (Cyperus rotundus L.)

SE - Sesbania (Sesbania exaltata)

MU - Mustard (Brassica kaber)

PI - Field Foxtail (Amaranthus retroflexus)

RW - Ambrosia herb (Ambrosia artemisiifolia)

MG - Purple Bindweed (Ipomoea purpurea)

BA - Millet (Echinochloa crusgalli)

CR - Blood finger millet (Digitaria sanguinalis)

FO - Green Bristle Millet (Setaria viridis)

WHERE - wind oat (Avena fatua)

TW - Tea herb (Sida spinosa)

VL - Indian Mallow (Abutilon theophrasti)

CN - maize (Zea mays)

CO - Cotton (Gossypium hirsutum)

SY - Soybean (Glycine max)

RI - Rice (Oryza sativa)

JW - Common Datura (Datura stramonium L.)

Table I

Efficacy of the compounds of the formula given as pre-emergence herbicides

639 957

12

Formula application quantity of plants

Rj R, R3 X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI

ch.,

-ch (ch3) 2

-ch2c = ch h

11.2

3rd

8th

8th

8th

5

8th

8th

9

7

7

6

9

-

-

-

-

4.48

7

9

9

9

5

9

9

9

3rd

3rd

8th

9

7

9

9

7

1.12

3rd

7

9

9

2nd

9

7

8th

3rd

3rd

3rd

6

7

9

9

5

0.56

1

3rd

9

9

2nd

8th

3rd

7

0

0

0

5

7

9

9

8th

0.25

3rd

0

9

9

3rd

7

5

6

5

-

6

7

9

9

7

-

ch3

-ch (ch3) 2

-ch2ch2ch3

H

11.2

0

0

5

5

0

2nd

3rd

5

0

0

0

0

-

-

-

-

4.48

-

9

7

8th

0

4th

2nd

1

0

1

1

-

0

9

2nd

0

1.12

-

3rd

3rd

8th

0

3rd

0

0

0

0

0

-

0

8th

1

0

0.56

-

0

1

6

0

2nd

0

0

0

0

0

-

0

8th

1

0

ch3

-ch (ch3) 2

/ \

H

11.2

0

1

7

7

0

2nd

5

7

0

4th

4th

4th

2nd

8th

5

1

pu - / A

4.48

-

7

8th

8th

1

7

7

2nd

1

2nd

2nd

-

0

9

3rd

1

2 \ //

1.12

-

9

8th

8th

0

7

2nd

2nd

0

0

0

-

0

9

3rd

0

\ '/

0.56

-

8th

8th

0

7

1

1

0

0

0

-

0

7

-

-

0

ch3

-ch (ch3) 2

- (ch2) 7ch3

H

11.2

0

7

5

7

0

0

4th

4th

0

4th

4th

0

-

-

-

-

ch3

-ch (ch3) 2

~ (ch2) 11ch3

H

11.2

0

5

3rd

7

0

0

1

1

0

1

1

0

-

-

-

-

ch3

-ch (ch3) 2

-ch2ch = ch2

H

11.2

0

1

7

8th

0

2nd

5

7

0

4th

4th

4th

-

-

-

-

4.48

-

3rd

9

8th

0

8th

8th

7

-

0

5

-

6

9

6

2nd

1.12

-

2nd

9

8th

0

7

2nd

2nd

0

0

0

-

2nd

8th

6

0

0.56

-

0

8th

8th

0

7

0

2nd

0

0

0

-

1

8th

6

0

ch3

-ch (ch3) 2

-ch3

H

11.2

1

8th

8th

8th

0

6

6

7

7

7

7

6

-

-

-

-

4.48

7

9

9

9

2nd

8th

6

9

7

2nd

8th

9

9

9

9

0

1.12

8th

6

9

9

1

8th

5

4th

3rd

0

2nd

9

8th

7

9

0

0.56

6

0

9

9

0

7

3rd

4th

0

0

0

9

9

7

9

0

ch3

-ch (ch3) 2

-c (ch3) ch = ch2

H

1.12

8th

9

9

9

6

9

6

9

7

9

9

8th

9

9

9

5

0.56

7

3rd

9

9

7

9

7

9

7

6

7

9

9

9

9

3rd

0.28

5

0

9

9

6

9

6

9

5

3rd

8th

9

9

8th

8th

2nd

ch3

-ch (ch3) 2

-c (ch3) 2c = ch h

4.48

2nd

0

9

9

4th

9

2nd

2nd

1

1

1

8th

7

8th

7

0

1.12

2nd

0

9

9

3rd

8th

1

2nd

0

1

1

6

7

7

7

-

0.56

2nd

0

8th

9

2nd

8th

0

2nd

0

0

2nd

0

7

7

6

-

ch3

-ch (ch3) 2

-ch (ch3) 2

H

11.2 *

3.5 2.5 4

8.5 1.5 6

5.5 4

3.5 4.5 4.5 4

-

-

-

-

ch3

-ch (ch3) 2

-c (ch3) 3

H

11.2

0

0

0

9

0

4th

0

0

0

0

0

0

-

-

-

-

ch3

-ch (ch3) 2

-ch2ch3

H

11.2

0

1

8th

8th

0

3rd

3rd

5

0

0

1

9

-

-

-

-

ch3

-ch2ch2ch3

-c (ch3) 2ch = ch2

H

11.2

2nd

8th

3rd

3rd

0

0

0

0

0

0

0

0

-

-

-

-

ch3

-ch (ch3) 2

-c (ch3) 2ch = ch2

H

11.2

9

9

9

9

9

9

9

9

9

9

9

9

-

-

-

-

4.48

9

9

9

9

8th

9

8th

9

9

9

9

9

9

9

9

8th

HCl salt

1.12

9

9

9

9

7

9

3rd

9

9

9

9

9

9

9

9

6

0.56

8th

7

9

9

6

9

1

9

7

5

8th

9

9

9

9

7

0.28

2nd

3rd

9

9

8th

9

1

5

3rd

5

5

5

9

9

7

7

ch3

-ch (ch3) 2

-c (ch3) 2c = ch h

11.2

7

7

9

9

9

9

8th

9

8th

9

9

9

-

-

-

-

4.48

3rd

9

9

9

7

9

9

9

3rd

2nd

6

9

9

9

8th

6

HCl salt

1.12

2nd

2nd

9

9

5

8th

1

5

2nd

0

5

6

9

8th

8th

6

0.56

2nd

2nd

9

9

0

9

0

8th

0

0

3rd

3rd

9

8th

8th

-

ch3

-ch (ch3) 2

-ch (ch3) c = ch h

11.2

7

9

9

9

7

9

7

9

7

7

6

9

-

-

-

-

ch,

-ch (ch3) 2

-ch2-c (ci) = ch2

h l'l, 2nd

9

9

9

9

9

9

8th

9

9

9

9

9

-

-

-

-

ch3

-ch (ch.,) 2

-ch2ch2c = ch h

11.2

6

-

4th

8th

0

5

4th

7

4th

4th

4th

9

-

-

-

-

ch,

-ch (ch3) 2

-ch (ch3) ch = ch2

H

11.2

0

3rd

7

7

0

3rd

4th

4th

2nd

2nd

2nd

0

-

-

-

-

- (ch2) 5—

-c (ch3) 2ch = ch2

H

11.2

0

2nd

6

6

4th

4th

4th

4th

4th

4th

4th

4th

-

-

-

-

-ch (ch3) ch2ch2ch2ch2-

-ch2c = ch h

11.2

0

0

4th

0

0

4th

0

0

8th

6

3rd

5

-

-

-

-

ch3

—Ch (ch3) 2

-ch (ch3) -c (ch3) = ch2

H

11.2

5

9

7

7

4th

4th

4th

4th

0

0

1

0

-

-

-

-

ch3

-ch (ch3) 2

-ch2ch = chch3

H

11.2

2nd

5

6

6

0

6

3rd

5

5

3rd

2nd

2nd

-

-

-

-

ch,

-ch (ch3) 2

-ch2c (ch3) = ch2

H

11.2

0

0

7

8th

0

0

1

3rd

0

0

0

0

-

-

-

-

ch,

-ch (ch3) 2

-ch2ch = c (ch3) 2

H

11.2

3rd

5

7

7

0

6

5

6

2nd

5

3rd

3rd

-

-

-

-

ch,

-ch (ch3) 2

-ch2 / \

H

11.2

0

0

3rd

7

0

5

2nd

3rd

0

0

0

0

-

-

-

-

\ /

»

ch,

-ch (ch,),

-ch (ch = ch,) 2

H

11.2

3rd

9

8th

9

4th

9

9

9

7

8th

8th

7

-

-

-

-

ch3

-ch (ch3) 2

-ch (ch3) -ch = chch3

H

11.2

3rd

7

9

9

2nd

8th

7

9

6

5

7

5

-

-

-

-

ch3

ch (ch3) 2

-ch2c (ch3) 2,

H

11.2

5

0

6

9

0

7

5

4th

0

0

0

0

ch,

ch (ch3) 2

-ch2ch, och3

H

11.2

2nd

0

9

9

7

0

6

8th

4th

0

4th

8th

8th

5

3rd

1

9

9

9

8th

8th

3rd

5

8th

8th

7

9

9

9

8th

3rd

7

7

5

5

9

8th

9

9

8th

8th

8th

8th

5

3rd

7

7

6

5

3rd

7

13

Applications- plant species

amount

X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN

~ QH) 3-n ch3

-c-c2h5 ch3

-ch2ch2och2h5

-chj-CH = ch- v_}

-ch2-c = c- \ _y

-CHj-c = c-ch3

-CH-

I.

CH

<3

-ch2-c = c-c7hls_n

-ch, cc13

-c (c2h5) 2ch = ch2

oi (cu3) 2

fc ^ CH -

Cl

I.

-ch, -c = ch,

-ch,

2.24

0

0

5

6

7

0

0

0

1

6

1.12

0

0

5

3rd

8th

0

0

0

0

0

0.56

0

0

3rd

0

8th

0

0

0

0

0

0.28

0

0

3rd

0

0

0

0

0

0

0

h 11.2

8.5 * 8

9

9

6 *

9

8th

9

9

9

9

2.24

8th

7

9

9

9

7

5

9

9

7

h 1.12

8th

8th

9

9

9

6

3rd

7

9

8th

0.56

7

3rd

8th

8th

9

3rd

0

6

7

7

0.28

3rd

2nd

6

7

9

2nd

0

0

2nd

7

h 11.2

2nd

0

3rd

9

0

5

4th

4th

0

0

0

1

11.2

6 *

0

9

9

0

7

6

6

2nd

0

0

8th

2.24

3rd

0

3rd

2nd

9

0

0

0

0

h 1.12

2nd

0

2nd

0

0

0

0

0

0

h 11.2

0

0

7

9

0

4th

5

6

4th

0

0

4th

2.24

2nd

2nd

7

8th

9

2nd

0

0

0

5

1.12

1

0

7

5

3rd

0

0

0

0

2nd

0.56

0

0

2nd

2nd

2nd

0

0

0

0

0

h 11.2

4.5 * 7.5 * 7.5 * 8.5 * 2

5 *

8.5 * 9

5

5

6

8.5

*

2.24

8th

3rd

7

7

9

7

2nd

7

6

7

1.12

7

2nd

6

2nd

9

2nd

0

3rd

2nd

7

0.56

8th

2nd

5

2nd

7

0

0

0

0

6

h 11.2

4.5 * 4

6.5 * 8 *

3 *

5.5 * 6 *

6.5 * 4

0

0

5.5

*

h 11.2

4.5 * 6.5 * 8.5 * 9

7.5 * 7.5 * 8.5 * 8.5 * 7 *

6.5 * 8.5 * 8.5

*

2.24

7

3rd

8th

8th

9

2nd

0

3rd

8th

9

1.12

3rd

0

8th

5

9

0

0

0

2nd

8th

0.56

3rd

0

7

5

9

0

0

0

0

7

11.2

6.5 * 3

9

9

5

7.5 * 7

8.5 * 4

4th

7

8th*

h 2.24

8th

0

6

0

8th

0

0

0

2nd

8th

1.12

7

0

6

0

0

0

0

0

0

7

0.56

5

0

5

0

0

0

0

0

0

7

h 11.2

3rd

6

8th

9

3rd

6

7

9

3rd

0

8th

5

2.24

0

0

6

2nd

6

0

0

0

2nd

3rd

1.12

0

0

5

0

7

0

0

0

0

3rd

0.56

0

0

3rd

0

6

0

0

0

0

3rd

h 11.2

2nd

9

8th

9

6

3rd

8th

8th

5

8th

8th

9

2.24

6

9

9

9

9

9

7

9

9

9

1.12

6

8th

9

8th

9

7

5

9

9

9

0.56

3rd

3rd

8th

5

8th

3rd

0

8th

9

9

0.28

2nd

3rd

7

3rd

8th

0

0

7

9

9

0.14

0

1

6

3rd

9

0

0

7

9

9

h 11.2

1

8th

7

9

5

0

6

8th

5

3rd

7

7

2.24

7

5

8th

6

9

2nd

2nd

5

7

9

1.12

1

3rd

7

3rd

9

0

0

2nd

6

9

0.56

1

0

8th

5

9

0

0

0

3rd

9

11.2

0

5

9

9

6

6

6

3rd

2nd

9

5

0

h 2.24

0

0

5

3rd

0

0

0

0

0

7

1.12

0

0

2nd

0

0

0

0

0

0

3rd

h 11.2

0

0

8th

9

0

6

0

3rd

0

0

0

0

4 (5) 11.2

2nd

7

9

9

8th

7

9

9

8th

8th

8th

9

ch3 2.24

0

8th

6

5

9

6

5

7

9

9

1.12

0

7

3rd

5

9

2nd

0

6

9

9

0.56

0

3rd

2nd

3rd

8th

0

0

1

9

7

0.28

0

3rd

0

0

7

0

0

0

9

3rd

4 (5) 11.2

2nd

7

9

3rd

7

7

8th

9

8th

2nd

8th

8th

ch, 2.24

0

2nd

2nd

3rd

8th

8th

0

0

2nd

2nd

1.12

0

0

0

2nd

7

0

0

0

0

3rd

SY

9

7

7

6

5

7

7

8th

8th

8th

7

9

9

9

8th

8th

8th

9

9

8th

9

7

8th

7

6

3rd

2nd

0

8th

8th

8th

8th

0

0

7

7

8th

8th

7

7

14

Applications- plant species

quantity in kg / ha PN SE MU PI RW MG TW VL BA CR FO

-ch2-c = ch

4 (5) 11.2

3rd

8th

9

9

8th

7

8th

9

8th

9

9

ch3 2.24

3rd

9

7

5

9

8th

6

8th

1.12

0

9

.3

5

9

2nd

2nd

6

0.56

0

3rd

3rd

3rd

9

2nd

0

6

0.28

0

3rd

0

0

8th

0

0

3rd

0.14

0

2nd

0

0

6

0

0

0

ch (chj),

11.2

2nd

7

9

9

6

7

7

8th

7

2nd

7

1

2.24

3rd

1

5

2nd

2nd

5

0

0

-c-ch = chi i

h 1.12

0

0

5

0

0

0

0

0

1

ch (ch3) 2

-c2hs

h 11.2

2nd

3rd

9

9

6

7

8th

9

6

0

7

2.24

7

3rd

6

8th

9

0

0

2nd

1.12

6

2nd

6

7

9

0

0

0

0.56

5

2nd

6

5

9

0

0

0

0.28

3rd

2nd

5

3rd

9

0

0

0

-ch2-c = ch

h 11.2

3rd

9

9

9

9

8th

9

9

7

9

9

2.24

8th

9

9

9

9

8th

7

9

1.12

8th

8th

9

7

9

8th

7

9

0.56

8th

8th

9

5

9

8th

2nd

9

0.28

7

7

9

5

9

6

2nd

5

0.14

7

7

8th

2nd

9

5

0

5

0.07

5

2nd

5

2nd

9

3rd

0

2nd

-ch, -c = ch2

h 11.2

2nd

9

9

9

9

9

9

9

9

9

9

" 1

2.24

7

8th

9

9

9

7

3rd

9

Cl

1.12

7

8th

9

9

9

6

0

9

0.56

6

8th

9

6

9

5

0

7

0.28

6

3rd

8th

5

9

3rd

0

5

0.14

5

0

8th

3rd

5

2nd

0

2nd

-ch (ch3) ch =

= chch3

4 (5) 11.2

2nd

8th

9

9

7

6

8th

9

8th

7

8th

ch3 2.24

6

7

3rd

7

8th

0

0

3rd

1.12

5

6

2nd

5

6

0

0

2nd

0.56

3rd

5

0

3rd

6

0

0

0

0.28

2nd

2nd

0

2nd

3rd

0

0

0

u

1

3 (6) 11.2

1

0

8th

9

7

6

5

5

0

0

0

Cl

X o iii u

1

X u

1

3 (6) 11.2

0

0

9

9

6

7

8th

9

0

0

0

Cl 2.24

0

0

5

3rd

0

0

0

2nd

1.12

0

0

5

2nd

0

0

0

0

-ch2-c = c-ch2oh h 11.2

3rd

8th

9

9

9

9

9

9

9

9

9

2.24

8th

8th

9

9

9

9

5

9

1.12

7

6

9

6

9

6

3rd

7

0.56

7

3rd

8th

6

9

2nd

0

6

0.28

6

3rd

8th

6

9

2nd

0

3rd

-CH -> - c = chi 1

3 (6) 11.2

0

0

7

8th

0

0

5

5

0

0

0

1

Cl

-ch (ch3) ch =

= ch-ch3

3 (6) 11.2

0

0

6

7

0

0

0

3rd

0

0

0

Cl

-C2hj

3 (6) 11.2

0

0

7

9

5

4th

6

5

3rd

7

1

no, 2.24

0

0

0

3rd

0

3rd

0

0

1.12

0

0

0

0

0

0

0

0

ch3

h 11.2

3rd

0

9

9

0

6

7

9

3rd

3rd

7

2.24

3rd

0

7

8th

9

0

0-

0

1.12

2nd

0

6

8th

9

0

0

0

X u iii u! -. X u

1

h 11.2

3rd

6

9

9

7

6

7

9

7

7

9

2.24

5

3rd

7

8th

9

8th

0

7

1.12

5

2nd

7

7

9

6

0

7

0.56

3rd

2nd

5

7

9

5

0

7

0.28

2nd

0

3rd

6

8th

0

0

3rd

15 639 957

formula

Ri

R:

Rî

X

Application quantity in kg / ha

Plant species PN SE MU PI

RW MG TW VL

BA

CR

FO

WOCN

CO

Sì

chj c2h5

-ch2-c = ch2

H

11.2

5

7

9

9

4th

4th

7

9

7

5

8th

7

2.24

3rd

0

8th

5

7

7

0

6

6

9

8th

8th

Cl

1.12

2nd

0

7

5

6

5

0

2nd

0

8th

7

7

0.56

1

0

7

0

2nd

3rd

0

2nd

0

7

6

7

0.28

0

0

7

0

0

0

0

0

0

7

5

6

ch.,

ch (ch3) 2

-ch2-c = chc1

H

11.2

3rd

8th

9

9

9

7

8th

9

7

8th

8th

1

2.24

8th

9

9

9

9

8th

8th

9

9

9

9

9

Cl

1.12

8th

8th

9

9

8th

8th

2nd

8th

9

9

9

9

0.56

8th

8th

9

7

9

5

0

7

9

9

9

9

0.28

8th

0

9

5

9

5

0

5

5

9

8th

9

ch,

c2h5

-ch (ch3) ch = chch3

H

11.2

2nd

2nd

9

8th

5

7

7

8th

7

5

6

7

2.24

3rd

0

8th

5

7

5

0

2nd

0

8th

7

7

1.12

3rd

0

6

2nd

5

5

0

0

0

7

6

5

0.56

1

0

5

1

5

3rd

0

0

0

7

7

3rd

ch3

ch (ch3) 2

-ch-c = ch,

3 (6) 11.2

0

0

9

9

3rd

3rd

7

4th

2nd

0

0

0

I.

no / 2 2.24

0

2nd

5

2nd

2nd

3rd

0

0

0

0

7

0

Cl

1.12

0

2nd

0

0

0

0

0

0

0

0

3rd

0

ch3

11.2

5

8th

9

9

9

7

8th

9

7

9

8th

9

1

2.24

9

9

9

9

9

9

9

9

9

9

9

9

ch3

ch (ch3) 2

-c-ch = ch2

H

1.12

9

8th

9

9

9

9

8th

9

9

9

9

9

1

0.56

9

8th

9

9

9

9

3rd

8th

9

9

9

9

ch3

0.28

8th

2nd

9

5

9

7

0

5

7

9

7

8th

0.14

3rd

0

9

5

5

7

0

0

3rd

8th

3rd

7

0.07

3rd

0

0

0

3rd

0

0

0

0

7

5

5

ch3

11.2

4th

4th

8th

8th

2nd

4th

4th

4th

4th

4th

4th

4th

1

2.24

9

0

9

7

9

9

3rd

9

7

9

7

9

ch3

c2h5

-c-ch = ch2

1.12

9

0

9

7

9

9

2nd

8th

7

9

7

9

1

0.56

8th

0

9

3rd

9

9

0

7

3rd

9

7

8th

ch3

0.28

2nd

0

8th

3rd

9

7

0

5

3rd

7

3rd

8th

0.14

2nd

0

6

1

9

3rd

0

3rd

0

6

2nd

7

ch3

ch (ch3) 2

H

4 (5) 11.2

1

3rd

6

8th

5

4th

8th

9

4th

4th

4th

4th

Cl

2.24

9

9

8th

8th

9

8th

9

9

9

9

9

9

1.12

5

8th

9

8th

9

8th

9

9

9

9

9

9

0.56

5

8th

8th

9

9

7

9

9

9

9

9

9

0.28

5

8th

6

7

9

7

8th

9

9

9

6

9

0.14

5

6

6

8th

9

6

6

8th

8th

6

9

9

0.07

0

6

5

7

8th

5

5

6

9

3rd

9

5

ch (ch3) 2

11.2

0

6

9

9

3rd

0

7

9

4th

7

4th

7

1

2.24

6

2nd

9

8th

9

7

7

3rd

8th

9

9

9

ch3

ch (ch3) 2

-c-c = ch h

1.12

5

1

9

7

9

5

3rd

3rd

9

9

9

9

1

0.56

5

0

9

6

8th

3rd

0

3rd

3rd

8th

9

9

ch (ch3) 2

0.28

3rd

0

9

5

7

3rd

0

1

3rd

3rd

7

5

ch3

ch (ch3) 2

-c2h5

4 (5) 11.2

0

0

9

9

7

2nd

7

7

4th

1

2nd

7

Cl

2.24

0

6

7

5

5

0

0

0

2nd

0

7

5

1.12

0

1

6

1

3rd

0

0

0

0

0

3rd

3rd

c2h5

ch (ch,) 2

ch3

H

11.2

0

0

6

8th

0

0

5

5

0

0

0

0

c; h5

ch (ch3) 2

-ch2-c = ch h

11.2

0

0

8th

8th

0

2nd

5

7

0

0

0

0

c2h5

ch (ch3) 2

-CHo-c = ch, 1

H

11.2

0

0

8th

8th

0

1

7

7

0

0

0

0

1

Cl

ch,

ch (ch,) 2

-ch2-c = ch

4 (5) 11.2

0

0

7

8th

3rd

0

5

5

4th

1

4th

4th

Cl

ch3

ch (ch,) 2

-ch (ch3) ch = chch,

4 (5) 11.2

2nd

6

8th

8th

4th

4th

7

9

7

4th

4th

4th

Cl

2.24

3rd

2nd

9

5

8th

5

0

2nd

7

6

6

7

1.12

3rd

2nd

6

6

6

5

0

2nd

2nd

5

5

7

0.56

3rd

7

6

5

5

5

0

0

0

0

5

5

ch3

c2h5

h h

11.2

3rd

8th

8th

8th

0

5

7

9

7

4th

7

7

ch,

ch (ch3) 2

h h

11.2

2nd

3rd

7

8th

1

5

7

8th

6

2nd

4th

4th

2.24

5

2nd

9

8th

9

7

7

7

9

8th

8th

8th

1.12

3rd

2nd

9

8th

9

7

5

7

8th

9

8th

6

0.56

3rd

0

9

3rd

9

6

0

5

6

8th

7

5

639 957

16

formula

Applications- plant species

amount

X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI

CH, CH (CH,) 2

CH3 CH (CH3) 2

CH3 CH (CH3) 2

CH3 CH (CH3) 2

H

-CH2-C = CH2 CI

CH = CHt

I.

-CH-C = CH CH3

I.

-c-ch = ch2 ch3

3 (6) 11.2 3 7976786247 Cl

4 (5) 11.2 278977786575 Cl

H 11.2 7

9 6 8 7 9 7

4 (5) 11.2 478766697379 Cl

* Average of two or more attempts Example 7

Efficacy as pre-emergence herbicides The efficacy of the compounds according to the invention as pre-emergence herbicides is shown by the following tests, for which seeds or reproductive organs of various monocotyledonous plants, cyperaceans and dicotyledonous plants are mixed separately with potting soil and the mixture thus obtained is then raised to an approximately 2.5 cm high Place the soil layer in separate cups. After planting you spray

25th

30th

the cups in such an amount with the respective solution of the active ingredient in mixtures of water and acetone that results in an amount of active ingredient per cup of about 0.28 to 11.2 kg per ha. The treated cups are then placed on hothouse tables, watered and kept in the usual way. The investigations are stopped three or four weeks after the treatment has been carried out, each cup being checked accordingly and rated on the evaluation scale given in Example 6. The data obtained here are shown in Table II below.

Table II

Efficacy of the compounds of the formula given as pre-emergence herbicides

.COOH.

x-

formula

R, R-,

Applications- plant species

quantity in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW

ch,

ch (ch3) 2

-ch2-c = ch h

11.2

9

8 8

9

9

9

8th

9

9

9

9

8th

4.48

9

9 9

9

9

9

9

8th

9

9

9

9 9 9

9

9 -

1.12 *

9

7.5 9

9

5

8th

8.5

8.5 9

9

9

9 8.5 9

8th

9 -

0.56 *

9

6.5 9

9

3rd

8th

7.5

8.5 7.5 7

9

8.5 7.5 8

8th

8.5 -

0.28

8th

0 9

9

3rd

7

5

6

5

-

6

7 9 9

7

- -

0.07

9

0 8

9

0

7

5

6

6

7

7

7 5 8

7

6 -

ch,

-ch (ch3) 2

-ch2ch2ch3

H

11.2

9

8 9

9

9

8th

8th

8th

7

8th

9

8th

4.48

6

8 8

9

2nd

8th

8th

8th

6

7

8th

8 7 9

8th

6 -

1.12

3rd

7 8

9

0

7

7

2nd

0

0

0

7 3 8

5

0 -

0.56

2nd

7 7

9

0

4th

5

1

0

0

0

4 1 7

1

0 -

ch,

-ch (ch3) 2

-ch2

H

11.2

9

8 9

9

8th

8th

9

9

9

9

9

8th

4.48

9

8 9

9

5

8th

9

8th

8th

8th

9

7 3 9

8th

9 -

1.12

8th

5 8

9

0

7

7

7

5

7

7

2 2 7

3rd

7 -

0.56

1

0 8

9

0

7

5

5

0

2nd

3rd

0 1 1

0

3 -

ch,

-entent

- (ch2) 7ch3

H

11.2

9

3 9

9

8th

7

8th

7

9

9

9

4th

4.48

9

9 8

9

0

7

7

6

7

8th

9

5 5 6

6

8th -

1.12

9

0 9

9

-

7

2nd

3rd

5

5

8th

2 2 2

3rd

7 -

0.56

8th

0 8

9

0

7

0

2nd

0

2nd

7

0 2 0

3rd

3 -

17th

639 957

formula

R?

Applications- plant species

quantity in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW

CH -CH (CH3) 2

CH3 -CH (CH3) 2

CH3 -CH (CH3) 2

CHj -CH (CH3) 2

ch3 -CH (CH3),

CH3 -CH (CH3) 2

CH3 -CH (CH3) 2

CH3 -CH (CH3) 2

ch3 -ch2ch2ch3

CH3 -encens),

CH3 -CH (CH3) 2

CH3 -CH (CH3) 2

CH3 -CH (CH3) 2 - (CH2) -

-CH (CH3) CH2CH2CH2CH2-

CH3 -CH (CH3) 2

CH, -entent,

CH3 -CH (CH3) 2

CH, -CH (CH3) 2

CH3 -CH (CH3) 2

CH3 -CH (CH3) 2

CH, -CH (CH3) 2

CH, -CH (CH3) 2

- (ch3) nch3

-ch2ch = ch2

-c <ch3) 2ch = ch2

-c (ch3) 2c = ch

-ch (ch3) 2 -c (ch3) 3

-ch2ch3

-c (ch3) 2ch = ch2 -ch (ch3) c = ch

-ch2c (c1) = ch2

-ch2ch2c = ch

-ch (ch3) chch2

-c (ch3) 2ch = ch2 -ch, c-ch

-ch2ch = chch3 -ch, c (ch3) = ch2 -ch2ch = c (ch3) 2

H

11.2

9

3rd

8th

9

0

7

7

8th

8th

9

9

4th

4.48

9

5

8th

9

0

7

7

7

7

8th

9

4th

1.12

9

0

8th

9

0

6

3rd

6

3rd

6

8th

2nd

0.56

6

0

7

9

0

2nd

0

2nd

2nd

2nd

7

0

H

11.2

9

8th

9

9

8th

8th

9

9

8th

9

9

8th

4.48

9

8th

8th

9

8th

8th

8th

9

9

9

9

8th

1.12

9

7

8th

9

0

8th

7

7

7

7

8th

7

0.56

9

0

8th

9

0

8th

2nd

6

5

5

7

7

H

11.2

9

9

9

9

7

8th

9

9

9

9

9

9

4.48

9

9

9

9

7

9

9

9

9

8th

9

9

1.12 *

7.6 3.5 9

9

2nd

7.6 5

8th

7.5 4.5 7

8.6

0.56 *

5.6 0

9

9

0

7.3 3.5 6.7 5.5 1

5

8.3

0.28

3rd

0

8th

8th

0

7

0

1

2nd

0

2nd

8th

H

11.2

9

8th

9

9

8th

8th

8th

8th

9

9

9

8th

4.48

9

9

9

9

8th

9

9

9

9

9

9

8th

1.12

9

8th

9

9

8th

8th

8th

8th

9

9

9

7

0.56

9

6

9

9

5

7

7

8th

7

8th

8th

6

0.07

9

0

8th

8th

0

7

2nd

5

0

2nd

6

0

H

11.2

9

8th

8th

9

8th

8th

8th

8th

8th

9

9

8th

0.56

8th

0

8th

9

0

8th

5

6

6

6

7

7

H

11.2

7

5

8th

9

3rd

8th

8th

8th

7

9

9

8th

11.2

9

5

8th

9

7

8th

9

9

6

7

8th

7

0.06

0

0

2nd

9

0

0

0

0

0

0

0

7

H

11.2

9

8th

8th

9

7

8th

9

9

7

7

7

9

1.12

9

5

8th

9

1

6

2nd

5

0

2nd

5

1

H

11.2

0

0

8th

6

0

4th

6

6

0

0

0

0

H

11.2

9

9

9

9

9

8th

9

9

9

9

9

8th

0.56

9

-

-

-

3rd

8th

9

8th

7

7

8th

8th

H

11.2

9

9

9

9

8th

9

8th

9

9

9

9

9

0.14

8th

-

-

-

0

8th

9

7

7

7

8th

8th

H

11.2

9

9

9

9

8th

9

9

9

9

9

9

8th

2.24

9

-

-

-

2nd

8th

8th

7

7

6

8th

8th

H

11.2

9

9

9

8th

8th

8th

8th

9

8th

7

8th

7

1.12

9

-

-

-

0

8th

9

8th

7

7

8th

7

H

11.2

9

0

8th

9

0

7

9

6

6

6

6

7

H

11.2

9

9

9

9

7

9

5

9

9

9

9

9

0.56

6

-

-

-

0

2nd

0

0

9

9

9

9

0.14

0

-

-

-

0

0

0

0

8th

9

7

0

H

11.2

9

9

9

9

8th

8th

9

9

8th

9

9

7

2.24

9

-

-

-

1

8th

8th

8th

7

6

8th

7

H

11.2

9

9

8th

8th

8th

8th

9

8th

8th

9

9

8th

2.24

9

-

-

-

2nd

8th

8th

8th

7

7

8th

8th

H

11.2

9

9

9

8th

8th

9

9

9

8th

8th

9

8th

0.56

8th

-

-

-

0

8th

9

7

6

7

7

2nd

H

11.2

9

9

9

9

8th

8th

9

8th

9

9

9

8th

0.28

9

-

-

-

0

7

9

8th

8th

9

9

7

H

11.2

3rd

8th

8th

8th

0

7

8th

8th

7

8th

9

0

2.28

8th

-

-

-

0

9

9

6

3rd

5

5

0

H

11.2

9

8th

8th

8th

8th

9

8th

8th

9

9

9

8th

1.12

9

-

-

-

0

8th

8th

8th

7

7

9

3rd

0.25

9

-

-

-

0

7

7

6

7

6

7

0

0.07

7

-

-

-

0

2nd

0

0

0

3rd

2nd

0

H

11.2

9

9

8th

8th

8th

9

8th

8th

9

9

9

8th

0.56

9

0

-

-

0

7

7

8th

7

7

9

6

H

11.2

8th

8th

8th

8th

0

8th

8th

8th

7

8th

8th

5

2.24

9

-

-

-

0

7

8th

6

6

6

7

2nd

9 9 9 -8 8 7 -

9 9 9 9 -9 8 9 9 -9 7 8 9 -

7 9 9

12 7-7

7 8 5

0 0 0 0

8 6

8 9 8

3-9

9 8 9

13 5-9

2 8 5 -

3 8 9

639 957

18th

Formula application- plant species quantity r1 r, r3 X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW

ch3

-CH (CHj) 2

-C (CHj) 2CH = CH2

H

11.2

9

9

9

9

8th

8th

8th

8th

9

9

9

9

HCl salt

1.12

9

6

8th

9

3rd

8th

7

8th

6

7

9

8th

8th

9

8th

9 -

0.56

9

0

8th

9

0

8th

7

7

3rd

8th

9

9

7

8th

7

9 -

0.14

9

0

8th

9

0

3rd

0

5

3rd

5

7

0

1

6

7

9 -

CHj

-CH (CHj) 2

-C (CHj) 2C = CH

H

11.2

9

8th

8th

9

6

8th

9

9

9

9

9

8th

HCl salt

1.12

9

0

8th

9

1

8th

6

7

8th

8th

8th

8th

7

8th

7

8th -

0.56

8th

0

8th

9

0

8th

0

3rd

7

7

3rd

7

3rd

8th

6

7 -

0.14

2nd

0

8th

9

0

7

0

1

2nd

0

2nd

1

0

7

1

1 -

CHj

CH (CHj) 2

-CH2C (CH3) j

H

11.2

8th

0

8th

9

3rd

8th

9

8th

3rd

3rd

5

6

2.24

2nd

0

7

7

5

0

0

0

2nd

1

7

2nd

7

1.12

0

0

0

5

1

0

0

0

2nd

0

7

0

7

CHj

CH (CHj) 2

-ch2ch2och3

H

11.2

9

7

9

9

3rd

8th

8th

8th

8th

8th

9

8th

2.24

5

0

8th

7

3rd

0

0

0

6

2nd

7

6

9

fî ~ \

1.12

5

0

2nd

0

1

0

0

0

2nd

1

1

2nd

7

CHj

CH (CHj) 2

H

11.2

9

8th

9

9

8th

9

9

9

9

9

9

8th

2.24

9

8th

8th

9

8th

9

9

9

8th

9

8th

8th

9

1.12

9

8th

8th

7

8th

7

8th

9

8th

8th

7

8th

9

0.56

9

2nd

8th

7

8th

3rd

7

9

7

8th

7

8th

8th

0.28

9

0

7

7

7

1

0

9

3rd

5

5

7

9

ch2

CH (CHj) 2

-QH13-n h

11.2

9

8th

9

9

7

8th

8th

8th

8th

8th

9

7

2.24

9

2nd

2nd

9

6

2nd

3rd

9

2nd

2nd

8th

6

9

1.12

9

0

0

3rd

5

0

0

0

1

1

2nd

2nd

7

CHj

H

11.2

9

8th

9

9

9

8th

9

9

9

9

9

8th

1

2.24

9

0

8th

9

8th

2nd

3rd

3rd

2nd

3rd

8th

7

9

CHj

CH (CHj) 2

-c-c2hs

1

1.12

9

0

5

9

3rd

0

0

0

0

2nd

5

3rd

9

CHj

CHj

CH (CHj) 2

-chjchjoqhj

H

11.2

9

8th

8th

9

5

8th

8th

8th

8th

8th

9

8th

2.24

9

0

2nd

1

5

0

0

2nd

5

6

5

6

8th

1.12

2nd

0

1

0

3rd

Q

0

0

1

0

0

4th

6

CHj

CH (CHj) 2

-CH2CH = CH-C6H5

H

11.2

9

9

9

9

7

8th

9

9

9

9

9

8th

2.24

8th

0

6

6

7

1

1

9

6

3rd

8th

5

8th

1.12

6

0

3rd

3rd

0

0

0

0

0

0

3rd

CHj

CH (CHj) 2

-CH2-C = C-C6Hs h

11.2

9

8th

9

9

8th

8th

8th

8th

9

9

9

7

2.24

9

3rd

8th

7

6

6

6

9

3rd

5

2nd

3rd

8th

1.12

8th

0

2nd

2nd

3rd

2nd

0

5

2nd

0

0

0

2nd

CHj

CH (CHj) 2

-ch2-c = c-ch3

H

11.2

9

9

9

9

9

9

9

9

9

9

9

8th

2.24

9

7

8th

9

9

6

8th

9

9

8th

8th

7

9

1.12

9

2nd

9

9

9

5

3rd

8th

8th

8th

7

7

9

0.56

9

0

3rd

9

9

2nd

0

7

2nd

8th

7

7

8th

0.28

6

0

5

7

3rd

0

0

0

0

3rd

7

5

7

CHj

CH (CHj) 2

-çh- <1

H

11.2

9

8th

9

9

9

8th

9

9

9

9

9

9

CH-,

2.24

9

5

8th

8th

9

7

7

9

8th

9

8th

8th

8th

3rd

1.12

9

0

6

- 7th

7

0

0

7

3rd

7

7

6

8th

0.56

9

0

3rd

5

2nd

0

0

0

0

1

7

5

2nd

CHj

CH (CHj) 2

-CH2-C = C-C7H15-n

H

11.2

9

1

8th

9

3rd

8th

8th

8th

8th

9

9

7

2.24

9

0

6

6

9

2nd

0

8th

9

5

5

6

7

1.12

9

0

3rd

2nd

7

0

0

7

5

2nd

2nd

5

7

0.56

0

0

2nd

0

3rd

0

0

0

2nd

1

1

3rd

3rd

CHj

CH (CHj) 2

-ch2cci3

H

11.2

9

8th

9

9

8th

8th

8th

9

8th

8th

9

8th

2.24

9

7

8th

9

9

8th

6

9

9

8th

8th

8th

8th

1.12

9

3rd

8th

5

9

5

2nd

8th

8th

8th

7

8th

7

0.56

9

0

7

5

7

3rd

0

7

7

7

7

7

6

0.28

9

0

6

5

2nd

3rd

0

5

5

3rd

7

6

3rd

CHj

CH (CHj),

-C (C2Hs) 2CH = CH,

H

11.2

9

9

8th

9

8th

9

9

9

9

8th

9

8th

2.24

9

5

8th

9

9

7

3rd

7

9

9

8th

8th

9

1.12

9

3rd

8th

5

7

5

0

7

9

8th

7

7

8th

0.56

9

0

7

0

6

0

0

3rd

5

7

7

7

6

19th

639 957

formula

R, R,

Applications- plant species

amount

X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI JW

CH3 CH (CH3) 2

ch (ch3) 2

H 11.2 0 0

04000030

CHj

CH (CHj) 2

OK

H 11.2

0

0

8th

9

0

7

6

7

3 5

6 3

j \ /

c = ch

CH,

CH (CHj) 2

-ch2-c = ch2

4 (5) 11.2

9

7

9

9

8th

8th

8th

8th

9 9

9 8

1

CHj 2.24

9

8th

8th

8th

8th

8 8

9 9

6

7

7

8th

Cl

1.12

7

7

5

7

7

8 5

8 9

1

5

6

8th

0.56

5

5

2nd

7

5

0 0

0 8

0

3rd

3rd

7

CHj

CH (CHj) 2

-CH3

4 (5) 11.2

9

8th

9

9

8th

7

8th

9

9 8

8 8

CH3 2.24

8th*

8th

7

4 *

7.5 * 7

7

8 * 4 *

5.5 * 9 *

8th

5

7

7

1.12

6 *

8th

2nd

3.5 * 3 *

7

6

5.5 * 0 *

4.5 * 9 *

2nd

2nd

7

7

0.56

3.5

*

8th

0

0 *

1*

3.5 * 0 *

0.5 * 9 *

CHj

CH (CHj) 2

-ch2-c = ch

4 (5) 11.2

9

8th

9

9

8th

8th

8th

9

9 9

9 8

CH3 2.24

9

8th

8th

8th

8th

8 7

9 9

9

1.12

9

8th

5

7

8th

6 3

7 9

8th

0.56

6

8th

2nd

6

7

3 0

2 9

8th

CH (CH3),

H 11.2

9

8th

9

9

8th

8th

8th

9

9 9

9 8

1

2.24

9

0

7

6

9

8 0

5 8

7

7

7

8th

CHj

CH (CH3) 2

-c-ch = ch2

1

1.12

9

0

5

5

6

3 0

2 2

6

6

6

8th

CH (CHj) 2

CH,

CH (CHj) 2

-CA

H 11.2

8th

6

8th

9

8th

8th

8th

9

7 6

8 8

(+) - isomer

1.12

8th

5

8th

8th

9

5 0

0 8

9

8th

8th

9

0.56

7

5

7

7

9

2 0

0 8

8th

8th

7

9

0.28

7

3rd

7

5

9

2 0

0 8

7

7

7

7

CHj

CH (CH3) 2

-ch2-c = ch

H 11.2

9

9

9

9

8th

8th

8th

8th

9 9

9 8

(-)-Isomer

1.12

9

8th

8th

8th

9

8 7

9 9

9

8th

8th

8th

0.56

9

8th

8th

8th

9

9 6

9 9

9

8th

8th

8th

0.28

8th

6

7

7

8th

6 3

8 8

8th

7

8th

8th

0.14

9

5

7

3rd

7

3 0

0 7

7

6

7

7

CHj

CH (CH3) 2

-CHj-C = CH2

H 11.2

9

8th

9

9

8th

8th

8th

9

9 9

9 8

]

2.24

9

8th

8th

9

8th

9 9

9 8

9

8th

8th

8th

(H -) isomer

Cl

1.12

9

8th

8th

8th

9

8 9

9 8

9

8th

8th

8th

0.56

9

8th

7

7

8th

7 5

8 8

8th

8th

7

8th

0.28

9

2nd

7

5

8th

5 2

7 8

8th

8th

7

8th

0.14

6

0

7

3rd

5

3 0

2 7

3rd

6

6

8th

0.07

3rd

0

6

0

2nd

0 0

0 3

2nd

3rd

3rd

7

CH,

CH (CHj) 2

-CH (CHj) CH = CHCH3

4 (5) 11.2

9

8th

9

9

8th

8th

8th

9

8 8

9 8

CH3 2.24

9

8th

7

8th

8th

6 6

7 9

8th

5

7

8th

1.12

9

6

6

7

6

3 0

2 8

5

2nd

6

8th

0.56

9

3rd

2nd

3rd

3rd

0 0

0 7

0

0

5

3rd

CHj

CH (CH3) 2

-ch3

3 (6) 11.2

0

0

8th

9

0

7

7

7

0 0

0 0

Cl

CH,

CH (CHj) 2

-ch2c = ch

3 (6) 11.2

7

0

8th

9

6

8th

8th

8th

0 0

0 0

Cl

CH.,

CH (CH3) 2

-ch2c = c-ch2oh

H 11.2

9

8th

9

9

8th

8th

8th

9

9 9

9 8

2.24

9

8th

8th

8th

8th

7 9

9 8

9

8th

8th

8th

1.12

9

5

8th

7

8th

3 6

8 8

8th

7

8th

8th

0.56

9

0

8th

5

3rd

2 2

7 7

7

6

7

7

0.28

9

0

8th

2nd

3rd

0 0

0 3

2nd

3rd

7

5

CH.,

CH (CHj) 2

-ch2-c = ch2

3 (6) 11.2

0

0

9

9

0

6

7

6

0 0

0 0

1

Cl

Cl

CH,

CH (CH3) 2

-CH (CH,) 2CH = CH-CH,

3 (6) 11.2

0

0

8th

9

0

4th

7

8th

0 0

0 0

Cl

639 957

20th

Formula application quantity of plants

R! R, R, X in kg / ha PN SE MU PI RW MG TW VL BA CR FO WO CN CO SY RI

ch.,

ch (ch3) 2

-qhs

3 (6) 11.2

5

0

8th

8th

1

8th

7

7

7

7

0

2nd

no2

ch3

c2hj

-ch3

H

11.2

9

5

9

8th

0

8th

8th

9

7

0

8th

9

2.24

7

0

8th

8th

9

3rd

0

3rd

8th

5

6

7

1.12

2nd

0

7

7

8th

0

0

0

7

0

3rd

5

ch3

c3h5

-ch2-c = ch h

11.2

9

8th

9

9

3rd

8th

8th

9

8th

8th

8th

9

2.24

9

0

8th

8th

9

7

6

9

8th

7

7

7

1.12

9

0

8th

6

8th

3rd

2nd

3rd

6

3rd

5

6

0.56

3rd

0

7

5

5

0

0

0

0

0

2nd

2nd

ch3

c2h5

-ch2-c = ch,

H

11.2

9

7

9

9

8th

8th

9

9

9

9

9

8th

1

2.24

9

0

8th

8th

8th

6

6

8th

8th

5

7

6

cl

1.12

7

0

8th

6

2nd

3rd

0

6

6

3rd

5

3rd

0.56

5

0

7

0

1

0

0

7

2nd

1

3rd

2nd

0.28

2nd

0

3rd

0

0

0

0

0

0

0

1

0

ch3

ch (ch3) 2

-CHi-C = CHCl h

11.2

9

8th

9

9

8th

8th

9

9

9

9

9

8th

" 1

2.24

9

8th

8th

8th

9

9

9

9

8th

8th

8th

8th

Cl

1.12

9

2nd

8th

7

8th

8th

5

8th

7

7

7

8th

0.56

9

0

6

6

7

3rd

2nd

5

3rd

7

6

7

0.28

8th

0

2nd

5

6

0

0

0

0

1

5

7

ch3

QHs ch3

11.2

9

6

9

9

0

8th

8th

9

8th

7

8th

8th

1

2.24

9

0

8th

8th

8th

5

2nd

5

3rd

7

7

7

-ch-ch = ch-ch3

H

1.12

9

0

7

5

2nd

2nd

0

2nd

0

2nd

5

5

ch3

ch (ch3) 2

-ch, -c = ch2

3 (6) 11.2

5

0

8th

8th

6

7

8th

8th

5

0

6

5

" 1

no,

Cl

ch3

ch (ch3) 2

ch3

11.2

9

7

9

9

8th

7

8th

9

8th

9

8th

8th

1

2.24

9

8th

8th

8th

9

9

8th

9

8th

9

8th

8th

-c-ch = ch2

H

1.12

9

0

8th

7

7

3rd

7

9

6

8th

7

6

1

0.56

8th

0

7

3rd

8th

0

0

8th

5

7

5

5

qhs

0.28

9

0

7

5

3rd

0

0

8th

3rd

6

3rd

2nd

0.14

9

0

2nd

0

1

0

0

0

0

6

2nd

1

ch3

c2h5

ch3

11.2

9

0

8th

8th

0

8th

8th

8th

7

8th

8th

8th

1

2.24

9

0

8th

8th

9

7

5

9

5

8th

8th

8th

-c-ch = ch,

H

1.12

9

0

7

7

7

2nd

1

6

2nd

5

6

7

1

0.56

7

0

5

3rd

1

0

0

0

0

1

2nd

5

ch3

ch3

ch (ch3) 2

ch (ch3),

H

11.2

9

9

8th

9

8th

8th

8th

9

8th

8th

8th

7

1

2.24

7

0

7

8th

8th

6

7

8th

3rd

3rd

5

5

-c-c = ch

1.12

3rd

0

6

6

8th

5

6

7

0

0

3rd

2nd

1

0.56

0

0

3rd

5

3rd

0

6

0

0

1

1

ch (ch3) 2

ch3

ch (ch3) 2

-C2hs

4 (5) 11.2

8th

1

8th

9

8th

8th

7

9

6

3rd

7

7

Cl

2.24

2nd

7

5

6

3rd

1

3rd

8th

0

6

3rd

1.12

1

0

5

5

2nd

0

0

1

8th

0

3rd

0

QHS

ch (ch3) 2

-ch3

H

11.2

3rd

0

8th

8th

0

6

3rd

6

1

1

1

1

c2h5

ch (ch3) 2

-ch2-c = ch h

11.2

7

0

8th

9

0

8th

8th

8th

7

6

8th

8th

c, h5

ch (ch3) 2

-ch2-c = ch2

H

11.2

3rd

0

8th

9

0

8th

8th

8th

6

7

8th

5

Cl

ch3

ch (ch3) 2

H

4 (5) 11.2

9

8th

9

9

8th

8th

8th

9

9

9

9

9

Cl

2.24

9

8th

8th

8th

8th

8th

8th

8th

8th

8th

8th

7

1.12

9

8th

8th

7

8th

8th

8th

9

8th

8th

8th

7

0.56

9

6

8th

7

8th

6

3rd

8th

8th

7

7

7

0.28

9

6

7

8th

7

5

3rd

5

6

5

5

6

0.14

9

0

5

3rd

6

3rd

1

2nd

5

3rd

3rd

5

ch3

ch (ch3) 2

-ch2-c = ch

4 (5) 11.2

9

8th

8th

9

8th

8th

8th

9

8th

8th

9

8th

Cl

2.24

8th

8th

8th

7

8th

8th

7

8th

6

8th

5

1.12

6

7

8th

5

7

7

7

8th

1

0

5

0.56

5

7

8th

2nd

5

5

6

7

0

1

1

0.28

3rd

7

7

0

2nd

0

3rd

7

0

0

1

JW

9

8th

9

8th

8th

8th

7

7

8th

8th

8th

8th

8th

8th

8th

8th

8th

8th

3rd

8th

8th

0

9

8th

7

8th

8th

8th

8th

5

8th

8th

8th

8th

21st

639 957

Formula R,

R,

R3

X

Application quantity in kg / ha

Plant species PN SE MU PI

RW MG TW VL

BA

CR

FO

WOCN

CO

SY RI

JW

ch,

ch (ch3) 2

ch3

4 (5) 11.2

9 8 8 8

8th

8th

8th

8th

8th

8th

8th

8th

1

2.24

9 cl

8th

7

2nd

6

7

7

7

7

6

5

6

7

-ch-ch = chch3

1.12

6

7

3rd

0

7

0

5

2nd

2nd

1

5

3rd

0.56

2nd

0

5

0

6

0

2nd

2nd

0

0

3rd

0

ch3

c2h5

h h

11.2

9 8 8 8

8th

8th

8th

8th

8th

8th

8th

8th

2.24

9

0

8th

8th

9

9

9

8th

8th

9

9

8th

1.12

9

0

8th

8th

8th

9

9

9

8th

7

9

8th

8th

0.56

9

0

8th

7

1

1

3rd

5

3rd

3rd

8th

8th

0.28

9

0

7

5

1

1

5

2nd

3rd

3rd

7

7

c2h5

ch (ch3) 2

h h

11.2

9 0 8 8

3rd

8th

8th

8th

7

8th

8th

5

2.24

9

0

8th

2nd

3rd

2nd

7

0

3rd

6

5

7

1.12

8th

0

6

0

7

0

0

3rd

0

3rd

5

2nd

1

0.56

9

0

3rd

0

0

0

0

0

0

1

2nd

2nd

0

ch3

ch (ch3) 2

H

3 (6) 11.2

9 8 8 8

8th

8th

8th

8th

9

8th

9

8th

Cl

2.24

9

9

8th

7

8th

9

8th

8th

9

9

8th

8th

1.12

9

8th

8th

3rd

7

6

3rd

7

7

8th

8th

8th

0.56

9

7

8th

2nd

3rd

1

1

2nd

6

8th

8th

7

0.28

9

7

8th

2nd

1

0

0

2nd

2nd

8th

7

7

ch3

ch (ch3) 2

-ch, -c = ch2

4 (5) 11.2

9 8 8 9

8th

8th

8th

9

8th

8th

8th

8th

" 1

Cl

2.24

9

8th

8th

7

7

9

9

8th

8th

7

8th

7

8th

cl

1.12

9

8th

5

6

8th

8th

7

8th

2nd

5

5

8th

0.56

8th

7

1

5

7

8th

6

5

0

6

2nd

8th

0.28

5

7

0

0

5

5

5

2nd

0

3rd

2nd

8th

0.13

0

7

3rd

0

0

0

3rd

3rd

0

0

3rd

1

7

ch3

ch (ch3) 2

ch2 = ch2

H

11.2

9 9 8 8

8th

8th

8th

8th

9

8th

9

8th

1

2.24

9

8th

8th

9

9

9

9

8th

9

8th

8th

8th

-ch-ch = ch

1.12

9

8th

8th

8th

8th

9

9

9

8th

7

8th

7

8th

0.56

9

8th

8th

8th

8th

9

8th

8th

8th

7

8th

7

8th

0.28

9

7

7

7

7

8th

7

6

5

8th

7

8th

0.14

9

7

5

7

7

8th

7

5

2nd

8th

6

8th

0.07

9

5

5

6

7

8th

6

3rd

2nd

7

2nd

7

ch3

ch (ch3) 2

ch3

4 (5) 11.2

9 7 8 8

8th

8th

8th

8th

8th

8th

8th

8th

1

2.24

9

8th

8th

8th

8th

8th

8th

8th

8th

8th

8th

8th

-c-ch = ch2

1.12

9

8th

5

5

7

8th

7

6

3rd

9

7

8th

1

cl

0.56

8th

8th

5

3rd

7

7

6

2nd

3rd

8th

7

7

ch3

0.28

8th

0

7

1

1

0

1

5

0

2nd

5

6

5

* = Average of two or more experiments Example 8

Efficacy as selective post-emergence herbicides The effectiveness of the compounds according to the invention as selective post-emergence herbicides is shown by the following tests, in which sorghum plants [Sorghum bicolor (L) Woeuch], spring wheat plants (Triticum aestiv-um, cv. Auza) and barley plants (Hordeum vulgare, cv .

43 Steptoe) treated with the corresponding active ingredients, which are dispersed in mixtures of water and acetone. The procedure described in Example 6 is followed in detail, the treated plants being examined as indicated in Example 6 and evaluated according to the evaluation scale 50 there. The results obtained in these experiments are shown in Table III below.

Table III

Efficacy of the compounds of the formula given as selective post-emergence herbicides

: oor-

formula

R>

R3

Application amount in kg / ha

Plant species sorghum auza

Steptoe

-CH, -CH (CH3),

-CHiCHIOCH,

H

2.24 1.12 0.56

639 957

22

formula

R, R,

Rs

X

Application amount in kg / ha

Plant species sorghum auza

Steptoe

-ch, -ch (ch,) 2

-ch,

-ch3

-CH,

-CH,

-CH,

-ch,

-CH,

-CH,

-CH,

-CH,

-ch,

-CH,

-CH (CH3) 2 -CH (CH3) 2 -CH (CH3) 2

-CH (CH3) 2 -CH (CH3) 2 -CH (CH3) 2

(+) - isomer

-CH (CH3) 2

-CH (CH3) 2

-C2Hs

-CH (CH3) 2

-CH (CH3) 2

-CH (CH3) 2

CH,

I '

-c-c2h5 ch3

-ch2ch2oc2hs

-çh <j ch3

-CH2-C = C-C7H15-n ch (ch3) 2

-CH,

-c2h5

-ch2-c = ch

-c2h5

-ch3

-ch, -c = ch,

"I"

Cl

-c2h5 ch3

-ch-ch = chch3

H H

H

H

H

2.24 1.12 0.56

2.24 1.12 0.56 2.24 1.12 0.56 2.24 1.12 0.56

H

2.24 1.12 1.12 4 (5) CH3 2.24 1.12 0.56 H 2.24 1.12 0.56 3 (6) CI 2.24 1.12 0.56 3 (6 ) N02 2.24 1.12 0.56 H 2.24 1.12 0.56 3 (6) NO, 2.24 1.12 0.56 4 (5) C12.24 1.12 0.56 4 (5) C12.24 1.12 0.56

3 3 0 3 0 0 2 0 0

0 0 0 2 2

0 2

1 0

2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6

3 0

2nd

2 0 6 5

3 3 2

2nd

3 0

0

1 0 0 9

2nd

2 0

3 0 0 0 0 0

2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0

0

6

7

1 0 0 0 0 0 0

50

Example 9 plants [Sorghum bicolor (L) Moeuch], spring wheat plants (Triticum aestivum, cv. Auza) and barley plants (Hor-deum vulgare, cv. Steptoe). The evaluation of the test results. According to the method described in Example 7, the effectiveness of the compounds according to the invention is carried out as 55 on the evaluation scale given in Example 6. The results obtained in these trials of selective pre-emergence herbicides using sorghum are shown in Table IV below.

Efficacy as selective pre-emergence herbicides

Table IV

Efficacy of the compounds of the formula given as selective pre-emergence herbicides

23

639 957

formula

Application amount

Plant species

R,

R:

R3

X

in kg / ha

Sorghum

Auza

Steptoe

-CH.,

-CH (CHj) 2

-CH2C (CHj) j

H

2.24

0

2nd

0

1.12

0

0

0

0.56

0

0

0

-CH,

-CH (CHj) 2

-CH2CH, OCHj

H

2.24

0

7

2nd

1.12

0

3rd

0

0.56

0

0

0

-CHj

-CH (CHj) 2

-céhij-n

H

2.24

3rd

2nd

0

1.12

0

0

0

0.56

0

0

0

-CHj

-CH (CHj) 2

CHj

H

2.24

2nd

5

2nd

1

1.12

0

3rd

0

-C-QHs

1

0.56

0

0

0

CHj

-CHj

-CH (CHj) 2

-CH2CH2OC2Hs

H

2.24

2nd

8th

7

1.12

0

5

0

0.56

0

3rd

0

-CHj

-CH (CHj) 2

-CH2CH = CH-C6Hs

H

2.24

3rd

7

3rd

1.12

2nd

0

0

0.56

0

0

0

-CH,

-CH (CHj) 2

-CHj

4 (5) CHj 2.24

8th

2nd

3rd

1.12

8th

0

0

0.56

2nd

0

0

-CHj

-CH (CHj) 2

-ch2-ch2-

H

2.24

0

6

3rd

1.12

0

0

0

0.56

0

0

0

-CHj

-QHs

-CHj

H

2.24

2nd

2nd

2nd

1.12

0

0

0

0.56

0

0

0

-CHj

-CH (CHj) 2

-c2h5

4 (5) C12.24

0

7

0

1.12

0

0

0

0.56

0

0

0

-CHj

-CH (CHj) 2

ÇH (CHj) 2

H

2.24

5

6

2nd

1

1.12

0

3rd

0

-CHj

-CH (CHj) 2

-C-C = CH

0.56

0

0

0

CH (CHj) 2

-CHj

-CH (CHj) 2

CHj

4 (5) CI 2.24

8th

7

2nd

1

1.12

2nd

5

0

-CH-CH = CHCHj

0.56

1

2nd

0

M

Claims (18)

639 957 2nd PATENT CLAIMS 1. Imidazolinylbenzoates of the formula: cook x wherein X is hydrogen Q-Cj-alkyl, halogen or nitro, R 1 is Q-C 1 alkyl, R2 represents QQ-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl, halophenyl or benzyl, or the substituents Rj and R2 together with the carbon atom to which they are attached mean Çr-Q-cycloalkyl, which is optionally substituted by methyl, R3 is hydrogen, C, -Cn-alkyl which is optionally substituted by a Q-Cj-alkoxy group or a C3-Q-cycloalkyl group or a phenyl group or a furyl group or 1 to 3 halogen substituents, C3-C5-alkenyl which is optionally substituted by 1 or 2 QQ-alkyl groups or a phenyl group or 1 to 2 halogen substituents, Q-C5-alkynyl which is optionally substituted by 1 to 2 C1-c3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, benzyl, cyclohexenylmethyl, Ethinylcyclohexyl, ethinylalkyl, pentadienyl or C3-C6-cycloalkyl, which is optionally substituted by 1 or 2 QQ-alkyl groups, or a salt-forming cation of alkali metals, ammonium or aliphatic ammonium ^ and, if the substituents Rj and R2 are not the same, the optical isomers thereof, and the acid addition salts of these compounds, if the substituent R3 is not a salt-forming cation. 2. Compounds according to claim 1, characterized in that X represents hydrogen, methyl, chlorine or nitro, Rj is Ci-C3-alkyl, R2 represents Ci-C3-alkyl or cyclohexyl or the substituents Rj and R2 together with the carbon atom to which they are attached mean cyclohexyl or methylcyclohexyl, R3 is hydrogen, Ci-C] 2-alkyl, C] -C5 alkenyl which is optionally substituted by 1 or 2 chlorine atoms or 1 or 2 Ci-C3-alkyl substituents, Q-c5-alkynyl which is optionally substituted by 1 or 2 QQ Alkyl substituent is benzyl, cyclohexenylmethyl or pentadienyl, and, if the substituents R 1 and R 2 are not identical, the optical isomers thereof and isomer mixtures thereof, and the acid addition salts of these compounds. 3. Compounds according to claim 1, characterized in that X represents hydrogen, methyl or chlorine, Ri is methyl, R2 represents isopropyl and R3 has the meaning given in claim 1. 4.2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid methyl ester, 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid 2-propinyl ester, 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid, 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) - n-propyl benzoate, 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid 1,1-dimethylallyl ester, Allyl 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate, Octyl 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate, (+) - 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid ethyl ester, (+) - 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid-2-chloroallyester, 2- (5-Ethyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acids according to Claim 1. The mixture of isomers according to claim 1 consisting of 6- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -m-toluic acid methyl ester and 2- (5-isopropyl-5-methyl-4-oxo-2 -imidazolin-2-yl) -p-toluic acid methyl ester. 6. isomer mixture according to claim 1 from 3-chloro-2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid and 6-chloro-2- (5-isopropyl- 5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid. 7. (-) - 2- (5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid 2-propinyl ester or 2- (5-isopropyl-5-methyl-4 -oxo-2-imidazolin-2-yl) -benzoic acid isopropylamine salt according to claim 1. 8. mixture of isomers according to claim 1 from 6- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -m-toluic acid and 2- (5-isopropyl-5-methyl-4- oxo-2-imidazolin-2-yl) -p-toluic acid. 9.2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid sodium salt or 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl -yl) -benzoic acid-l-methyl-2-butenyl ester according to claim 1. 10. Herbicidal composition for combating undesirable plant species, which contains a herbicidally effective amount of a corresponding active ingredient, characterized in that it contains a compound of the formula I as active ingredient: wherein X is hydrogen, Q-Q-alkyl, halogen or nitro, R 1 is C 1 -C 4 -alkyl, R2 represents Q-Q-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, phenyl, halophenyl or benzyl, or the substituents R] and R2 together with the carbon atom to which they are attached mean C3-C6-cycloalkyl which is optionally substituted by methyl, R3 is hydrogen, Q-Cn-alkyl which is optionally substituted by a C1-C3-alkoxy group or a C3-C6-cycloalkyl group or a phenyl group or a furyl group or 1 to 3 halogen substituents, C3-C5-alkenyl which is optionally substituted by 1 or 2 Q-c3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, c3-c5-alkynyl which is optionally substituted with 1 to 2 C1-c3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, benzyl, cyclohexenylmethyl, ethynylcyclohexyl , Ethynylalkyl, pentadienyl or C3-C6-cycloalkyl, which is optionally substituted by 1 or 2 Q-Cj-alkyl groups, or a salt-forming cation of alkali metals, ammonium or aliphatic ammonium. 5 10th 15 20th 25th 30th 35 40 45 50 55 60 65 3rd 639 957 or, if the substituents R and R2 are not the same, an optical isomer or a mixture of isomers thereof, or an acid addition salt of these compounds, if the substituent R3 is not a salt-forming cation. 11. Agent according to claim 10, characterized in that it is used for pre-emergence control of undesirable plant species in application amounts of 0.07 to 11.2 g of active ingredient per ha for the treatment of a soil which contains seeds, seedlings or other reproductive organs of the plants to be controlled. 12. Composition according to claim 10, characterized in that it is applied to control cyperaceans or other annual plants in application amounts of 0.56 to 25 kg of active ingredient per hectare on a soil which contains seeds or other reproductive organs of the cyperaceas to be controlled or annual plants. 13. Composition according to claim 10 for post-emergence control of undesirable plants, characterized in that it is applied in application amounts of 0.28 to 25 kg of active ingredient per hectare to the foliage of the plants to be controlled. 14. Composition according to claim 10, characterized in that it is a compound of formula I as active ingredient, wherein X is hydrogen, methyl, chlorine or nitro, R is [Ci-C3-alkyl, R2 represents Q-Q-alkyl or cyclohexyl or the substituents R] and R2 together with the carbon atom to which they are attached mean cyclohexyl or methylcyclohexyl, R3 is hydrogen, Ci-Ci2-alkyl, C3-C5-alkenyl which is optionally substituted by 1 or 2 chlorine atoms or 1 or 2 Q-c3-alkyl substituents, C3-C5-alkynyl which is optionally substituted by 1 or 2 QQ-alkyl substituents is benzyl, cyclohexenylmethyl or pentadienyl, or, if the substituents Rj and R2 are not the same, an optical isomer thereof or an isomer mixture thereof, or an acid addition salt of these compounds. 15. Composition according to claim 10, characterized in that it contains as active ingredient a compound of formula I in which X is hydrogen, methyl or chlorine, Ri is methyl, R2 represents isopropyl and R3 has the meaning given in claim 8. 16. Composition according to claim 10, characterized in that it contains 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid 2-propynyl ester as active ingredient, Methyl 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate, 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid, the mixture of isomers 6- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -m-toluyl acid remethyl ester and 2- (5-isopropyl-5-methyl-4-oxo-2-imidazoIin-2-yI) -p-toIuyIic acid methyl ester, (+) - 2- (5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid ethyl ester or (+) - 2- (5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -benzoic acid 2-chloroallyl ester. 17. Process for the preparation of imidazolinyl benzoates of the formula: ^ fOOR ^ X- - - H (I), wherein X is hydrogen, Q-Q-alkyl, halogen or nitro, Ri is Q-C4-alkyl R2 represents QQ-alkyl, QQ-cycloalkyl, C2-C4-alkenyl, phenyl, 5 halophenyl or benzyl, or the substituents Ri and R2 together with the carbon atom to which they are attached mean C3-C6-cyclic, which if appropriate is substituted by methyl, 10 R3 is hydrogen, Q-Q2-alkyl which is optionally substituted by a QQ-alkoxy group or a QQ-cycloalkyl group or a phenyl group or a furyl group or 1 to 3 halogen substituents, C3-C5-alkenyl which is optionally substituted by 1 or 2 Ci C3-alkyl groups or a phenyl group or 1 to 2 halogen substituents, QQ-alkynyl, which is optionally substituted by 1 to 2 QQ-alkyl groups or a phenyl group or 1 to 2 halogen substituents, benzyl, cyclohexenylmethyl, ethynylcyclohexyl, ethynylalkyl, pentadienyl or 20 QQ-cycloalkyl, which is optionally substituted by 1 or 2 QQ-alkyl groups, or denotes a salt-forming cation of alkali metals, ammonium or aliphatic ammonium, and, if the substituents Rx and R2 are not the same, the 25 optical isomers and isomer mixtures thereof, and the acid addition salts of these compounds, if the substituent R3 is not a salt-forming cation, characterized in that an imidazoisoindoldione of the formula II: 30th 35 (II) 40 wherein X, Rx and R2 have the meanings given above, with an alcohol of the formula: R3OH, 45 wherein R3 has the meaning given above, in the presence of an alkali metal or an alkali metal hydride at 20 to 50 ° C. 18. The method according to claim 17, characterized in that one works at a ratio of alcohol to imidazoisoindoldione of 1.1 to 1.0: 5.0 to 1.0 and carries out the reaction under inert gas protection. 19. The method according to claim 17, characterized in that 50 that the reaction mixture of imidazoisoindoldione, alcohol and alkali metal or alkali metal hydride is mixed with such an amount of a non-protic solvent that the ratio of non-protic solvent to alcohol does not exceed 4: 1, and the reaction is carried out under inert gas protection 55. 20. Process for the preparation of imidazolinylbenzoic acids of the formula: COOK 60 65 ^ 0 where n ~ - ~~ ^ 0 X represents hydrogen, Q-Q-alkyl, halogen or nitro. Ri Ci ~ C4 alkyl. 639 957 4th R 1 is C 1 -C 6 -alkyl, C3-C6-cycloalkyl, c2-c4-alkenyl, phenyl, halophenyl or benzyl, or the substituents Rj and R2 together with the carbon atom to which they are attached, C3-C6- Cycloalkyl, which is optionally substituted by methyl, 5 and, if the substituents R 1 and R 2 are not the same, the optical isomers thereof and mixtures of isomers thereof, characterized in that an imidazoisoindoldione of the formula II: .n (Ii) « 15 wherein X, Ri and R2 have the meanings given above, treated with excess hydrochloric acid in such a way that the corresponding lactone hydrochloride is formed, and this lactone hydrochloride is then reacted with an equivalent of a base to form the desired imidazolonic acid. 25th No. 3,717,659 relates to salicylic acid derivatives substituted in the 5-position by a heteroaryl radical and having pharmacological effects. U.S. Patent No. 3905,996 relates to N-phenyl derivatives of cyclized ureas. U.S. Patent No. 4,055,409 relates to pyrazole derivatives. GB-PS No. 1360.982 relates to pharmacologically active 2-phenyl-5-aminoimidazoles. U.S. Patent No. 3,882,138 relates to oxazole and oxadiazole derivatives. US Pat. No. 3,448,074 relates to 4-oxoimidazolidine-1-oxides which can be used as stabilizers for polyolefins. U.S. Patent No. 4,067,718 relates to tricyclic compounds with 2 lactam functions. GB-PS No. 876.015 relates to mono- and di-alkyl-substituted ureas or cyclically substituted ureas with plant growth-regulating action.