DE3618501A1 - Herbicidally active unsaturated lactams - Google Patents

Abstract

Novel N-(2-fluoro-4-halophenyl)hexahydroisoindole compounds of the formula I below have good selective herbicidal properties when used pre- and post-emergence, and furthermore affect, i.e. inhibit, the growth of plants. The compounds have the formula I <IMAGE> in which n denotes the number zero or 1, Hal denotes fluorine, chlorine, bromine or iodine, R and R1 independently of one another in each case denote hydrogen or C1-C8-alkyl, C3-C8-cycloalkyl, C3-C8-alkenyl or C3-C8 -alkynyl radicals, each of which is optionally substituted by halogen or C1-C4-alkoxy, B denotes a radical -COXR1, -YR2, X and Y in each case denote oxygen, sulphur or a radical -N(R3), R2 denotes hydrogen or a C1-C8-alkyl, C3-C8-alkenyl or C3-C8 -alkynyl radical, each of which is optionally substituted by halogen, C1-C4-alkoxy, cyano or a radical -COXR1, and R3 denotes hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl, or a C3-C8-alkenyl or C3-C8-alkynyl radical which is bonded via a saturated carbon atom.

Description

Unsaturated lactams with herbicidal properties

DE-A 2 831 770 discloses unsaturated lactams of the formula wherein X, Y and Z are each independently hydrogen, halogen, alkyl, haloalkyl, methoxy, ethoxy, phenoxy, chlorophenoxy, the cyano or nitro group, A is hydrogen, halogen or a group QR or -Q - (Q ") R n Q, Q 'and Q, independently of one another, each represent an oxygen or sulfur atom or a group -N-, n the R' number is zero or 1 and the radicals R and R 'independently of one another are hydrogen, optionally substituted alkyl radicals, cycloalkyl or alkenyl 1 or 2 double compounds or alkynyl, B represents the -CH group or a nitrogen atom.

Such compounds are also postulated in EP-A-68 822, but not described in detail. The compounds described are characterized by a herbicidal action and can be used to control weeds. Depending on the dosage, they act as total or selective herbicides, and can be used to control weeds in crops of useful plants. Some compounds also have fungicidal effects against phytopathogenic fungi.

Surprisingly, it has now been found that hitherto unknown N- (2-fluoro-4-halophenyl) -hexahydro-isoindole compounds of the formula below I the compounds known from DE-A 2 831 770 in their herbicidal and the Plant growth regulating effects are clearly superior.

The new N- (2-fluoro-4-halophenyl) -hexahydro-isoindole compounds correspond to formula I. wherein A is hydrogen, halogen or a group QR or # -QC- (Q ") nR where Q, Q 'and Q" are each independently an oxygen or sulfur atom or the group -N-R1 n is the number zero or 1 Hal fluorine , Chlorine, bromine or iodine R and R1 independently of one another each hydrogen or optionally C1-Cs-alkyl, C§-C8-Cxcloalkyl-, C3-Ce-alkenyl- or C3-C8- substituted by halogen or C1-C4-alkoxy Alkynyl radicals, B a radical -COXR1, -YR2, X and Y each oxygen, sulfur or a radical -N (R3).

R2 is hydrogen or an optionally substituted by halogen, C1-C4-alkoxy, Cyan or a -COXR1-substituted C1-C8-alkyl, C3-Cs-alkenyl or C3-Cs-alkynyl radical and R3 hydrogen, Cl-Ca-alkyl, C3-Cs-cycloalkyl, one over one C3-Cg-alkenyl or C3-Cg-alkynyl radical bonded to a saturated carbon atom.

The present invention relates to the N- (2-fluoro-4-halophenyl) -hexahydro-isoindole compounds of the formula I with herbicidal and plant growth-regulating effects, as well as the Making these new connections. It also concerns means that the new Contain compounds and their use for the selective control of weeds or to regulate plant growth.

Those N- (2-fluoro-4-halophenyl) -hexahydro-isoindoles have proven to be particularly active of formula I, in which Hal represents a chlorine atom and B represents the isopropoxy radical while A has the meaning given under formula I; - also those in which A and Hal each represent a chlorine atom, while B has the meaning given in claim 1 has, - further compounds in which B is the methoxycarbonylmethoxy radical and Hal represent a bromine atom while A has the meaning given in claim 1 - and and finally those in which B is isopropoxy and Hal is fluorine represent, while A has the meaning given in claim 1.

The preferred individual compounds are N- (2-fluoro-4-chloro-5-isopropoxyphenyl) -2,3,4,5,6,7-hexahydroisoindol-1 (1H) one, N- (2-fluoro-4-chloro-5-isopropoxyphenyl) -3-hydroxy-2,3,4,5,6,7-hexahydro-isoindole-1 (lH) on, N- (2-fluoro-4-chloro-5-isopropoxyphenyl) -3-chloro-2, 3,4,5,6, 7-hexahydro-isoindol-1 (1H) one.

If A represents a halogen atom, chlorine is preferred. examples for Groups -Q-R and Q-8- (Q ") n-R at the point of A are: hydroxyl alkyl-, haloalkyl- and dialkylamino, acyl, haloacyl, alkylthio, alkoxy, alkenyloxy, -O-CO-NH-alkyl, -O-CO-N (dialkyl), -O-CO-NH-cycloalkyl, -O-CO-S-alkyl, -S-CO-O-alkyl, -O-CO-NH-alkenyl, Etc.

The preparation of the N- (2-fluoro-4-halophenyl) -hexahydro-isoindoles according to the invention of the formula I takes place - depending on the meaning of A - in different process stages.

1) Compounds in which A represents the OH group are obtained from the N- (2-fluoro-4-halophenyl) -tetrahydrophthalimides of the formula II wherein B and Hal have the meaning given under formula I, by reduction with a hydrogenating agent, in particular with metal hydrides, such as sodium borohydride Nach4, according to the Polish Rocz literature. Chem. 49, 1671 (1975), or with LiA1H4 and other hydrogen-evolving metal hydrides.

Lower alkanols, in particular Ethanol, but also ether, tetrahydrofuran or water can be used. Such Reductions can be carried out under normal pressure in conventional apparatus.

2) The reduced hydroxy compounds obtained according to 1) (A = OH) can be with halogenating agents such as thionyl chloride, etc. in compounds of Convert formula I, in which A is chlorine or bromine. By exchanging the Chlorine by fluorine by means of potassium fluoride leads to the corresponding fluorine derivatives (A = fluorine).

3) From the halides described under 2), especially the chlorides (A = C1) the corresponding Make compounds where A is represented by hydrogen.

4) To compounds of the formula I in which A is a group -QR, where R is an optionally substituted alkyl or alkenyl radical, one arrives at starting from a halogen compound described under 2) (e.g. A = C1) Reaction with a compound RQH or RQ Me in the presence or absence of a base, where Q is as defined under formula I and Me represents a metal cation.

5) Finally, the hydroxyl compounds obtained according to 1) can be used (A = OH) acylate with acid halogens of the R-CO-Hal type (A = O-CO-R) or through Conversion with isocyanates of the type R-NCO or isothiocyanates R-NCS into end products convert, in which A respectively a radical -O-CO-NH-R1. -O-CS-NH-R1 represents.

For the production of all described variants of the end products is the first stage, namely the reduction of N- (2-fluoro-4-halophenyl) -tetrahydrophthalimides of formula II necessary. Most of the starting materials of the formula II are known, e.g. from Chem. Ber. 1903, pages 996 to 1007 and can in the usual way from the tetrahydrophthalic anhydride by reaction with an appropriately substituted one Aniline can be easily produced.

The process for the preparation of the N- (2-fluoro-4-halophenyl) -hexahydro-indoles of the formula I is characterized in that a 2-fluoro-4-halophenyl-tetrahydrophthalic acid imide of the formula II in which B and Hal have the meaning given under formula I, reduced with a hydrogenating agent to a hydroxyl compound in which A in formula I of the end products represents the OH group, and that this hydroxyl compound can, if desired, be incorporated by methods known per se another derivative of the formula I with the meaning given there for A converted.

Some of the starting materials of formula II are in US Pat. No. 3,984 435 have been proposed as herbicides, but are nowhere near as effective and the spectrum of activity of the new unsaturated lactams of the formula I present Sign up.

A metal hydride is particularly advantageous as the hydrogenating agent Sodium borohydride is used.

The invention relates to all diastereomeric and enantiomeric isomers of the compounds of formula I.

The active ingredients of the formula I are generally used with application rates from 0.005 to 4 kg / ha, in particular 0.01 to 1 kg / ha, have been used successfully.

At lower application rates, the compounds of the formula stand out I have good selective-growth-inhibiting and selective-herbicidal properties that they are ideal for use in crops of useful plants, especially in cereals, Cotton, soy, corn and rice, empower. In some cases, weeds are also involved damaged, which so far could only be dealt with with total herbicides.

The mode of action of these active ingredients is unusual. Many are translocatable, i.e. they are taken up by the plant and transported to other places, where they then come into effect. This is how it works, for example, through surface treatment Damaging perennial weeds down to the roots. The new connections of formula I already have an effect - in comparison to other herbicides and growth regulators - very low application rates.

The compounds of formula I also have strong plant growth inhibiting, Properties. There will be both monocots and dicots in theirs Impaired growth.

For example, those in agriculture in tropical areas can often as cover crops "(ground cover) planted legumes through the connections of formula I are selectively inhibited in their growth, so that although soil erosion between the cultivated plants is prevented, but the cover crops do not compete for culture can be.

Inhibition of vegetative growth is possible in many cultivated plants a denser planting of the culture, so that a higher yield, based on the soil area, can be achieved.

Another mechanism of increasing yield with growth inhibitors is based on the fact that the nutrients in greater measure of the flower and fruit formation benefit while vegetative growth is restricted.

If larger amounts are used, all plants tested are used in their Development is so damaged that it dies.

The invention also relates to herbicidal and plant growth regulating agents Means which contain a new active ingredient of the formula I, as well as methods for pre- and post-emergent weed control and to inhibit the Plant growth of monocotyledonous and dicotyledonous plants, especially grasses, tropical Ground cover and tobacco shoots.

The compounds of the formula I are used in unchanged form or, preferably used as a means together with the auxiliaries customary in formulation technology and therefore become e.g. emulsion concentrates, directly sprayable or dilutable Solutions, diluted emulsions, wettable powders, soluble powders, dusts, Granules, also encapsulations in e.g. polymeric materials, processed in a known manner. The application methods such as spraying, misting, dusting, scattering or pouring become the same as the nature of the means, the desired goals and the given circumstances chosen accordingly.

The formulations, i.e. the active ingredient of the formula I and optionally agents, preparations or containing a solid or liquid additive Compositions are prepared in a known manner, for example by intimate mixing and / or grinding the active ingredients with extenders, such as solvents, solid carriers, and optionally surface-active compounds (surfactants).

The following solvents can be used: aromatic hydrocarbons, preferably the fractions Cs to Clz, such as xylene mixtures or substituted naphthalenes, Phthalic acid esters such as dibutyl or dicotyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and optionally epoxidized vegetable oils, such as epoxidized Coconut oil or soybean oil; or water.

As solid carriers, e.g. for dusts and dispersible powders, As a rule, natural rock flour is used, such as calcite, talc, kaolin, Montmorillonite or Attapulgite. To improve physical properties highly disperse silica or highly disperse absorbent polymers can also be added will. As granular, adsorptive granulate carriers, porous types such as pumice stone, Broken bricks, sepiolite or bentonite, as non-sorptive carrier materials e.g. calcite or sand in question. In addition, a large number of pregranulated materials can be used inorganic or organic nature such as in particular dolomite or crushed Plant residues are used.

As surface-active compounds come depending on the type of the to be formulated Active ingredient of the formula I with nonionic, cationic and / or anionic surfactants good emulsifying, dispersing and wetting properties are considered. Among surfactants are also to understand surfactant mixtures.

Suitable anionic surfactants can be so-called water-soluble soaps as well as water-soluble synthetic surface-active compounds.

The soaps are alkali, alkaline earth or optionally substituted Ammonium salts of higher fatty acids (C1o-C22), such as the Na or K salts of the Oleic or stearic acid, or natural fatty acid mixtures, e.g. from coconut or tallow oil can be obtained called. The fatty acid methyl taurine salts are also used to mention.

However, so-called synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty sulfates or sulfates are usually as alkali, alkaline earth or optionally substituted ammonium salts and have an alkyl radical 8 to 22 carbon atoms, with alkyl also the alkyl part of acyl radicals includes, e.g. the Na or Ca salt of ligninsulphonic acid, the dodecylsulphuric acid ester or a fatty alcohol sulfate mixture made from natural fatty acids.

This subheading also includes the salts of sulfuric acid esters and sulphonic acids of fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives contain preferably 2 sulfonic acid groups and a fatty acid residue with 8-22 carbon atoms. Alkyl aryl sulfonates are e.g.

the Na, Ca or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulphonic acid or of a naphthalenesulphonic acid-formaldehyde condensation product.

There are also corresponding phosphates such as salts of the phosphoric acid ester a p-nonylphenol- (4-14) -ethylene oxide adduct or phospholipids in question.

Polyglycol ether derivatives are primarily used as non-ionic surfactants of aliphatic or cycloaliphatic alcohols, saturated or unsaturated Fatty acids and alkylphenols in question, the 3 to 10 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms may contain in the alkyl radical of the alkylphenols.

Other suitable nonionic surfactants are the water-soluble, 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups containing polyethylene oxide adducts with polypropylene glycol, ethylene diamino polypropylene glycol and alkyl polypropylene glycol having 1 to 10 carbon atoms in the alkyl chain. the compounds mentioned usually contain 1 to per propylene glycol unit 5 ethylene glycol units.

Examples of nonionic surfactants are nonylphenol polyethoxyethanols, Castor oil polyglycol ether, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethanol Polyethylene glycol and Octylphenoxypolyäthoxyäthanol mentioned.

Furthermore, there are also fatty acid esters of polyoxyethylene sorbitan like that Polyoxyethylene sorbitan trioleate into consideration.

The cationic surfactants are mainly quaternary Ammonium salts which have at least one alkyl radical with 8 to 22 as N-substituent Contain carbon atoms and, as further substituents, lower ones, optionally halogenated ones Have alkyl, benzyl or lower hydroxyalkyl radicals. The salts are preferably as halides, methyl sulfates or ethyl sulfates, e.g. stearyltrimethylammonium chloride or benzyldi (2-chloroethyl) ethylammonium bromide.

The surfactants commonly used in formulation technology are, among others, in the following publications described: "Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood, New Jersey, 1979.

Dr. Helmut Stache "Tensid Taschenbuch" Carl Hanser Verlag, Munich / Vienna 1981.

Such preparations usually contain 0.1 to 95%, in particular 0.1 to 80%, active ingredient of the formula I, 1 to 99.9% of a solid or liquid additive and 0 to 25%, especially 0.1 to 25% of a surfactant.

In particular, preferred formulations are set as follows together: (% ~ weight percent) Emulsifiable concentrates: Active ingredient of formula 1: 1 to 20% preferably 5 to 10% surfactant: 5 to 30%, preferably 10 to 20% liquid vehicle: 50 to 94%, preferably 70 to 85%.

Dusts: Active ingredient of the formula I: 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99%.

Suspension concentrates: Active ingredient of the formula I: 5 to 75%, preferably 10 to 50% water: 94 to 25%, preferably 90 to 30% surfactant: 1 to 40%, preferably 2 to 30%.

Wettable powder: Active ingredient of the formula I: 0.5 to 90%, preferably 1 to 80% surfactant: 0.5 to 20%, preferably 1 to 15% solids Carrier: 5 to 95%, preferably 15 to 90%.

Granules: Active ingredient of the formula I: 0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%.

While concentrated products are preferred as a commodity, the end user usually uses diluted agents. The application forms can be diluted down to 0.001% active ingredient. The application rates are usually 0.005 to 5 kg As / ha.

The agents can also contain other additives such as stabilizers, defoamers, Viscosity regulators, binders, adhesives and fertilizers or other active ingredients included to achieve special effects.

The following examples illustrate the preparation of some unsaturated lactams of the formula I. Others prepared in a corresponding manner Active ingredients are listed in the tables below. Refer to temperature information in degrees Celsius, pressures are given in millibars.

Example 1: Preparation of N- (2-fluoro-4-chloro-5-isopropoxy) -phenyl-3-hydroxy-2,3,4,5,6,7-hexahydro-isoindol-1 (1H) -one 33.75 g (0.1 mol) of N- (2-fluoro-4-chloro-5-isopropoxy) phenyl-3,4,5,6-tetrahydrophthalimide in 75 ml of methanol are placed in a 1 liter sulphonation flask. 5.6 g (0.148 mol) of sodium borohydride are added in portions to the clear solution at room temperature. A slightly exothermic reaction occurs with strong foaming and gas evolution. After this has subsided, a suspension is obtained which is allowed to stir for a further 30 minutes at room temperature and then mixed with 200 ml of ice water. The rubbery substance soon crystallizes. The reaction mixture is refined in a mixer and filtered. The residue is washed with water and dried over phosphorus pentoxide. This gives 30.5 g (90.0%) of N- (2-fluoro-4-chloro-5-isopropoxy) phenyl-3-hydroxy-2, 3,4, 5,6, 7-hexahydroisoindole-1 ( lH) on with a melting point 83-840C.

Example 2: Preparation of N- (2-fluoro-4-chloro-5-isopropoxy) -phenyl-3-hydroxy-2,3,4,5,6,7-hexahydro-isoindol-1 (1H) -one 25.5 g (0.075 mol) of the compound obtained in Example 1 are dissolved in 25 ml of methylene chloride at room temperature. 8.1 ml (0.11 mol) of thionyl chloride are added dropwise with stirring. A slightly exothermic reaction occurs with vigorous evolution of gas. As the temperature drops, it is kept at 250C with a bath. When the addition is complete, the mixture is stirred for 30 minutes at 50 ° C. The reaction mixture is gently evaporated and N- (2-fluoro-4-chloro-5-isopropoxy) phenyl-3-chloro-2,3,4 is obtained in quantitative yield > 5,6,7-hexahydro-isoindol-l (1H) one as a dark, thick oil.

Example 3: Preparation of N- (2-fluoro-4-chloro-5-isopropoxy) -phenyl-2,3,4,5,6,7-hexahydro-isoindol-1 (1H) -one 8.4 g (0.0235 mol) of the compound obtained in Example 2 are dissolved in 90 ml of tetrahydrofuran and 2.51 g of 2,6-lutidine and 2.5 g of Pd / C 5% are added. The reaction mixture is then hydrogenated by adding hydrogen. After the uptake of 116% hydrogen, the reaction is interrupted. The reaction mixture is filtered and the filtrate is evaporated. The oily residue is dissolved in methylene chloride and the solution is filtered through a small silica gel column.

After the filtrate has been evaporated, the oily residue is dissolved in little ether, the solution is mixed with petroleum ether until it becomes cloudy and leaves that Crystallize product. 4.6 g (60.5%) of N- (2-fluoro-4-chloro-5-isopropoxyphenyl-2,3,4,5,6, 7-hexahydro-isoindol-1 (1H) one with a m.p. 78-800C.

According to these examples, the following N- (2-fluoro-4-halophenyl) -2,3,4,5,6,7-hexahydro-isoindol-1 (1H) one compounds of the formula I are prepared: Table 1 No. AB Hal 1.01 OH OCH (CH3) 2 Cl m.p. 83-84 ° 1.02 Cl OCH (CH3) 2 Cl Oel 1.03 H OCH (CH3) 2 Cl m.p. 78-80 ° 1.04 SCH3 OCH (CH3) 2 Cl 1.05 NHCH ( CH3) 2 OCH (CH3) 2 Cl 1.06 OCH2CH = CH2 OCH (CH3) 2 Cl 1.07 OCON (CH3) 2 OCH (CH3) 2 Cl 1.08 SCOOC2H5 OCH (CH3) 2 Cl 1.09 OCOCH3 OCH (CH3) 2 Cl 1.10 OCONHCH3 OCH (CH3) 2 Cl 1.11 Cl OCH3 Cl 1.12 Cl OC2H5 Cl 1.13 Cl OCH2CH = CH2 Cl 1.14 Cl OCH2C = CH Cl 1.15 Cl OCH2-CN Cl 1.16 Cl OCH2COOCH2 Cl 1.17 Cl OCH2COOC2H5 Cl 1.18 Cl OCH (CH3) COOCH3 Cl 1.19 Cl OCH (CH3) COOC2H5 Cl 1.20 Cl SCH3 Cl 1.21 Cl SC2H5 Cl 1.22 Cl SCH2CH = CH2 Cl 1.23 Cl SCH2C = CH Cl 1.24 Cl SCH2COOCH3 Cl 1.25 Cl SCH2COOC2H5 Cl 1.26 Cl NHCH3 Cl 1.27 Cl N (CH3) 2 Cl Table 1 (continued) No. AB Hal 1.28 Cl NHCH2COOCH3 Cl 1.29 Cl NHCH2COOC2H5 Cl 1.30 Cl N (CH2) CH2COOCH3 Cl 1.31 Cl COOCH3 Cl 1.32 Cl COOC2H5 Cl 1.33 OH OCH2COOCH3 Br 1.34 OCH3 OCHzCOOCH3 Br 1.35 OCOCOCH3 OCHCOOCH3 Br 1.35 OCOCH3 OCHCOOCH3 Br 1.35 Br 1.35 OCOCH3 OCHCOOCH3 Br 1.36 Br 1.36 Br 1.35 OCOCH3 OCHCOOCH3 Br 1.36 1.39 H OCHCOOCH3 Br 1.40 OH OCH (CH3) 2 F 1.41 OCH3 OCH (CH3) 2 F 1.42 Cl OCH (CH3) 2 F 1.43 H OCH (CH3) 2 F Formulation examples: Example 4: Formulation examples for active ingredients of the formula I (% = Percentage by weight) a) wettable powder a) b) c) active ingredient according to table 1 20% 60% 0.5% sodium lignin sulfonate 5% 5% 5% sodium lauryl sulfate 3% - -Na-diisobutylnaphthalene sulfonate - 6% 6% octylphenol polyethylene glycol ether (7 -8 mol AeO) - 2% 2% highly disperse silica 5% 27% 27% kaolin 67% - -sodium chloride - - 59.5% The active ingredient is mixed well with the additives and ground well in a suitable mill. Wettable powders are obtained which can be diluted with water to form suspensions of any desired concentration.

b) Emulsion concentrate a) b) Active ingredient according to Table 1 10% 1% Octylphenol polyethylene glycol ether (4-5 mol AeO) 3% 3% calcium dodecylbenzenesulfonate 3% 3% castor oil polyglycol ether (36 mol AeO) 4% 4% cyclohexanone 30% 10% xylene mixture 50% 79% This concentrate can be diluted with water Emulsions of any desired concentration can be prepared.

c) Dusts a) b) Active substance according to Table 1 0.1% 1% talc 99.9% kaolin - 99% Ready-to-use dusts are obtained by adding the active ingredient mixed with the carrier and ground on a suitable mill.

d) Extruder granules a) b) Active ingredient according to Table 1 10% 1% Na lignin sulfonate 2 2% carboxymethyl cellulose 1% 1% kaolin 87% 96% The active ingredient is mixed with the Additives mixed, ground and moistened with water. This mixture will extruded and then dried in a stream of air.

e) Coating granulate active ingredient according to Table 1 3% polyethylene glycol (MG 200) 3% Kaolin 94% The finely ground active ingredient is in a mixer the kaolin moistened with polyethylene glycol is applied evenly. To this In this way, dust-free coating granules are obtained.

f) suspension concentrate a) b) active ingredient according to table 1 40% 5 % Ethylene glycol 10 æ 10% nonylphenol polyethylene glycol ether (15 mol AeO) 6% 1 % Na lignin sulfonate 10% 5% Carboxymethyl cellulose 1% 1% 37% aqueous formaldehyde solution 0.2% 0.2% silicone oil in the form of a 75% aqueous Emulsion 0.8% 0.8% Water 32% 77% The finely ground active ingredient is mixed with the Additives intimately mixed. A suspension concentrate is obtained from which by diluting with water suspensions of any desired concentration are prepared can be.

g) saline solution active ingredient according to table 1 5% isopropylamine 1% octylphenol polyethylene glycol ether 3% (78 mol AeO) water 91% biological examples: Example 5: Pre-emergent herbicidal effect In the greenhouse, the test plants are placed in seed trays immediately after sowing the earth's surface with an aqueous dispersion of the active ingredients obtained from a 25% emulsion concentrate treated. There are concentrations of 4 kg of active substance / hectare applied. The seed trays are in the greenhouse at 22-250C and 50-70% relative Maintained humidity and evaluated the test after 3 weeks. In this attempt the compounds of Table 1 show strong herbicidal activity.

Example 6: Post-emergent herbicidal action (contact herbicide) One Number of weeds, both monocotyledon and dicotyledonous, were determined after emergence (im 4- to 6-leaf stage) with an aqueous active ingredient dispersion in one dose of 4 kg of active substance per hectare sprayed onto the plants and these at 24 "-260C and 45-60% relative humidity. 15 days after treatment will be the experiment is evaluated according to the above grading scale. Also show in this experiment the compounds of Table 1 have a strong to very strong herbicidal action.

Example 7: Herbicidal action before the plants emerge. Plastic pots are filled with expanded vermiculite (density: 0.135 g / cm3, water absorption capacity: 0.565 1/1) filled. After saturating the non-adsorptive vermiculite with a aqueous active ingredient emulsion in deionized water, which combines the active ingredients in a Containing concentration of 70.8 ppm, seeds of the following plants will be on the Sown surface. Nasturtium offcinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis. The test vessels are then placed in a climatic chamber at 200C, a lighting of approx. 20 kLux and a relative humidity of 70% held. During the germination phase of 4 to 6 days, the pots are raised the local humidity covered with translucent material and covered with watered with deionized water.

After the 5th day, 0.5% of a commercially available liquid fertilizer is added to the watering water (Greenzit) added. The experiment is evaluated 12 days after sowing evaluated the effect on the test plants. The checked connections of the table 1 show good to very good herbicidal action.

Example 8 Herbicidal activity for water rice (paddy) The aquatic weeds Echinochloa crus galli and Monocharia vag.

are sown in plastic cups (60 cm2 surface, 500 ml volume). After sowing, water is added to the surface of the earth filled up. 3 days after sowing, the water level is raised to slightly above the surface of the earth (3-5 mm). The application takes place 3 days after sowing with an aqueous emulsion the test substances by spraying them onto the vessels. The dose used corresponds to an amount of active ingredient of 0.5 to 4 kg of AS per hectare (amount of spray mixture - 550 1 / ha. The plant cups are then placed in the greenhouse under optimal growing conditions Set up for the rice weeds, i.e. at 25 "-30" C and high humidity.

The tests are evaluated 3 weeks after application.

The compounds in Table 1 do not damage the weeds but the rice.

Example 9: Inhibition of growth in tropical ground cover legumes (cover crops).

The test plants (centrosema plumieri and centrosema pubescens) are used to the adult stage and up to a height of 60 cut back cm. After 7 days, the active ingredient is injected as an aqueous emulsion. The test plants are exposed to 70% relative humidity and 6000 lux artificial light, 14 hours per day, held at temperatures of 270 ° C. during the day and 210 ° C. at night. The experiment is evaluated 4 weeks after application. There will be the New growth compared to the control estimated and weighed and the phytotoxicity rated. In this experiment, show the application rates with the active ingredients in Table 1 of 50-3000 g / ha treated plants a significant reduction in new growth (less than 20% of the new growth in untreated control plants) without the test plants were damaged.

Example 10: Growth regulation on soybeans in plastic containers with an earth-peat-sand mixture in a ratio of 6: 3: 1, soybeans become of the variety "Hark" sown and placed in a climatic chamber. Through optimal choice of temperature, lighting, Addition of fertilizer and watering, the plants develop after approx.

5 weeks to the 5-6 trifolia leaf stage. At this point will be the plants with the aqueous broth of an active ingredient of the formula I up to the good Wetting sprayed. The active ingredient concentration is up to 100 g AS / ha. The evaluation takes place approx.

5 weeks after application of the active ingredient. In comparison to untreated The active compounds according to the invention in Table 1 have a more noticeable effect on control plants Increase in the number and weight of the pods in the main shoot.

Example 11: Growth inhibition in cereals In plastic pots with sterilized Soil are grown in cereals Hordeum vulgare (spring barley) and Secale (summer rye) Sown in the greenhouse and watered as needed. The offspring will grow approx.

21 days after sowing with the aqueous spray mixture of an active ingredient of Table 1 sprayed. The amount of active ingredient is up to 100 g per each Hectares. The growth of the grain is assessed 21 days after application. the treated plants show a reduction compared to untreated controls of new growth (60-90% of the control), as well as an increase in stem diameter in some cases on.

Example 12: Growth inhibition in grasses in plastic dishes with a mixture of earth, peat and sand (6: 3: 1) are the grasses Lolium perenne, Poa pratensis, Festuca ovina, Dactylis Glomerate and Cynodon dactylon are sown in the greenhouse and watered as needed. The grass that has emerged is cut back weekly to a height of 4 cm and approx. 50 days after sowing and one day after the last cut with the aqueous spray liquor of an active ingredient of Table 1 sprayed. The amount of active ingredient is the equivalent of up to 500 g of active ingredient per hectare. 21 days after application the growth of the grass is assessed.

The tested compounds of the formula I cause a reduction the new growth of around 10-30% compared to the untreated control.

Example 13: Desiccation and defoliation effects in a greenhouse Cotton plants of the Deltapine variety were grown in clay pots. After completed They were capsule formation with aqueous preparations of the active ingredient No. 1 in one Application rate corresponding to 1.2, 0.6 and 0.3 kg / ha in the field, sprayed. Untreated Plants were left as controls. The evaluation of the experiment was carried out 3, 7 and 14 days after application of the active substance by determining the degree of defoliation (% fallen leaves) and on dessication (% drying out of those remaining on the plant Leaves).

In this experiment, the tested compounds from Table 1 at application rates of 0.6 and 1.2 kg / ha only a few dried up after 7 days Leaves on the plants (more than 80% leaf fall and desiccation).

Claims (16)

Claims 1. N- (2-fluoro-4-halophenyl) -hexahydro-isoindole compounds of the formula I. wherein A is hydrogen, halogen or a group QR or where Q, Q 'and Q "independently of one another each have an oxygen or sulfur atom or the group -N-R1 n is the number zero or 1 Hal fluorine, chlorine, bromine or iodine R and R1 independently of one another are each hydrogen or optionally halogen or C1 -C4-alkoxy-substituted C1-Ca-alkyl, C3-C8-cycloalkyl, C3-Cs-alkenenyl or C3-C8-alkynyl radicals, B a radical -COXR1, -YR2, X and Y each being oxygen, sulfur or a radical -N (R3). Rz is hydrogen or an optionally substituted by halogen, C1-C4-alkoxy, Cyan or a -COXR1-substituted C1-C8-alkyl, C3-Cs-alkenyl or C3-Cg-alkynyl radical and R3 is hydrogen, C1-Cs-alkyl, C3-C8-cycloalkyl, one via a saturated carbon atom bonded C3-Cg-alkenyl or C3-C8-alkynyl radical. 2. N- (2-fluoro-4-halophenyl) -hexahydro-isoindole compounds according to Claim 1 of the formula I, in which B is the isopropoxy radical and Hal is a chlorine atom, while A has the meaning given in claim 1. 3. N- (2-Fluoro-4-chloro-5-isopropoxyphenyl) -2, 3,4,5,6,7-hexahydroisoindol-1 (1H) one according to claim 1. 4. N- (2-Fluoro-4-chloro-5-isopropoxyphenyl) -3-hydroxy-2,3,4,5,6,7-hexahydro-isoindol-1 (1H) one according to claim 1. 5. N- (2-Fluoro-4-chloro-5-isopropoxyphenyl) -3-chloro-2, 3,4,5,6,7-hexahydro-isoindol-1 (1H) one according to claim 1. 6. N- (2-fluoro-4-halophenyl) -hexahydro-isoindoles according to claim 1 of the formula I, in which A and Hal are each extended by a chlorine atom, while B has the meaning given in claim 1. 7. N- (2-fluoro-4-halophenyl) -hexahydro-isoindoles according to claim 1 of the formula I, in which B represents the Hethoxydarbonylmethoxyrest and Hal represents a bromine atom while A have the meaning given in claim 1. 8. N- (2-fluoro-4-halophenyl) -hexahydro-isoindoles according to claim 1 of the formula I, in which B is the isopropoxy radical and Hal is a halogen atom, while A have the meaning given in claim 1. 9. Process for the preparation of the N- (2-fluoro-4-halophenyl) -hexahydro-indoles of the formula I, claim 1, characterized in that a 2-fluoro-4-halophenyl-tetrahydrophthalic acid imide of the formula II in which B and Hal have the meaning given under formula I, reduced with a hydrogenating agent to a hydroxyl compound in which A in formula I of the end products represents the OH group, and that this hydroxyl compound can, if desired, be incorporated by methods known per se another derivative of the formula I with the meaning given there for A converted. 10. The method according to claim 9, characterized in that one a metal hydride, in particular sodium borohydride, is used as the hydrogenating agent. 11. A herbicidal and plant growth regulating agent, thereby characterized in that it is used as an active ingredient in addition to carriers and / or other additives an N- (2-fluoro-4-halophenyl) -hexahydro-isoindole of the formula I according to claim 1 contains. 12. The use of an active ingredient according to claim 1, or one agent containing such for controlling undesired plant growth. 13. The use of an active ingredient according to claim 1 or one agent containing such for inhibiting plant growth. 14. The use of an active ingredient according to claim 1, or one such containing agent for influencing plant growth for the purpose of Increase in yield. 15. Method for the selective pre- or post-emergence control of Weeds in crops of useful plants, characterized in that one is the crops of useful plants or their cultivation area with an effective amount of an N- (2-fluoro-4-halophenyl) -bexahydro-isoindole of formula I, claim 1 or an agent containing such a compound. 16. Method of suppressing plant growth beyond the 2-leaf stage also, characterized in that you use the plants while they are growing an effective amount of an N- (2-fluoro-4-halophenyl) -hexahydro-isoindole of Formula I claim 1 or an agent containing such an active ingredient treated.