DE19517597A1 - New 3-(tetra:hydro-phthalimido)cinnamyl alcohol derivs. - Google Patents

Abstract

3-Tetrahydrophthalimidocinnamyl alcohol derivs. of formula (I) and their salts are new. R1 = halo, NO2, CN or CF3; R2 = H or halo; R3 = H, CN, halo or alkyl; R4 = H, halo, alkyl, haloalkyl or alkoxy; R5, R6 = H, 1-6C alkyl, haloalkyl or phenyl; R7 = H, alkyl, 3-6C alkenyl, 3-6C alkynyl, COR, alkylsulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl; R = alkyl, haloalkyl, 3-8C cycloalkyl, 2-6C alkenyl, 2-6C alkynyl, alkoxy, haloalkoxy, 3-8C cycloalkoxy, alkylthio, haloalkylthio, 3-8C cycloalkylthio, alkylamino, haloalkylamino, 3-8C cycloalkylamino, alkylcarbonyloxy alkylcarbonyl, alkylcarbonylthioalkyl, alkoxycarbonylalkyl, alkylthiocarbonylalkyl, phenyl, phenylamino, phenoxy; phenylthio or a 3-8 membered opt. unsatd. or heteroaromatic ring contg. 1-3 heteroatoms selected from 2 oxygen, 2 sulphur, 2 nitrogen and 1 N-methyl; phenyl gps. are opt. substd. by 1-3 of CN, NO2 halo, alkyl, haloalkyl, alkoxy and alkoxycarbonyl. Alkyl, haloalkyl and alkoxy contain 1-6C. Also new are intermediates of formula (III) and (VI).

Description

The present invention relates to new 3- (tetrahydrophthal imido) cinnamon alcohol derivatives of the formula I.

in which the substituents have the following meaning:
R1 halogen, nitro, cyano or trifluoromethyl;
R² is hydrogen or halogen;
R³ is hydrogen, cyano, halogen or C₁-C₆ alkyl;
R⁴ is hydrogen, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl or C₁-C₆ alkoxy;
R⁵, R⁶ independently of one another hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or the phenyl group, which may be unsubstituted or carry one to three radicals, selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl , C₁-C₆ halo alkyl, C₁-C₆ alkoxy and (C₁-C₆ alkoxy) carbonyl;
R⁷ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkyl) carbonyl, (C₁-C₆-haloalkyl) carbonyl, (C₃-C₈-cycloalkyl) carbonyl, (C₂ -C₆-alkenyl) carbonyl, (C₂-C₆-alkynyl) carbonyl, (C₁-C₆-alkoxy) carbonyl, (C₁-C₆-haloalkoxy) carbonyl, (C₃-C₈-cycloalkoxy) carbonyl, (C₁-C₆-alkylthio ) carbonyl, (C₁-C₆-haloalkyl) thiocarbonyl, (C₃-C₈-cycloalkyl thio) carbonyl, (C₁-C₆-alkyl) aminocarbonyl, (C₁-C₆-haloalkyl) aminocarbonyl, (C₃-C₈-cycloalkyl) aminocarbonyl, (C₁-C₆-alkyl) carbonyloxy- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkyl) carbonylthio- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkoxy) carbonyl- (C₁-C₆- alkyl) carbonyl, (C₁-C₆-alkylthio) carbonyl- (C₁-C₆-alkyl) carbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl, di- (C₁-C₆-alkyl) aminosulfonyl, the phenylcarbonyl, phenylaminocarbonyl -, Phenoxycarbonyl- or Phenylthio carbonylgruppe, the phenyl ring if desired one to three radicals can be selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy) carbonyl, or a bonded via a carbonyl group 3 up to 8-membered, saturated, unsaturated or aromatic heterocycle which contains one to three heteroatoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms, two nitrogen atoms and one nitrogen atom which carries a methyl group,
and the agriculturally useful salts of the compounds I, if they exist.

The invention also relates to

• - The use of the compounds I as herbicides and for de siccation and / or defoliation of plants,
• - herbicidal agents and agents for desiccation and / or Defoliation of plants which the compounds I act as contain same substances,
• - Process for the preparation of these herbicidal compositions for desiccation and / or defoliation of plants, and
• - methods of controlling undesirable plant growth and for desiccation and / or defoliation of plants with the Connections I.

Furthermore, the invention relates to new 3-amino cinnamon alcohol Derivatives of formula III and new 3-nitrocinnamic alcohol derivatives Formula VI

where the substituents have the following meaning:
R1 halogen, nitro, cyano or trifluoromethyl;
R ^{2 is} hydrogen or halogen;
R³ is hydrogen, cyano, halogen or C₁-C₆ alkyl;
R⁴ is hydrogen, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl or C₁-C₆ alkoxy;
R⁵, R⁶ independently of one another hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or the phenyl group, which may be unsubstituted or carry one to three radicals, selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl , C₁-C₆ halo alkyl, C₁-C₆ alkoxy and (C₁-C₆ alkoxy) carbonyl;
R⁷ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkyl) carbonyl, (C₁-C₆-haloalkyl) carbonyl, (C₃-C₈-cycloalkyl) carbonyl, (C₂ -C₆-alkenyl) carbonyl, (C₂-C₆-alkynyl) carbonyl, (C₁-C₆-alkoxy) carbonyl, (C₁-C₆-haloalkoxy) carbonyl, (C₃-C₈-cycloalkoxy) carbonyl, (C₁-C₆-alkylthio ) carbonyl, C₁-C₆-haloalkyl) thiocarbonyl, (C₃-C₈-cycloalkyl thio) carbonyl, (C₁-C₆-alkyl) aminocarbonyl, (C₁-C₆-haloalkyl) aminocarbonyl, (C₃-C₈-cycloalkyl) aminocarbonyl, ( C₁-C₆-alkyl) carbonyloxy- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkyl) carbonylthio- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkoxy) carbonyl- (C₁-C₆-alkyl) ) carbonyl, (C₁-C₆-alkylthio) carbonyl- (C₁-C₆-alkyl) carbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl, di- (C₁-C₆-alkyl) aminosulfonyl, the phenylcarbonyl, phenylaminocarbonyl -, Phenoxycarbonyl- or Phenylthiocarbo nylgruppe, the phenyl ring if desired one to three radicals can wear, selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-halo alkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy) carbonyl, or a bonded via a carbonyl group 3- to 8-membered, saturated, unsaturated or aromatic heterocycle which contains one to three heteroatoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms, two nitrogen atoms and one nitrogen atom which carries a methyl group,
and the salts of the compounds III and V, if these exist.

From JP-OS-59/155358 it is already known that compounds of Formula IIa

where X and Y are hydrogen or methyl and Ra is a lower alkyl group, in particular methyl or ethyl, mean herbicidal activity are sam.

In addition, EP-A 300 387 u. a. Cinnamic acids and acid esters of formulas IIb and IIc

in which
R ^{b is} hydrogen or fluorine, Hal is chlorine or bromine and R ^{c is} hydrogen or C₁-C₄-alkyl and R ^{d is} hydrogen, C₁-C₆-alkyl, C₅ / C₆-cycloalkyl, (C₁-C₄-alkoxy) - or (C₁-C₄ -Alkylthio) -C₂-C₄-alkyl mean, and their use as herbicides.

The selectivity of these known herbicides in terms of harmful however, plants can only satisfy to a limited extent. Task of The present invention was therefore to develop new herbicidally active To provide connections with which a good contract better than unwanted plants for crops have been targeted so far.

Accordingly, the 3- (tetrahydrophthalimido) cinnamon alcohol deri vate of formula I found. Herbicidal agents have also been found those that contain the compounds I and a very good one  Have an effect. In addition, processes for making the This means and methods to combat unwanted Plant growth with the compounds I found.

The compounds I according to the invention are also suitable for Defoliation and desiccation of plant parts for e.g. B. Tree wool, potato, rapeseed, sunflower, soybean or field beans, especially for cotton. In this regard, funds for Desiccation and / or defoliation of plants, method of manufacture provision of these means and methods for desiccation and / or Defoliation of plants with the compounds I found.

With regard to the use of the 3- (tetrahydrophthal imido) cinnamon alcohol derivatives I as herbicidal compounds
R¹ preferably for halogen such as fluorine, chlorine, bromine and iodine, especially chlorine;
R² is preferably hydrogen, fluorine or chlorine;
R³ preferably for hydrogen and
R⁴ preferably for halogen or C₁-C₄-alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl, especially methyl.

The for the substituents R¹ to R⁷ or as residues on phenyl rings mentioned organic molecule parts - like the meaning Halogen - collective terms for individual enumeration of the individual group members. All carbon chains, so all alkyl, alkylcarbonyl, alkenyl, alkynyl, haloalkyl, Haloalkenyl, haloalkynyl, alkoxy, alkoxycarbonyl and Alkylthio parts can be straight-chain or branched.

Halogenated substituents preferably carry one to five identical che or different halogen atoms.

In detail, for example:

• - Halogen for: fluorine, chlorine, bromine and iodine, preferably for Fluorine and chlorine;
• - C₁-C₆-alkyl and the alkyl parts of (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkylamino) carbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl, di- (C₁-C₆-alkyl) aminosulfonyl, (C₁-C₆-alkyl) carbonyloxy- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkyl) carbonylthio- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkoxy) carbonyl- (C₁- C₆-alkyl) carbonyl and (C₁-C₆-alkyl thio) carbonyl- (C₁-C₆-alkyl) carbonyl for:
  Methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methyl propyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2.2 -Dimethyl propyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2 -Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-tri methylpropyl, 1,2,2- Trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, preferably for methyl, ethyl and 1-methylethyl;
• - C₃-C₆-alkenyl for: prop-1-en-1-yl, prop-2-en-1-yl, 1-methyl ethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, n-penten-1-yl, n- Penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl but-1-en-1-yl, 2-methyl-but-1-en-1-yl, 3-methyl but-1-en-1-yl, 1-methyl-but-2-en-1-yl, 2-methyl but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3-methyl but-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl prop-1-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl prop-1-en-2-yl, 1-ethyl-prop-2-en-1-yl, n-hex-1-en-1-yl, n- Hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n- Hex-5-en-1-yl, 1-methyl-pent-1-en-1-yl, 2-methyl pent-1-en-1-yl, 3-methyl-pent-1-en-1-yl, 4-methyl pent-1-en-1-yl, 1-methyl-pent-2-en-1-yl, 2-methyl pent-2-en-1-yl, 3-methyl-pent-2-en-1-yl, 4-methyl pent-2-en-1-yl, 1-methyl-pent-3-en-1-yl, 2-methyl pent-3-en-1-yl, 3-methyl-pent-3-en-1-yl, 4-methyl pent-3-en-1-yl, 1-methyl-pent-4-en-1-yl, 2-methyl pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl pent-4-en-1-yl, 1,1-dimethyl-but-2-en-1-yl, 1,1-dimethyl but-3-en-1-yl, 1,2-dimethyl-but-1-en-1-yl, 1,2-dimethyl but-2-en-1-yl, 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl but-1-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl but-3-en-1-yl, 2,2-dimethyl-but-3-en-1-yl, 2,3-dimethyl but-1-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl but-3-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl but-2-en-1-yl, 1-ethyl-but-1-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1,1,2-trimethyl prop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl, 1-ethyl-2-methyl-prop-1-en-1-yl and 1-ethyl-2-methyl prop-2-en-1-yl, preferably for ethenyl and prop-2-en-1-yl;
• - The alkenyl part of (C₂-C₆-alkenyl) carbonyl for: vinyl and for C₃-C₆ alkenyl as mentioned above,  
• - C₃-C₆-alkynyl for: prop-1-in-1-yl, prop-2-in-3-yl, n - But-1-in-1-yl, n-but-1-in-4-yl, n-but-2-in-1-yl, n- Pent-1-in-1-yl, n-Pent-1-in-3-yl, n-Pent-1-in-4-yl, n- Pent-1-in-5-yl, n-Pent-2-in-1-yl, n-Pent-2-in-4-yl, n- Pent-2-in-5-yl, 3-methyl-but-1-in-1-yl, 3-methyl but-1-in-3-yl, 3-methyl-but-1-in-4-yl, n-hex-1-in-1-yl, n- Hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl, n- Hex-1-in-6-yl, n-hex-2-in-1-yl, n-hex-2-in-4-yl, n- Hex-2-in-5-yl, n-hex-2-in-6-yl, n-hex-5-in-1-yl, n- Hex-3-in-2-yl, 3-methyl-pent-1-in-1-yl, 3-methyl pent-1-in-3-yl, 3-methyl-pent-1-in-4-yl, 3-methyl pent-1-in-5-yl, 4-methyl-pent-1-in-1-yl, 4-methyl pent-2-in-4-yl and 4-methyl-pent-2-in-5-yl, preferably for Ethynyl and prop-2-in-1-yl;
• - The alkynyl part of (C₂-C₆-alkynyl) carbonyl for: ethynyl and for C₃-C₆ alkynyl as mentioned above;
• - C₁-C₆ haloalkyl and the haloalkyl part of (C₁-C₆-haloalkyl) carbonyl, (C₁-C₆-haloalkyl) thiocarbonyl and (C₁-C₆-haloalkyl) aminocarbonyl for: C₁-C₆-alkyl such as mentioned above, partially or completely by Fluorine, chlorine and / or bromine is substituted, ie z. B. chlorine methyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, Chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoro ethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 3-chloropropyl, hepta fluoropropyl, preferably trifluoromethyl, chloromethyl and Dichloromethyl;
• - C₁-C₆-alkoxy and the alkoxy part of (C₁-C₆-alkoxy) carbonyl and (C₁-C₆-alkoxy) carbonyl- (C₁-C₆-alkyl) carbonyl for: methoxy, Ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methyl butoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n- Hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-tri methylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methyl propoxy and 1-ethyl-2-methylpropoxy, preferably for Methoxy, ethoxy and 2-methylethoxy;  
• - The haloalkoxy part of (C₁-C₆-haloalkoxy) carbonyl for: C₁-C₆ alkoxy as mentioned above, the partial or full is constantly substituted by fluorine, chlorine and / or bromine, so z. B. chloromethoxy, dichloromethoxy, trichloromethoxy, Fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluorine methoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-fluorine ethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoro ethoxy, 3-chloropropoxy and heptafluoropropoxy;
• - The alkylthio part of (C₁-C₆-alkylthio) carbonyl and (C₁-C₆-alkylthio) carbonyl- (C₁-C₆-alkyl) carbonyl for: methyl thio, ethylthio, n-propylthio, 1-methylethylthio, n-butyl thio, 1-methyl-propylthio, 2-methylpropylthio, 1,1-dimethyl ethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutyl thio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethyl propylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentyl thio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethyl butylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethyl butylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-tri methylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, preferably for methylthio and ethylthio;
• - The cycloalkyl part of (C₃-C₈-cycloalkyl) carbonyl, (C₃-C₈-cycloalkyl) oxycarbonyl, (C₃-C₈-cycloalkyl) thiocarbonyl and of (C₃-C₈-cycloalkyl) aminocarbonyl for: cyclopropyl carbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclo hexylcarbonyl, cycloheptylcarbonyl and cyclooctylcarbonyl, preferably for cyclopentyl and cyclohexylcarbonyl.

The phenyl, phenylcarbonyl, phenylaminocarbonyl, phenoxy carbonyl and phenylthiocarbonyl group can be on any substi usable carbon atom of the phenyl ring tra one of the following residues gene:

• - cyano, nitro,
• - Halogen, preferably fluorine or chlorine;
• - C₁- or C₂-alkyl, preferably methyl;
• - C₁- or C₂-haloalkyl, preferably trifluoromethyl and tri chloromethyl;
• - C₁-C₄ alkoxy, preferably methoxy or ethoxy;  
• - C₁-C₄ alkoxycarbonyl, preferably methoxycarbonyl or Ethoxycarbonyl.

The phenyl rings are preferably unsubstituted or carry one Nitro, halogen, trifluoromethyl, methoxy or ethoxy substituents do.

Among the 3- to 8-membered, saturated, unsaturated or aromatic heterocycles, the following rings are particularly be prefers:

• - Saturated and partially unsaturated, 4- to 6-membered Heterocycles, each with one or two rings in addition to carbon atoms wear limbs selected from the group consisting of one Oxygen or sulfur atom and one or two nitrogen atoms and one or two groups -N (CH₃) -, especially oxes tanyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydro thienyl, tetrahydrothiopyranyl, pyrrolidinyl, isoxazolidinyl, Isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, Imidazolidinyl, 1,2,4-oxadiazolidinyl, 1,3,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl, 1,3,4-thiadiazolidinyl, 1,2,4-triazo lidinyl, 1,3, 4-triazolidinyl, 2,3-dihydrofuryl, dihydro pyranyl, 2,4-dihydrofuryl, 2,3-dihydrothienyl, 2,4-dihydro thienyl, dihydrothiopyranyl, 2,3-pyrrolinyl, 2,4-pyrrolinyl, 2,3-isoxazolinyl, 3,4-isoxazolinyl, 4,5-isoxazolinyl, 2,3-isothiazolinyl, 3,4-isothiazolinyl, 4,5-isothiazolinyl, 2,3-dihydropyrazolyl, 3,4-dihydropyrazolyl, 4,5-dihydropyra zolyl, 2,3-dihydrooxazolyl, 3, 4-dihydrooxazolyl, thiazolyl, Imidazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thia diazolyl, 1,3,4-thiadiazolyl, 1,2,4-triazolyl and 1,3,4-tri azolyl, 1,3-dioxolanyl, piperidinyl, tetrahydropyridazinyl, Tetrahydropyrimidinyl, tetrahydropyrazinyl, 1,3,5-tetrahydro triazinyl and 1,2,4-tetrahydrotriazinyl;
• - 5- or 6-membered aromatic heterocycles with 1 or 2 Heteroatoms selected from a group consisting of 2 Nitrogen atoms and an oxygen or sulfur atom, in particular 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxa zolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-tri azol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,  3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-tri azin-3-yl.

Among the heterocyclic bound via a carbonyl group Substituents R⁷ are tetrahydrofuranylcarbonyl, tetrahydropyra nylcarbonyl and tetrahydrothiopyranylcarbonyl be particularly prefers.

Both the 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of For mel I as well as the 3-amino cinnamon alcohol derivatives III and the 3-Ni Trozimtalkohol-Derivatives VI can in the form of their agriculture Lich useful salts are present, especially when R⁷ is hydrogen means.

As agriculturally useful salts generally come Salts of such bases into consideration, which have the herbicidal effect of I do not adversely affect.

Particularly suitable as basic salts are those of the alkali metals talle, preferably the sodium and potassium salts, the Erdal potassium metals, preferably calcium, magnesium and barium salts, and that of the transition metals, preferably manganese, copper, Zinc and iron salts, as well as the ammonium salts, the one to three C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl substituents and / or one Can carry phenyl or benzyl substituents, preferably Diisopropylammonium, tetramethylammonium, tetrabutylammonium, Trimethylbenzylammonium and trimethyl (2-hydroxyethyl) ammonium salts, furthermore the phosphonium salts, the sulfonium salts, preferably tri- (C₁-C₄-alkyl) sulfonium salts, and the sulfoxonium salts, preferably tri- (C₁-C₄-alkyl) sulfoxonium salts.

The substituted 3- (tetrahydrophthalimido) cinnamon alcohol derivatives Formula I are available in various ways, namely before preferably by one of the following methods:  

a) reaction of 3,4,5,6-tetrahydrophthalic anhydride with a 3-Amino cinnamon alcohol derivative of the formula III in a solution medium

For example, short-chain solvents are suitable Alkanoic acids such as acetic acid, propionic acid and isobutyric acid, the esters of these alkanoic acids, e.g. B. ethyl acetate, higher boiling hydrocarbons such as toluene and xylene and Dimethylformamide. Mixtures of the solvents mentioned is being brought up for consideration.

The reaction normally takes place at a reaction temperature rature from 25 ° C to the boiling point of the respective reaction mixture, preferably at 40 to 110 ° C. At reaction in an aprotic solvent, it is recommended to continuously remove the water formed during the reaction distant.

About stoichiometric amounts are expediently used on anhydride and on 3-aminocinnamic alcohol derivative III or, for. B. to optimize sales of III, a surplus Anhydride up to about 10 mol%.

Depending on the 3-amino cinnamon alcohol deri used vat III can add a condensing agent like Thionyl chloride, phosphorus oxychloride and phosgene, or one Acid accelerates the reaction.

Acids which can be used for this purpose are in particular organic Acids, e.g. B. alkane carboxylic acids such as acetic and propionic acid, Sulfonic acids such as methanesulfone and p-toluenesulfonic acid, or Mineral acids such as hydrochloric acid, sulfuric acid and nitric acid.

The amount of condensing agent and / or acid is not critical. Already a catalytic amount of e.g. B. 0.01 mol Equivalents can already have a positive effect on the course of the reaction rivers. On the other hand, there is also the possibility of one large excess to use that the condensing agent or the acid can also serve as a solvent.  

For those compounds of formula I in which R⁷ for (C₁-C₆-alkyl) carbonyl, (C₃-C₈-cycloalkyl) carbonyl or (C₂-C₆-alkenyl) carbonyl, it has to be special partially proven, a compound of formula III, wherein R⁷ Hydrogen means with 3,4,5,6-tetrahydrophthalic acid anhy drid in a (C₁-C₆-alkyl) carboxylic acid, (C₃-C₈-cyclo-al kyl) carboxylic acid or (C₂-C₆-alkenyl) carboxylic acid or in one to implement inert solvents in the presence of these acids.

b) reduction of an ester, aldehyde or ketone of the formula IV Compounds I, wherein R⁷ is hydrogen

R⁸ stands for hydroxyl, lower alkoxy, phenoxy or one of the meanings of R⁵ or R⁶.

If R⁸ stands for one of the meanings of R⁵ or R⁶, then Obtain compounds I in which one of the substituents R⁵ and R⁶ also has this meaning and the other Stands for hydrogen.

The use of starting materials of the formula IV, where R⁸ stands for hydroxyl, lower alkoxy or phenoxy Compounds I in which R⁵ and R⁶ are hydrogen.

The reduction is usually carried out in an inert solution or diluents, for example in one aliphatic, cyclic or aromatic hydrocarbon substance such as n-pentane, petroleum ether, cyclohexane, benzene, toluene and o-, m-, p-xylene, in an aliphatic or cyclic Ethers such as diethyl ether, tert-butyl methyl ether, dimethoxy ethane and tetrahydrofuran, in an aliphatic or aroma halogenated hydrocarbons such as dichloromethane, chloro form, chorbene, 1,2-dichloroethane and dichlorobenzenes, in an alcohol such as ethanol, methanol and tert-butanol, in an amide such as dimethylformamide and N-methylpyrrolidone, or  in an amine like ammonia. Mixtures of these solutions means are considered.

As a reducing agent such. B. metal hydrides such Lithium and sodium hydride, silanes such as diethylsilane, boranes such as diborane, borane complexes with z. B. pyridine or dimethyl sulfide, also aluminum hydride, diisobutyl aluminum hydride, complex metal hydrides such as lithium aluminum hydride, lithium, Sodium, zinc borohydride and sodium cyanoborohydride, alkali talle such as sodium and potassium in the presence of an alcohol, so like hydrogen in the presence of a precious metal catalyst, e.g. B. palladium or platinum.

Depending on the starting compound IV, it can particularly be advantageous in the presence of a catalyst or an aid promoting the chemoselectivity of the reaction work. As catalysts and / or auxiliaries are z. B. lanthanoid salts such as cerium trichloride, Terbi umtrichloride and samarium halides, or other metal halides, e.g. B. zinc chloride, aluminum trichloride, cesium fluoride, dicyclopentadienyltitanium dichloride, vanadium trichlo rid, boron trifluoride etherate or titanium tetrachloride. In terms of the exact reaction procedure when using a catalytic converter tors or auxiliary is, for example, to that of R.C. Larock in "Comprehensive Organic-Transformations", 1 edition 1989, VCH Publishers, Inc., p. 537 ff. And p. 549 ff put literature referenced.

The starting compound IV and the reducing agent expediently used in approximately equimolar amounts; to However, optimizing the course of the reaction can be advantageous be to use one of the two components in excess up to about 10 times the molar amount.

The reaction temperature depends on the one used Starting compound IV. It is generally from (-78) to about 100 ° C, preferably between (-70) ° C and the reflux temperature of the solvent used.

c) alkylation or acylation of a compound of formula I, in the R₇ means hydrogen

Acid chlorides are particularly suitable as acylating agents R⁷-Cl, where R⁷ is not hydrogen, alkyl, alkenyl or Alkynyl is considered. Also the free acids R⁷-DH the Carboxylic acid chlorides, their anhydrides (R⁷) ₂D and isocyanates (for the production of I with R⁷ = alkyl, cycloalkylaminocarbo nyl- or the phenylaminocarbonyls) are suitable. With Ver When using the free acids, working in Presence of a condensing agent such as carbonyldiimidazole and dicyclohexylcarbondiimide, usually about especially equimolar amounts of acid and condensing agent are appropriate.

The alkylation is advantageously carried out in the presence of a inert organic solvent, especially in one aprotic solvent, e.g. B. an aliphatic or cy clical ether, preferably 1,2-dimethoxyethane, tetrahydro furan and dioxane, an aliphatic ketone, preferably Acetone, amides, preferably dimethylformamide, or sulfoxi the, preferably dimethyl sulfoxide.

For acylation with one of the above Halides are the ge named solvents are also suitable. Particularly advantageous is to in the presence of a base such as sodium hydride under Ver using an aprotic solvent.

The reaction is generally at a temperature of 0 ° C can be carried out up to the boiling point of the reaction mixture. It is preferred to work at 0 to 40 ° C.

The compounds of the formulas III are new. You can z. B. according to the method described in method b) or c) put. For this purpose, compounds of Formulas V or III with R⁷ = hydrogen:

Furthermore, the compounds of formula III are also from 3-Ni trocinnamic alcohol derivatives of the formula VI

in a manner known per se (see, for example, DE-A 37 24 399) by hydrogenation of the nitro group using hydrogen on a Me tall catalyst such as Raney nickel, palladium and platinum, or by reduction with a reducing agent, e.g. B. a tin II salt or iron, producible.

The compounds of formula VI are also new and in turn analogous to methods b) or c) described above bar. Starting products for this are e.g. B. Compounds of the formulas VII or VI with R⁷ = hydrogen:

In addition, the compounds VI can be prepared in a manner known per se by nitration of allylbenzenes VIII

getting produced.  

As further methods with which compounds of the formulas I, III or VI can be produced, for example, the alkylation with an organometallic reagent, the Wittig reaction or to call the Peterson olefination.

The reactions described above are convenient all at atmospheric pressure or under their own pressure gen made reaction mixture.

The reaction mixtures are usually worked up after methods known per se, for example by removing the Solvent, distribute the residue in a mixture Water and a suitable organic solvent and insulation ren of the product from the organic phase.

Unless otherwise stated, the are for the production of the 3- (tetrahydrophthalimido) cinnamon alcohol derivatives I, the 3-aminozim talc alcohol derivatives III and the 3-nitrocinnamic alcohol derivatives VI be necessary raw materials and auxiliaries known or can can be produced by methods known per se.

The 3- (tetrahydrophthalimido) cinnamon alcohol derivatives 1,3-aminozim Talkohol derivatives III and 3-nitrocinnam alcohol derivatives VI can incurred in the preparation as mixtures of isomers, however if desired, using the usual methods such as crystal lization or chromatography, also on an optically active ad sorbate, into which pure isomers can be separated. Pure op Table-active isomers can advantageously be obtained from corresponding Manufacture optically active starting products.

Alkali metal salts of the 3- (tetrahydrophthalimido) cinnamon alcohol deri vate I, the 3-amino cinnamon alcohol derivatives III and the 3-nitro cinnamon alcohol derivatives VI can be prepared by treating compounds I, III or VI with R⁷ = hydrogen with sodium hydroxide, potassium hydroxide, sodium hydride or potassium hydride in aqueous solution or in an organic solvent such as methanol, ethanol, acetone and toluene can be obtained.

Salt formation normally takes place at around 20 ° C sufficient speed.

The salt can e.g. B. by cases with a suitable inert Solvent or isolated by evaporation of the solvent become.  

Salts of the 3- (tetrahydrophthalimido) cinnamon alcohol derivatives I, the 3-amino cinnamon alcohol derivatives III and the 3-nitro cinnamon alcohol derivative Derivatives VI whose metal ion is not an alkali metal ion can usually by salting the corresponding alkali metal salt can be prepared in aqueous solution. In this way can generally be metal salts of the compounds I. places that are insoluble in water.

Other metal salts such as manganese, copper, zinc, iron, calcium, Magnesium and barium salts can from the sodium salts in übli be produced in the same way, as well as ammonium and phosphonium salts with ammonia, phosphonium, sulfonium or Sulfoxonium hydroxides.

The compounds I and their agriculturally useful salts are suitable, both as isomer mixtures and in the form of pure isomers, as herbicides. You can in cultures like Wei zen, rice, corn, soybeans and cotton weeds and grass weeds fight very well without appreciably damaging the crops dig. This effect occurs especially at low application rates on.

Depending on the particular application method, the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. The following cultures are examples:
Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoealumisisumisum , Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacum (N.ru stica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prun avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifo lium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I are in cultures by Breeding and / or using genetic engineering methods against the we I have largely been made resistant, can be used.

The substituted 3- (tetrahydrophthalene imido) cinnamon alcohol derivatives I also for desiccation and / or Defoliation of plants.

As desiccants, they are particularly suitable for drying out the aerial parts of crops such as potatoes, rapeseed, Sunflower and soybean. So that a completely mechani harvests these important crops.

Ease of harvest is also of economic interest, which are caused by the temporally concentrated falling or decreasing of the Adhesion to the tree with citrus fruits, olives or other other types and varieties of pome, stone and shell fruit becomes. The same mechanism, that is, the promotion of training Formation of separating tissue between the fruit or leaf and sprout part of the plants is also for a well controlled defoliation of useful plants, especially cotton.

It also leads to the shortening of the time interval in which the individual cotton plants mature, to an increased fiber quality after harvest.

The compounds I or the herbicidal compositions comprising them can, for example, in the form of directly sprayable aqueous Solutions, powders, suspensions, including high-proof aqueous oily or other suspensions or dispersions, emulsions, Oil dispersions, pastes, dusts, spreading agents or granules by spraying, atomizing, dusting, scattering or pouring be used. The application forms depend on the Uses; in any case, they should be as fine as possible Ensure the distribution of the active substances according to the invention.

As inert auxiliaries for the production of directly sprayed solutions, emulsions, pastes or oil dispersions come in essential considerations: mineral oil fractions from medium to high boiling point such as kerosene and diesel oil, as well as coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. paraffins, Tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, Ethanol, propanol, butanol and cyclohexanol, ketones such as cyclo  hexanone, strongly polar solvents, e.g. B. amines such as N-methylpyr rolidon and water.

Aqueous use forms can be obtained from emulsion concentrates, Sus pensions, pastes, wettable powders or water-dispersible Granules can be prepared by adding water. For the manufacture Emulsions, pastes or oil dispersions can be sub strate as such or dissolved in an oil or solvent, using wetting agents, adhesives, dispersants or emulsifiers in water be homogenized. But it can also be made from an active substance, Wetting, adhesive, dispersing or emulsifying agents and possibly Concentrates containing solvents or oil are produced, which are suitable for dilution with water.

The alkali, alkaline earth, Ammonium salts of aromatic sulfonic acids, e.g. B. lignin, Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acids, alkyl and alkyl aryl sulfonates, alkyl and lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers, condensates products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxy ethylenoctylphenolether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethyleno xid condensates, ethoxylated castor oil, polyoxyethylene or Po lyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, Sorbitol ester, lignin sulfite liquor or methyl cellulose in Be dress.

Powders, materials for spreading and dusts can be mixed or mixed joint grinding of the active substances with a solid Carrier are manufactured.

Granules, e.g. B. coating, impregnation and homogeneous granules can Herge by binding the active ingredients to solid carriers be put. Solid carriers are mineral soils like pebbles acids, silica gels, silicates, talc, kaolin, limestone, lime, Chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and Magnesium sulfate, magnesium oxide, ground plastics, fertilizer tel such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urine substances and vegetable products such as flour, tree bark, Wood and nutshell flour, cellulose powder or other solid Carriers.  

The concentrations of the active ingredients I in the ready-to-use Preparations can be varied in a wide range, for example between 0.01 and 95% by weight, preferably between 0.5 and 90 % By weight. The active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum) is used.

The following formulation examples illustrate the manufacturer such preparations:

• I. 20 parts by weight of compound no. I.01 are in one Dissolved mixture that alkylated from 80 parts by weight Benzene, 10 parts by weight of the adduct from 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 Parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 Parts by weight of the adduct of 40 moles of ethylene oxide on 1 mole of castor oil. By pouring out and fine Distribute the solution in 100,000 parts by weight of water an aqueous dispersion containing 0.02% by weight of the active ingredient contains.
• II. 20 parts by weight of compound no. I.05 are in one Dissolved mixture consisting of 40 parts by weight of cyclohexanone, 30 Parts by weight of isobutanol, 20 parts by weight of the addition product of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles There is ethylene oxide in 1 mol of castor oil. By pouring and finely distribute the solution in 100,000 parts by weight of water an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient contains.
• III. 20 parts by weight of active ingredient No. I.10 are in one Dissolved mixture consisting of 25 parts by weight of cyclohexanone, 65 Parts by weight of a mineral oil fraction from boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 Moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight Water is obtained in an aqueous dispersion containing 0.02% by weight of the Contains active ingredient.
• IV. 20 parts by weight of active ingredient no. I.12 are added with 3 Parts by weight of the sodium salt of diisobutyl naphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt a lignin sulfonic acid from a sulfite waste liquor and 60 Parts by weight of powdered silica gel mixed well and ground in a hammer mill. Through fine distribution  the mixture in 20,000 parts by weight of water contains one Spray liquor containing 0.1% by weight of the active ingredient.
• V. 3 parts by weight of active ingredient no. I.20 are 97 Parts by weight of finely divided kaolin mixed. You get on this way a dusting agent containing 3% by weight of the active ingredient holds.
• VI. 20 parts by weight of active ingredient no Parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 Parts by weight of fatty alcohol polyglycol ether, 2 parts by weight Sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil intimately mixed. A stable oily dispersion is obtained.

The application of the active ingredients 1 or the herbicidal compositions can pre-emergence or post-emergence. Are the Active ingredients for certain crops less tolerable, so application techniques can be used in which the herbicidal agents are sprayed with the help of sprayers, that the leaves of sensitive crops if possible not to be taken while the active ingredients are on the leaves including growing unwanted plants or the uncovered Floor space (post-directed, lay-by).

Depending on the target, the amount of active ingredient applied is Season, target plants and stage of growth 0.001 to 3.0 preferably 0.01 to 1 kg / ha of active substance (a.S.).

To broaden the spectrum of activity and to achieve syner The substituted 3- (tetrahydrophthal imido) cinnamon alcohol derivatives I with numerous representatives of others herbicidal or growth-regulating active ingredient groups mixed and be applied together. For example, come as Mi Research partners diazines, 4H-3,1-benzoxazine derivatives, benzothia diazinone, 2,6-dinitroaniline, N-phenyl carbamate, thiol carbamate, Halogen carboxylic acids, triazines, amides, ureas, diphenyl ethers, Triazinones, uraciles, benzofuran derivatives, cyclohexane-1,3-dione derivatives in the 2-position z. B. a carboxy or carbimino Group wear, quinoline carboxylic acid derivatives, imidazolinones, sul fonamides, sulfonylureas, aryloxy, heteroaryloxyphenoxy propionic acids and their salts, esters and amides and others in Consideration.

It may also be useful to use the compounds I alone or in combination with other herbicides also with others Plant protection products mixed, to apply together, at  for example with means to control pests or phytopathogenic fungi or bacteria. It is also of interest the miscibility with mineral salt solutions, which are used to eliminate Nutritional and trace element deficiencies are used. It can non-phytotoxic oils and oil concentrates can also be added.

Manufacturing examples example 1 4-chloro-3- (2-chloro-3-hydroxypropenyl) nitrobenzene {No. VI.1}

25 ml of a 1.0 molar solution of diisobutylaluminum hydride in Toluene, diluted with 30 ml of tetrahydrofuran, were at (-70) to (-75) ° C within 30 minutes to a solution of 2.9 g 4-chloro-3- (2-chloro-2-ethoxycarbonyl-ethenyl) nitrobenzene in 120 ml Dropped tetrahydrofuran. After 5 hours of stirring at (-70) - (-75) ° C the mixture was at 25 ° C within 12 hours warms. Since no complete turnover was observed, at (-70) - (- 75) ° C diisobutylaluminium hydride (10.0 ml a 1.0 M solution in toluene) was added. After another 5 hours of stirring at (-70) - (- 75) ° C, the reaction mixture was heated again to about 20 ° C over a period of 12 hours. Then 50 ml a 10 percent Hydrochloric acid added, after which it is 12 hours. stirred. The product was separated from the aqueous phase extracted with 50 ml of toluene. The combined organic phases were washed twice with 50 ml of water, over sodium sulfate dries and finally concentrated. Yield: 2.5 g (as an oil).

Example 2 4-chloro-3- (3-hydroxy-2-methyl-propenyl) nitrobenzene {No. VI.3}

17 g of sodium boranate, dissolved in 150 ml of water, became one Solution of 67.65 g of 4-chloro-3- (2-formyl-propenyl) nitrobenzene in 600 ml of methanol were added dropwise. The mixture was then stirred another 5 hours, after which 40 ml of conc. Hydrochloric acid were added.

Then the low-boiling fractions were removed. The residue was washed with 200 ml of a mixture of ethyl acetate and water (approx 1: 1) added. From the mixture obtained, the organic Phase separated, washed with water and ge over sodium sulfate dries. After removing the solvent, 68.3 g were obtained of the product. M.p .: 82-84 ° C.

The following Table 1 shows further 3-nitrocinnamic alcohol Derivatives VI listed that are produced in the same way were or can be produced:  

Table 1

Example 3 4-chloro-3- (2-chloro-3-hydroxy-propenyl) aniline {No. III.1}

5.0 g of 4-chloro-3- (2-chloro-3-hydroxypropenyl) nitrobenzene, herge represents according to Example 1, were made using Raney nickel hydrogenated as a catalyst in 150 ml of ethanol. The product received one as oil.

Example 4 4-chloro-3- (2-chloro-3-hydroxy-propenyl) aniline {No. III.1}

To a suspension of 0.46 g lithium aluminum hydride in 120 ml Tetrahydrofuran became a solution of 2.6 g under nitrogen 4-chloro-3- (2-chloro-2-ethoxycarbonylethenyl) nitrobenzene in 30 ml Given tetrahydrofuran. The reaction mixture was stirred for 2 hours at about 20 ° C and then added 50 ml of a 10 % by weight sodium hydroxide solution. The aqueous phase was then removed separated and washed twice with 100 ml ether each. The unite The organic phases were in turn three times with 50 ml each Washed water, then dried over sodium sulfate and finally narrowed down. Yield: 1.5 g (as an oil).

In the following Table 2 are still 3-amino cinnamon alcohol Derivatives III listed that are made in the same way were or can be produced:  

Table 2

Example 5 N- [4-chloro-3- (2-chloro-3-hydroxypropenyl) phenyl] -3,4,5,6-tetra hydrophthalimide {no. I.06}

To a solution of 1.5 g of 3,4,5,6-tetrahydrophthalic anhydride and 0.5 g of p-toluenesulfonic acid in 200 ml of toluene became 2.2 g 4-Chloro-3- (2-chloro-3-hydroxypropenyl) aniline added. To Heating the reaction mixture to reflux for 20 hours temperature was reduced to dryness. Cleaning the raw product was carried out using flash chromatography (eluent: first dichloromethane, then successive dichloromethane / ethyl acetate 9/1). Yield: 1.5 g (as an oil).

Example 6 N- [3- (3-Acetoxy-2-chloropropenyl) -4-chlorophenyl] -3,4,5,6-tetra hydrophthalimide {no. 1.07}

To a solution of 0.76 g of 3,4,5,6-tetrahydrophthalic anhydride 1.09 g of 4-chloro-3- (2-chloro-3-hydroxy-pro penyl) aniline. The reaction mixture was then heated Schung 20 hours at reflux temperature, after which 50 ml of water were given. The aqueous phase was then separated off and ex she married twice with 100 ml dichloromethane each. The United organic phases were dried over sodium sulfate and then constricted. After flash chromatography (eluent: dichloromethane) was obtained in addition to 0.2 g of N- [4-chloro-3- (2-chloro-3-hydroxy-prope nyl) phenyl] -3,4,5,6-tetrahydrophthalimide (oil) 1.0 g of the ge desired product. M.p .: 84-87 ° C.  

Example 7 N- [3- (3-Acetoxy-2-chloropropenyl) -4-chlorophenyl] -3,4,5,6-tetra hydrophthalimide {I.07}

To a solution of 3.5 g of N- [4-chloro-3- (2-chloro-3-hydroxy propenyl) phenyl] -3,4,5,6-tetrahydrophthalimide and 1.2 g tri ethylamine in 80 ml of toluene was 0.9 g of acetyl chloride, dissolved in 20 ml of toluene. After 5 hours of stirring at about 20 ° C, the organic phase washed three times with 30 ml of water each, over Na Triumsulfat dried and concentrated. By careful addition diisopropyl ether was used to crystallize the product. Yield: 2.0 g.

In Table 3 below there are still more substituted ones 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I. performed in the same way or can be produced:  

Table 3

Examples of use

The herbicidal effects of 3- (tetrahydrophthalimido) cinnamon alcohol Derivatives of the formula I could be shown by greenhouse experiments:

Plastic flower pots with loamy sand also served as culture vessels about 3.0% humus as a substrate. The seeds of the test plants were sown separately according to species.

In pre-emergence treatment, the or suspended in water emulsified active ingredients directly after sowing by means of a fine distribution lender nozzles applied. The vessels were irrigated slightly To promote germination and growth, and then with covered plastic hoods until the plants had grown This cover causes the test to germinate evenly plant, unless this is affected by the active ingredients has been.

For the purpose of post-emergence treatment, the test plants were each according to growth habit, only tightened to a height of 3 to 15 cm and only then with those suspended or emulsified in water Active substances treated. The test plants were either di sown right and grown in the same containers or they become only grown separately as seedlings and a few days before Treatment transplanted into the test vessels. The application rate for post-emergence treatment was 0.125 and 0.063 kg active sub punch per hectare.

The plants became species-specific at temperatures of 10-25 ° C or kept at 20-35 ° C. The trial period extended over 2 to 4 weeks. During this time the plants were ge nurses, and their response to individual treatments has been evaluated.

It was rated on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal Growth course.

The plants used in the greenhouse experiments settled composed of the following types:

With an application rate of 0.125 and 0.063 kg / ha a.S. let themselves be with compound no. I.10, I.12 and I.20 unwanted broad Control leafy plants very well using the post-emergence method.

Examples of use for desiccative / defolian effectiveness of compounds I:

Young, 4-petals (without cotyledons) served as test plants Cotton plants grown under greenhouse conditions den (relative humidity 50 to 70%; day / night temperature 27/20 ° C).

The young cotton plants were dripping wet with water-based treatments the active ingredients (with the addition of 0.15% by weight of the fat alcohol alkoxylate Plurafac LF 700, based on the spray mixture) leaf treated. The amount of water applied was converted 1000 l / ha. After 13 days, the number of leaves dropped ter and the degree of defoliation determined in%.

No leaf fall occurred in the untreated control plants.

Claims (16)

1. 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I. in which the substituents have the following meaning:
R1 halogen, nitro, cyano or trifluoromethyl;
R² is hydrogen or halogen;
R³ is hydrogen, cyano, halogen or C₁-C₆ alkyl;
R⁴ is hydrogen, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl or C₁-C₆ alkoxy;
R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or the phenyl group, which may be unsubstituted or carry one to three radicals, selected from the group consisting of cyano, nitro, halogen, C₁-C₆- Alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy and (C₁-C₆ alkoxy) carbonyl;
R⁷ hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkyl) carbonyl, (C₁-C₆-haloalkyl) carbonyl, (C₃-C₈-cycloalkyl) carbonyl, ( C₂-C₆-alkenyl) carbonyl, (C₂-C₆-alkynyl) carbonyl, (C₁-C₆-alkoxy) carbonyl, (C₁-C₆-halogeno alkoxy) carbonyl, (C₃-C₈-cycloalkoxy) carbonyl, (C₁-C₆- Alkylthio) carbonyl, (C₁-C₆-haloalkyl) thio carbonyl, (C₃-C₈-cycloalkylthio) carbonyl, (C₁-C₆-alkyl) aminocarbonyl, (C₁-C₆-haloalkyl) aminocarbonyl, (C₃-C₈-cycloalkyl) aminocarbonyl , (C₁-C₆-alkyl) carbonyloxy- (C₁-C₆-alkyl) carbonyl,
(C₁-C₆-alkyl) carbonylthio- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkoxy) carbonyl- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkylthio) carbonyl- (C₁-C₆- alkyl) carbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl, di- (C₁-C₆-alkyl) aminosulfonyl, the phenylcarbonyl, phenylaminocarbonyl, phenoxycarbonyl or phenyl thiocarbonyl group, the phenyl ring, if desired, carrying one to three radicals can be selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy) carbonyl,
or a 3- to 8-membered, saturated, unsaturated or aromatic heterocycle bonded via a carbonyl group and containing one to three heteroatoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms, two nitrogen atoms and one nitrogen atom, that carries a methyl group,
and the agriculturally useful salts of the compounds I, if they exist. 2. 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I. according to claim 1, wherein R¹ is halogen. 3. 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I. according to claim 1, wherein R² is hydrogen, fluorine or chlorine stands. 4. 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I. according to claim 1, wherein R³ is hydrogen. 5. 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I. according to claim 1 wherein R⁴ is halogen or C₁-C₄ alkyl. 6. Use of the 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I and the agriculturally useful salts of I, according to claim 1, as herbicides. 7. Use of the 3- (tetrahydrophthalimido) cinnamon alcohol derivatives of the formula I and the agriculturally useful salts of I, according to claim 1, for desiccation and / or defoliation of Plants. 8. Herbicidal composition containing a herbicidally effective amount at least one 3- (tetrahydrophthalimido) cinnamon alcohol deri vates of formula I or an agriculturally useful  Salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired at least one adjuvant. 9. means for the desiccation and / or defoliation of plants, containing a desiccant and / or defoliant effective amount at least one 3- (tetrahydrophthalimido) cinnamon alcohol deri vates of formula I or an agriculturally useful Salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired at least one adjuvant. 10. Process for the preparation of herbicidally active agents, since characterized in that a herbicidally effective amount at least one 3- (tetrahydrophthalimido) cinnamon alcohol deri vates of formula I or an agriculturally useful Salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired mixes at least one adjuvant. 11. Process for the production of desiccant and / or defoliant effective means, characterized in that a de siccant and / or defoliant effective amount of at least one 3- (tetrahydrophthalimido) cinnamon alcohol derivative of the formula I. or an agriculturally useful salt of I, according to An claim 1, and at least one inert liquid and / or fe most carrier and, if desired, at least one adju vants mixes. 12. A method for controlling undesirable plant growth, since characterized in that a herbicidally effective amount at least one 3- (tetrahydrophthalimido) cinnamon alcohol derivative tes of formula I or an agriculturally useful Salt of I, according to claim 1, on plants, their life room or on seeds. 13. Process for the desiccation and / or defoliation of plants, characterized in that a defoliant and / or de siccant effective amount of at least one 3- (tetrahydrophthal imido) cinnamon alcohol derivative of formula I or a country economically usable salt of I, according to claim 1, can act on plants. 14. The method according to claim 13, characterized in that one Cotton treated.   15. 3-Amino cinnamon alcohol derivatives of the formula III in which the substituents have the following meaning:
R1 halogen, nitro, cyano or trifluoromethyl;
R² is hydrogen or halogen;
R³ is hydrogen, cyano, halogen or C₁-C₆ alkyl;
R⁴ is hydrogen, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl or C₁-C₆ alkoxy;
R⁵, R⁶ independently of one another hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or the phenyl group, which may be unsubstituted or carry one to three radicals, selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl , C₁-C₆ haloalkyl, C₁-C₆ alkoxy and (C₁-C₆ alkoxy) carbonyl;
R⁷ hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkyl) carbonyl, (C₁-C₆-haloalkyl) carbonyl, (C₃-C₈-cycloalkyl) carbonyl, ( C₂-C₆-alkenyl) carbonyl, (C₂-C₆-alkynyl) carbonyl, (C₁-C₆-alkoxy) carbonyl, (C₁-C₆-halogeno alkoxy) carbonyl, (C₃-C₈-cycloalkoxy) carbonyl, (C₁-C₆- Alkylthio) carbonyl, (C₁-C₆-haloalkyl) thio carbonyl, (C₃-C₈-cycloalkylthio) carbonyl, (C₁-C₆-alkyl) aminocarbonyl, (C₁-C₆-haloalkyl) aminocarbonyl, (C₃-C₈-cycloalkyl) aminocarbonyl , (C₁-C₆-alkyl) carbonyloxy- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkyl) carbonylthio- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkoxy) carbonyl- (C₁-C₆ -alkyl) carbonyl, (C₁-C₆-alkylthio) carbonyl- (C₁-C₆-alkyl) carbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl, di- (C₁-C₆-alkyl) aminosulfonyl, the phenylcarbonyl, Phenylaminocarbonyl, phenoxycarbonyl or phenyl thiocarbonyl group, the phenyl ring being desired if one to three radicals e can be selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy) carbonyl, or a bonded via a carbonyl group 3 - Up to 8-membered, saturated, unsaturated or aromatic heterocycle, which contains one to three heteroatoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms, two nitrogen atoms and a nitrogen atom which carries a methyl group;
and the salts of compounds III, if these exist. 16. 3-nitrocinnamic alcohol derivatives of the formula VI in which the substituents have the following meaning:
R1 halogen, nitro, cyano or trifluoromethyl;
R² is hydrogen or halogen;
R³ is hydrogen, cyano, halogen or C₁-C₆ alkyl;
R⁴ is hydrogen, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl or C₁-C₆ alkoxy;
R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or the phenyl group, which may be unsubstituted or carry one to three radicals, selected from the group consisting of cyano, nitro, halogen, C₁-C₆- Alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy and (C₁-C₆ alkoxy) carbonyl;
R⁷ hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkyl) carbonyl, (C₁-C₆-haloalkyl) carbonyl, (C₃-C₈-cycloalkyl) carbonyl, ( C₂-C₆-alkenyl) carbonyl, (C₂-C₆-alkynyl) carbonyl, (C₁-C₆-alkoxy) carbonyl, (C₁-C₆-halogeno alkoxy) carbonyl, (C₃-C₈-cycloalkoxy) carbonyl, (C₁-C₆- Alkylthio) carbonyl, (C₁-C₆-haloalkyl) thio carbonyl, (C₃-C₈-cycloalkylthio) carbonyl, (C₁-C₆-alkyl) aminocarbonyl, (C₁-C₆-haloalkyl) aminocarbonyl, (C₃-C₈-cycloalkyl) aminocarbonyl , (C₁-C₆-alkyl) carbonyloxy- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkyl) carbonylthio- (C₁-C₆-alkyl) carbonyl, (C₁-C₆-alkoxy) carbonyl- (C₁-C₆ -alkyl) carbonyl, (C₁-C₆-alkylthio) carbonyl- (C₁-C₆-alkyl) carbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl, di- (C₁-C₆-alkyl) aminosulfonyl, the phenylcarbonyl, Phenylaminocarbonyl, phenoxycarbonyl or phenyl thiocarbonyl group, the phenyl ring being desired if one to three radicals e can be selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy) carbonyl, or a bonded via a carbonyl group 3 - Up to 8-membered, saturated, unsaturated or aromatic heterocycle, which contains one to three heteroatoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms, two nitrogen atoms and a nitrogen atom which carries a methyl group;
and the salts of the compounds VI, if they exist.