DE4230933A1 - Hydroxylamino-phenylsulfonylureas, preparation and use as herbicides and plant growth regulators - Google Patents

Abstract

The sulphonyl ureas of formula (I) and their salts are suitable as selective herbicides to combat weeds in the cultivation of useful plants. The intermediate products of formulae (II) and (IV) may be used for their production.

Description

The invention relates to the technical field of herbicides and Plant growth regulators, especially herbicides for selective Control of weeds and grass weeds in crops.

It is known that heterocyclically substituted phenylsulfonylureas, which am Phenyl ring carry an amino or a functionalized amino group, herbicidal and have plant growth regulating properties (US Pat. No. 4,892,946; US Pat. A-4,981,509; EP-A-169 815).

Furthermore, from WO-89/10921 phenylsulfonylurea herbicides are known, in which the phenyl ring is 2,4-disubstituted or 2,4,6-trisubstituted and in the 4-position include an alkylamino or (substituted) hydroxylamino group can.

Surprisingly, it has now been found that certain heterocyclic substituted phenylsulfonylureas, which is an unsubstituted or a substituted hydroxylamino function, as herbicides or Plant growth regulators are particularly well suited.

The present invention relates to compounds of the formula (1) or their salts,

wherein
R ¹ CO-R ⁵ , CO-OR ⁶ , CO-NR ⁷ R ⁸ , CS-R ⁹ , CS-OR ¹⁰ , CS-NR ⁷ R ⁸ , SO ₂ R ¹¹ , SOR ¹¹ , SO ₂ NR ⁷ R ⁸ or CO-COR ¹² ,
R ^{2 is} hydrogen, C ₁ -C ₅ -alkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, the latter 3 radicals independently being unsubstituted or by one or more radicals from the group halogen, C ₁ - C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
R ³ halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy or C ₂ -C ₆ - Alkynyloxy, where the latter 6 radicals are independently unsubstituted or substituted by one or more radicals from the group halogen, C ₁ -C ₄ -alkoxy and alkylthio, or CO-CO-R ¹⁶ , CS-R ¹⁶ , CO-CO- OR ¹⁷ , CS-OR ¹⁷ , CS-SR ¹⁷ , CO-NR ¹⁸ R ¹⁹ , CS-NR ¹⁸ R ¹⁹ , NR ¹⁸ R ¹⁹ , SO ₂ NR ¹⁸ R ¹⁹ , Cyano, S (O) ₀ -R ²⁰ , CO-R ¹⁶ , CO-OR ¹⁷ , NO ₂ or C (R ²¹ ) = NR ²² or
a 5- or 6-membered saturated, unsaturated or heteroaromatic heterocycle with up to 4 heteroatoms from the group N, O and S, which is unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, CN, NO ₂ , CHO, (C ₁ -C ₄ alkyl) carbonyl and (C ₁ -C ₄ alkoxy) carbonyl is substituted and in which up to 2 C ring positions can be replaced by GO and up to two S hetero ring atoms by SO ₂ , or
R ^{4 is} hydrogen or C ₁ -C ₄ alkyl,
R ^{5 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -G ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ ₂ , or C ₃ -C ₇ cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ - Alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ ₂ , or benzyl, unsubstituted or substituted aryl or an unsubstituted or substituted heterocyclic radical,
R ^{6 is} C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy , C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted,
R ^{7 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₁ -C ₆ alkoxy, the latter 4 radicals being unsubstituted or by one or more radicals from the Halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and NR ¹³ R ^{14 are} substituted,
R ^{8 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ Alkoxy and C ₁ -C ₄ -alkylthio are substituted, or COR ²³ , CO ₂ R ²⁴ , CONR ¹³ R ¹⁴ or SO ₂ R ¹¹ ,
R ^{9 is} analogous to R ⁵ , preferably hydrogen, C ₁ -C ₆ alkyl or C ₃ -C ₆ alkenyl, the latter 2 radicals being unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ -alkoxy, alkylthio and NR ¹³ R ^{14 are} substituted,
R ¹⁰ analogous to R ⁶ , preferably C ₁ -C ₆ alkyl or C ₃ -C ₆ alkenyl, the latter 2 radicals being unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ - Alkoxy and C ₁ -C ₄ alkylthio are substituted,
R ^{11 is} C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
R ^{12 is} hydrogen, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, the latter 2 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
the R ¹³ independently of one another are hydrogen or C ₁ -C ₆ alkenyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted, or COR ²⁵ or CO ₂ R ²⁶ ,
the R ¹⁴ independently of one another are hydrogen or C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
NR ¹⁵ ₂ independently of one another is a heterocyclic 3- to 7-membered ring which, in addition to the N atom, can also contain one or two further hetero ring atoms from the group N, O and S and is unsubstituted or substituted,
R ¹⁶ analogous to R ⁵ ,
R ^{17 is} hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted,
R ¹⁸ analogous to R ⁷ ,
R ¹⁹ analogous to R ⁸ ,
R ²⁰ analogous to R ¹¹ ,
R ^{21 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ -Alkoxy and C ₁ -C ₄ alkylthio are substituted, or C ₁ -C ₄ alkoxy, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, CO-R ¹⁶ , CO ₂ -R ¹⁷ or SO ₂ -R ²⁰ ,
R ^{22 is} hydrogen, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, the latter 2 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
R ²³ analogous to R ⁹ ,
R ²⁴ analogous to R ¹⁰ ,
R ²⁵ analogous to R ⁹ ,
R ²⁶ analogous to R ¹⁰ ,
X, Y independently of one another are hydrogen, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy or C ₁ -C ₆ -alkylthio, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted, or mono- or di- (C ₁ -C ₄ alkyl) amino, C ₃ - C ₆ cycloalkyl, C ₃ -C ₅ alkenyl , C ₃ -C ₆ alkynyl, C ₃ -C ₅ alkenyloxy or C ₃ -C ₅ alkynyloxy,
Z CH or N,
WHERE or S,
n 0, 1, 2 or 3 and
o 0, 1, 2 or 3
mean.

In the formula (1) and below, the radicals alkyl, alkoxy, haloalkyl, Haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or be branched. Unless specifically stated, these residues are the Carbon skeletons with 1 to 4 carbon atoms, or 2 to 4 for unsaturated groups 4 carbon atoms preferred. Alkyl radicals, also in their composite meanings such as alkoxy, haloalkyl, etc. mean e.g. B. methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Have alkenyl and alkynyl radicals the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, Alkenyl means e.g. B. allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2- en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; Alkynyl means z. B. Propargyl, But-2-in-1-yl, But-3-in-1-yl, 1-Methyl-but-3-in-1-yl.

Halogen means fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are partially or fully substituted alkyl, alkenyl or alkynyl, for example by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine. B. CF ₃ , CHF ₂ , CH ₂ F, CF ₃ CF ₂ , CH ₂ FCHCl, CCl ₃ , CHCl ₂ , CH ₂ CH ₂ Cl; Haloalkoxy is e.g. B. OCF ₃ , OCHF ₂ , OCH ₂ F, CF ₃ CF ₂ O, OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl. The same applies to haloalkenyl and other halogen-substituted radicals.

Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, Fluorenyl and the like, preferably phenyl; Aryloxy preferably means that the aryl radicals corresponding to oxy radicals, in particular phenoxy.

Heteroaryl means a mono-, bi- or polycyclic aromatic system, in which contains at least 1 ring one or more heteroatoms, for example Pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, Pyrrolyl, pyrazolyl and imidazolyl, but also bicyclic or polycyclic aromatic or araliphatic compounds, e.g. B. quinolinyl, benzoxazolyl etc.

Substituted aryl, heteroaryl, phenyl, benzyl or substituted bicyclic radicals with aromatic portions mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals from the group halogen, alkyl, haloalkyl , Alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, mono- and dialkylamino, alkylsulfinyl and alkylsulfonyl and, in the case of radicals with carbon atoms, those with 1 to 4 C Atoms, in particular 1 or 2 carbon atoms, are preferred. Preferred are usually substituents from the group halogen, z. B. fluorine and chlorine, C ₁ -C ₄ alkyl, preferably methyl or ethyl, C ₁ -C ₄ haloalkyl, preferably trifluoromethyl, C ₁ - C ₄ alkoxy, preferably methoxy or ethoxy, C ₁ -C ₄ haloalkoxy , Nitro and cyano. The substituents methyl, methoxy and chlorine are particularly preferred.

Optionally substituted phenyl is, for example, phenyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - Haloalkyl, C ₁ -C ₄ haloalkoxy and nitro is substituted, for. B. o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl, 2,4-, 3,5-, 2, 5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

A heterocyclic radical is preferably 5- or 6-membered and heteroaromatic, saturated or unsaturated and contains 1, 2 or 3 heteroatoms, preferably from of groups N, O and S. The rest can be benzo-condensed. There are leftovers such as oxiranyl, pyrrolidyl, piperidyl, dioxolanyl, pyrazolyl, morpholyl, furyl, Tetrahydrofuryl, indolyl, quinolinyl, pyrimidyl, azepinyl, imidazolyl, triazolyl, thienyl and oxazolyl in question.

The invention also relates to all stereoisomers encompassed by formula (I) are, and their mixtures. Such compounds of formula (I) contain one or several asymmetric carbon atoms or double bonds in the general formulas (I) are not specified separately. Which by their specific Spatial form defined possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers are all encompassed by the formula I and can be prepared according to customary methods Methods obtained from mixtures of the stereoisomers or by stereoselective reactions in combination with the use of stereochemical pure raw materials are produced.

The compounds of the formula (I) can form salts in which the hydrogen of the —SO ₂ —NH group or also other acidic hydrogen atoms (for example from COOH and others) is replaced by a cation suitable for agriculture. These salts are, for example, metal, in particular alkali or alkaline earth metal salts, or also ammonium salts or salts with organic amines. Salt formation can also be caused by the addition of an acid to basic groups such as e.g. B. amino and alkylamino. Suitable acids for this are strong inorganic and organic acids, for example HCl, HBr, H ₂ SO ₄ or HNO ₃ .

Especially for reasons of higher herbicidal activity, better selectivity, and / or better producibility, compounds of the formula (I) or their salts are of particular interest, in which
R ¹ CO-R ⁵ , CO-OR ⁶ , CO-NR ⁷ R ⁸ , CS-R ⁹ , CS-NR ⁷ R ⁸ , SO ₂ R ¹¹ , SO ₂ NR ⁷ R ⁸ or CO-COR ¹² ,
R ^{2 is} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₅ alkenyl or C ₃ -C ₅ alkynyl, the latter 3 radicals being independently unsubstituted or by one or more halogen atoms or by one or two radicals from the Group C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted, or
R ³ halogen, C ₁ -C ₄ alkyl, C ₂ -C ₅ alkenyl, C ₂ -C ₅ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₅ alkenyloxy or C ₃ -C ₅ - Alkynyloxy, where the latter 6 radicals are independently unsubstituted or substituted by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ -alkoxy and alkylthio, or CO-CO-R ¹⁶ , CO-CO-OR ¹⁷ , CO-NR ¹⁸ R ¹⁹ , NR ¹⁸ R ¹⁹ , SO ₂ NR ¹⁸ R ¹⁹ , Cyano, S (O) ₀ -R ²⁰ , CO-R ¹⁶ , CO-OR ¹⁷ , NO ₂ or C (R ²¹ ) = NR ²² or
a 5- or 6-membered saturated, unsaturated or heteroaromatic heterocycle with up to 3 heteroatoms from the group N, O and S, which is unsubstituted or by one or more radicals from the group halogen, C ₁ - C ₄ -alkyl, such as methyl, C ₁ -C ₄ alkoxy, such as methoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, such as CF ₃ , CN, NO ₂ , CHO, (C ₁ -C ₄ alkyl) carbonyl, such as Acetyl, and (C ₁ -C ₄ alkoxy) carbonyl, such as CO ₂ CH ₃ , is substituted and in which up to 2 C ring positions can be replaced by CO and up to two S hetero ring atoms by SO ₂ ,
R ^{4 is} hydrogen or methyl or
R ^{5 is} hydrogen or C ₁ -C ₆ alkyl which is unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 is} substituted, or C ₃ -C ₇ cycloalkyl, benzyl, unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl, preferably H, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ -cycloalkyl, benzyl, phenyl, which is unsubstituted or substituted by one or more, preferably up to 3, radicals from the group halogen, methoxy or methyl, or a 5- or 6-membered heteroaromatic radical which contains up to 4 heteroatoms from the group N. , Contains O and S and is unsubstituted or substituted by one or more radicals from the group halogen, NO ₂ , CN, CHO, COCH ₃ , CO ₂ CH ₃ , OCH ₃ and SCH ₃ , or
R ⁶ C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted, preferably C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ haloalkenyl, or
R ^{7 is} hydrogen or C ₁ -C ₆ alkyl which is unsubstituted or substituted by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and NR ¹³ R ¹⁴ is, preferably H, C ₁ -C ₄ alkyl or C ₁ - C ₄ haloalkyl, or
R ^{8 is} hydrogen or C ₁ -C ₄ alkyl which is unsubstituted or substituted by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio, or COR ²³ , CO ₂ R ²⁴ or SO ₂ R ¹¹ , preferably H, CH ₃ , C ₂ H ₅ , CHO, COCH ₃ or CO ₂ CH ₃ , or
R ⁹ analogous to R ⁵ , preferably hydrogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or
R ¹⁰ analogous to R ⁶ , preferably C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, or
R ^{11 is} C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl or
R ^{12 is} hydrogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ haloalkyl, preferably H or C ₁ -C ₄ alkyl, or
the R ¹³ independently of one another are hydrogen or C ₁ -C ₄ alkyl, COR ²⁵ or CO ₂ R ²⁶ , preferably H, CH ₃ , C ₂ H ₅ , CHO, COCH ₃ , CO-OCH ₃ or CO-OC ₂ H ₅ , or
the R ¹⁴ independently of one another are hydrogen or C ₁ -C ₄ alkyl, preferably H, CH ₃ or C ₂ H ₅ , or
NR ¹⁵ ₂ independently of one another is a heterocyclic 3- to 7-membered ring which, in addition to the N atom, can also contain a further hetero ring atom from the group N, O and S and is unsubstituted or by radicals from the group C ₁ -C ₄ alkyl and oxo is substituted, e.g. B. heterocyclic radicals of the formula A ₁ to A ₉

or
R ¹⁶ analogous to R ⁵ ,
R ^{17 is} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted, preferably H, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ Alkenyl or C ₃ -C ₆ haloalkenyl,
R ¹⁸ analogous to R ⁷ ,
R ¹⁹ analogous to R ⁸ ,
R ²⁰ analogous to R ¹¹ ,
R ^{21 is} hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, OH, NH ₂ , mono- or di- (C ₁ -C ₄ -alkyl) -amino, preferably H, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, hydroxy, amino, methylamino or dimethylamino,
R ^{22 is} hydrogen, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkyl or C ₁ - C ₄ alkoxy, preferably H, OH, NH ₂ , NHCH ₃ , N (CH ₃ ) ₂ , CH ₃ or OCH ₃ ,
R ²³ analogous to R ⁹ ,
R ²⁴ analogous to R ¹⁰ ,
R ²⁵ analogous to R ⁹ ,
R ²⁶ analogous to R ¹⁰ ,
X, Y independently of one another are hydrogen, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, the latter 3 radicals being unsubstituted or substituted by one or more halogen atoms, or mono - or di- (C ₁ -C ₂ alkyl) amino, preferably one of the radicals X and Y CH ₃ , C ₂ H ₅ , OCH ₃ or OC ₂ H ₅ and the other radical CH ₃ , C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , Cl, CF ₃ , OCF ₃ C, OCF ₂ H, N (CH ₃ ) ₂ , NHCH ₃ or N (C ₂ H ₅ ) ₂ , or
Z CH or N or
WO or S, preferably O, or
n 0.1 or 2 or
o 0.1 or 2
mean or preferably those compounds of the formula (I) or their salts in which one or more of the above-mentioned particular or preferred meanings for the general radicals or indices R ¹ to o are present in combination in formula (I).

Preference is given to compounds of the formula I mentioned or their salts, in which
R ¹ COR ⁵ , CO ₂ R ⁶ , CO-NR ⁷ R ⁸ , CO-CO-R ¹² , CS-NR ⁷ R ⁸ , SO ₂ R ¹¹ or SO ₂ -NR ⁷ R ⁸ and / or
R ^{2 is} hydrogen or C ₁ -C ₄ alkyl, preferably H, CH ₃ , C ₂ H ₅ , n- or iC ₃ H ₇ , in particular H,
mean.

Compounds of the formula (I) according to the invention or salts thereof are also preferred, wherein
R ^{5 is} hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, such as CF ₃ , cyclopropyl, cyclopentyl, cyclohexyl, benzyl, phenyl, which is unsubstituted or by 1 to 3 radicals from the group halogen, preferably fluorine or Chlorine, methyl and methoxy is substituted, or thienyl, furyl or pyridyl, the above heteroaromatic radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy, or
R ⁶ C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl,
R ^{7 is} H, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl or
R ⁸ H, C ₁ -C ₄ alkyl, COCH ₃ , CO ₂ CH ₃ or CO ₂ C ₂ H ₅
mean or in which a combination of the above-mentioned preferred radicals is contained.

Preferred compounds are also compounds of the formula (1) according to the invention or their salts, in which the group of the formula N (OR ² ) R ^{1 is} in the 2-, 3-, 5- or 6-position on the phenyl ring and n is 0 or 1.

The group of the formula N (OR ² ) R ¹ on the phenyl ring is particularly preferably in the 2-position and n is 0 or 1 or the group of the formula N (OR ² ) R ¹ is in the 5-position (or 3-position) on Phenyl ring, n means 0 or 1 and the radical R ³ is in the 2-position (or 6-position) on the phenyl ring.

The present invention further relates to processes for producing the Compounds of formula (I) according to the invention or their salts, thereby characterized that one

• a) a compound of the formula (II), with a heterocyclic carbamate of the formula (III), wherein R is optionally substituted phenyl or (C ₁ -C ₄ ) alkyl, or
• b) provided that R ^{2 is} not hydrogen, a sulfonyl isocyanate of the formula (IV) with an amino heterocycle of the formula (V) implements.

The compounds of the formulas (II) and (III) are preferably reacted base catalyzed in an inert organic solvent, such as. B. Dichloromethane, acetonitrile, dioxane or THF at temperatures between 0 ° C, preferably 20 ° C and the boiling point of the solvent. As a base here, for example, organic amine bases, such as 1,8-diazabicyclo- [5.4.0] undec-7-ene (DBU), especially when R * = (subst.) Phenyl (cf. EP-A-44 807), or Trimethylaluminium or triethylaluminium, the latter especially when R * = alkyl (cf. EP-A-166 516) is used.

The sulfonamides (II) are new compounds. You and their manufacture are also subject of the invention.

The compounds of formula (II) z. B. starting from connections of the formula (VI)

by reacting with a strong acid.

As strong acids such. B. mineral acids such as H ₂ SO ₄ or HCl, or strong organic acids such as trifluoroacetic acid in question. The t-butyl protective group is cleaved off, for example, at temperatures of -20 ° C. and the respective reflux temperature of the reaction mixture, preferably at 0 ° C. to 40 ° C. The reaction can be carried out in bulk or in an inert solvent, such as. B. dichloromethane or trichloromethane.

The compounds of formula (VI), wherein R ^{2 is} not hydrogen (hydroxylamine ether), z. B. from the compounds of formula (VI), wherein R ² = hydrogen, obtained analogously to known O-alkylation reactions, alkylating agents in the presence of a base, such as. As potassium carbonate or sodium hydride, in an inert solvent such as. B. DMF (dimethylformamide) or DMSO (dimethyl sulfoxide), THF (tetrahydrofuran) or 1,2-dimethoxyethane can be used. Dialkyl sulfates or corresponding alkyl halides are suitable as alkylating agents (cf. Houben-Weyl-Klamann, "Methods of Organic Chemistry", 4th edition, Vol. E XVI / a, p. 271, Thieme Verlag Stuttgart, 1990).

The introduction of the substituent R ¹ can by reaction of the hydroxylamine aromatics (VI), wherein R ¹ = R ² = H, with appropriate electrophiles, such as. B. acid chlorides, acid anhydrides, isocyanates and thioisocyanates (see. Houben-Weyl-Klamann, "Methods of Organic Chemistry", 4th ed., Vol. E XVIa / 1, p. 199ff., Thieme Verlag Stuttgart, 1990).

The hydroxylamine derivative of formula (VI), in which R ¹ = R ² = H, is from the corresponding nitro compound (VII) by reduction, for. B. with zinc powder in ethanol buffered with ammonium chloride, available. Other suitable reducing agents for this transformation are, for example: platinum / tributyl phosphite / 4-dimethylamino-pyridine, hydrazine hydrate or hydrogen / Raney nickel / ethanol, hydrazine hydrate / rhodium, sodium dihydrogen phosphate / palladium, etc. (cf. here: Houben-Weyl-Klamann , "Methods of Organic Chemistry", 4th ed., Vol. E XVIa / 1, p. 49ff., Thieme Verlag Stuttgart, 1990).

The nitro compound of the formula (VII) mentioned can be obtained from the corresponding Nitrobenzenesulfonic acid (VIII) can be produced.

The sulfonic acid group of the compounds (VIII) is first converted into the sulfochlorides, e.g. B. according to standard methods such as implementation of  Phosphorus oxychloride or thionyl chloride with potassium salts of the corresponding Sulfonic acids in inert solvents such as acetonitrile and / or sulfolane or in Substance by heating to reflux (cf. Houben-Weyl-Klamann, "Methods der organic chemistry ", 4th ed., vol. E XI / 2, pp. 1067-1073, Thieme Verlag Stuttgart, 1985).

The sulfonamide formation from the sulfochlorides with tert-butylamine in ethanol provides the compounds (VII) in good yields (cf. analogous reactions in WO 89/10921).

Alternatively, the sulfonamides of the formula II in which R ¹ and R ^{2 are} not equal to H can be obtained by aminolysis of the corresponding sulfochlorides of the formula (IXb)

are obtained, which in turn from the sulfonic acids (IXa) by the above Standard methods (see conversions from (VIII) to (VII)) are readily available.

The compounds (IXa) can in turn be derived from the nitrobenzenesulfonic acid (VIII) as a result of reactions
(1) reduction analogous to the reduction of (VII),
(2) N-acylation and
(3) O-acylation,
the latter as described in the preparation of (VI) can be obtained.

The starting compounds of the formula (VIII) or their sulfochlorides mentioned are either known or commercial connections or can be easily Create ways, e.g. B. by

• - Nitration (see Houben-Weyl-Müller, "Methods of Organic Chemistry, 4th Ed., Vol. X / 1, pp. 463ff., Thieme Verlag Stuttgart, 1971),  
• - Sulfonation (Houben-Weyl-Klamann, "Methods of Organic Chemistry, 4th Ed., Vol. E XI / 2, pp. 1055ff., Thieme Verlag Stuttgart, 1985; Houben-Weyl Müller, "Methods of Organic Chemistry", 4th ed., Vol. IX, p. 435ff., Thieme Verlag Stuttgart, 1955),
• - sulfochlorination (Houben-Weyl-Klamann, "Methods of Organic Chemistry", 4th edition, vol. E XI / 2, pp. 1067ff., Thieme Verlag Stuttgart, 1985; Houben-Weyl Müller, "Methods of Organic Chemistry", 4th ed., Vol. IX, pp. 563ff., Thieme Verlag Stuttgart, 1955),
• - Introduction of a residue R ³ z. B. by halogenation (Houben-Weyl-Müller, "Methods of Organic Chemistry", 4th Edition, Vol. V / 3, pp. 213ff., Thieme Verlag Stuttgart, 1962; Houben-Weyl-Müller, "Methods of Organic Chemistry ", 4th ed., Vol. V / 3, pp. 556-561 and 845-853, Thieme Verlag Stuttgart, 1962; Houben-Weyl-Müller," Methods of Organic Chemistry ", 4th ed., Vol. V / 4, pp. 233-299 and 437-447, Thieme Verlag Stuttgart, 1960; Houben-Weyl-Müller, "Methods of Organic Chemistry", 4th edition, Vol. V / 4, pp. 557-593 and 639-647, Thieme Verlag Stuttgart, 1960) or alkylation (GA Olah, "Friedel-Crafts-Chemistry", Wiley-Interscience, New York, 1973),
• - Or by derivatizing an existing third substituent, such as. B. by oxidation of an alkyl group (R ³ ) to a carboxylic acid, followed by an esterification (R ³ = CO ₂ alkyl) (Houben-Weyl-Falbe, "Methods of Organic Chemistry", 4th ed., Vol. EV / 1, Thieme Verlag Stuttgart, 1985, pp. 199-202 and literature cited there).

Those required for the implementation of the compounds (II) according to variant a) Carbamates of the formula (III) are known from the literature or can be known analogously Prepare the process (see EP-A-70804 or US-A-4,480,101).

From the compounds of the formulas (III) and (VIII) mentioned and their Precursors can also be used for process variant b) Compounds of the formulas (IV) and (V) according to or analogously known Create methods.  

The phenylsulfonyl isocyanates of the formula (IV) with R ² not equal to H can, for. B. analogously to the process from EP-A-184 385 from compounds (II), for. B. with phosgene.

The reaction of the compounds (IV) with the amino heterocycles (V) is carried out preferably in inert, aprotic solvents such as. B. dioxane, acetonitrile or tetrahydrofuran at temperatures between 0 ° C and the boiling temperature of the solvent.

The salts of the compounds of formula (I) are preferably in inert solvents such as. B. water, methanol, acetone, dichloromethane, tetrahydrofuran, toluene or heptane, at temperatures from 0 to 100 ° C. Suitable bases for the preparation of the salts according to the invention are, for example, alkali carbonates, such as potassium carbonate, alkali and alkaline earth metal hydroxides, ammonia or a suitable amine base, such as triethylamine or ethanolamine. Suitable acids for salt formation are, for. B. HCl, HBr, H ₂ SO ₄ or HNO ₃ .

With the "inert" designated in the above process variants Solvents "are solvents that are meant under the respective Reaction conditions are inert, but not under any Reaction conditions must be inert.

The compounds of formula (I) or their salts according to the invention have a excellent herbicidal activity against a broad spectrum economically important mono- and dicotyledonous harmful plants. Even difficult to fight perennial weeds made from rhizomes, rhizomes or others Expelling permanent organs are well captured by the active ingredients. It is regardless of whether the substances are pre-seeding, pre-emergence or post-emergence be applied. Some of the representatives of the mono- and called dicotyledonous weed flora, caused by the invention Connections can be checked without a Restriction to certain types should take place.  

On the side of the monocot weed species, e.g. B. Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and on the part of the perennial species Agropyron, Cynodon, Imperata as well as sorghum and perennial cyperus species well recorded.

In dicotyledon weed species, the spectrum of activity extends to species such as: B. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annual side as well as Convolvulus, Cirsium, Rumex and Artemisia in the perennial weeds.

Weeds occurring in rice under the specific crop conditions such as e.g. B. Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus are from the Active ingredients according to the invention also fought excellently.

Are the compounds of the invention prior to germination on the Applied earth surface, so is either the emergence of the weed seedlings completely prevented or the weeds grow up to the cotyledon stage, however, they stop growing and eventually die after three up to four weeks.

When applying the active ingredients to the green parts of the plant in a post-emergence process there is also a drastic growth stop very quickly after the treatment and the weed plants remain in the existing at the time of application Stages of growth stand or die completely after a certain time, so that in this way weed competition harmful to crops very early and is permanently eliminated.

Although the compounds of the invention are excellent herbicidal Have activity against mono- and dicotyledon weeds Cultivated plants of economically important crops such as B. wheat, barley, Rye, rice, maize, sugar beet, cotton and soy only marginally or not at all not harmed. The present compounds are suitable for these reasons  very good for selective control of undesired plant growth in agricultural crops.

In addition, the substances according to the invention have excellent properties growth regulatory properties in crops. You grab regulate the plant's own metabolism and can thus targeted influencing of plant ingredients and to facilitate harvesting, e.g. B. by triggering desiccation and stunted growth. They are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. A Inhibition of vegetative growth plays in many mono- and dicotyledons Cultures play a major role, as this reduces or completely prevents storage can be.

The compounds according to the invention can be in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or Granules can be used in the usual preparations. Subject of Invention are therefore also herbicidal and plant growth regulating agents, contain the compounds of formula (I) or their salts.

The compounds of formula (I) or their salts can in various ways be formulated, depending on which biological and / or chemical physical parameters are specified. As formulation options Examples include: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as Oil-in-water and water-in-oil emulsions, sprayable solutions, Suspension concentrates (SC), oil- or water-based dispersions, oil-miscible Solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for the spreading and soil application, granules (GR) in the form of micro, spray, Elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.  

These individual types of formulation are known in principle and will described for example in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids such as inert materials, surfactants, Solvents and other additives are also known and will be described for example in: Watkins, "Handbook of Insecticide Dust Diluent and Carriers ", 2nd Ed., Darland Books, Caldwell N.J .; H. v. Olphen," Introduction to Clay Colloid Chemistry ", 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden," Solvents Guide ", 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual ", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood," Encyclopedia of Surface Active Agents ", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Surface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, combinations with others can also be made pesticidal substances, such as. B. insecticides, acaricides, herbicides, Manufacture fungicides, safeners, fertilizers and / or growth regulators, e.g. B. in the form of a finished formulation or as a tank mix.

Spray powders are preparations which are uniformly dispersible in water Active substance in addition to a diluent or an inert substance or ionic surfactants and / or nonionic type (wetting agents, dispersing agents), e.g. B. polyoxyethylated Alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, Fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2′-dinaphthylmethane-6,6′-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltauric acid sodium contain. The herbicidal active ingredients are used to produce the wettable powders for example in conventional equipment such as hammer mills, fan mills and  Air jet mills finely ground and simultaneously or subsequently with the Formulation aids mixed.

Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures the organic solvent with the addition of one or more surfactants ionic and / or nonionic type (emulsifiers). As emulsifiers can be used for example: alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. B. sorbitan fatty acid esters or polyoxethylene sorbitan esters such. B. Polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active ingredient with finely divided solid Fabrics, e.g. B. talc, natural clays, such as kaolin, bentonite and pyrophyllite, or Diatomaceous earth.

Suspension concentrates can be water or oil based. You can for example by wet grinding using commercially available pearl mills and optionally addition of surfactants, such as. B. above with the others Formulation types already listed can be produced.

Emulsions e.g. B. oil-in-water emulsions (EW) can be used, for example Stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as z. B. already listed above for the other formulation types.

Granules can either by spraying the active ingredient adsorbable, granulated inert material or by Applying active ingredient concentrates using adhesives, e.g. B. polyvinyl alcohol,  polyacrylic acid sodium or mineral oils, on the surface of Carriers such as sand, kaolinite or granulated inert material. Can too suitable active ingredients in the usual for the production of fertilizer granules Way - if desired in a mixture with fertilizers - granulated.

Water-dispersible granules are generally made using the customary methods such as spray drying, fluidized bed granulation, plate granulation, mixing with High speed mixers and extrusion made without solid inert material.

The agrochemical preparations usually contain 0.1 to 99 % By weight, in particular 0.1 to 95% by weight, of active compound of the formula (I) or its Salts.

In wettable powders, the active ingredient concentration is e.g. B. about 10 to 90 wt .-% of The remainder to 100 wt .-% consists of conventional formulation components. At emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80 wt .-%. Dusty formulations contain 1 to 30, preferably mostly 5 to 20 wt .-% of active ingredient, sprayable Solutions about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient. At water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, Fillers, etc. are used. For water-dispersible granules the active ingredient content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active ingredient formulations mentioned optionally contain the usual adhesive, wetting, dispersing, emulsifying, penetration, preservation, Antifreeze and solvents, fillers, carriers and dyes, defoamers, Evaporation inhibitors and agents that affect pH and viscosity.

As a combination partner for the active substances according to the invention in mixture formulations or in the tank mix, known active substances can be used, for example, as described in e.g. B. from Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Bracknell, England, and literature cited therein. As herbicides known from the literature, which can be combined with the compounds of formula (I), z. For example, the following active substances are to be mentioned (note: the compounds are identified either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name, possibly together with a usual code number):
acetochlor; acifluorfen; aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino -] - oxy] - acetic acid and methyl acetate; alachlor; alloxydim; ametryn; amidosulfuron; amitrole; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin; butylates; carbetamide; CDAA, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie 2-chloroallyl ester of diethyldithiocarbamic acid; CGA 184927, ie 2- [4 - [(5-chloro-3-fluoro-2-pyridinyl) -oxy] phenoxy] propanoic acid and 2-propynyl ester; chlomethoxyfen; chloramben; chlorazifop-butyl, pirifenop-butyl; chlorbromuron; chlorobufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuronethyl; chloronitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlororthal dimethyl; chlorothiamide; cinmethylin; cinosulfuron; clethodim; clomazone; clomeprop; cloproxydim; clopyralid; cyanazine; cycloate; cycloxydim; cycluron; cyperquat; cyprazine; cyprazole; 2,4-DB; dalapon; desmediphan; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop; diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethazone; e clomazone; dimethipin; dimetrasulfuron; cinosulfuron; dinitramine; dinoseb; dinoterb; diphenamide; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 177, ie 5-cyano-1- (1,1-dimethylethyl) -N-methyl-3H-pyrazole-4-carboxamide; endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; F5231, ie N- [2-chlorofluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] phenyl] ethanesulfonamide; F6285, ie 1- [5- (N-methylsulfonyl) amino-2,4-dichlorophenyl] -3-methyl-4-difluoromethyl-1,2,4-triazol-5 - one; fenoprop; fenoxan, p. clomazone; fenoxaprop-ethyl; fenuron; flamprop-methyl; flazasulfuron; fluazifop and its ester derivatives; fluchloralin; flumetsulam; N- [2,6-difluorophenyl] -5-methyl- (1,2,4) -triazolo [1,5a] pyrimidine-2-sulfonamide; flumeturon; flumipropyn; fluorodifen; fluoroglycofen-ethyl; fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halosates; haloxyfop and its ester derivatives; hexazinone; Hw 52, ie N- (2,3-dichlorophenyl) -4- (ethoxymethoxy) benzamide; imazamethabenz-methyl; imazapyr; imazaquin; imazethamethapyr; imazethapyr; imazosulfuron; ioxynil; isocarbamide; isopropaline; isoproturon; isouron; isoxaben; isoxapyrifop; carbutilates; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidide; metamitrol; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metobromuron; metolachlor; metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine, MT 5950, ie N- [3-chloro-4- (1-methylethyl) -phenyl] -2-methylpentanamide, naproanilide, napropamide, naptalam, NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitraline; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenmedipham; phenisopham; phenmedipham; picloram; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn; propachlor; propanil; propaquizafop and its ester derivatives; propazine; propham; propyzamide; prosulfalin; prosulfocarb; prynachlor; pyrazolinates; pyrazone; pyrazosulfuron-ethyl; pyrazoxyfen; pyridate; quinclorac; quinmerac, quinofop and its ester derivatives, quizalofop and its ester derivatives; quizalofop-ethyl; quizalofop-p-tefuryl; renriduron; dymron; S 275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -4,5,6,7-tetrahydro-2H-i-ndazole; S 482, ie 2- [7-fluoro-3,4-dihydro-3-oxo-4- (2-propynyl) -2H-1,4-benzoxazin-6-yl] - 4,5,6,7 - tetrahydro-1H-isoindole-1,3 (2H) -dione; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propanoic acid and methyl ester; sulfometuron-methyl; sulfazuron; flazasulfuron; TCA; tebutam; tebuthiuron; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, ie N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1,2,4-triazole-1-carboxamide; thiazafluron; thifensulfuron-methyl; thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin; trimeturon; vernolate; WL 110547, ie 5-phenoxy-1- [3- (trifluoromethyl) phenyl] -1H-tetrazole.

The formulations available in commercial form are used optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, ground or scatter granules as well as sprayable Solutions are usually no longer combined with other solutions before use inert substances diluted.

With the external conditions such as temperature, humidity, the type of used herbicide u. a. the required application rate varies Compounds of formula (I). It can fluctuate within wide limits, e.g. B. between 0.001 and 10.0 kg / ha or more of active substance, preferably it is however between 0.005 and 5 kg / ha.

A. Chemical examples a) 2-carboxy-5-nitro-benzenesulfonic acid

To a solution of 106.0 g (0.40 mol) of 2-methyl-5-nitro-benzenesulfonic acid and 80.0 g (0.58 mol) of potassium carbonate in 1300 ml of water are at 80 ° C. 400.0 g (2.53 mol) of potassium permanganate were added in portions over the course of 2 hours. The reaction temperature is kept between 80 and 95 ° C. To the resulting solid is filtered off for a further 4 h of stirring. The filtrate is acidified with concentrated hydrochloric acid (pH = 1). The fancy, colorless 2-  Carboxy-5-nitro-benzenesulfonic acid is suctioned off via a Büchner funnel and dried at approx. 50 ° C / 100 torr (82.0 g; 83.7% of theory). Mp <300 ° C.

b) 2-methoxycarbonyl-5-nitro-benzenesulfonic acid

A suspension of 190.0 g (0.77 mol) of 2-hydroxycarbonyl-5-nitro- benzenesulfonic acid, 10 ml of dimethylformamide, and 250 ml (3.43 mol) of thionyl chloride is heated to boiling for 3 h. After the removal of insoluble components the filtrate is concentrated by filtration. To the residue so obtained 200 ml (4.94 mol) of methanol are added dropwise. When the addition is complete, it will Cooled reaction mixture to 0 ° C. The precipitated solid is filtered off and dried. This gives 70.9 g (35.3% of theory) of the colorless, crystalline 2- Methoxycarbonyl-5-nitro-benzenesulfonic acid (mp: 92-94 ° C).

By distilling off the volatile parts of the mother liquor on the rotary evaporator a second fraction is obtained (62.5 g, 31.1% of theory).

c) 2-methoxycarbonyl-5-nitro-benzenesulfochloride

A solution of 70.9 g (0.27 mol) of 2-methoxycarbonyl-5-nitro-benzenesulfonic acid in 300 ml of methanol is carefully stirred with a solution of 17.3 with vigorous stirring g (0.27 mol) of potassium hydroxide (88%) and 100 ml of methanol were added. After this Cooling to 0 ° C, the salt formed is filtered off, dried and then in 150 ml sulfolane, 150 ml acetonitrile and 10 ml dimethylformamide suspended. After the dropwise addition of 100 ml (1.07 mol) of phosphorus oxychloride the mixture is heated to boiling for 2.5 h and then on ice water poured. The precipitated 2-methoxycarbonyl-5-nitro-benzenesulfochloride (60.1 g, 70% of theory) is suctioned off via a Büchner funnel and reduced Traces of solvent are removed from the print. Mp: 86-88 ° C.  

d) N-tert-butyl-2-methoxycarbonyl-5-nitro-benzenesulfonamide

To a solution of 34.4 g (0.12 mol) of 2-methoxycarbonyl-5-nitro-benzenesulfochloride in 200 ml of ethyl acetate and 250 ml of ethanol, 50 ml (0.48 Mol) slowly added dropwise tert-butylamine. Then the reaction solution stirred for a further 10 min at room temperature. After adding 500 ml Water crystallizes out as a colorless solid. After filtering and drying 28.1 g (89%) of N-tert-butyl-2-methoxycarbonyl-5-nitro-benzenesulfonamide receive. Mp: 121-124 ° C.

e) N-tert-butyl-5-hydroxylamino-2-methoxycarbonyl-benzenesulfonamide

23.4 g (0.08 mol) of N-tert-butyl-2-methoxycarbonyl-5-nitro-benzenesulfonamide submitted at 40 ° C in 600 in ethanol. After buffering with 42.1 g (0.79 mol) Ammonium chloride and 170 ml of water are added in portions to 32.0 g (0.49 mol) Zinc powder added. The mixture is then stirred for a further 4 h at approx. 55 ° C. Of the Solid is filtered off and the filtrate is concentrated on a rotary evaporator. Of the The residue is taken up in 800 ml of ethyl acetate and with 300 ml Washed water. The aqueous phase is washed three times with 300 ml of dichloromethane re-extracted. The combined organic phases are over magnesium sulfate dried. Then volatile components on the rotary evaporator distilled off. The crystalline residue is mixed with a little ethyl acetate: heptane (1: 1) stirred. In this way, 17.2 g (77%) of N-tert-butyl-5- hydroxylamino-2-methoxycarbonyl-benzenesulfonamide obtained. Mp: 190-195 ° C.

f) N-tert-butyl-5- (N-acetyl-hydroxylamino) -2-methoxycarbonyl-benzenesul-fonamide

3.31 g (0.01 mol) of N-tert-butyl-5-hydroxylamino-2-methoxycarbonyl- benzenesulfonamide are briefly warmed in 20 ml acetonitrile to obtain a homogeneous To get solution. With ice bath cooling, 0.94 g (0.01 mol) Acetyl chloride and 1.30 g (0.01 mol) of triethylamine were added. After 2 hours it will Mixture taken up in ethyl acetate and successively with 1 N  Hydrochloric acid and sat. Washed sodium chloride solution. After drying the organic phase over magnesium sulfate, the solvent is Distilled off rotary evaporator. After recrystallization of the residue Ethyl acetate / heptane gives 3.12 g (82%) of N-tert-butyl-5- (N-acetyl- hydroxylamino) -2-methoxycarbonyl-benzenesulfonamide. Mp: 168-169 ° C.

g) 5- (N-acetyl-hydroxylamino) -2-methoxycarbonyl-benzenesulfonamide

1.70 g (4.9 mmol) N-tert-butyl-5- (N-acetyl-hydroxylamino) -2-methoxycarbonyl- benzenesulfonamide are dissolved in 20 ml of trifluoroacetic acid. After 18 h at 25 ° C the volatile parts are distilled off under reduced pressure. This gives 1.48 g of 5-N- (acetyl-hydroxylamino) -2-methoxycarbonyl-benzenesulfonamide. Mp: 246-247 ° C.

h) 5- (N-acetyl-hydroxylamino) -N - [(dimethoxypyrimidin-2-yl) aminocarbony-l] -2- methoxycarbonyl-benzenesulfonamide (corresponds to example 192 in table 1)

To a mixture of 1.00 g (4.4 mmol) of 5- (N-acetyl-hydroxylamino) -2- methoxycarbonyl-benzenesulfonamide and 0.65 g (2.4 mmol) 4,6-dimethoxy-2- (phenoxycarbonylamino) pyrimidine in 50 ml acetonitrile are 0.8 ml DBU added. After stirring for 18 h, the solvent is on a rotary evaporator distilled off. The residue is taken up in water and with diethyl ether washed. The aqueous phase is acidified with concentrated hydrochloric acid (pH = 1). The colorless solid is filtered off and stirred with a little methanol. That so 5- (N-acetyl-hydroxylamino) -N - [(dimethoxypyrimidin-2-yl) -aminocarbony-1] obtained - 2-methoxycarbonyl-benzenesulfonamide (0.81 g, 79% of theory) has one Melting point of 205-208 ° C.  

The compounds described in Tables 1-3 are obtained in analogy Wise.

The following abbreviations are used in the tables:
Et = ethyl (C ₂ H ₅ )
Me = methyl (CH ₃ )
Ph = phenyl
c-Pr = cyclopropyl
n-Pr = n-propyl
i-Pr = i-propyl.

B. Examples of formulation

• a) A dusting agent is obtained by mixing 10 parts by weight of a compound of Formula (I) and 90 parts by weight of talc as an inert substance and mixed in one Crushed crushing mill.
• b) A water-dispersible, wettable powder is contained by 25 parts by weight of a compound of the formula (I), 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight ligninsulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as Mixes wetting and dispersing agents and grinds them in a pin mill.
• c) A dispersion concentrate which is easily dispersible in water is obtained by 20 parts by weight of a compound of formula (I) with 6 parts by weight Alkylphenol polyglycol ether (®Trition X 207), 3 parts by weight Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (Boiling range e.g. approx. 255 to above 277 ° C) mixes and in a friction ball mill ground to a fineness of less than 5 microns.
• d) An emulsifiable concentrate is obtained from 15 parts by weight of one Compound of formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethylated nonylphenol as an emulsifier.
• e) A water-dispersible granulate is obtained by:
  75 parts by weight of a compound of the formula (I),
  10 parts by weight of calcium lignosulfonic acid,
  5 parts by weight of sodium lauryl sulfate,
  3 parts by weight of polyvinyl alcohol and
  7 parts by weight of kaolin
  mixes, grinds on a pin mill and granulates the powder in a fluidized bed by spraying water as granulating liquid.
• f) A water-dispersible granulate is also obtained by
  25 parts by weight of a compound of the formula (I),
  5 parts by weight of 2,2′-dinaphthylmethane-6,6′-disulfonic acid sodium,
  2 parts by weight of oleoylmethyl tauric acid sodium,
  1 part by weight of polyvinyl alcohol,
  17 parts by weight of calcium carbonate and
  50 parts by weight of water
  homogenized on a colloid mill and pre-comminuted, then ground on a bead mill and the suspension thus obtained is atomized and dried in a spray tower using a single-component nozzle.

Biological examples 1. Pre-emergence weed action

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were grown in Plastic pots laid out in sandy loam and covered with earth. The in shape of wettable powders or emulsion concentrates Compounds according to the invention were then in the form of an aqueous suspension or Emulsion with a water application rate of the equivalent of 600 to 800 l / ha in different doses applied to the surface of the earth.

After the treatment, the pots were placed in the greenhouse and under good growing conditions for the weeds. The optical rating of the Plant damage or the emergence damage occurred after the emergence of the Test plants after a test period of 3 to 4 weeks compared to untreated controls. As the test results show, the  Compounds according to the invention have a good herbicidal pre-emergence activity a wide range of grasses and weeds. For example, they have Compounds of Examples 61, 192, 217, 256 and 262 from Table 1 are very good herbicidal activity against harmful plants such as Sinapis alba, Chrysanthemum segetum, Avena sativa, Stellaria media, Echinochloa crus-galli and Lolium multiflorum pre-emergence with an application rate of 0.3 kg and less Active ingredient per hectare.

2. Post-emergence weed action

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were found in Plastic pots laid out in sandy clay soil, covered with earth and in Greenhouse grown under good growing conditions. Three weeks after During sowing, the test plants were treated at the three-leaf stage.

The formulated according to the invention as wettable powder or as emulsion concentrates Compounds were made in different dosages with one Water application rate of the equivalent of 600 to 800 l / ha on the green Plant parts sprayed and after about 3 to 4 weeks standing time of the test plants in the greenhouse under optimal growth conditions the effect of Preparations rated optically in comparison to untreated controls. The Agents according to the invention have good herbicidal properties even after emergence Efficacy against a wide range of economically important grasses and Weeds on. For example, the compounds of Examples 61, 192, 217, 256 and 262 from Table 1 very good herbicidal activity against harmful plants such as Sinapis alba, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Chrysanthemum segetum and Avena sativa post-emergence in one Application rate of 0.3 kg and less active substance per hectare.

Claims (11)

1. Compounds of the formula (I) or their salts, wherein
R ¹ CO-R ⁵ , CO-OR ⁶ , CO-NR ⁷ R ⁸ , CS-R ⁹ , CS-OR ¹⁰ , CS-NR ⁷ R ⁸ , SO ₂ R ¹¹ , SOR ¹¹ , SO ₂ NR ⁷ R ⁸ , CO-COR ¹² ,
R ^{2 is} hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, the latter 3 radicals being independently unsubstituted or by one or more radicals from the group halogen, C ₁ - C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
R ³ halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy or C ₂ -C ₆ - Alkynyloxy, where the latter 6 radicals are independently unsubstituted or substituted by one or more radicals from the group halogen, C ₁ -C ₄ -alkoxy and alkylthio, or CO-CO-R ¹⁶ , CS-R ¹⁶ , CO-CO- OR ¹⁷ , CS-OR ¹⁷ , CS-SR ¹⁷ , CO-NR ¹⁸ R ¹⁹ , CS-NR ¹⁸ R ¹⁹ , NR ¹⁸ R ¹⁹ , SO ₂ NR ¹⁸ R ¹⁹ , Cyano, S (O) ₀ -R ²⁰ CO -R ¹⁶ , CO-OR ¹⁷ , NO ₂ or C (R ²¹ ) = NR ²² or
a 5- or 6-membered saturated, unsaturated or heteroaromatic heterocycle with up to 4 heteroatoms from the group N, O and S, which is unsubstituted or by one or more radicals from the group halogen, C ₁ - C ₄ -alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, CN, NO ₂ , CHO, (C ₁ -C ₄ alkyl) carbonyl and (C ₁ -C ₄ alkoxy) carbonyl is substituted and in which up to 2 C ring positions can be replaced by CO and up to two S hetero ring atoms by SO ₂ ,
R ^{4 is} hydrogen or C ₁ -C ₄ alkyl,
R ^{5 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ ₂ , or C ₃ -C ₇ cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ - Alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ ₂ , or benzyl, unsubstituted or substituted aryl or an unsubstituted or substituted heterocyclic radical,
R ^{6 is} C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy , C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted,
R ^{7 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₁ -C ₆ alkoxy, the latter 4 radicals being unsubstituted or by one or more radicals from the Halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and NR ¹³ R ^{14 are} substituted,
R ^{8 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ Alkoxy and C ₁ -C ₄ -alkylthio are substituted, or COR ²³ , CO ₂ R ²⁴ , CONR ¹³ R ¹⁴ or SO ₂ R ¹¹ ,
R ⁹ analogous to R ⁵ ,
R ¹⁰ analogous to R ⁶ ,
R ^{11 is} C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
R ^{12 is} hydrogen, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, the latter 2 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
the R ¹³ independently of one another are hydrogen or C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted, or COR ²⁵ or CO ₂ R ²⁶ ,
the R ¹⁴ independently of one another are hydrogen or C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
NR ¹⁵ ₂ independently of one another is a heterocyclic 3- to 7-membered ring which, in addition to the N atom, can also contain one or two further hetero ring atoms from the group N, O and S and is unsubstituted or substituted,
R ¹⁶ analogous to R ⁵ ,
R ^{17 is} hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted,
R ¹⁸ analogous to R ⁷ ,
R ¹⁹ analogous to R ⁸ ,
R ²⁰ analogous to R ¹¹ ,
R ^{21 is} hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ -Alkoxy and C ₁ -C ₄ alkylthio are substituted, or C ₁ -C ₄ alkoxy, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, CO-R ¹⁶ , CO ₂ -R ¹⁷ or SO ₂ -R ²⁰ ,
R ^{22 is} hydrogen, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, the latter 2 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted,
R ²³ analogous to R ⁹ ,
R ²⁴ analogous to R ¹⁰ ,
R ²⁵ analogous to R ⁹ ,
R ²⁶ analogous to R ¹⁰ ,
X, Y independently of one another are hydrogen, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy or C ₁ -C ₆ -alkylthio, the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted, or mono- or di- (C ₁ -C ₄ alkyl) amino, C ₃ - C ₆ cycloalkyl, C ₃ -C ₅ alkenyl , C ₃ -C ₆ alkynyl, C ₃ -C ₅ alkenyloxy or C ₃ -C ₅ alkynyloxy,
Z CH or N,
WHERE or S,
n 0, 1, 2 or 3 and
o 0, 1, 2 or 3
mean. 2. Compounds of formula (I) or their salts according to claim 1, characterized in that
R ¹ CO-R ⁵ , CO-OR ⁶ , CO-NR ⁷ R ⁸ , CS-R ⁹ , CS-NR ⁷ R ⁸ , SO ₂ R ¹¹ , SO ₂ NR ⁷ R ⁸ , CO-COR ¹² ,
R ^{2 is} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₅ alkenyl or C ₃ -C ₅ alkynyl, the latter 3 radicals being independently unsubstituted or by one or more halogen atoms or by one or two radicals from the Group C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio are substituted, or
R ³ halogen, C ₁ -C ₄ alkyl, C ₂ -C ₅ alkenyl, C ₂ -C ₅ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₅ alkenyloxy or C ₃ -C ₅ - Alkynyloxy, where the latter 6 radicals are independently unsubstituted or substituted by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ -alkoxy and alkylthio, or CO-CO-R ¹⁶ , CO-CO-OR ¹⁷ , CO-NR ¹⁸ R ¹⁹ , NR ¹⁸ R ¹⁹ , SO ₂ NR ¹⁸ R ¹⁹ , Cyano, S (O) ₀ -R ²⁰ , CO-R ¹⁶ , CO-OR ¹⁷ , NO ₂ or C (R ²¹ ) = NR ²² , or
a 5- or 6-membered saturated, unsaturated or heteroaromatic heterocycle with up to 3 heteroatoms from the group N, O and S, which is unsubstituted or by one or more radicals from the group halogen, C ₁ -C ₄ alkyl, such as methyl, C ₁ -C ₄ alkoxy, such as methoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, such as CF ₃ , CN, NO ₂ , CHO, (C ₁ -C ₄ alkyl) carbonyl, such as Acetyl, and (C ₁ -C ₄ alkoxy) carbonyl, such as CO ₂ CH ₃ , is substituted and in which up to 2 C ring positions can be replaced by CO and up to two S hetero ring atoms by SO ₂ ,
R ^{4 is} hydrogen or methyl or
R ^{5 is} hydrogen or C ₁ -C ₆ alkyl which is unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ^{15 is} substituted, or C ₃ -C ₇ cycloalkyl, benzyl, unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl, preferably H, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ Cycloalkyl, benzyl, phenyl, which is unsubstituted or substituted by one or more radicals from the group halogen, methoxy or methyl, or a 5- or 6-membered heteroaromatic radical which contains up to 4 heteroatoms from the group N, O and S and is unsubstituted or substituted by one or more radicals from the group halogen, NO ₂ , CN, CHO, COCH ₃ , CO ₂ CH ₃ , OCH ₃ and SCH ₃ , or
R ⁶ C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted, or
R ^{7 is} hydrogen or C ₁ -C ₆ alkyl which is unsubstituted or substituted by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio and NR ¹³ R ¹⁴ is, or
R ^{8 is} hydrogen or C ₁ -C ₄ alkyl which is unsubstituted or substituted by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy and C ₁ -C ₄ alkylthio, or COR ²³ , CO ₂ R ²⁴ or SO ₂ R ¹¹ or
R ⁹ analogous to R ⁵ or
R ¹⁰ analogous to R ⁶ or
R ^{11 is} C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl or
R ^{12 is} hydrogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ haloalkyl or
the R ¹³ independently of one another are hydrogen or C ₁ -C ₄ alkyl, COR ²⁵ or CO ₂ R ²⁶ or
the R ¹⁴ independently of one another hydrogen or C ₁ -C ₄ alkyl or
NR ¹⁵ ₂ independently of one another is a heterocyclic 3- to 7-membered ring which, in addition to the N atom, can also contain a further hetero ring atom from the group N, O and S and is unsubstituted or by radicals from the group C ₁ -C ₄ alkyl and oxo is substituted, or
R ¹⁶ analogous to R ⁵ ,
R ^{17 is} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, the latter 3 radicals being unsubstituted or by one or more halogen atoms or by one or two radicals from the group C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ _{2 are} substituted, preferably H, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ Alkenyl or C ₃ -C ₆ haloalkenyl,
R ¹⁸ analogous to R ⁷ ,
R ¹⁹ analogous to R ⁸ ,
R ²⁰ analogous to R ¹¹ or
R ^{21 is} hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino or
R ^{22 is} hydrogen, OH, NH ₂ , mono- or di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy or
R ²³ analogous to R ⁹ ,
R ²⁴ analogous to R ¹⁰ ,
R ²⁵ analogous to R ⁹ ,
R ²⁶ analogous to R ¹⁰ or
X, Y independently of one another are hydrogen, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, the latter 3 radicals being unsubstituted or substituted by one or more halogen atoms or mono- or di (C ₁ -C ₂ alkyl) amino or
n 0.1 or 2 or
o 0.1 or 2
mean or in which one or more of the meanings given above for the general radicals or indices R ¹ to o are present in combination in formula (I). 3. Compounds of formula (1) or their salts according to claim 1 or 2, characterized in that
R ¹ COR ⁵ , CO ₂ R ⁶ , CO-NR ⁷ R ⁸ , CO-CO-R ¹² , CS-NR ⁷ R ⁸ , SO ₂ R ¹¹ or SO ₂ -NR ⁷ R ⁸ or
R ^{2 is} hydrogen or C ₁ -C ₄ alkyl or
R ^{5 is} hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, such as CF ₃ , cyclopropyl, cyclopentyl, cyclohexyl, benzyl, phenyl, which is unsubstituted or by 1 to 3 radicals from the group halogen, methyl and methoxy is substituted, or thienyl, furyl or pyridyl, the above heteroaromatic radicals being unsubstituted or substituted by one or more radicals from the group halogen, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -alkoxy, or
R ⁶ C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl,
R ^{7 is} H, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl or
R ⁸ H, C ₁ -C ₄ alkyl, COCH ₃ , CO ₂ CH ₃ or CO ₂ C ₂ H ₅
mean or in which a combination of the above-mentioned preferred radicals is contained. 4. Compounds of formula (I) or their salts according to one of claims 1 to 3, characterized in that the group of formula N (OR ² ) R ^{1 is} in the 2-, 3-, 5- or 6-position on the phenyl ring and n represents 0 or 1. 5. A process for the preparation of the compounds of formula (I) or their salts according to claim 1, characterized in that

• a) a compound of the formula (II), with a heterocyclic carbamate of the formula (III), wherein R * denotes optionally substituted phenyl or (C ₁ -C ₄ ) alkyl, or
• b) provided that R ^{2 is} not hydrogen, a sulfonyl isocyanate of the formula (IV), with an amino heterocycle of the formula (V) implements.

6. Herbicidal or plant growth-regulating agents, characterized in that that there is at least one compound of formula (I) or its salt after a of claims 1 to 4 and formulation auxiliaries customary in crop protection contains. 7. Processes for controlling harmful plants or for regulating growth of plants, characterized in that an effective amount of at least one compound of formula (I) or its salts according to one of the Claims 1 to 4 on the harmful plants or plants, their plant seeds or applied the acreage. 8. Use of the compounds of formula (I) or their salts according to one of the Claims 1 to 4 as herbicides or plant growth regulators. 9. Compounds of the formula (II), wherein R ¹ , R ² , R ³ and n are as defined in formula (I) according to any one of claims 1 to 4. 10. A process for the preparation of the compounds of formula (II) according to claim 9, characterized in that

• a) compounds of the formula (VI) wherein R ¹ , R ² , R ³ and n are as defined in formula (II), with a strong acid or
• b) compounds of the formula (IXb) wherein R ¹ , R ² , R ³ and n are as defined in formula (II), subject to aminolysis.

11. Compounds of the formula (IV), wherein R ¹ , R ² , R ³ and n are as defined in any one of claims 1 to 4.