JPH08501542A - Hydroxylamino-phenylsulfonylureas, their manufacture and their use as herbicides and plant growth regulators - Google Patents

Abstract

  (57) [Summary] The sulfonylureas represented by formula (I) and salts thereof are suitable as selective herbicides for controlling weeds in the cultivation of useful plants. Intermediate products of formulas (II) and (IV) can be used for their preparation.

Description

Detailed Description of the Invention Hydroxylamino-phenylsulfonylureas, their preparation and herbicides and And their use as plant growth regulators   The present invention is a herbicide and a plant growth regulator, and in particular, broad leaves in cultivation of useful plants. To the technical field of herbicides for selective control of weeds and grass weeds Related.   Amino group or functionalized amino group having herbicidal and plant growth regulating properties Heterocyclic-substituted phenylsulfonylureas having phenyl on the phenyl ring are known (US National patent application No. 4,892,946; No. 4,981 509; European patent (See Japanese Patent Application Publication No. 169,815).   Furthermore, from WO-89 / 10921, the phenyl ring is 2,4-disubstituted or 2 , 4,6-trisubstituted and, above all, alkylamido at the 4-position. Or phenylsulfonylurea compounds which may have (substituted) hydroxylamino groups Herbs are known.   Surprisingly, we have now found that one unsubstituted or substituted hydroxy! Some heterocyclic-substituted phenylsulfonylureas with silamino functional groups are herbicides It has also been found that it is particularly suitable as a plant growth regulator.   The subject of the present invention is the formula (I) [In the above formula, R¹Is CO-R^Five, CO-OR⁶, CO-NR⁷ R⁸, CS-R⁹, CS-OR^Ten, CS-NR⁷ R⁸, SO₂ R¹¹, SOR¹¹, SO₂ NR⁷ R⁸Or CO- COR¹² Means R² Is hydrogen, C₁-C₆-Alkyl, C₂-C₆-Alkenyl or C₂-C₆-Alkynyl Where the three radicals listed below are, independently of one another, unsubstituted or Rogen, C₁-C_Four-Alkoxy and C₁-C_Four-Selected from the group consisting of alkylthio Substituted by one or more groups R³Is halogen, C₁-C₆-Alkyl, C₂-C₆-Alkenyl, C₂-C₆-Alkynyl , C₁-C₆-Alkoxy, C₂-C₆-Alkenyloxy or C₂-C₆-Arkiniro Xy (the six groups listed below are independently of each other unsubstituted or halogenated). N, C₁-C_Four-One selected from the group consisting of alkoxy and alkylthio; Are substituted by further groups), or CO-CO-R¹⁶, CS-R¹⁶ , CO- CO- OR¹⁷, CS-OR¹⁷, CS-SR¹⁷, CO-NR¹⁸R¹⁹, C S-NR¹⁸R¹⁹, NR¹⁸R¹⁹, SO₂ NR¹⁸R¹⁹, Cyano, S (O). -R²⁰, CO-R¹⁶, CO-OR¹⁷, NO₂Or C (R^{twenty one}) = N-R^{twenty two}Means Or having up to 4 heteroatoms selected from the group consisting of N, O and S 5- or 6-membered saturated or unsaturated, or heteroaromatic heterocycles (which are non-substituted Or halogen, C₁-C_Four-Alkyl, C₁-C_Four-Alkoxy, C₁-C_Four -Alkylthio, C₁-C_Four-Haloalkyl, CN- NO₂-CHO, (C₁-C_Four-Al Kill) carbonyl and (C₁-C_Four-Alkoxy) -carbonyl Substituted by one or more selected groups, and then up to two The position of the C- ring at is by CO and up to two S- heterocycle atoms are SO₂ To Therefore, it may be replaced) R^Four Is hydrogen or C₁-C_Four-Means alkyl, R^FiveIs hydrogen or C₁-C₆-Alkyl, C₂-C₆-Alkenyl or C₂-C₆-Archi Nyl (the three radicals mentioned herein are unsubstituted or halogen, C₁-C_Four-A Lucoxy, C₁-C_Four-Alkylthio, NR¹³R¹⁴And NR^Fifteen ₂Selected from the group consisting of Substituted by one or more selected groups) or C₃-C₇-Siku Lower alkyl (which may be unsubstituted or halogen, C₁-C_Four-Alkyl, C₁-C_Four -Alkoxy, C₁-C_Four-Alkylthio, NR¹³R¹⁴And NR^Fifteen ₂A group of Substituted by one or more groups selected from ), Or benzyl, unsubstituted or substituted aryl or unsubstituted or Means a substituted heterocyclic group, R⁶ Is C₁-C₆-Alkyl, C₂-C₆-Alkenyl or C₂-C₆-Alkynyl (here The three radicals listed under are unsubstituted or halogen, C₁-C_Four-Alkoxy, C₁-C_Four-Alkylthio, NR¹³R¹⁴And NR^Fifteen ₂1 selected from the group consisting of Substituted by one or more groups), R⁷ Is hydrogen or C₁-C₆-Alkyl, C₂-C₆-Alkenyl, C₂-C₆-Alkynyl Or C₁-C₆-Alkoxy (the four groups listed below are unsubstituted or halogenated N, C₁-C_Four-Alkoxy, C₁-C_Four-Alkylthio and NR¹³R¹⁴A group of Substituted by one or more groups selected from R⁸ Is hydrogen or C₁-C₆-Alkyl, C₂-C₆-Alkenyl or C₂-C₆-Archi Nyl (the three radicals mentioned herein are unsubstituted or halogen, C₁-C_Four-A Lucoxy and C₁-C_Four-One or it selected from the group consisting of alkylthio Substituted by any of the above groups), or COR^{twenty three}, CO₂ R^{twenty four}, CONR¹³ R¹⁴Or SO₂ R¹¹Means R⁹ Is R^Five Similarly, preferably hydrogen, C₁-C₆-Alkyl or C₃-C₆-Arque Nyl (the two radicals listed herein are unsubstituted or one or more By a halogen atom or C₁-C_Four-Alkoxy, alkylthio and NR¹³R¹⁴ Substituted by 1 or 2 groups selected from the group consisting of Then R^TenIs R⁶And preferably C₁-C₆-Alkyl or C₃-C₆-Alkenyl ( The two radicals mentioned here below may be unsubstituted or one or more halogens. By atom or C₁-C_Four-Alkoxy and C₁-C_Four-Consisting of alkylthio Substituted by 1 or 2 groups selected from the group), R¹¹Is C₁-C₆-Alkyl, C₂-C₆-Alkenyl or C₂-C₆-Alkynyl (here The three radicals listed under are unsubstituted or halogen, C₁-C_Four-Alkoxy And C₁-C_Four-One or it selected from the group consisting of alkylthio Substituted by the above groups), R¹²Is hydrogen, OH, NH₂, Mono- or di- (C₁-C_Four-Alkyl) -amino, C₁ -C_Four-Alkyl or C₁-C_Four-Alkoxy (the last two groups mentioned here are Or halogen, C₁-C_Four-Alkoxy and C₁-C_Four-Alkylthio Substituted by one or more groups selected from the group Taste, R¹³Independently of one another, hydrogen or C₁-C₆-Alkyl, C₃-C₆-Alkenyl again Is C₃-C₆-Alkynyl (the three radicals mentioned here being unsubstituted or halo Gen, C₁-C_Four-Alkoxy and C₁-C_Four-Selected from the group consisting of alkylthio Substituted by one or more groups), or COR^{twenty five}Or C O₂ R²⁶Means R¹⁴Independently of one another, hydrogen or C₁-C₆-Alkyl, C₃-C₆-Alkenyl again Is C₃-C₆-Alkynyl (the last three radicals mentioned here are unsubstituted or Rogen, C₁-C_Four-Alkoxy and C₁-C_Four-Selected from the group consisting of alkylthio Substituted by one or more groups selected from NR ¹⁵ ₂Are independently of each other, in addition to the N- atom, a group consisting of N, O and S May have one or two other heterocyclic atoms selected from and are unsubstituted Or a substituted 3- to 7-membered heterocyclic ring, R16Is R^FiveMeans a group similar to R¹⁷Is hydrogen, C₁-C₆-Alkyl, C₂-C₆-Alkyl or C₂-C₆-Alkynyl ( The three radicals mentioned here are unsubstituted or halogen, C₁-C_Four-Arukoki Si, C₁-C_Four-Alkylthio, NR¹³R¹⁴And NR^Fifteen ₂Selected from the group consisting of Substituted by one or more groups) R¹⁸Is R⁷Means a group similar to R¹⁹Is R⁸Means a group similar to R²⁰Is R¹¹Means a group similar to R^{twenty one}Is hydrogen or C₁-C₆-Alkyl, C₂-C₆-Alkenyl or C₂-C₆-Archi Nyl (the three radicals mentioned here are unsubstituted or halogen, C₁-C_Four-A Lucoxy and C₁-C_Four-One selected from the group consisting of alkylthio Or substituted by more groups), or C₁-C_Four-Alkoxy, O H, NH₂, Mono- or di- (C₁-C_Four-Alkyl) -amino, CO-R¹⁶, CO-R¹⁷Or SO₂-R²⁰Means R^{twenty two}Is hydrogen, OH, NH₂, Mono- or di- (C₁-C_Four-Alkyl) -amino, C₁ -C_Four-Alkyl or C₁-C_Four-Alkoxy (the last two groups listed here are Or halogen, C₁-C_Four-Alkoxy and C₁-C_Four-Alkylthio Substituted by one or more groups selected from the group Taste, R^{twenty three}Is R⁹Means a group similar to R^{twenty four}Is the group R^TenMeans a group similar to R^{twenty five}Is the group R⁹Means a group similar to R²⁶Is the group R^TenMeans a group similar to X and Y are independently of each other hydrogen, halogen, C₁-C₆-Alkyl, C₁-C₆-A Lucoxy or C₁-C₆-Alkylthio (the last three groups mentioned here are unsubstituted Present or halogen, C₁-C_Four-Alkoxy and C₁-C_Four-More than alkylthio Substituted by one or more groups selected from the group Mono-or di- (C₁-C_Four-Alkyl) amino, C₃-C₆-Cycloalkyl, C₃-C_Five -Alkenyl, C₃-C₆-Alkynyl, C₃-C_Five-Alkenyloxy or C₃-C_Five- Means alkynyloxy, Z means CH or N, W means O or S, n means 0, 1, 2 or 3; and o means 0, 1, 2, or 3] Is a compound represented by or a salt thereof.   In formula (I) and below, the groups alkyl, alkoxy, haloalkyl, halo Alkoxy, alkylamino and alkylthio and the corresponding unsaturated, And / or groups substituted in the carbon skeleton are linear or branched chains, respectively. It can be a state. Unless otherwise specified, there is no 1 carbon skeleton in these groups. Has 4 C atoms and, in the case of unsaturated groups, 2 to 4 C atoms Preferably. Alkyl groups are compound groups such as alkoxy, haloalkyl and others. In a synthetic sense, for example, methyl, ethyl, n- or i-propyl, n- , I-, t- or 2-butyl, pentyl, hexyl such as n-hexyl, i- Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1- Means methylhexyl and 1,4-dimethylpentyl: alkenyl and a A alkynyl group has the meaning of a possible unsaturated group corresponding to an alkyl group, Is, for example, allyl, 1-methylpropenyl- (2), 2-methylpropenyl- (2) , Butenyl- (2), butenyl- (3), 1-methylbutenyl- (3) and 1-me Tilbutenyl- (2); alkynyl is, for example, propargyl, butynyl- It means (2), butynyl- (3), 1-methylbutynyl- (3).   Halogen means fluorine, chlorine, bromine or iodine. Haloalkyl, ha Ralkenyl and haloalkynyl are halogen, preferably fluorine, chlorine and And / or bromine, especially fluorine or chlorine, partially or completely substituted Alkyl, alkenyl or alkynyl, eg CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl CCl₃, CHCl₂, CH₂CH₂Means Cl : Haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O , OCH₂CF₃And OCH₂CH₂It is Cl. The same applies to haloalkenyl And other halogen-substituted radicals.   Aryl is a monocyclic, bicyclic or polycyclic aromatic system such as phenyl, naphthyl. , Tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl And the like, preferably phenyl, aryloxy is preferably Or, it means an oxy group corresponding to the above aryl group, particularly phenoxy.   Heteroaryl or heteroaromatic groups have at least one ring which is either one or Mono-, bi- or polycyclic aromatic systems having more than one heteroatom, eg pyridinium , Pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxa Zolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, and also bicyclic Or polycyclic aromatic or araliphatic compounds such as quinolinyl, benzoxa It means zolyl and the like.   Substituted aryl, heteroaryl, phenyl, benzyl or aromatic moieties Substituted bicyclic groups having, for example, are derived from an unsubstituted basic skeleton. Substituents, in which case these substituents are, for example, halogen, alkyl. , Haloalkyl, alkoxy, haloalkoxy, alkylthio, hydroxy, a Mino, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, formyl , Carbamoyl, mono- and dialkylaminocarbonyl, mono- and dial Selected from the group consisting of: kylamino, alkylsulfinyl and alkylsulfonyl. Means one or more selected groups, preferably 1, 2 or 3 groups, And in the case of radicals having C atoms, 1 to 4 C atoms, in particular 1 or 2 C atoms Those having a C atom are preferred. Generally, halogens such as fluorine and Chlorine, C₁-C_Four-Alkyl, preferably methyl or ethyl, C₁-C_Four-Halo Archi , Preferably trifluoromethyl, C₁-C_Four-Alkoxy, preferably methoxy Or ethoxy, C₁-C_Four-From the group consisting of haloalkoxy, nitro and cyano Selected substituents are preferred. At that time, particularly preferred are the methyl substituent and methyl substituent. Toxic and chlorine.   Optionally substituted phenyl is, for example, unsubstituted or halogen, C₁-C_Four-Alkyl, C₁-C_Four-Alkoxy, C₁-C_Four-Halogenalkyl, C₁-C_Four- Identical or different selected from the group consisting of halogenalkoxy and nitro Mono-substituted or poly-substituted, preferably tri-substituted by a group Phenyl, such as o-, m- and p-tolyl, dimethylphenyl, 2- 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoromethyl- and -Trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichloro Lophenyl, o-, m- and p-methoxyphenyl.   Heterocyclic groups are preferably 5- or 6-membered, heteroaromatic, saturated or unsaturated. Saturated and having 1, 2 or 3 heteroatoms, preferably N, O or And S selected from the group consisting of: The above groups are benzo-fused May be. Oxiranyl, pyrrolidyl, piperidyl, dioxolanyl, pyrazo Ril, morpholyl, furyl, tetrahydrofuryl, indolyl, quinolinyl, phenyl Rimidyl, azepinyl, imidazolyl, triaryl, thienyl and oxazo Groups such as ril are important.   The subject of the invention is also all stereoisomers of the formula (I) and their It is a mixture. Those compounds represented by the formula (I) are different from each other in the general formula (I). Also has one or more asymmetric carbon atoms or double bonds not shown To do. Their identification, such as enantiomers, diastereomers, Z- and E isomers The possible stereoisomers defined by the spatial shape of are all encompassed by formula (I) And obtained by conventional methods from a mixture of the above stereoisomers or Also produced by stereoselective reactions combined with the use of stereochemically pure starting materials Can be done.   The compound represented by the formula (I) is -SO₂-NH group hydrogen or other acidic hydrogen atom Substituted (eg from COOH or the like) by agriculturally suitable cations It can form salts. These salts are, for example, metal salts, especially alkali metal salts (for example, , Na- or K-salt) or alkaline earth metal salt, or ammonium salt Alternatively, it is a salt with an organic amine. Similarly, salt formation may occur, for example, with amino and alkenyl. It is also done by the addition of an acid to a basic group such as ruamino. In this case, Acids are strong inorganic and organic acids such as HCl, HBr, H₂SO_FourOr HNO₃ Is.   Higher herbicidal activity, better selectivity and / or better manufacturability For reasons of performance, among other things, of particular importance is in formula (I): R¹Is CO-R^Five, CO-OR⁶, CO-NR⁷R⁸, CS-R⁹, CS-NR⁷R⁸, SO₂ R¹¹, SO₂NR⁷R⁸Or CO-COR¹²Means or R²Is hydrogen, C₁-C₆-Alkyl, C₃-C_Five-Alkenyl or C₃-C_Five-Alkynyl (The three last-mentioned groups are independently of one another unsubstituted or one or more. Or more halogen atoms, or C₁-C_Four-Alkoxy and C₁-C_Four -Substituted by 1 or 2 groups selected from the group consisting of alkylthio Meaning) or R³Is halogen, C₁-C_Four-Alkyl, C₂-C_Five-Alkenyl, C₂-C_Five-Alkynyl , C₁-C_Four-Alkoxy, C₃-C_Five-Alkenyloxy or C₃-C_Five-Arkiniro Xy (the last six groups listed here are independently of one another unsubstituted or By one or more halogen atoms, or C₁-C_Four-Alkoxy and Substituted by 1 or 2 groups selected from the group consisting of alkylthio ), Or CO-CO-R¹⁶, CO-CO-OR¹⁷, CO-NR¹⁸R¹⁹, NR¹⁸R^{1 9} , SO₂NR¹⁸R¹⁹, Cyano, S (O)_o-R²⁰, CO-R¹⁶, CO-OR¹⁷, NO₂ Or C (R^{twenty one}) = N-R^{twenty two}Or a group consisting of N, O and S 5- or 6-membered saturated or unsaturated having up to 3 heteroatoms selected from Or of a heteroaromatic heterocycle (which may be unsubstituted or halogen, C₁-C_Four -Alkyl, eg methyl, C₁-C_Four-Alkoxy, eg methoxy, C₁-C_Four-A Luquilcio, C₁-C_Four-Haloalkyl, eg CF₃, CN, NO₂, CHO, (C₁ -C_Four-Alkyl) -carbonyl, such as acetyl, and (C₁-C_Four-Alkoxy ) -Carbonyl, eg CO₂CH₃One or more selected from the group consisting of Is substituted by groups of and the positions of up to two C-ring atoms are CO And up to two S-heterocycle atoms are SO₂Even if replaced by Good) or R^FourMeans hydrogen or methyl R^FiveIs hydrogen or C₁-C₆-Alkyl (which may be unsubstituted or C₁-C_Four-Al Coxy, C₁-C_Four-Alkylthio, NR¹³R¹⁴And NR^Fifteen ₂Select from the group consisting of Substituted by one or two groups), or C₃-C₇-Cycloal Kill, benzyl, unsubstituted or substituted aryl or unsubstituted or substituted-heteroa Reel; preferably H, C₁-C₆-Alkyl, C₁-C₆-Haloalkyl, C₃-C₆-Shi Chloroalkyl, benzyl, phenyl (which may be unsubstituted or halogen, methoxy or Or one or more, preferably 3 selected from the group consisting of Substituted by a group) or a 5- or 6-membered heteroaromatic group (which is It has up to 4 heteroatoms selected from the group consisting of N, O and S Unsubstituted or halogen, NO₂, CN, CHO, COCH₃, CO₂C H₃, OCH₃And SCH₃One or more groups selected from the group consisting of Has been replaced by) or R⁶Is C₁-C₆-Alkyl, C₃-C₆-Alkenyl or C₃-C₆-Alkynyl (here The last three groups in 1 are unsubstituted or one or more halogen Atom, or C₁-C_Four-Alkoxy, C₁-C_Four-Alkylthio, NR¹³R¹⁴ And NR^Fifteen ₂Substituted by one or two groups selected from the group consisting of ), Preferably C₁-C₆-Alkyl, C₁-C₆-Haloalkyl, C₃-C₆-Arque Nil or C₃-C₆-Means haloalkenyl, or R⁷Is hydrogen or C₁-C₆-Alkyl (which may be unsubstituted or one or More than one halogen atom, or C₁-C_Four-Alkoxy, C₁-C_Four-Alkyl Thio and NR¹³R¹⁴Substituted by 1 or 2 groups selected from the group consisting of ), Preferably H, C₁-C_Four-Alkyl or C₁-C_Four-Haloalkyl Means or R⁸Is hydrogen or C₁-C_Four-Alkyl (which may be unsubstituted or one or More halogen atoms or C₁-C_Four-Alkoxy and C₁-C_Four-Alkylthio Substituted by 1 or 2 groups selected from the group consisting of OR^{twenty three}, CO₂R^{twenty four}Or SO₂R¹¹, Preferably H, CH₃, C₂H_Five, CHO, COCH₃Or CO₂CH₃Or means R⁹Is R^FiveAnd preferably hydrogen, C₁-C₆-Alkyl or C₁-C₆-Halo Means alkyl, or R^TenIs R⁶And preferably C₁-C_Four-Alkyl or C₁-C_Four-Haloal Means kill or R¹¹Is C₁-C_Four-Alkyl or C₁-C_Four-Means haloalkyl, or R¹²Is hydrogen, OH, C₁-C_Four-Alkyl, C₁-C_Four-Alkoxy or C₁-C_Four-Ha Lower alkyl, preferably H or C₁-C_Four-Alkyl, or R¹³Independently of each other hydrogen or C₁-C_Four-Alkyl, COR^{twenty five}Or CO₂R²⁶ , Preferably H, CH₃, C₂H_Five, CHO, COCH₃, CO-OCH₃Or CO -OC₂H_FiveOr means R¹⁴Independently of each other hydrogen or C₁-C_Four-Alkyl, preferably H, CH₃Also Is C₂H_FiveOr means NR^Fifteen ₂Independently of one another, in addition to the N atom, also from the group consisting of N, O and S It may have other heterocyclic atoms selected and is unsubstituted or C₁- C_Four-One or more selected from the group consisting of alkyl and oxo 3- to 7-membered heterocycles substituted by groups, eg formula A₁Through A₉ Or a heterocyclic group represented by R¹⁶Is R^FiveMeans a group similar to R¹⁷Is hydrogen, C₁-C₆-Alkyl, C₃-C₆-Alkenyl, C₃-C₆-Alkynyl The three radicals listed below are unsubstituted or one or more halogens. By atom or C₁-C_Four-Alkoxy, C₁-C_Four-Alkylthio, NR¹³R¹⁴ And NR^Fifteen ₂Substituted by one or two groups selected from the group consisting of ), Preferably H, C₁-C₆-Alkyl, C₁-C₆-Haloalkyl, C₃-C₆-A Lucenyl or C₃-C₆-Means haloalkenyl, R¹⁸Is R⁷Means a group similar to R¹⁹Is R⁸Means a group similar to R²⁰Is R¹¹Means a group similar to R^{twenty one}Is hydrogen, C₁-C_Four-Alkyl, C₁-C_Four-Haloalkyl, C₁-C_Four-Alkoxy, OH, NH₂, Mono- or di- (C₁-C_Four-Alkyl) -amino, preferably H, Tyl, ethyl, n- or i-propyl, methoxy, ethoxy, hydroxy, Means amino, methylamino or dimethylamino, R^{twenty two}Is hydrogen, OH, NH₂, Mono- or di- (C₁-C_Four-Alkyl) -amino, C₁- C_Four-Alkyl or C₁-C_Four-Alkoxy, preferably H, OH, NH₂, NHC H₃, N (CH₃)₂, CH₃Or OCH₃Means R^{twenty three}Is R⁹Means a group similar to R^{twenty four}Is R^TenMeans a group similar to R^{twenty five}Is R⁹Means a group similar to R²⁶Is R^TenMeans a group similar to X and Y are independently of each other hydrogen, halogen, C₁-C_Four-Alkyl, C₁-C_Four-Al Coxy or C₁-C_Four-Alkylthio (the three radicals mentioned here are unsubstituted) Or substituted by one or more halogen atoms), or Mono-or di- (C₁-C₂-Alkyl) -amino, preferably of the groups X and Y One is CH₃, C₂H_Five, OCH₃Or OC₂H_FiveAnd the other group is CH₃ , C₂H_Five, OCH₃, OC₂H_Five, Cl, CF₃, OCF₃C, OCF₂H, N (CH₃ )₂, NHCH₃Or N (C₂H_Five)₂And Z means CH or N, W means O or S, preferably O, n means 0, 1 or 2, o means 0, 1 or 2 A compound or a salt thereof, or, preferably, a general group in formula (I) Or code R¹To a combination of two or more of the preferred ones of the groups o to o. Is a compound of formula (I) or a salt thereof.   In formula (I), R¹Is COR^Five, CO₂R⁶, CO-NR⁷R⁸, CO-CO-R¹², CS-NR⁷R⁸, S O₂R¹¹Or SO₂-NR⁷R⁸And / or R²Is hydrogen or C₁-C_Four-Alkyl, preferably H, CH₃, C₂H_Five, N- or i-C₃H₇, Especially means H The compounds or their salts are preferred.   In formula (I), R^FiveIs hydrogen, C₁-C_Four-Alkyl, C₁-C_Four-Haloalkyl, eg CF₃, Cyclop Ropil, cyclopentyl, cyclohexyl, benzyl, phenyl (which is unsubstituted Or halogen, preferably fluorine or chlorine, methyl and methoxy Substituted by 1 to 3 groups selected from the group consisting of), or Thienyl, furyl or pyridyl (wherein the above heteroaromatic group is unsubstituted Or halogen, C₁-C_Four-Alkyl and C₁-C_Four-From the group consisting of alkoxy Substituted by one or more selected groups) or Or R⁶Is C₁-C_Four-Alkyl, C₁-C_Four-Haloalkyl, C₃-C₆-Alkenyl or C₃ -C_Four-Means alkynyl, R⁷Is H, C₁-C_Four-Alkyl or C₁-C_Four-Means haloalkyl or R⁸Is H, C₁-C_Four-Alkyl, COCH₃, CO₂CH₃Or CO₂CH_FiveMeans Or having a combination of the above preferred groups, The compounds according to the invention of the formula (I) above are also preferred. Preferred compounds also have the formula N (OR²) R¹The group represented by Means at the 2-, 3-, 5- or 6-position of the enyl ring and n is 0 or 1 A compound according to the present invention represented by formula (1) or a salt thereof.   Particularly preferred is the formula N (OR²) R¹The group represented by is at the 2-position of the phenyl ring. Is present and n is 0 or 1, or   Formula N (OR²) R¹A group represented by is present in the 5-position (or 3-position) of the phenyl ring , N means 0 or 1 and the radical R³Is the 2-position (or 6-position) of the phenyl ring Is present in.   Particularly preferred is R³Is the formula CO-OR¹⁷The group represented by 2- is a phenyl group Or compounds in which the N is 1 at the 6-position.   Another subject of the invention is the compounds according to the invention of the formula (I) or To produce these salts, a) Formula (II) The compound represented by the formula (III) (In the above formula, R^*Is an optionally substituted phenyl or (C₁-C_Four) Alkyl Or a heterocyclic carbamate represented by b) R²Is different from hydrogen, formula (IV) A sulfonyl isocyanate represented by the formula (V) Or react with an amino heterocycle represented by or c) a compound represented by the formula (II) is represented by the formula (X) Is reacted with (thio) isocyanate represented by the formula (1) in the presence of a base. In II) to (V) and (X) the group R¹Through R^FourAnd n are the same as in formula (I) As defined above, and in methods a) and b) above, first in formula (I) A compound represented by the above formula (I), characterized in that a compound in which W = O is obtained Alternatively, it is a method for producing a salt thereof.   The reaction of the compounds of formula (II) and (III) is preferably, for example dichloromethane 0 in an inert organic solvent, such as acetonitrile, acetonitrile, dioxane or THF. A basic catalyst at a temperature between 0 ° C, preferably 20 ° C and the boiling point of the solvent. Be done. In that case, as the base, for example, an organic amine base, for example, R^* = (Substituted) phenyl (see European Patent Application Publication No. 44807) ) 1,8-diazabicyclo- [5.4.0] undecene- (7) (DBU) Used, or especially R^*= Alkyl (European Patent Application Publication No. 16 6516) Trimethyl aluminum or triethyl aluminum is used Is done.   Sulfonamide (II) is a new compound. These compounds and their production Methods are also the subject of the present invention.   The compound represented by the formula (II) is, for example, a compound represented by the formula (VI) It is obtained by starting from the compound represented by and reacting with a strong acid.   As the strong acid, for example, H₂SO_FourOr a mineral acid such as HCl or trifluoro A strong organic acid such as acetic acid is used. Cleavage of the tert-butyl protecting group can be accomplished, for example, by- A temperature from 20 ° C. to the respective reflux temperature of the reaction mixture, eg 0 ° C. to 40 It is carried out at ° C. The reaction can be in bulk or for example dichloromethane or It can be carried out in an inert solvent such as trichloromethane.   R²A compound of formula (VI) in which is not hydrogen (hydroxylamine ether) is an example For example, R²Is similar to the known O-alkylation reaction from a compound of formula (VI) where The alkylating agent is potassium carbonate or sodium hydride. In the presence of a base such as DMF (dimethylformamide) or DM SO (dimethyl sulfoxide), THF (tetrahydrofuran) or 1,2- Used in an inert solvent such as dimethoxyethane. At that time, alkyl As the agent, dialkyl sulfate or the corresponding alkyl halide is preferable. [Houben-Weyl-Claman ed. "Methoden der Organischen Hemmy 4th Edition, EXVI / a Volume 271, page 271 Taime Publishing Company, 1990 (Houben-W eyl-Klamann, “Methoden der organischen Chemie, 4. Aufl. Bd. EXVI / aS. 271, Thieme Verlag Stuttgart, 1990)].   Substituent R¹Introduction of R¹= R²= H, the hydroxylamine aromatic compound ( VI) and corresponding electrophiles such as acid chlorides, oxyhydrides, isocyanates and the like. And a reaction with thioisocyanate [Houben-Weyl-Klama Ed. "Methoden der Organissien Chemie" 4th edition EXVIa / 1   199 pages or less, published by Taime Publishing Company, 1990 (Houben-Weyl-Klamann, “M ethoden der organischen Chemie ”, 4 Aulf. Bd. EXla / 1 S. 199ff., ThiemeVe rlag Sttugart, 1990)].   R¹= R²= H, the hydroxylamine derivative of formula (VI) has the corresponding nitro Starting from compound (VII), eg in ethanol buffered with ammonium chloride For example, it can be obtained by reduction with zinc powder. Other for this conversion Suitable reducing agents include, for example, the following: platinum / tributyl phosphite / 4-Dimethylamino-pyridine, hydrazine hydrate or hydrogen / Ranenicke / Ethanol, hydrazine hydrate / rhodium, sodium dihydrogen phosphate / Palladium and others [For that, Houben-Weyl-Claman, ed., “Metthoden” ・ Dare Organisienne Hemmy ", 4th edition, EXVIa / 1, p. 49 et seq. , Taime Publisher, 1990 (Houben-Weyl-Klamann, “Methoden der organi schen Chemie ”, 4 .Aufl. Bd. EXVIa / 1 S.49ff., Thieme Verla g Stuttgart 1990)].   The above nitro compound represented by the formula (VII) is the corresponding nitrobenzenesulfon. It can be produced from acid (VIII).   First, the conversion of the sulfo group of compound (VIII) to sulfonyl chloride can be performed by Phosphorus oxychloride or an inert solvent such as nitrile and / or sulfolane. Or the standard reaction such as the reaction of thionyl chloride with the corresponding potassium salt of the sulfonic acid. Method or by heating to the reflux temperature in bulk. Uben-Weyl-Claman ed "Tomaden der Organissien Chemie", Fourth Edition, EXI / 2, pages 1067-1073, published by Theime Publishing Co. in 1985 (Ho uben-Weyl-Klamann, “Methoden der organischen Chemie”, 4. Aufl. Bd. E XI / 2, S.I. 1067-1073, Thieme Verlag Stuttgart, 1985) See).   Sulfones from sulfonyl chlorides and tert-butylamine in ethanol The formation of the amide gives compound (VII) in excellent yield (WO89 / 10). (See similar reaction in 921).   Or R¹And R²Sulfonamides of formula II when H is other than H have the formula (IX b) Obtained by aminolysis of the corresponding sulfonyl chloride represented by Sulfonyl is obtained by the standard method (compound (VII) above from sulfonic acid (IXa). (See the reaction of compound (VIII)) for   The compound (IXa) is the same as nitrobenzenesulfonic acid (VIII) Order, ie, 1) Similar to the reduction of compound (VII) as described in the preparation of compound (VI) Return to 2) N-acylated and 3) O-acylation, Obtained by   The above starting compounds of formula (VIII) or sulfonyl chlorides derived therefrom are , A known or commercially available compound, or in a simple manner For example, it can be manufactured by the following method: -Nitration [Houben-Weill-Muller, "Methoden der Organissi" En Hemmy ", 4th edition, Volume X / 1, pages 463 et seq., Theme Publishing Company, 1971. Published (Houben-Weyl-Mueller, “Methoden der organischen Chemie”, 4. Aufl. B d X / 1 S. 463ff., Thieme Verlag Stuttgart, 1971)), -Sulfonation [Houben-Weyl-Klamann ed., "Methoden der Organics" "En-Hemi", 4th edition, EXI / 2, pages 1055 and below, 1987 5 years (Houben-Weyl-Klamann, “Methoden der organischen Chemie, Bd. EXI / 2 , S. 1055ff., Thieme Verlag Stuttgart 1985; Houben-Weil-Muller, "Methoden der Organissien Chemie", 4th Edition, Volume IX, pp. 435 Below, Theme Publisher 1955 (Houben-Weyl-Mueller, “Methoden der organischen Chemie”, 4. Aufl. Bd. IX S. 435ff., Thieme V erlag Stuttgart, 1955)), -Sulfochlorination [Houben-Weyl-Claman, ed., "Methoden der Organik" Cien Hemmy, "4th edition, EXI / 2, pp. 1067 and below, Time Publisher 19 1985 (Houben-Weyl-Klamann, “Methoden der organischen Chemie”, 4. A ufl. Bd. EXI / 2, S. 1067ff., Thieme Verlag Stuttgart, 1985); Houben-wa Ill-Muller ed., "Methoden der Organissien Chemie", 4th edition. Volume IX, pages 563 et seq., Published by Theime Publisher, 1955 (Houben-Weyl-Mueller, “Methoden der organischen Chemie”, 4. Aufl. Bd. IX, S. 563ff., Thieme Verlag Stuttgart 1955)], The radical R, for example by halogenation³Introduction [Houben-Weyl-Muller Edition "Meteau Den der Organissien Chemie ", 4th edition, Volume V / 3, pages 213 and below, Published by Time Publishing Company, 1962 (Houben-Weyl-Mueller, “Methoden der organisc hen Chemie ”, 4. Aufl. Bd. V / 3, S. 213ff., Thieme Verlag Stuttgart, 1962 ); Houben-Weil-Muller, “Mettoden der Organissien Hemi” -", 4th Edition, Volume V / 3, pages 556-561 and 845-853, Tee Published by Me Publisher, 1962 (Houben-Weyl-Mueller, “Methoden der organischen Ch emie ”, 4. Aufl. Bd V / 3, S. 556-561 und 845-853, Thieme Verlag Stuttgart , 1962); Houben-Weil-Muller eds. "Methoden der Organissien" -Hemi ", 4th edition, V / 4, pages 233-299 and 437-447. Ime publisher 1960 (Houben-Weyl-Mueller, “Methoden der organischen  Chemie ”, 4. Aufl. Bd V / 4, S. 557-593 und 639-647, Thieme Verlag Stuttga rt, 1960) or Alkylation (Gie Oller, Friedel-Crafts-Ke. Mistry ", Willie-Interscience, 1973 (G.A. Olah,“ Friedel- Craft-Chemistry ”, Wiley-lnterscience, New York, 1973), -Or a derivatization of an already existing third substituent, such as an alkyl group (R³)of Oxidation to carboxylic acid and subsequent esterification (R³= CO₂-Alkyl) Ruhou-Weil-Farbe ed. "Methoden der Organissienho "Hemmy", 4th edition, EV / 1 volume, 1985, 199-202, Teime Publishing Co. Page and references cited therein (Houben-Weyl-Falbe: “Methoden der organisc hen Chemie ”, 4. Aufl. Bd. EV / 1, Thieme Verlag Stuttgart, 1985, S. 199-2 02)].   The carbamate of formula (III) required for the reaction of compound (II) according to method a) is: Manufactured by a known method or a similar known method (Europe). See Patent Application Publication No. 70804 or US Pat. No. 4,480,101).   The compounds of formulas (IV) and (V) which may be used in process b) also have the formulas above. Commonly known from (III) and (VIII) compounds and their precursors Can be manufactured by a similar method or a similar method.   R³A phenylsulfonylisocyanate of formula (IV) in which is other than H: For example, a method similar to that described in European Patent Application Publication No. 184,385 may be used. Can be produced from compound (II) by using, for example, phosgene.   The reaction of compound (IV) with aminoheterocycle (V) is preferably, for example, diox An inert aprotic solvent such as sun, acetonitrile or tetrahydrofuran It is carried out in a medium at a temperature between 0 ° C. and the boiling point of the solvent.   The (thio) isocyanate of formula (X) can be prepared by methods known in the literature. (European Patent Application Publication No. 232067A and European Patent Application Publication No. 166, 516).   The reaction of the compound of formula (X) with the sulfonamide of formula (II) can be performed, for example, by triethyl In the presence of a suitable base such as an amine or potassium carbonate, for example acetone or Is -10 ° C to 10 ° C in an inert aprotic solvent such as acetonitrile. It is carried out at a temperature of 0 ° C., preferably 20 to 80 ° C.   The salts of the compounds of formula (I) are preferably at a temperature of 0 to 100 ° C, for example Water, methanol, acetone, dichloromethane, tetrahydrafuran, toluene Alternatively, it is prepared in an inert solvent such as heptane.   Suitable bases for the preparation of the salts according to the invention described above are, for example, potassium carbonate. Una carbonate of alkali metal, alkali metal and alkaline earth metal hydroxides, Suitable amine salts such as monia or triethylamine or ethanolamine Group. Acids for salt formation include, for example, HCl, HBr, H₂SO_FourOr HNO₃Is preferred.   The term "inert solvent" used in each of the above methods refers to specific reaction conditions. Inert under, but need not be inactive under any reaction conditions It means such a solvent.   The compounds of formula (I) or their salts according to the invention have a wide range of Shows excellent herbicidal activity against economically important monocotyledonous and dicotyledonous harmful plants . Difficult to control germination from rhizomes, root fragments or other perennial organs Various perennial weeds are also effectively controlled by the active substances according to the invention. So In these cases, these active substances may be treated before seeding, before germination or after germination. It is not important that they have been applied. By the compound according to the invention Some representative examples of monocotyledonous and dicotyledonous weed groups that can be controlled are listed as individual examples. List, but by listing it means limiting to a particular species Not something.   Weeds belonging to monocotyledons include, for example, oats (Av ena), Dokumugi (Lolium), Sparrow (Alopecurus), Reed (Phalar) is), barnyardgrass (Echinochloa), crabgrass (Digitoria), green locust (Setaria) And the genus Cyperus, and from the perennial genus, pyron), cynodon (Cynodon), cypress (Imperata), sorghum (Sorghum) It also effectively controls the perennial Cyperus.   In the case of dicotyledon weed species, the range of action is, for example, Galm. Millet (Viola), Scutellaria baicalensis (Veronica), Heartwort (Lamium), Stellari (Stellari) a), Amaranthus, Mustard (Sinapis), Bindweed (Ipomoea), Kamil Le (Matricaria), Abutilon (Abutilon) and Fern (Sida) and perennial weeds Convolvulus (Convolvulus), Leopard fox thistle (Cirsium), It extends to sorrel (Rumex) and mugwort (Artemisia).   For example, Urikawa (Saglttarla), which occurs under specific cultivation conditions in rice cultivation, Omodaka (Alisma), Pine pine (Eleocharia), Firefly (Scirpus) and Cyper Weeds such as grass (Cyperus) are also significantly controlled by the active substances according to the invention. Is done.   When the compounds according to the invention are applied to the surface of the soil before germination, weed seedlings Germination is completely arrested or weeds grow to the cotyledon stage, which then They cease to grow and eventually die completely after 3 to 4 weeks.   If the active substance was applied to the green plant parts in the post-emergence treatment method, the treatment A very rapid stoppage of growth likewise occurred very soon after, and these weeds It will either remain in the growth stage present at the time of application or die after a period of time. Since we die, weeds, which are harmful to cultivated plants, are thus very early in competition. Persistently blocked.   The compounds according to the invention have excellent herbicidal action against monocotyledonous and dicotyledonous weeds. , But wheat, barley, rye, rice, corn, te No toxic effects on economically important crops such as sugar beet, cotton and soybean. Give it only insignificantly so that it cannot be ignored. For these reasons, the present invention The compounds are selective for unwanted plant growth in the cultivation of useful agricultural plants. Very suitable for control.   Furthermore, the substances according to the invention have a very good growth-regulating action in cultivated plants. Show. They are regulatoryly involved in the plant's natural metabolism and therefore plant composition. It influences the tissue contents in a controlled manner and also prevents, for example, desiccation and growth. It can be used to facilitate harvesting by stopping. Moreover, they are also desirable To generally regulate and suppress the growth of non-plants without killing the plants Suitable for Inhibition of plant growth in many monocot and dicot crops Plays a major role because it reduces or completely prevents recumbence. Because it can be stopped.   The compounds according to the invention are in the form of wettable powders, emulsions, spray solutions, powders or granules. It can be used as a normal formulation. The subject of the invention is therefore also represented by the formula (I) And a plant growth regulator containing the compound or a salt thereof.   The compounds of formula (I) or their salts are biologically and / or chemically-physically A wide variety can be prepared by defining the parameters. As a possible suitable formulation Are, for example: Wettable powder (WP), water-soluble powder (SP), water-soluble concentrate, emulsifiable concentrate (emulsion) ( EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, Sprayable solutions, suspension concentrates (SCs), oil- or water-based dispersions, oil-miscible solutions Liquid, capsule suspension (CS), powder (DP), seed dip, spraying and soil application Granules (GR, micro granules, spray granules, coated granules and adsorbent granules (GR ), Water-dispersible granules (WG), water-soluble granules (SG), ULV-formulation, microca Pousel and wax.   These individual formulation forms are known in principle and include, for example: It is described in: Winacker-Kuchler, "Chemical Technology," Volume 7, Hauser Publishing, 4th Edition, 1986 ( Winnacker-Kuechler, “Chemische Technologie”, Band 7, C. Hauser Verlag,  Muenchen, 4. Aufl. 1986); Warde van Falkenburg, "Pesticide Formulation. Marcel Decker, 1973 (Wade van Valkenburg, “Pesticide Fo rmulations ”, Marcel DekKer, N. Y., 1973): Martens,“ Spray Drying Handbook ” Third Edition 1979 Goodwin Publishing (K. Martens, “Spray Drying Handbook”, 3rd Ed. 1979, G. Goodwin Ltd., London).   Required formulation aids such as inerts, surfactants, solvents and other additives Are also known, for example as described below: Watkins, "Handbook of Insecticide Powder Diluents and Carriers," Second Edition, Dhahran De Books (Watkins, “Handbook of lnsecticide Dust Diluents and Car riers ”, 2nd Ed., Darland Books, Caldwell N.J.); "Introduction to Chemistry", 2nd edition, published by Willie (H.v. Olphen, “Introduction to Clay Colloid C hemistry ”, 2nd Ed., J. Willey & Sons, N.Y.); Marsden's" Solvent Guide, "second Edition Interscience, 1963 (C. Marsden, “Solvents Guide”, 2nd Ed., lnterscience, N.Y. 1963): MacCution Edition "Detergent and Emulsifier Yearbook, MC Publishing" Published by McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Rid gewood N.J.); Sisley, Wood, "Surfactants Encyclopedia," Chemical Publishing 19 1988 (Sisley and wood, “Encyclopedia of Surface Active Agents”, Chem. Publ.Co.lnc., N.Y.1964): Schienfel "Surface Active Ethylene Oxide Adducts" by Toh, Vissen Shaft Publishing Company 1976 Annual (Schoenfeldt, “Grenzflaechenaktive Aethylenoxidaddukte”, Wiss. Verla gsgesell., Stuttgart 1976); Winacker-Kuchler, "Chemical Technology," Volume 7, Ha The 4th edition published by Uzersha, 1986 (Winnacker-Kuechler, “Chemische Technologie”, Band 7, C. Hauser Verlag, Muenchen, 4. Aufl. 1986).   Based on these formulations, other pesticidal active substances such as insecticides, acaricides, control Combinations with herbicides, fungicides, safeners, fertilizers and / or growth regulators are also For example, it is prepared in the form of ready mix or tank mix.   Wettable powders are preparations that can be evenly dispersed in water and contain the active substance as a diluent. Or in addition to inert substances, ionic and / or nonionic surfactants ( Wetting agents, dispersants), eg polyoxyethylated alkylphenols, polyoxy Ethylated fatty alcohol, polyoxyethylated fatty amine, fatty alcohol poly Glycol ether sulphur, alkane sulfonate, alkylbenzenes Ruphonate, sodium lignin sulfonate, 2,2'-dinaphthylmethane-6,6 6'-sodium disulfonate, dibutylnaphthalene-sodium sulfonate or Contains sodium oleylmethyl taurate. To make wettable powder , Herbicidal active substances are, for example, hammer mills, blowing mills and air jets. Milled in conventional equipment, such as Mixed.   Emulsions contain active substances in organic solvents such as butanol, cyclohexanone, dimethyi. One in the formaldehyde, xylene or high boiling aromatic compounds or hydrocarbons. Or more ionic and / or nonionic surfactants (emulsifiers) added While being dissolved. Examples of emulsifiers include Can be used: Alkyl aryls such as calcium dodecylbenzene sulfonate Calcium salt of sulfonic acid, or nonionic emulsifiers such as aliphatic polyglycol Ester, alkylaryl polyglycol ether, fatty alcohol poly Glycol ether, propylene oxide-ethylene oxide-condensation product, al Kill polyethers, sorbitan esters such as sorbitan fatty acid esters or Is a polyoxyethylene sorbitan ester, such as polyoxyethylene sorbitan Tan fatty acid ester.   Dusts are finely divided solid substances of the active substance, for example talc, natural clay, eg Grind with kaolin, bentonite and pyrophyllite, or diatomaceous earth, for example Obtained by   Suspension concentrates can be water-based or oil-based. These are, for example, commercially available beads beads. Wet-milled with a rubber and optionally in other formulations such as those mentioned above. It can be prepared by adding a surfactant as mentioned immediately above.   Emulsions, such as oil-in-water emulsions (EWs), are, for example, stirrers, rollers. Using an Idmill and / or stationary mixer, the aqueous organic solvent and optionally Of the use of surfactants such as those already mentioned for other formulations above. Manufactured below.   Granules are prepared by spraying the active substance on adsorptive granular inert substances or by sand, kaolina. On the surface of a carrier material, such as aluminum or granular inert material, for example polyvinylalcohol. Active substances with adhesives such as Cole, sodium polyacrylate or mineral oil It can be produced by applying a concentrate. Producing granular fertilizers with appropriate active substances If desired, it can also be granulated as a mixture with fertilizers in a customary manner for Wear.   Water dispersible granules are generally spray dried, fluid bed granulated, disk granulated, high speed mixers. By conventional methods such as mixing with a mixer and extrusion without solid inerts. Is manufactured.   The agrochemical formulations according to the invention are in principle provided with the active substances of the formula (I) or their It contains 0.1 to 99% by weight of salt, in particular 0.1 to 95% by weight.   In wettable powders, the active substance concentration is, for example, about 10 to 90% by weight. The remainder, up to 100% by weight, consists of customary formulation components. Effective in case of emulsion The concentration of the substance may be about 1 to 90% by weight, preferably 5 to 80% by weight It Dusts are effective at about 1 to 30% by weight, preferably 5 to 20% by weight The substance-containing solution for spraying is about 0.05 to 80% by weight, preferably not 2 It contains 50% by weight of the active substance. In the case of water dispersible granules, the inclusion of active substances The amount depends, in part, on whether the active compound is a liquid or a solid and what the granulation is. Auxiliaries, It depends on whether a filler or the like is used. In the case of water dispersible granules, The content of the active substance is, for example, 1 to 95% by weight, preferably 10 to 80% by weight. The amount is%.   In addition, the active substance formulations mentioned above may, in each case, be customary in each case. Adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezing agents, solvents, fillers , Carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity modifiers .   Combination for active substances according to the invention in mixed formulations or tank mixes Examples of the sauce component include "Weed Research" Vol. 26, pages 441-445. (1986) (Weed Research, 26, 441-445 (1986)), or "Pesticide Handbook", No. 9 Edition by The British Crop Protection Council (“The Pesticide Manual”, 9th Ed. The British Crop Protection Council, 1990/91, Bracknell, England) and references cited therein. The active substances listed under can be used. Statements that may be combined with compounds of formula (I) Known herbicides include, for example, the following effective substances (Note: The compound is the International Organization for Standardization ( ISO) "common name or, in some cases, normal code number Along with the issue, by chemical name): Acetochlor: Acifluoren; Acronifen: AKH7088, Sun That, [[[1- [5- [2-chloro-4- (trifluoromethyl) -phenoxy] ] -2-Nitrophenyl] -2-methoxyethylden] -amino-] oxy] -acetic acid And-acetic acid methyl ester; alachlor; alloxydim; ametrine; Dosulfuron: Amitrole; AMSN, ie ammonium sulfamate Anilophos: Aslam: Atrazine; Adiprothrin; Barban; BAS51 6H, ie 5-fluoro-] 2-phenyl-4H-3,1-benzoxazine -4-On; Benazoline: Benfluralin; Benfresate: Bensulfuron-M Chill; Benthlide; Bentazone; Benzofenap; Benzofluor; Benzo Ilprop-Ethyl; Benzthiazurone; Bialaphos; Bifenox; Bro Masil; Bromobutide; Bromophenoxime; Bromoxynil; Bromuron; Minafos: Busoxynone; Butachlor; Butamiphos; Butenachlor; Butida Sol; butralin: butyrate; carbetamide; CDAA, 2-chloro-N, N-di-2-propenylacetamide; CDEC, that is Chi diethyldithiocarbamic acid-2-chloroallyl ester: CGA1849 27, ie 2- [4- [5-chloro-3-fluoro-2-pyridinyl) -oxy [] -Phenoxy] -propanoic acid and 2-propynyl ester; En; chloramben; chloradiop-butyl: pyriphenop-butyl; Lolbromuron: Chlorphenac; Chlorflurecol-Methyl; Chloridazo Chlorimuron-Chill: Chloronitrophene; Chlorotoluron; Chloroxyuro Chlorpropham; Chlorsulfuron; Chlortal-dimethyl; Chlorthia Mido; Symmethyline: Cinosulfuron; Cresodymium; Chromazone; Chromeprot Clocloproxydim; Clopyralid; Cyanazine: Cycloate: Cycloxy Jim; Cycurlon: Cyperquat: Ciprazine: Ciprazole: 2,4-DB Derapong; Desmejiuan: Desmethrin; Di-Alate; Zicamba; Ziclo Benil; Dichlorprop: Diclofop-methyl; Diethyl: Diphenox Ulong; Difuenzoquat: Diflufenican; Dimefron; Dimethachlor: Dimethamethrin: Dimethasone; Chromazone: Dimethipine: Dimetrasulfuron; Cinosulfuron: Dinithramine; Dinoceb; Dinoterb; Diphenamide: Dipro Petrin; Diquat; Dithiopyr; Diuron; DNOC; Eglinazine-Ethi Le: EL177, that is, 5-cyano-1- (1,1-dimethylethyl) -N- Methyl-3H-pyrazole-4-carboxamide; Endothal: EPTC; Sprocarb: etalfluralin; etamethosulfuron-methyl; etizimurone Ethiodine; Etofumesate; F5231, ie, N- [2-chloro-4- Fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo- 1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide; F62 85, ie 1- [5- (N-methylsulfonyl) -amino-2,4-dichloro Phenyl] -3-methyl-4-difluoromethyl-1,2,4-triazole-5-   On; Phenoprop; Phenoxane; Chromazone; Phenoxaprop-E
Chi Le; fenuron; flamprop-methyl: flazasulfuron: fluazifop And its ester derivatives: fluchloralin; flumethoslam; N- [2,6- Difluorophenyl] -5-methyl- (1,2,4) -triazolo [1, 5a] pyrimidine-2-sulfonamide; flumethuron; flumipropyne; Luorodiphene: Fluoroglycophene-Ethyl: Fluridone; Flurochloride Fluroxypeal; Fultamon; Homesafhuen; Hosamine; Furyloxy Fuen; Glufosinate; Glyphosate; Halosafuene; Haloxifop and Its ester derivative; hexadinone; HW52, ie, N- (2,3-dic Lolophenyl) -4- (ethoxymethoxy) -benzamide; Ilzametabenz- Methyl; Imazapeel: Imazaquin; Imazeta Metapeel; Imazetapeel; Mazosulfuron; Ioxynil; Isocarbamide; Isopropaline; Isoproti Uron; isouron; isoxaben; isoxapyrihop; carbutyrate; LA Ctofuen; Renacil; Linuron; MCPA; MCPB; Mecoprop; Mef Enaset: Mefluidid: Metamitron; Metazachlor; Metabenzcia Zuron; Metam; Metazole; Methoxyphenone: Methyldimurone; Metobrom Ron: metolachlor; methoxuron; metribuzin; metsulfuron-methyl MH: molinate: monalide; dihydrogen sulfate monocarbamide; monolinuron; Nuron: MT128, ie 6-chloro-N- (3-chloro-2-propeny ) -5-Methyl-N-phenyl-3-pyridazinamine; MT5950, that is N- [3-chloro-4- (1-methylethyl) -phenyl] -2-methylpenta Namide; Naproanilide; Napropamide; Naptham; NC310, that is, 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazo Le; Nebulon; Nicosulfuron; Nipiraclofen; Nitraline: Nitrophen Nitrofluor: Norflurazon; Orbencarb: Oryzalin: Oki Thasiazone; Oxyfluorphene; Paraquat; Pebrate; Pendimetari Perfluidon; Fuengmedjiam: Fuenisofuam; Fuengmedjiam: Picloram; Piperofos; Pyributicarb: Piriphenop-butyl: Pretila Chlor: Primisulfuron-methyl; Procyanidin; Prodiamine; Proflula Phosphorus; Proglinazine-ethyl; Promethone; Promethrin; Propachlor; Ropanil; Propaxazahop and its ester derivatives; Propazine; Propizzamide; Prosulfualin; Prosulfocarb: Prinachlor; Pyram Zolinate; Pyrazone; Pyrazosulfuron-ethyl; Pyrazoxyphene; Pyride Quinclolac; quinmelac; quinofop and its ester derivatives, Quizalofop and its ester derivative: Quizalofop-ethyl; Quizalofop -p- Tefril; Lenrizuron: Jimuron: S275, that is, 2- [4-black Le-2-fluoro-5- (2-propynyloxy) -phenyl] -4,5,6,7-   Tetrahydro-2H-indazole; S482, that is, 2- [7-fluoro
- 3,4-Dihydro-3-oxo-4- (2-propynyl) -2H-1,4-benz Oxazin-6-yl] -4,5,6,7-tetrahydro-1H-isoindole Le-1,3 (2H) -dione; Secbumetone; Setoxydim; Shizuron; Shimaji Cimetrin; SN106279, that is, 2-[[7- [2-chloro-4- (Trifluoro-methyl) -phenoxy] -2-naphthalenyl] -oxy] -pro Panic acid and methyl ester; Sulfometuron-methyl; Flufazuron: F Lazasulfuron: TCA; Tebutam: Tebutyuron: Terbacil: Telcarb Terbuchlor; Terbumetone: Terbutyrazine; Terbutrin; TFH450, That is, N, N-diethyl-3- [2-ethyl-6-methylphenyl) -sulfo Nil] -1H-1,2,4-triazole-1-carboxamide; thiazafluron Thiophensulfuron-methyl; thiobencarb: thiocarbazyl; tralkoki Cysimium; tri-allate; triasulfuron; triazophenamide; trivenu Ron-Methyl; Triclopeal; Tridiphane: Triethazine; Trifluralin Trimeturon; Vuelnorate: WL110547, 5-Feno Xy-1- [3- (trifluoromethyl) -phenyl] -1H-tetrazole.   Formulations that are present in commercially available forms may be prepared using conventional methods With water, for example in the case of wettable powders, emulsions, dispersions and water dispersible granules . Dusts, soils or dusting granules and spray solutions are generally inert before use. It is no longer diluted with active substances.   The required amount of compound of formula (I) used depends on the temperature, humidity, type of herbicide used and It depends on external conditions such as others. It has a wide range, for example, 0.001 to 10.0 kg / ha or more, but preferably It is 0.005 to 5 kg / ha. A. Compound production example a) 2-carboxy-5-nitro-benzenesulfonic acid   2-Methyl-5-nitro-benzenesulfonic acid 106.0 in 1300 ml of water g (0.40 mol) and potassium carbonate 80.0 g (0.58 mol) solution Then, 400.0 g (2.53 mol) of potassium permanganate is added at 80 ° C. to 2 Add over time. At that time, the reaction temperature is maintained at 80 to 95 ° C. After stirring for a further 4 hours, the solid formed is filtered. Acidify the filtrate with concentrated hydrochloric acid (PH = 1). Precipitated colorless 2-carboxy-5-nitro-benzene Rufonic acid was filtered off using a Buchner funnel and smelled at about 50 ° C / 100 torr. And dry (82.0 g: 83.7% of theory). Melting point> 300 ° C. b) 2-methoxycarbonyl-5-nitro-benzenesulfonic acid   2-hydroxycarbonyl-5-nitro-benzenesulfonic acid 190.0 g ( 0.77 mol), 10 ml of dimethylformamide and 250 m of thionyl chloride. 1 (3.43 mol) of the suspension is heated to boiling temperature for 3 hours. Insoluble components are filtered After removal by filtration, the filtrate is concentrated. 200m of methanol in the obtained residue 1 (4.94 mol) is added dropwise. After the addition is complete, cool the reaction mixture to 0 ° C. To reject. The precipitated solid is filtered off and dried. Thus colorless crystalline 2-meth Xycarbonyl-5-nitro-benzenesulfonic acid 70.9 g (theoretical amount of 35. 3%) (melting point: 92-94 ° C).   The second fraction (62.) was removed by distilling off the volatile constituents of the mother liquor on a rotary evaporator. 5 g, theoretical 31.1%) are obtained. c) 2-methoxycarbonyl-5-nitro-benzenesulfonyl chloride   2-Methoxycarbonyl-5-nitro-benzenesulfate in 300 ml of methanol 70.9 g (0.27 mol) solution of phosphonic acid was added to potassium hydroxide ( A solution of 17.3 g (0.27 mol) of concentration 88%) and 100 ml of methanol Mix with. After cooling to 0 ° C., the salt formed is filtered off, dried and then sprayed. Lufolan 150 ml, acetonitrile 150 ml and dimethylformamide 1 Suspend in 0 ml. 100 ml (1.07 mol) of phosphorus oxychloride was added dropwise. After that, the mixture is heated to boiling temperature for 2.5 hours and then poured into ice water. Sinking 2-methoxycarbonyl-5-nitro-benzenesulfonyl chloride (60.1 g, 70% of theory) is filtered off with suction using a Buchner funnel and reduced pressure. Remove traces of solvent below. Melting point: 86-88 ° C. d) N-tert-butyl-2-methoxycarbonyl-5-nitro-benzenesulfone Amide   2-Methoxycarbonyl in 200 ml of ethyl acetate and 250 ml of ethanol To 34.4 g (0.12 mol) of le-5-nitro-benzenesulfonyl chloride 50 ml (0.48 mol) of tert-butylamine is gradually added dropwise at 0 ° C. . The reaction solution is then kept stirring at room temperature for a further 10 minutes. Add 500 ml of water After that, a colorless solid crystallizes. After filtration and drying, N-tert-butyl- 2-Methoxycarbonyl-5-nitro-benzenesulfonamide 28.1 g (8 9%) is obtained: melting point 121-124 ° Co. e) N-tert-butyl-5-hydroxylamino-2-methoxycarbonyl-ben Zensulfonamide   N-tert-butyl-2-methoxycarbonyl-5-nitro-benzenesulfone 23.4 g (0.08 mol) of the amide in 600 ml of ethanol at 40 ° C. Introduce. Ammonium chloride 42.1 g (0.79 mol) and water 170 ml After buffering with, add 32.0 g (0.49 mol) of zinc powder little by little. . Stirring is then continued for a further 4 hours at about 55 ° C. The solid is filtered off and the filtrate Is concentrated on a rotary evaporator. The residue is taken up in 800 ml of ethyl acetate and water 3 Wash with 00 ml. The aqueous phase is extracted 3 times with 300 ml of dichloromethane. one The combined organic phases are dried over magnesium sulphate. Then using a rotary evaporator The volatile constituents are distilled off. The crystalline residue was washed with a small amount of ethyl acetate: heptane (1: 1). Stir with. Thus, N-tert-butyl-5-hydroxylamino- 2-methoxycarbonyl-benzenesulfonamide (17.2 g, 77%) was obtained. Be done. Melting point: 190-195 ° C. f) N-tert-butyl-5- (N-acetyl-hydroxylamino) -2-methoxy Carbonyl-benzenesulfonamide   N-tert-butyl-5-hydroxylamino-2-methoxycarbonyl-benze In order to obtain a homogeneous solution, 3.31 g (0.01 mol) of sulfone amide was added to the acetonamide. Heat briefly in 20 ml of trinitrile. Next, 0.94 g of acetyl chloride (0. 01 mol) and 1.30 g (0.01 mol) of triethylamine are cooled in an ice bath. Add while rejecting. After 2 hours the mixture was taken up in ethyl acetate and treated with 1N Wash successively with hydrochloric acid and saturated sodium chloride solution. Organic phase over magnesium sulphate After drying at 4, the solvent is distilled off using a rotary evaporator. The residue is ethyl acetate / After recrystallization from butane, N-tert-butyl-5- (N-acetylhydroxy) Lumino) -2-methoxycarbonyl-benzenesulfonamide 3.12 g (8 2%). Melting point: 168-169 [deg.] C. g) 5- (N-acetyl-hydroxylamino) -2-methoxycarbonyl-ben Zensulfonamide   N-tert-butyl-5- (N-acetyl-hydroxylamino) -2-methoxyca Rubonyl-benzenesulfonamide (1.70 g, 4.9 mmol) was added to trifluoro Dissolve in 20 ml of acetic acid. Volatile components under reduced pressure after 18 hours at 25 ° C Distill off. Thus, 5-N- (acetyl-hydroxylamino) -2-methoxy 1.48 g of carbonyl-benzenesulfonamide are obtained. Melting point: 246-24 7 ° C h) 5- (N-acetyl-hydroxylamino) -N-[(4,6-dimethoxypyri Midin-2-yl) -aminocarbonyl] -2-methoxycarbonyl-benzenes Lefonamide (corresponding to Example 192 in Table 1)   5- (N-acetyl-hydroxylamino) -2- in 50 ml of acetonitrile Methoxycarbonyl-benzenesulfonamide (1.00 g, 4.4 mmol) And 4,6-dimethoxy-2- (phenoxycarbonylamino) -pyrimidine 0. 0.8 ml of DBU is added to the mixture consisting of 65 g (2.4 mmol). 18 After stirring for a period of time, the solvent is distilled off in a rotary evaporator. Put the residue in water , And then washed with diethyl ether. Acidify the aqueous phase with concentrated hydrochloric acid ( pH = 1). The colorless solid is filtered off and stirred with a little methanol. Was 5- (N-acetyl-hydroxylamino) -N-[(dim Toxypyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonyl- Benzenesulfonamide (0.81 g, 79% of theory) was 205-208 ° C. Having a melting point of. i) N-[(4,6-dimethoxypyrimidin-2-yl) -aminocarbonyl] -2 -Methoxycarbonyl-5- (N-methoxycarbonyl-hydroxylamino)- Benzenesulfonamide (Table 1, Example 238)   CH₃2-Methoxycarbonyl-5- (N-methoxycarbo in 50 ml of CN Nyl-hydroxylamino) -benzenesulfonamide 0.74 g (2.43 m) mol) and 4,6-dimethoxy-2- (phenoxycarbonylamino) -pyrimidi 0.75 ml DBU to a mixture with 0.67 g (2.43 mmol) . After stirring for 18 hours, the solvent is distilled off using a rotary evaporator. Put the residue in water And wash with diethyl ether. After acidifying the aqueous phase with concentrated hydrochloric acid (pH = 1), a colorless solid precipitates. After suction filtration and washing with methanol, 0.66 g of the above-mentioned sulfonylurea was obtained as colorless crystals with a melting point of 192-193 ° C. Be done. j) N- [4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2- Methoxycarbonyl-4- (N-methoxycarbonyl-hydroxyamino) -ben Zensulfonamide (Table 3, Examples 3-9)   CH₃2-Methoxycarbonyl-4- (N-methoxycarbonyl) in 30 ml of CN -Hydroxyamino) -benzenesulfonamide 1.2 g and 4,6-dime Tooxy-2- (phenoxycarbonylamino) -pyrimidine 1.1 g suspension D Add 1.2 ml BU dropwise. After a reaction time of 4 hours, the treatment is carried out as in example i). U 1.09 g of the above-mentioned sulfonylurea was converted into colorless crystals having a melting point of 171-174 ° C. Obtained. k) N-[(4,6-dimethoxypyrimidin-2-yl) -aminocarbonyl]- 2-Methoxycarbonyl-5- (N-methoxycarbonyl-hydroxyamino)- Sodium salt of benzenesulfonamide (Table 4, Examples 4-10)   CH₂Cl₂20 ml and CH₃N-[(4,6-dimethoxy in 20 ml of CN Pyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonyl-5- ( N-methoxycarbonyl-hydroxyamino) -benzenesulfonamide 0.5 To 7 g of solution is added 1.2 ml of 1N sodium hydroxide solution. 2 hours of stirring After stirring, the reaction mixture is concentrated by evaporation under reduced pressure. The product thus obtained (0 ． 61 g) is the above-mentioned sulfonylurea having a melting point of 175-180 ° C. The remaining compounds listed in Tables 1 to 4 are prepared in a similar manner to Examples a) to k) above. can get. The following abbreviations are used in these tables: M. p. = Melting point expressed in ° C No. = Example number Et = Ethyl (C₂H_Five) Me = methyl (CH₃) Ph = phenyl c-Pr = cyclopropyl n-Pr = n-propyl i-Pr = i-propyl B. Formulation example a) 10 parts by weight of the compound of formula (I) and 90 parts by weight of talc as an inert substance A powder is obtained by mixing and grinding with a hammer mill. b) Wettable powders which are easily dispersible in water include 25 parts by weight of a compound of formula (I), inert 64 parts by weight of quartz containing kaolin as a substance, 10 parts by weight of potassium lignin sulfonate Parts and sodium oleoylmethyl taurate as a wetting agent and dispersing agent Obtained by mixing parts and comminuting with a pin disk mill. c) A dispersion concentrate which can be easily dispersed in water contains 20 parts by weight of a compound of formula (I). Rukiruphenol polyglycol ether [^(R)Triton X207] 6 Parts by weight, 3 parts by weight of isotridecanol polyglycol ether (EO 8 units) And paraffinic mineral oils (boiling range, eg, about 255 to 277 ° C. or above Top) Mix 71 parts by weight and mill in a ball mill to a fineness of less than 5 microns. It is obtained by doing. d) The emulsion comprises 15 parts by weight of the compound of formula (I) and 75 parts by weight of cyclohexanone as a solvent. And 10 parts by weight of oxyethylated nonylphenol as an emulsifier can get. e) The water dispersible granules are   75 parts by weight of compound of formula (I)   Calcium lignin sulfonate 10〃   Sodium lauryl sulfate 5〃   Polyvinyl alcohol 3〃   And kaolin 7 〃 Are mixed, ground in a pin disc mill, and the powder is granulated in a fluidized bed. It is obtained by granulating by spraying water as. f) Water dispersible granules   25 parts by weight of compound of formula (I)   2,2'-Dinaphthylmethane-6,6'-sodium disulfonate 5 〃   Oleoyl methyl taurate sodium salt 2〃   Polyvinyl alcohol 1 〃   Calcium carbonate 17 parts by weight   And water 50〃 Is homogenized in a colloid mill and premilled, then finely milled in a bead mill and then The suspension thus obtained is then atomized in a spray tower by means of a single substance nozzle. It is also obtained by liquefying and drying. C. Biological test example 1. Herbicidal effect of pre-emergence treatment   Seed or rhizome fragments of monocotyledonous and dicotyledonous weed plants in plastic pots. It was planted in sandy loamy soil and covered with soil. Wettable powder or emulsion form The compound of the present invention, which is prepared into a liquid phase, is converted into 600 to 800 L / ha. As a suspension or emulsion in water usage, the soil cover can be It was applied on the surface.   After treatment, place the above pots in a greenhouse and under good growth conditions for weeds. Kept at. No damage to plant and germination after test plant germinated 3 Visual assessment by comparison with untreated controls after a 4-week test period went. As the results of the tests show, the compounds according to the invention show a wide range of rice. Excellent pre-emergence herbicidal effect against weeds belonging to the family and other weeds. An example For example, Table 1, Example 61, 192, 217, 238, 256 and 262, Table 3 -9 and 3-29 and compounds 4-9 in Table 4 are the mustard (Sinapis alba), Chrysanthemum segetum, oats (Avena sativa), chickweed (Stella) ria media), barnyard grass (Echinochloa crus-galli) and murine wheat (Lolium mult) per hectare in pre-emergence treatment for harmful plants such as iflorum) Excellent herbicidal effect when used with 0.3 kg or less of active substance Show. 2. Herbicidal effect of post-emergence treatment   Monocotyledonous and dicotyledonous weed seeds or rhizome fragments in plastic pots Planted in sandy loamy soil, covered with soil and in a greenhouse in good growing conditions Cultivated in. Three weeks after sowing, the test plants were treated at the trifoliate stage.   The compound according to the present invention prepared as a wettable powder or as an emulsion is converted to 6 Water amount of 00 to 800 L / ha to green parts of plants at various application rates Spray and test plants were left in the greenhouse under optimal growth conditions for about 3-4 weeks The effect of the formulation was later evaluated visually by comparing it to an untreated control. The agents according to the invention are suitable for a wide range of economically important grasses and other weeds. It also shows an excellent post-emergence herbicidal effect on the weeds of P. For example, Examples 61 and 1 of Table 1 92, 217, 238, 256 and 262, 3-9 and 3-29 in Table 3 The compounds 4-9 in Table 4 are the mustard (Sinapis alba) and chickweed (Stellaria media ), Inubiri (Echinochloa crus-galli), murine wheat (Lolium multiflorum), Harmful such as rye (Chrysanthemum segetum) and oats (Avena sativa) For plants, in the post-emergence treatment method, 0.3 kg of active substance per hectare It also shows a very good herbicidal effect when the amount used is less than that. 3. Tolerance for cultivated plants   In yet another greenhouse test, a large number of cultivated plants and weed seeds were sanded. Seeded and covered with thick loamy soil. Some of the pots above 1. To Immediately as described above, and the remaining pot with 2 to 3 leaves. Place in the greenhouse until Book as described in The active substances of the formula (I) according to the invention were sprayed on at different application rates. Applied and After being placed in the greenhouse for 4 to 5 weeks, the compounds according to the invention were evaluated visually. But dicotyledons such as soybean, cotton, rapeseed, sugar beet and potato Higher application rates of active substances are used in pre-emergence and post-emergence treatments for It proved to be harmless even when used. In addition, some Examples of the active substance include barley, wheat, rye, sorghum and corn. It also did not harm crops of rice plants such as rice. Therefore, it is expressed by the formula (I). Compounds are used to control unwanted plant growth in crops. Shows high selectivity.

[Procedure Amendment] Patent Law Article 184-8 [Date of submission] September 19, 1994 [Amendment content] c) The compound represented by the formula (II) is represented by the formula (X). By reacting (thio) isocyanate represented by the formula (II) in the presence of a base, wherein the groups R ¹ to R ⁴ and n in the formulas (II) to (V) and (X) are defined as in the formula (I). And a method for producing a compound represented by the above formula (I) or a salt thereof, which is characterized in that in the above methods a) and b), a compound in which W = 0 in the formula (I) is first obtained. Is. The reaction of compounds of formula (II) and formula (III) is preferably carried out in an inert organic solvent such as dichloromethane, acetonitrile, dioxane or THF at 0 ° C, preferably 20 ° C to the boiling point of the solvent. It is carried out with a basic catalyst at a temperature in between. In that case, the base is, for example, an organic amine base, for example, in the case of R ^* = (substituted) phenyl (see European Patent Application Publication No. 44807), 1,8-diazabicyclo- [5.4.0]. Undecene- (7) (DBU) 2 is used, or trimethylaluminium or triethylaluminum, especially when R ^* = alkyl (see EP 166516). Two kinds of sulfonamides represented by the formula (II), that is, 4- (N-acetyl-N-hydroxy- or -N-methoxy-amino) -benzenesulfonamide, are available in Chemical Abstracts (Chem. Abstr.) 99: 37857e (1983). The novel compounds (II) and their production methods are also an object of the present invention. The compound represented by the formula (II) is, for example, a compound represented by the formula (VI) It is obtained by starting from the compound represented by and reacting with a strong acid. Claim 10. Formula (II) (Wherein R ¹ , R ² , R ³ and n have the meaning defined in formula (I) according to any one of claims 1 to 5), However, 4- (N-acetyl-N-hydroxy-amino) -benzenesulfonic acid amide and 4- (N-acetyl-N-methoxy-amino) -benzenesulfonic acid amide are excluded.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI C07C 311/65 7419-4H C07D 239/47 A 8615-4C 239/52 8615-4C 251/14 7431-4C 251 / 16 F 7431-4C 251/18 H 7431-4C 251/46 G 7431-4C 409/12 239 7602-4C (72) Inventor Wims Rothal Germany, Dei-65719 Hofheim, Königsteiner Strah SE, 50 (72) Inventor Bauer Klaus Germany, De-63456 Hanau, Dorner Strasse, 53-day (72) Inventor Bilinger Hermann, Federal Republic of Germany, DE-65817 Epp Stein / Taunus, Eichen Weh Ku, 26 (72) Inventor Schulz Arno, Germany, Day-658 17 Epp Stein / Taunus, In den Am Tomannswiesen, 5

Claims (1)

[Claims] 1. Formula (I) [In the above formula, R ¹ is 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 means R ² , hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl, after which The three radicals mentioned are, independently of one another, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkylthio. R ³ is 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 - or halogen six groups listed later in alkynyloxy (here, an independent non-substituted each other, ₁ -C ₄ - alkoxy and may be substituted by one or more groups selected from the group consisting of 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 ) = N-R ²² , or having up to 4 heteroatoms selected from the group consisting of N, O and S Or a 6-membered saturated or unsaturated, or heteroaromatic heterocycle, which is unsubstituted or 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 one or more groups selected from the group consisting of (C ₁ -C ₄ -alkoxy) -carbonyl, and up to two C-ring positions are replaced by CO, and Up to 2 S-heterocycle atoms optionally substituted by SO ₂ ), R ⁴ means 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 last three radicals mentioned here being unsubstituted or halogen, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, substituted by one or more groups selected from the group consisting of NR ¹³ R ¹⁴ and NR ¹⁵ ₂ ) or C ₃ -C ₇ -cycloalkyl (which is unsubstituted or halogen, C ₁ -C ₄ - alkyl, C ₁ - C ₄ - alkoxy , C ₁ -C ₄ - alkylthio, substituted by one or more groups selected from the group consisting of NR ¹³ R ¹⁴ and NR ¹⁵ _2), or benzyl, unsubstituted or substituted aryl or unsubstituted or A substituted heterocyclic group, R ⁶ is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl (the last three radicals here being unsubstituted) Or halogen, substituted with one or more groups selected from the group consisting of C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ ₂ ). 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 last four radicals mentioned here being Unsubstituted or halogen, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -Alkylthio and NR ¹³ R ¹⁴ substituted by one or more groups selected from the group consisting of), R ⁸ is hydrogen or C ₁ -C ₆ -alkyl, C ₂ -C _6- Alkenyl or C ₂ -C ₆ -alkynyl (the three radicals mentioned here being unsubstituted or selected from the group consisting of halogen, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkylthio). Or substituted by one or more groups), or COR ²³ , CO ₂ R ²⁴ , CONR ¹³ R ¹⁴ or SO ₂ R ¹¹ , and R ⁹ has the same meaning as R ⁵ . R ¹⁰ has the same meaning as R ⁶ and R ¹¹ is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl (of the three radicals mentioned here). halogen or is unsubstituted, C ₁ -C ₄ - alkoxy and C ₁ -C ₄ - a Means to have) been substituted by one or more groups selected from the group consisting of Kiruchio, 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 (where do the two groups mentioned last is unsubstituted or halogen, C ₁ -C ₄ - alkoxy and C ₁ -C ₄ -Substituted by one or more groups selected from the group consisting of: alkylthio, 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 last three radicals mentioned here being unsubstituted or selected from the group consisting of halogen, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkylthio). Substituted by one or more groups) or Or COR ²⁵ or CO ₂ R ²⁶ , R ¹⁴ independently of one another is hydrogen or C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl or C ₃ -C ₆ -alkynyl (wherein The three radicals listed under are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkylthio. NR ¹⁵ ₂ independently of one another has, in addition to the N-atom, one or two other heterocyclic atoms selected from the group consisting of N, O and S. And optionally represents an unsubstituted or substituted 3- to 7-membered heterocyclic ring, R ¹⁶ represents a group similar to R ⁵ , R ¹⁷ represents hydrogen, C ₁ -C _6- alkyl, C ₁ -C ₆ - alkenyl or C ₂ -C ₆ - alkynyl (three radicals mentioned last here is the unsubstituted Or halogen, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ are substituted by one or more groups selected from the group consisting of ₂₎ means R ¹⁸ represents a group similar to R ⁷ , R ¹⁹ represents a group similar to R ⁸ , R ²⁰ represents a group similar to R ^11, and R ²¹ represents hydrogen or C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl (the last three radicals mentioned here being unsubstituted or halogen, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ - substituted by one or more groups selected from the group consisting of alkylthio), or C ₁ -C ₄ - alkoxy, OH, NH _2, mono- - or di - (C ₁ -C ₄ - alkyl) - amino, means a _{^{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 (two groups mentioned last Here unsubstituted Or substituted by one or more groups selected from the group consisting of halogen, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkylthio), R ²³ is R ⁹ and It means a similar group, R ²⁴ means the same groups as R ^10, R ²⁵ means the same group as the group R ^9, R ²⁶ means the same group as the group R ^10, X And 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 last three radicals mentioned here being unsubstituted). there or halogen, C ₁ -C ₄ - alkoxy and C ₁ -C ₄ - ₁ one or selected from the group consisting of alkylthio Is substituted by group above), 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 is meant, Z is CH or N, W is O or S, n is 0, 1, 2 or 3 And o means 0, 1, 2, or 3.] or a salt thereof. 2. In the formula (I), R ¹ is 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 or R ² is hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₅ -alkenyl or C ₃ -C ₅ -alkynyl (the last three radicals mentioned here being each independently of the other unsubstituted or is one or more halogen atoms or by C ₁ -C ₄ - substituted by 1 or 2 groups selected from the group consisting of alkylthio - alkoxy and C ₁ -C ₄ Or R ³ is 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 (six radicals mentioned last here It is substituted by one or two groups selected from alkoxy and the group consisting of alkylthio) - independently unsubstituted or is one or more halogen atoms or by C ₁ -C ₄ to have 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 , N O ₂ or C (R ²¹ ) = N-R ²² , or 5- or 6-membered having up to 3 heteroatoms selected from the group consisting of N, O and S Saturated or unsaturated, or heteroaromatic heterocycles, which are unsubstituted or 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 - A Kill) - carbonyl and (C ₁ -C ₄ - alkoxy) - and substituted by one or more groups selected from the group consisting of carbonyl, and the position of that time of up to two C- ring atoms CO And up to 2 S-heterocycle atoms may be substituted by SO ₂ ), R ⁴ represents hydrogen or methyl, or R ⁵ represents hydrogen or C ₁ -C ₆ -alkyl (which is unsubstituted or substituted by C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio, substituted by one or two groups selected from the group consisting of NR ¹³ R ¹⁴ and NR ¹⁵ ₂ Or C ₃ -C ₇ -cycloalkyl, benzyl, unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl, or R ⁶ is C ₁ -C ₆ -alkyl, C ₃ -C _6- Alkenyl or ₃ -C ₆ - alkynyl (by three groups unsubstituted or one or more halogen atoms mentioned later herein or C ₁ -C _4, - alkoxy, _C-1 C ₄ - alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ ₂ are substituted by 1 or 2 groups selected from the group consisting of, or R ⁷ is hydrogen or C ₁ -C ₆ -alkyl (which is unsubstituted) by or is one or more halogen atoms is or C ₁ -C _4, - alkoxy, C ₁ -C ₄ - by one or two groups selected from alkylthio and NR ¹³ R ¹⁴ group consisting of substituted R ⁸ is hydrogen or C ₁ -C ₄ -alkyl (which may be unsubstituted or one or more halogen atoms or C ₁ -C ₄ -alkoxy and C ₁ than alkylthio - -C ₄ That is substituted by 1 or 2 groups selected from the group), or means C OR ^23, CO ₂ R ²⁴ or SO ₂ R ^11, or R ⁹ has the same meaning as R ⁵ Or R ¹⁰ has the same meaning as R ⁶ , or R ¹¹ means C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl, or R ¹² is hydrogen, OH, C ₁ Means -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, or C ₁ -C ₄ -haloalkyl, or R ¹³ independently of one another is hydrogen or C ₁ -C ₄ -alkyl, COR ²⁵ or CO _2. R ^{26 represents} , or R ¹⁴ independently of one another hydrogen or C ₁ -C ₄ -alkyl, or NR ¹⁵ ₂ independently of one another, in addition to the N atom, also N, O and S May have other heterocyclic atoms selected from the group consisting of and are unsubstituted There or C ₁ -C ₄ - or means a heterocycle alkyl and one selected from the group consisting of oxo or more 7-membered to 3 without being substituted by a group, or R ¹⁶ is R ⁵ And R ¹⁷ is hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl (the three radicals mentioned here being unsubstituted) by some or one or more halogen atoms or C ₁ -C _4, - alkoxy, C ₁ -C ₄ - alkylthio, NR ¹³ R ¹⁴ and NR ¹⁵ 1 or 2 selected from the group consisting of ₂ R ¹⁸ represents a group similar to R ⁷ , R ¹⁹ represents a group similar to R ⁸ and R ²⁰ represents a group similar to ^{11. 21} are hydrogen, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - alkoxy, OH, N _2, mono- - or di - (C ₁ -C ₄ - alkyl) - refers to amino, 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 is meant, R ²³ is a group similar to R ⁹ , R ²⁴ is a group similar to R ^10, and R ²⁵ is R ⁹ . Means a similar group, R ²⁶ means a group similar to R ¹⁰ , or X and 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 last three radicals mentioned here being unsubstituted or substituted by one or more halogen atoms), or mono- or di- (C _1- C ₂ -alkyl) -amino, n means 0, 1 or 2 and o means 0, 1 or 2 Compounds or their salts. 3. In formula (I), R ¹ is 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 Means 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 substituted by 1 to 3 groups selected from the group consisting of halogen, methyl and methoxy) or thienyl, furyl or pyridyl (wherein The above heteroaromatics are unsubstituted or substituted by one or more groups selected from the group consisting of halogen, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -alkoxy). Mean Or R ⁶ is C ₁ -C ₄ - alkyl, C ₁ -C ₄ - haloalkyl, C ₃ -C ₄ - alkenyl or C ₃ -C ₄ - and alkynyl, R ⁷ is H, C ₁ -C ₄ -Alkyl or C ₁ -C ₄ -haloalkyl or R ⁸ represents H, C ₁ -C ₄ -alkyl, COCH ₃ , CO ₂ CH ₃ or CO ₂ C ₂ H ₅ or the abovementioned preferences A compound of formula (I) or a salt thereof according to claim 1 or 2 containing a combination of groups. 4. A group represented by the formula (I), wherein the group represented by the formula N (OR ² ) R ¹ is present at the 2-, 3-, 5- or 6-position of the phenyl ring and n is 0 or 1. A compound represented by formula (I) or a salt thereof according to any one of items 1 to 3. 5. In the formula (I), R ³ is a group represented by the formula CO-OR ¹⁷ and n = 1, and R ³ is represented by the formula (I) according to any one of claims 1 to 4. Compounds or salts thereof. 6. To prepare a compound of formula (I) or a salt thereof according to claim 1, a) formula (II) The compound represented by the formula (III) (Where R ^* is optionally substituted phenyl or (C ₁ -C ₄ ) alkyl) or b) R ² is different from hydrogen In case, the formula (IV) A sulfonyl isocyanate represented by the formula (V) Or by reacting the compound represented by the formula (II) with a compound represented by the formula (X) In represented by (thio) reacted in the presence of an isocyanate and a base, in which, in the formulas (II) no (V) and (X), the radicals R ¹ R ⁴ and n are as for formula (I) Preparation of a compound of the above formula (I) or a salt thereof, which is defined and in the above methods a) and b) firstly obtains a compound of formula (I) in which W = 0. Method. 7. A herbicide or a plant, which comprises at least one compound represented by formula (I) or a salt thereof according to any one of claims 1 to 5 and a formulation aid commonly used in plant protection. Growth regulator. 8. An effective amount of at least one compound of formula (I) or a salt thereof according to claims 1 to 5 is applied to harmful plants or plants, plant seeds or cultivated land. A method for controlling harmful plants or controlling the growth of plants. 9. A method of using a compound represented by formula (I) or a salt thereof according to any one of claims 1 to 5 as a herbicide or a plant growth regulator. 10. Formula (II) (Wherein R ¹ , R ² , R ³ and n have the meanings defined in formula (I) according to claims 1 to 5). 11. To prepare a compound of formula (II) according to claim 10, a) formula (VI) (Wherein R ¹ , R ² , R ³ and n have the same meanings as in formula (II)), or the compound represented by formula (IXb) is reacted with a strong acid. (Wherein R ¹ , R ² , R ³ and n have the same meanings as in formula (II)) and are subjected to aminolysis and are represented by the above formula (II). Method for producing compound. 12. Formula (IV) (Wherein R ¹ , R ² , R ³ and n have the meanings defined in claims 1 to 5).