Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/42—One nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

• Hydroxylamino-phenylsulfonylureas their preparation and their use as herbicides and plant growth regulators
• Plant growth regulators especially herbicides for selective inhibition
• WO-89/10921 discloses phenylsulfonylurea herbicides in which the phenyl ring is 2,4-disubstituted or 2,4,6-trisubstituted and, in the 4-position, can carry, inter alia, an alkylamino or (substituted) hydroxylamino group.
• Plant growth regulators are particularly well suited.
• the present invention relates to 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 1 1 , SOR 1 1 ,
• R 2 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, the
• radicals are independently unsubstituted or substituted by one or more radicals from the group halogen, C 1 -C 4 alkoxy and C 1 - C 4 alkylthio,
• 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 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,
• 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 1 1 ,
• R 9 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
• R 1 1 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 -alkynyl, the latter 3 R este unsubstituted or substituted 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 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 substituted by one or more radicals from the group halogen, C 1 -C 4 -alkoxy and C 1 - C 4 -alkylthio, 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
• 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 is a radical 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
• R 18 is a radical analogous to R 7 ,
• R 19 is a radical analogous to R 8 ,
• R 20 is a radical 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 is a radical analogous to R 9 ,
• R 24 is a radical analogous to R 10 .
• R 25 is a residue analogous to R ⁇
• R 26 is a radical 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,
• W is O or S, n is 0, 1, 2 or 3 and o is 0, 1, 2 or 3.
• alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched. Unless specifically stated, these residues are the
• Carbon skeletons with 1 to 4 carbon atoms, or in the case of unsaturated groups with 2 to 4 carbon atoms are preferred.
• Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl, etc. mean z. B.
• alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, alkenyl means e.g.
• Alkynyl means e.g. 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 partly or completely substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF, by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine 3 CF 2 , CH 2 FCHCI, CCI 3 , CHCI 2 , CH 2 CH 2 CI;
• Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI.
• 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 the oxy radicals corresponding to the aryl radicals mentioned, in particular phenoxy.
• Heteroaryl or a heteroaromatic radical means a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains 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 components mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents
• Substituents from the group halogen e.g. 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.
• halogen e.g. 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 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 -Halogenalkyl, C 1 -C 4 -haloalkoxy and nitro is substituted, for example 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-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 the group N, O and S. The rest can be benzofused. There are residues such as oxiranyl, pyrrolidyl, piperidyl, dioxolanyl, pyrazolyl, morpholyl, furyl,
• the invention also relates to all stereoisomers which are encompassed by formula (I) and mixtures thereof.
• Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not indicated separately in the general formulas (I).
• the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula I and can be obtained from mixtures of the stereoisomers by conventional methods or else by
• ⁇ ereoselective reactions can be produced in combination with the use of stereochemically pure starting materials.
• the compounds of formula (I) can form salts in which the hydrogen of the -SO 2 -NH group or other acidic hydrogen atoms (for example from COOH and others) is replaced by a cation suitable for agriculture.
• These salts are, for example, metal salts, in particular alkali metal salts (for example Na or K salts) or alkaline earth metal salts, or also ammonium salts or salts with organic ones
• Amines. Salt formation can also take place by addition of an acid to basic groups such as amino and alkylamino.
• Suitable acids for this are strong inorganic and organic acids, for example HCl, HBr, H 2 SO 4 or HNO 3 .
• 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
• R 2 is hydrogen, C 1 -C 6 alkyl, C 3 -C 5 alkenyl or C 3 -C 5 alkynyl, the
• 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 C 1 -C 4 alkylthio, or
• 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 , or
• R 4 is hydrogen or methyl
• 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 is 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, O and S and is unsubstituted or by one or more radicals from the group halogen, NO 2 , CN, CHO, COCH 3 , CO 2 CH 3 , OCH 3 and SCH 3 is substituted, 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 1 1 C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
• R 12 is hydrogen, OH, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkyl
• 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 COOC 2 H 5 , or
• the R 14 independently of one another are hydrogen or C 1 -C 4 -alkyl, preferably H,
• 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 one or several residues from the group C 1 -C 4 alkyl and oxo are substituted, for example heterocyclic residues of the formulas A 1 to A 9
• R 16 is a radical analogous to R 5 , R 1 7 hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, the
• 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 is a radical analogous to R 7 ,
• R 19 is a radical analogous to R
• R 20 is a radical 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 is a radical analogous to R 9 ,
• R 24 is a radical analogous to R 10
• R 25 is a radical analogous to R 9 ,
• R 26 is a radical 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
• W O or S preferably O, or
• n 0, 1 or 2 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,
• 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
• Preferred compounds are also compounds of the formula (I) 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 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
• R 1 is in the 5-position (or 3-position) on
• Phenyl ring, n means 0 or 1 and the rest
• R 3 is in the 2-position (or 6-position) on the phenyl ring.
• R 3 particularly preferably denotes a group of the formula CO-OR 17 in the 2- or 6-position on the phenyl radical and n is 1.
• 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),
• reaction of the compounds of formulas (II) and (III) is preferably base-catalyzed in an inert organic solvent, such as. B.
• the sulfonamides (II) are new compounds. They and their manufacture are also the subject of the invention.
• the t-butyl protective group is split off, for example, at temperatures from -20 ° C. to 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
• Dialkyl sulfates or corresponding alkyl halides are as
• Suitable alkylating agents cf. Houben-Weyl-Klamann, "Methods of Organic Chemistry", 4th edition, Vol. E XVI / a, p. 271, Thieme Verlag Stuttgart, 1990).
• electrophiles such as, for example, acid chlorides, acid anhydrides, isocyanates and thioisocyanates
• 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. (see: Houben-Weyl-Klamann , "Methods of Organic Chemistry", 4th ed., Vol. E
• the sulfonic acid group of the compounds (VIII) is converted into the sulfochlorides, e.g. using standard methods such as implementation of
• 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)
• the starting compounds of the formula (VIII) or their sulfochlorides mentioned are either known or commercially available compounds or can be prepared in a simple manner, e.g. by
• Preliminary stages can also be used for those which can be replaced for process variant b)
• the phenylsulfonyl isocyanates of the formula (IV) with R 2 not equal to H can be prepared, for example, from compounds (II), for example using phosgene, analogously to the processes from EP-A-184 385.
• reaction of the compounds (IV) with the amino heterocycles (V) is preferably carried out in inert, aprotic solvents such as. B. dioxane, acetonitrile or tetrahydrofuran at temperatures between 0 ° C and the boiling point of the solvent.
• aprotic solvents such as. B. dioxane, acetonitrile or tetrahydrofuran at temperatures between 0 ° C and the boiling point of the solvent.
• the (thio) isocyanates of the formula (X) can be prepared by processes known from the literature (cf. EP-A-232 067A, EP-A-166 516).
• reaction of compounds of formula (X) with sulfonamides of formula (II) takes place at temperatures between -10 ° C and 100 ° C, preferably between 20 and 80 ° C, in an inert aprotic solvent such as e.g. Acetone or acetonitrile, in the presence of a suitable base, e.g. Triethylamine or potassium carbonate.
• aprotic solvent such as e.g. Acetone or acetonitrile
• the salts of the compounds of formula (I) are preferably inert
• Solvents such as B. water, methanol, acetone, dichloromethane,
• 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 example, HCl, HBr, H 2 SO 4 or HNO 3 .
• Solvents are solvents that are meant under the respective
• Reaction conditions are inert, but not under any
• the compounds of formula (I) or their salts according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
• Connections can be checked without being limited to certain types by the name.
• the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene to regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, e.g. by triggering desiccation and stunted growth.
• a Inhibition of vegetative growth plays a major role in many mono- and dicotyledon crops, as this can reduce or completely prevent storage.
• 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.
• the invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I) or their salts.
• the compounds of formula (I) or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: 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 ,
• WP wettable powder
• SP water-soluble powder
• EC emulsifiable concentrates
• EW emulsions
• sprayable solutions emulsions
• SC Suspension concentrates
• CS capsule suspensions
• DP dusts
• pickling agents granules for spreading and soil application
• granules GR
• WG water-dispersible granules
• SG water-soluble granules
• the necessary formulation aids such as inert materials, surfactants,
• Solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colioid Chemistry "; 2nd Ed., J. Wiley & Sons, NY; C. Marsden,” Solvents Guide “; 2nd Ed., Interscience, NY 1963; McCutcheon's” Detergents and Emulsifiers Annual “, MC Publ. Corp., Ridgewood NJ ; Sisley and Wood, “Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt,
• Manufacture fungicides, safeners, fertilizers and / or growth regulators e.g. in the form of a finished formulation or as a tank mix.
• Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines,
• the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and simultaneously or subsequently with the
• Formulation aids mixed.
• Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
• organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
• ionic and / or nonionic surfactants emulsifiers
• emulsifiers which can be used are: 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, for. B. sorbitan fatty acid esters or polyoxethylene sorbitan esters such. B.
• Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• finely divided solid substances e.g. 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 bead mills and optionally adding surfactants, such as z. B. above with the others
• Emulsions e.g. B. oil-in-water emulsions (EW) can be, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as z. B. are already listed above for the other types of formulation.
• Granules can either by spraying the active ingredient
• Carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
• Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
• the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active compound of the formula (I) or salts thereof.
• the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components.
• the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
• Dust-like formulations contain 1 to 30, preferably mostly 5 to 20% by weight of active ingredient, sprayable
• Solutions about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient.
• the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
• the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight,
• the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
• Active substances can be used, as in e.g. from Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Brackneil, England, and the literature cited therein.
• Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Brackneil, England, and the literature cited therein.
• acetochlor acifiuorfen; aclonifen
• AKH 7088 ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidenes] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim; ametryn;
• busoxinone busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin; butylates; carbetamide; CDAA, i.e. H. 2-chloro-N, N-di-2-propenylacetamide; CDEC, i.e. H.
• chlomethoxyfen chloramben; chlorazifop-butyl, pirifenop-butyl; chlorbromuron; chlorobufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl;
• 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, clomazone; dimethipin; dimetrasulfuron, cinosulfuron; dinitramine; dinoseb; dinoterb; diphenamide; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 177, i.e. H.
• 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; halosafen; haloxyfop and its ester derivatives; hexazinone; Hw 52, ie N- (2,3-dichlorophenyl) -4- (ethoxymethoxy) benzamide; imazamethabenz-methyl; imazapyr; imazaquin;
• met.zthiazuron metham; methazole; methoxyphenone; methyldymron;
• nitrofluorfen norflurazon; orbencarb; oryzalin; oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenmedipham; phenisopham;
• phenmedipham phenmedipham; picloram; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodiamine; profluralin; proglinazine-ethyl;
• prometon prometryn; propachlor; propanil; propaquizafop and its
• terbumeton terbuthylazine; terbutryn; TFH 450, i.e. H. N, N-Diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1 H-1,2,4-triazole-1-carboxamide; thiazafluron;
• thifensulfuron-methyl thifensulfuron-methyl
• thiobencarb tiocarbazil
• tralkoxydim tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin;
• the formulations present in commercial form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Preparations in the form of dust, ground or scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
• herbicide used i.a. varies the required application rate of
• Compounds of formula (I) can fluctuate within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but it is preferably between 0.005 and 5 kg / ha.
• Ph phenyl
• n-Pr n-propyl
• i-Pr i-propyl
• a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
• a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I),
• a readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of formula (I) with 6 parts by weight of alkylphenol polyglycol ether (Triton ® X 207), 3 wt. parts by
• a water-dispersible granulate is obtained by:
• Homogenize 50 "water on a colloid mill and pre-crush it, then grind it on a bead mill and atomize and dry the suspension thus obtained in a spray tower using a single-component nozzle.
• Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy loam in plastic pots and covered with soil.
• the compounds according to the invention formulated in the form of wettable powders or emulsion concentrates were then applied as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l / ha in different dosages to the surface of the covering earth. After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the weeds. The visual assessment of the damage to the plants and the emergence occurred after the emergence of the
• Compounds according to the invention have a good herbicidal pre-emergence activity against a broad spectrum of grasses and weeds.
• the compounds of Examples 61, 192, 217, 238, 256 and 262 from Tables 1, 3-9 and 3-29 from Tables 3 and 4-9 from Table 4 have very good herbicides Effect against harmful plants such as Sinapis alba, Chrysanthemum segetum, Avena sativa, Stellaria media, Echinochloa crus-galli and Lolium multiflorum in the pre-emergence process with an application rate of 0.3 kg and less
• Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in plastic pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions. The test plants were treated at the three-leaf stage three weeks after sowing.
• Test plants in a greenhouse under optimal growth conditions optically rated the effect of the preparations compared to untreated controls.
• the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, even after emergence. For example, the connections of
• Harmful plants such as Sinapis alba, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Chrysanthemum segetum and Avena sativa im
• Cultures such as Soy, cotton, rapeseed, sugar beet and potatoes were left undamaged in the pre- and post-emergence process, even with high active ingredient doses. Some substances are particularly gentle on Gramineae crops, e.g. Barley, wheat, rye, sorghum, corn or rice.

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• 1992
  • 1992-09-16 DE DE4230933A patent/DE4230933A1/de not_active Withdrawn
• 1993
  • 1993-09-13 AU AU48161/93A patent/AU4816193A/en not_active Abandoned
  • 1993-09-13 KR KR1019950701009A patent/KR950703538A/ko not_active Application Discontinuation
  • 1993-09-13 BR BR9307062A patent/BR9307062A/pt not_active Application Discontinuation
  • 1993-09-13 WO PCT/EP1993/002469 patent/WO1994006778A1/de not_active Application Discontinuation
  • 1993-09-13 JP JP6507781A patent/JPH08501542A/ja not_active Withdrawn
  • 1993-09-13 EP EP93920708A patent/EP0660828A1/de not_active Withdrawn
  • 1993-09-13 CA CA002144769A patent/CA2144769A1/en not_active Abandoned
  • 1993-09-15 CN CN93117530A patent/CN1112922A/zh active Pending

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