WO2019121547A1 - Thiophényluraciles substitués, leurs sels et leur utilisation comme agents herbicides - Google Patents

Thiophényluraciles substitués, leurs sels et leur utilisation comme agents herbicides Download PDF

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WO2019121547A1
WO2019121547A1 PCT/EP2018/085267 EP2018085267W WO2019121547A1 WO 2019121547 A1 WO2019121547 A1 WO 2019121547A1 EP 2018085267 W EP2018085267 W EP 2018085267W WO 2019121547 A1 WO2019121547 A1 WO 2019121547A1
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alkyl
methyl
aryl
haloalkyl
cycloalkyl
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PCT/EP2018/085267
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German (de)
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Jens Frackenpohl
Ines Heinemann
Lothar Willms
Roland Beffa
Hansjörg Dietrich
Elmar Gatzweiler
Anu Bheemaiah MACHETTIRA
Christopher Hugh Rosinger
Peter Lümmen
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Bayer Aktiengesellschaft
Bayer Cropscience Aktiengesellschaft
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    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • this invention relates to substituted thiophenyluracils and their salts, processes for their preparation and their use as herbicides, in particular for controlling weeds and / or weeds in crops and / or as plant growth regulators for influencing the growth of crops.
  • Lactic acid groups can also be used as herbicidal active compounds (compare JP2000 / 302764, JP2001 / 172265, US6403534, EP408382). It is furthermore known that N-aryluracils with optionally further substituted thiolactic acid groups likewise exhibit herbicidal effects (compare WO2010 / 038953, KR2011110420, WO2013 / 154396, EP2343284).
  • An object of the present invention are thus substituted thiophenyluracils of the general formula (I) or salts thereof
  • R 1 is (C 1 -C 8 -alkyl, amino, bis - [(C 1 -C 8 ) -alkyl] -amino,
  • R 2 is hydrogen, (C i -CT) -alkyl
  • R 3 is hydrogen, halogen, (CT-Cx) -alkoxy,
  • R 4 is halogen, cyano, NO 2 , C (O) NH 2 , C (S) NH 2 , (CT-Cx) -haloalkyl, (CT-Csj-alkynyl,
  • R 5 and R 6 independently of one another represent hydrogen, halogen, (CT-Cx) -alkyl, (CT-Cx) -cycloalkyl,
  • R 5 and R 6 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
  • R 5 and R 6 with the carbon atom to which they are attached form a optionally substituted by R 81 and R 82 double bond, according to the following formula (G)
  • R 20 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C 1 -C 6) -alkoxy, m is 0, 1, 2,
  • a 7 and A 8 are each as defined below and wherein arrow is a bond to the carbonyl group, X is O (oxygen) or the groups NR 69 or NOR 70 and wherein R 69 and R 70 in the grouping NR 69 and NOR 70 independently of one another have the meanings according to the following definitions
  • R 7 is (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) - alkynyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C3-Cio) halocycloalkyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, hydroxyalkyl, aryl (Ci-C 8) alkoxy (Ci-C 8) alkyl, Heteroryl- (Ci-C 8) alkoxy (Ci-C 8) - alkyl, heterocyclyl- (Ci-C 8) alkoxy (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyloxy- (C 1
  • R 5 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 8-membered monocyclic or bicyclic ring,
  • R 8 is (C 1 -C 8 ) -alkoxy, (C 2 -C 8 ) -alkenyloxy, (C 2 -C 8 ) -alkynyloxy, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) - cycloalkyl (Ci-C8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -Alkmyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) - haloalkynyl , (C 3 -C 10) -halocycloalkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, hydroxyalkyl, aryl- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, Hetero
  • R 9 and R 69 are independently hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, cyano (Ci-C 8) - alkyl, (C 3 -C 8) cycloalkyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl, arylsulfonyl,
  • R 10 and R 11 with the carbon atom to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • R 12 and R 13 are each independently fluorine, (Ci-Cg) alkyl, (C3-Cg) -cycloalkyl, (C3-Cg) -cycloalkyl- (Ci-Cg) -alkyl, (C 2 -Cg) -alkenyl , (C 2 -C 9) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -Cg) -haloalkenyl, (C 2 -C 6) -haloalkynyl, (C 1 -C 6) -alkoxy- (C 1 -C 8) - alkyl, (Ci-Cg) -alkoxy- (Ci-Cg) -haloalkyl, (Ci-Cg) -haloalkoxy- (Ci-Cg) -haloalkyl, (Ci-Cg) -haloalkoxy- (Ci-
  • R 12 and R 13 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
  • R 12 and R 13 form an exomethylene group with the carbon atom to which they are attached
  • R 14 is hydrogen, (Ci-C 8) -alkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) - alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) - haloalkoxy ( C 1 -C 9) -alkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6) -alkyl, (C 1 -C 8) ) Alkylthio (Ci-Cg) -alkyl, (C
  • a 1 is a direct bond, O (oxygen), S (sulfur), CR 71 R 72 , NH or the groups NR 69 or NOR 70 , and wherein R 69 , R 70 , R 71 and R 72 in the group CR 71 R 72 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R ' ⁇ R 16, R 17, R 18, R 28, R 29, R 30 and R 31 are independently hydrogen, (Ci-Cg) alkyl, (C 3 -C 8) - cycloalkyl, (C 3 - C 8) cycloalkyl (Ci-C8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-Cio) - haloalkyl, (Ci-C 8) - Alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 4) -haloalkyl; 8) alkyl, heterocyclyl, heterocyclyl (Ci-C8)
  • R 19, R 27, R 32, R 39 and R 48 are independently hydrogen, (Ci-C 8) -alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (C 2 - C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C8) haloalkyl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl- ( C 1 -C 8 ) -alkyl, R 85 0- (C 1 -C 8 ) -alkyl, R 86 S- (C 1 -C 8 ) -alkyl, R 83 R 84 N- (C 1 -C 8 ) -alkyl,
  • a 2 is O (oxygen), S (sulfur), SO, SO 2 , CR 71 R 72 , NH, or the NR 69 or N-OR 70 moieties, and where R 69 , R 70 , R 71 and R 72 in the grouping CR 71 R 72 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 33 , R 34 , R 35 , R 36 , R 37 and R 38 independently of one another are hydrogen, (C 1 -C 8 ) -alkyl, ( C 3 -C 8) -cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C8) alkyl, (C 2 -C 8) alkenyl, (Ci-Cio) -haloalkyl, aryl, aryl (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl,
  • a 3 and A 4 independently represent a direct bond, O (oxygen), S (sulfur), NH or the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 or NOR 70 , wherein R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 and R 76 in the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or subsequent definitions and wherein A 3 and A 4 are not simultaneously oxygen, sulfur or a combination of sulfur and oxygen,
  • R 42, R 43, R 44 and R 45 are independently hydrogen, (Ci-C 8) -alkyl, (C3-C8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C 8) -alkyl, (C 2 -C 8 ) -alkenyl, (C 1 -C 10) -haloalkyl, R 85 0- (C 1 -C 8 ) -alkyl, R 86 is S- (C 1 -C 8 ) -alkyl, C (O) 0R 85 , C (O) NR 83 R 84 , R 85 0 (0) C- (C 1 -C 8 ) -alkyl, R 83 R 84 N (0) C- (Ci-C 8) - alkyl, R stand 83 R 84 N- (Ci-C 8) alkyl, or
  • R 44 and R 45 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • a 5 represents O (oxygen), S (sulfur), NH or the groups CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 or NOR 70 , where R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 and R 76 in the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R 48, R 49, R 50, R 51, R 54 and R 55 are independently hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) -
  • R 62 is (Ci-C8) -haloalkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C 2 -C 8) alkenyl , (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -halocycloalkyl, R 85 0- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) - alkyl, hetero
  • R 83 R 84 N C (N H) NH (Ci-Cg) alkyl, R 86 S- (Ci-Cg) alkyl, R 86 S (0) - (Ci-Cg) alkyl, R 86 S0 2 - (Ci-Cg) - alkyl, and wherein R 63 and R 64 are different in at least one case of (Ci -Cg) - alkyl,
  • a 6 and A 8 are independently a group CR 65 R 66 , wherein R 65 and R 66 in the
  • Grouping CR 65 R 66 independently of one another have the meanings according to the following definitions,
  • R 65 and R 66 independently of one another are hydrogen, (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C 1 -C 6) -haloalkyl,
  • R 67 , R 68 , R 77 , R 78 , R 79 and R 80 independently of one another represent hydrogen, (Ci-Cg) -alkyl, (C 3 -Cg) -
  • Cycloalkyl (Ci-Cg) -haloalkyl, (Ci-Cg) -alkoxy (Ci-Cg) -alkyl, aryl, aryl (Ci-Cg) -alkyl,
  • R 70 is hydrogen, (Ci-Cg) -alkyl, (C 3 -Cg) -cycloalkyl (Ci-Cg) -alkyl, (C 2 -Cg) -alkenyl, (C 2 -Cg) -alkynyl, (Ci -Cg) -alkoxy- (Ci-Cg) -alkyl, (Ci-Cg) -haloalkoxy- (Ci-Cg) -alkyl, (Ci-Cg) -alkylthio (Ci-Cg) -alkyl, aryl, aryl (Ci-Cg) -alkyl, R 85 0 (0) C- (Ci-Cg) -alkyl, R 83 R 84 N (0) C- (Ci-Cg) -alkyl,
  • R 14 and R 69 in the case that X is NR 69 , with the nitrogen atom to which they are attached, a fully saturated or optionally interrupted by heteroatoms and
  • R 14 and R 70 when X is NOR 70 , form a fully saturated and optionally further substituted 4 to 10 membered monocyclic or bicyclic ring with the nitrogen atom to which they are attached,
  • R 71 and R 72 are independently hydrogen, halogen, hydroxy, (Ci-C 8) alkyl, (CN-Cx) - cycloalkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) alkenyl, (haloalkoxy, (Ci-C8) alkylthio, (Ci-C8) alkoxy- Ci-C - (C 2 -C 8) alkynyl, (Ci-C 8) alkoxy, (Ci-C 8) 8) alkyl, (Ci-C8) haloalkoxy (Ci-C 8) - alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, aryl, aryl (Ci-C 8 ) -alkyl, R 85 0 (0) C- (C 1 -C 8 ) -alkyl, R 83 R 84 N (0) C- (C 1 -C 8 ) -
  • R 73 , R 74 , R 75 and R 76 independently of one another represent hydrogen, halogen, hydroxy, (C 1 -C 8 ) -alkyl,
  • R 81 and R 82 are independently hydrogen, halogen, (Ci-C 8) -alkyl, (C3-C8) cycloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl, (Ci-Cio) -haloalkyl, aryl or stand
  • R 81 and R 82 with the carbon atom to which they are attached form a saturated or optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring.
  • R 83 and R 84 are identical or different and independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl,
  • R 85 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) - haloalkyl , (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C3-Cio) cycloalkyl, (C3-C10) - Halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C 4 -Cio) -Halocycloalkenyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) alkoxy (Ci C 8) haloalkyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci
  • R 86 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) - haloalkyl , (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C3-Cio) cycloalkyl, (C3-C10) - halocycloalkyl, (C4-Cio) cycloalkenyl, (C4-Cio) -Halocycloalkenyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) alkoxy (Ci-C 8) haloalkyl, aryl, aryl (Ci-C8) - alkyl, heteroaryl, heteroaryl (
  • the compounds of general formula (I) can be prepared by addition of a suitable organic compound.
  • inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 S0 4 , H 3 P0 4 or HNO 3 , or organic acids, e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C 4 ) -trialkylsulfonium and (Ci-C 4 ) -Trialkylsulfoxoniumsalze.
  • the compounds used in the invention are the
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • R 1 is (C 1 -C 7 ) -alkyl, amino, bis - [(C 1 -C 7 ) -alkyl] -amino,
  • R 2 is hydrogen, (C 1 -C 7 ) -alkyl
  • R 3 is hydrogen, halogen, (C 1 -C 7 ) -alkoxy,
  • R 4 is halogen, cyano, NO 2 , C (O) NH 2 , C (S) NH 2 , (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) -alkynyl,
  • R 5 and R 6 are independently hydrogen, halogen, (Ci-C7) alkyl, (C3-C 7) -cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, (C2-C7) haloalkenyl, (C2-C7) haloalkynyl, (C3-C 7 ) -Halocycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 4 -C 7 ) -halocycloalkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, ( Ci-C7) alkoxy (Ci-C7) haloalkyl, (C
  • R 5 and R 6 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
  • R 5 and R 6 with the carbon atom to which they are attached form a optionally substituted by R 81 and R 82 double bond, according to the following formula (G)
  • R 20 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C 1 -C 4) -alkoxy, m is 0, 1, 2,
  • a 8 each have the meaning according to the following definitions is a bond to the carbonyl group, X represents O (oxygen), NH or the groupings NR 69 or NOR 70 and wherein R 69 and R 70 in the grouping NR 69 and NOR 70 independently of one another have the meanings according to the definitions below,
  • R 7 is (C 3 -C 7) cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) - alkynyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C 3 -C 7) halocycloalkyl, (Ci-C7) alkoxy (Ci-C7) - alkyl, hydroxyalkyl, aryl- (Ci-C7) alkoxy (Ci-C7) alkyl, Heteroryl- (Ci-C7) alkoxy (Ci-C7) - alkyl, heterocyclyl- (Ci-C 7) alkoxy (Ci-C7) alkyl, (C 2 -C 7) alkenyloxy (Ci-C7) alkyl, (C 2 -C 7)
  • R 5 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 8-membered monocyclic or bicyclic ring,
  • R 8 is (Ci-C7) alkoxy, (C 2 -C 7) alkenyloxy, (C 2 -C 7) alkynyloxy, (C3-C 7) -cycloalkyl, (C3-C7) - cycloalkyl (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) -alkynyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) - haloalkynyl, ( C 3 -C 7 -halocycloalkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxyalkyl, aryl- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, heteroryl- (Ci-C7) alkoxy (Ci-C7) alkyl,
  • R 9 and R 69 are independently hydrogen, (Ci-C7) alkyl, (C3-C 7) cycloalkyl, cyano (Ci-C7) - alkyl, (C3-C7) -cycloalkyl- (Ci -C 7) alkyl, (Ci-C7) alkylsulphonyl, arylsulphonyl,
  • R 10 and R 11 are independently (Ci-C7) alkyl, (C3-C 7) -cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C7) - alkyl, (C 2 -C 7 ) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) - haloalkynyl, (Ci-C7) - Alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalky
  • R 10 and R 11 with the carbon atom to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • R 12 and R 13 independently of one another represent fluorine, (Ci-C7) alkyl, (C3-C 7) -cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C7) alkyl, (C 2 - C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (Ci-C 7 ) -Alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, ( C 1 -C 7 ) -haloalkoxy- (C 1 -
  • R 12 and R 13 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
  • R 12 and R 13 form an exomethylene group with the carbon atom to which they are attached
  • R 14 is hydrogen, (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) - alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) - haloalkoxy ( C 1 -C 7 ) -alkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) -alkyl, Heterocyclyl, heterocyclyl (C 1 -C 4) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7
  • a 1 is a direct bond, O (oxygen), S (sulfur), CR 71 R 72 , NH or the groups NR 69 or NOR 70 , and wherein R 69 , R 70 , R 71 and R 72 in the group CR 71 R 72 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R 15, R e i n R R I R 2 8J 8J r »R3 and R O n una epending another represent hydrogen, (Ci-C7) alkyl, (C 3 -C 7) - cycloalkyl, (C 3 - C 7) -cycloalkyl- (Ci-C 7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) -alkynyl, (C 1 -C 7) - haloalkyl, (Ci-C7) Alkoxy- (C 1 -C 7) -haloalkyl, (C 1 -C 7) -haloalkoxy- (C 1 -C 7) -haloalkyl, aryl, aryl- (C 1 -C 7) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7) -alkyl , heterocyclyl, heterocyclyl (Ci-C
  • R 19, R 27, R 32, R 39 and R 48 are independently hydrogen, (Ci-C7) alkyl, (C3-C7) -cycloalkyl- (Ci-C 7) alkyl, (C 2 -C 7 ) alkenyl, (C 2 -C 7) alkynyl, (Ci-C7) haloalkyl, aryl (Ci-C7) alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci- C 7 ) -alkyl, R 85 0- (C 1 -C 7 ) -alkyl, R 86 S- (C 1 -C 7 ) -alkyl, R 83 R 84 N- (C 1 -C 7 ) -alkyl,
  • a 2 is O (oxygen), S (sulfur), SO, SO 2 , CR 71 R 72 , NH, or the NR 69 or N-OR 70 moieties, and where R 69 , R 70 , R 71 and R 72 in the grouping CR 71 R 72 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 33 , R 34 , R 35 , R 36 , R 37 and R 38 are each independently hydrogen,
  • a 3 and A 4 independently represent a direct bond, O (oxygen), S (sulfur), NH or the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 or NOR 70 , wherein R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 and R 76 in the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or subsequent Have definitions and where A 3 and A 4 are not simultaneously oxygen, sulfur or a combination of sulfur and oxygen,
  • R 42 , R 43 , R 44 and R 45 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) - alkyl, (C 2 -C 7) alkenyl, (Ci-C7) haloalkyl, R 85 0- (Ci-C7) alkyl, R 86 S- (Ci-C7) alkyl, C (0 ) 0R 85, C (0) NR 83 R 84, R 85 0 (0) C- (Ci-C 7) alkyl, R 83 R 84 N (0) C- (Ci-C7) - alkyl, R 83 R 84 is N- (C 1 -C 7 ) -alkyl, or
  • R 44 and R 45 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • a 5 represents O (oxygen), S (sulfur), NH or the groups CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 or NOR 70 , where R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 and R 76 in the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R 48, R 49, R 50, R 51, R 54 and R 55 are independently hydrogen, (Ci-C7) alkyl, (C 3 -C 7) - cycloalkyl, (C 2 -C 7) alkenyl , (Ci-C 7 ) -haloalkyl, R 85 0- (Ci-C 7 ) -alkyl, R 86 S- (Ci-C 7 ) -alkyl, C (0) 0R 85 , C (0) NR 83 R 84 , R 85 0 (0) C- (C 1 -C 7 ) -alkyl, R 83 R 84 N (0) C- (C 1 -C 7 ) -alkyl, R 83 R 84 N- (C 1 -C 7 ) alkyl, or
  • R 50 and R 54 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring,
  • R 56 , R 57 , R 58 , R 59 , R 60 and R 61 independently of one another are hydrogen, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl , (C 2 -C 7) alkenyl, (C 2 -C 7) -alkynyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) - haloalkynyl, (Ci-C7) alkoxy (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) alkyl, heterocyclyl
  • R 62 is (Ci-C7) haloalkyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 2 -C 7) alkenyl , (C 2 -C 7 ) alkynyl, (C 2 -C 7 ) haloalkenyl, (C 2 -C 7 ) haloalkynyl, (C 3 -C 7 ) -halocycloalkyl, R 85 0- (Ci-C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, aryl, Aryl- (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) al
  • R 63 and R 64 independently of one another represent fluorine, (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C3-C 7) -cycloalkyl, (C 3 -C 7) cycloalkyl (Ci- C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 - C 7 ) -halocycloalkyl, R 85 0- (Ci-C 7 ) -alkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) - haloalkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C 7 ) -haloalkyl, aryl
  • R 83 R 84 N C (N H) NH- (C 1 -C 7 ) -alkyl, R 86 S- (C 1 -C 7 ) -alkyl, R 86 S (0) - (C 1 -C 7 ) -alkyl , R 86 S0 2 - (Ci-C 7 ) - alkyl, and wherein R 63 and R 64 in at least one case of (Ci-C 7 ) alkyl, are different,
  • a 6 and A 8 are independently a group CR 65 R 66 , wherein R 65 and R 66 in the
  • Grouping CR 65 R 66 independently of one another have the meanings according to the following definitions,
  • R 65 and R 66 are independently hydrogen, (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl, (Ci-C 7) - are haloalkyl,
  • R 67, R 68, R 77, R 78, R 79 and R 80 are independently hydrogen, (Ci-C7) alkyl, (C 3 -C 7) -
  • Cycloalkyl, (Ci-C7) haloalkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, aryl, aryl (Ci-C7) - alkyl, are,
  • R 70 is hydrogen, (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) Alkynyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 4 ) -alkyl C 7 ) -alkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, R 85 0 (0) C- (C 1 -C 7 ) -alkyl, R 83 R 84 N (0) C- (C 1 -C 4) -alkyl C 7 ) alkyl, R 14 and R 69 in the
  • R 14 and R 70 when X is NOR 70 , form a fully saturated and optionally further substituted 4 to 10 membered monocyclic or bicyclic ring with the nitrogen atom to which they are attached,
  • R 71 and R 72 are independently hydrogen, halogen, hydroxy, (Ci-C7) alkyl, (C3-C7) - cycloalkyl, (Ci-C7) haloalkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-Cv) alkoxy, (Ci-C7) - haloalkoxy, (Ci-C7) -alkylthio, (Ci-C7) alkoxy (Ci-C 7 ) alkyl, (Ci-C7) haloalkoxy (Ci-C7) - alkyl, (Ci-C7) -alkylthio (Ci-C 7) alkyl, aryl, aryl (Ci-C 7) alkyl, R 85 0 (0) C- (Ci-C 7) alkyl, R 83 R 84 N (0) C- (C 1 -C 7) alkyl, C (0)
  • R 73 , R 74 , R 75 and R 76 independently of one another represent hydrogen, halogen, hydroxy, (C 1 -C 7 ) -alkyl,
  • R 81 and R 82 are independently hydrogen, halogen, (Ci-C7) alkyl, (C3-C 7) -cycloalkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7 ) haloalkyl, aryl or
  • R 81 and R 82 with the carbon atom to which they are attached form a saturated or optionally heteroatom-interrupted and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • R 83 and R 84 are identical or different and are each independently hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (Ci-C7) haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C3-C 7) -cycloalkyl, (C3-C 7) halocycloalkyl, (C4-C7) cycloalkenyl, (C4-C7) -Halocycloalkenyl, (C iC 7) - alkoxy- (C iC 7) alkyl, (C iC 7) haloalkoxy (C 1 -C 7) - alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 )
  • R 85 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (Ci-C7) - Haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) - cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl- (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7)
  • R 86 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (Ci-C7) - Haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) - cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl- (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C
  • R 1 is (C 1 -C 6) -alkyl, amino, bis - [(C 1 -C 6) -alkyl] -amino,
  • R 2 is hydrogen, (C 1 -C 6) -alkyl
  • R 3 is hydrogen, halogen, (Ci-G,) - alkoxy,
  • R 4 is halogen, cyano, NO 2 , C (O) NH 2 , C (S) NH 2 , (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -alkynyl,
  • R 5 and R 6 independently of one another represent hydrogen, halogen, (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl,
  • R 5 and R 6 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
  • R 5 and R 6 with the carbon atom to which they are attached form a optionally substituted by R 81 and R 82 double bond, according to the following formula (G)
  • R 20 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (GG) alkoxy, m is 0, 1, 2, Q is the groupings Ql to Q-16
  • a 8 each have the meaning given in the definitions below
  • R 7 is (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl , (C 2 -C 6) haloalkenyl, (C 2 -C 6) haloalkynyl, (C3-C6) halocycloalkyl, (Ci-C6) alkoxy (Ci-C 6) - alkyl, hydroxyalkyl, aryl - (Ci-C6) alkoxy (Ci-C 6) alkyl, Heteroryl- (Ci-C6) alkoxy (Ci-C 6) - alkyl, heterocyclyl- (Ci-C 6) alkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyloxy (Ci-C 6) alkyl, (C 2 -C
  • R 5 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 8-membered monocyclic or bicyclic ring,
  • R 8 is (GG) -alkoxy, (C 2 -Ce) -alkenyloxy, (C 2 -C 6 ) -alkynyloxy, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (Ci -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 6) halocycloalkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, hydroxyalkyl, aryl (Ci-C6) alkoxy (Ci-C 6) alkyl, Heteroryl- ( Ci-C 6) alkoxy (Ci-C 6) alkyl, heterocyclyl (GC
  • R 9 and R 69 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, cyano- (GG) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, arylsulfonyl,
  • R 10 and R 11 with the carbon atom to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • R 12 and R 13 independently of one another represent fluorine, (Ci-C 6) -alkyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) haloalkynyl, (Ci-C 6) - Alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, C 6 ) -haloalkoxy- (C 1 -C
  • R 12 and R 13 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
  • R 12 and R 13 form an exomethylene group with the carbon atom to which they are attached
  • R 14 is hydrogen, (GC 6 ) -alkyl, (GC 6 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6 ) alkyl, aryl, aryl (GC 6 ) alkyl, heteroaryl, heteroaryl (C 1 -C 6 ) alkyl, heterocyclyl, heterocyclyl (C 1 -C 6 ) alkyl, (GC 6 ) alkylthio (GC 6 ) -alkyl, (GG) - haloalkylthio (C 1 -C 6 )
  • a 1 is a direct bond, O (oxygen), S (sulfur), CR 71 R 72 , NH or the groups NR 69 or NOR 70 and wherein R 69 , R 70 , R 71 and R 72 in the group CR 71 R 72 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R ' ⁇ R 16, R 17, R 18, R 28, R 29, R 30 and R 31 are independently hydrogen, (Ci-C 6) -alkyl, (C 3 -C 6) - cycloalkyl, (C3- C 6) -cycloalkyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - haloalkyl, (Ci-C 6) Alkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (ci) C 6) alkyl, heterocyclyl, heterocyclyl (Ci-C 6) - alkyl, R 85 0-
  • R 19, R 27, R 32, R 39 and R 48 are independently hydrogen, (Ci-C 6) -alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) alkynyl, (Ci-C 6) -haloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci -C 6 ) -alkyl, R 85 0- (C 1 -C 6 ) -alkyl, R 86 S- (C 1 -C 6 ) -alkyl, R 83 R 84 N- (C 1 -C 6 ) -alkyl,
  • a 2 is O (oxygen), S (sulfur), SO, SO 2 , CR 71 R 72 , NH, or the NR 69 or N-OR 70 moieties , and where R 69 , R 70 , R 71 and R 72 are in the Grouping CR 71 R 72 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 33 , R 34 , R 35 , R 36 , R 37 and R 38 are each independently hydrogen,
  • a 3 and A 4 independently represent a direct bond, O (oxygen), S (sulfur), NH or the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 or NOR 70 , wherein R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 and R 76 in the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or subsequent definitions and wherein A 3 and A 4 are not simultaneously oxygen, sulfur or a combination of sulfur and oxygen,
  • R 42 , R 43 , R 44 and R 45 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6) alkenyl, (Ci-C 6) -haloalkyl, R 85 0- (Ci-C 6) alkyl, R 86 is S- (C 1 -C 6 ) -alkyl, C (O) 0R 85 , C (O) NR 83 R 84 , R 85 0 (0) C- (C 1 -C 6 ) -alkyl, R 83 R 84 N (0) C- (Ci-C 6) - alkyl, R 83 R 84 are N- (Ci-C 6) alkyl, or
  • R 44 and R 45 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • a 5 represents O (oxygen), S (sulfur), NH or the groups CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 or NOR 70 , where R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 and R 76 in the groupings CR 71 R 72 , CR 73 R 74 CR 75 R 76 , NR 69 and NOR 70 independently of one another have the meanings according to the preceding or following definitions,
  • R 48, R 49, R 50, R 51, R 54 and R 55 are independently hydrogen, (Ci-C 6) -alkyl, (C3-C6) - cycloalkyl, (C 2 -C 6) alkenyl, ( C 1 -C 6 ) -haloalkyl, R 85 0- (C 1 -C 6 ) -alkyl, R 86 S- (C 1 -C 6 ) -alkyl, C (O) 0R 85 , C (O) N-R 83 R 84 , R 85 0 (0) C- (C 1 -C 6 ) -alkyl, R 83 R 84 N (0) C- (C 1 -C 6 ) -alkyl, R 83 R 84 N- (C 1 -C 6 ) -alkyl stand, or
  • R 50 and R 54 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, j ⁇ 6 o untj j ⁇ 6i una bi q ä n gig another represent hydrogen, (C3-C6) -cycloalkyl, (C3-C6) -
  • R 62 is (Ci-C 6) -haloalkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, ( C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -halocycloalkyl, R 85 0- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroary
  • R 83 R 84 NC (N H) NH- (C 1 -C 6 ) -alkyl, R 86 S- (C 1 -C 6 ) -alkyl, R 86 S (0) - (C 1 -C 6 ) -alkyl, R 86 S0 2 - (Ci-C 6) - alkyl, and wherein R 63 and R 64 are different in at least one case of (Ci-C 6) alkyl,
  • a 6 and A 8 are independently a group CR 65 R 66 , wherein R 65 and R 66 in the
  • Grouping CR 65 R 66 independently of one another have the meanings according to the following definitions,
  • R 65 and R 66 are independently hydrogen, (Ci-C 6) -alkyl, (C3-C6) cycloalkyl, (CI-C ⁇ ) - haloalkyl stand,
  • R 67 , R 68 , R 77 , R 78 , R 79 and R 80 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -
  • Cycloalkyl, (Ci-C 6) -haloalkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, aryl, aryl (Ci-C 6) - alkyl, are,
  • R 70 is hydrogen, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) Alkynyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (Ci C 6 ) -alkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, R 85 0 (0) C- (C 1 -C 6 ) -alkyl, R 83 R 84 N (0) C- (C 1 -C 4) -alkyl C 6 ) alkyl,
  • R 14 and R 69 in the case that X is NR 69 , with the nitrogen atom to which they are attached, a fully saturated or optionally interrupted by heteroatoms and
  • R 14 and R 70 when X is NOR 70 , form a fully saturated and optionally further substituted 4 to 10 membered monocyclic or bicyclic ring with the nitrogen atom to which they are attached,
  • R 71 and R 72 are independently hydrogen, halogen, hydroxy, (Ci-C 6) -alkyl, (C3-C6) - cycloalkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (Ci-C 6) alkoxy, (Ci-C6) - haloalkoxy, (Ci-C 6) alkylthio, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) haloalkoxy (Ci-C 6) - alkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, aryl, aryl (Ci-C 6 ) -alkyl, R 85 0 (0) C- (C 1 -C 6
  • R 71 and R 72 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • R 73 , R 74 , R 75 and R 76 independently of one another represent hydrogen, halogen, hydroxy, (C 1 -C 6 ) -alkyl,
  • R 81 and R 82 are independently hydrogen, halogen, (Ci-C 6) -alkyl, (C3-C6) cycloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, ( Ci-C 6 ) -haloalkyl, aryl or
  • R 81 and R 82 with the carbon atom to which they are attached form a saturated or optionally heteroatom-interrupted and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
  • R 83 and R 84 are identical or different and are each independently hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) Cyanoalkyl, (C 1 -C 6 ) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C4 -C6) cycloalkenyl, (C4-C6) -Halocycloalkenyl, (C 1 - C 6) - A 1 k 0 xy - (C 1 - C 6) - a 1 ky 1, (C iC 6) haloalkoxy ( C 1 -C 6) alkyl,
  • R 85 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) - haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C3-C6) -cycloalkyl, (C3-C6) - halocycloalkyl, (C4-C ö) cycloalkenyl, (C4-C6) -Halocycloalkenyl , (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl
  • R 86 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) - Haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 4 -C 6 ) -Halocycloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl
  • R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-
  • R 2 is hydrogen, methyl, ethyl, n-propyl, iso-propyl,
  • R 3 is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy
  • R 4 is halogen, cyano, NO 2 , C (O) NH 2 , C (S) NH 2 , difluoromethyl, trifluoromethyl, ethynyl, propynyl-1, propyn-1-yl, 1-butynyl-yl, pentyne l-yl, hexynyl,
  • R 5 and R 6 independently of one another are hydrogen, fluorine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,
  • Fluoromethyl difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl,
  • Chloromethyl bromomethyl, methoxy, ethoxy, n-propyloxy, isopropoxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, iso-propyloxymethyl,
  • Methylcarbonylethyl hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl,
  • Ethoxycarbonylmethyl n-propyloxycarbonylmethyl, iso-propyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl,
  • Cyclohexylaminomethyl methoxycarbonylaminomethyl, ethoxycarbonylaminomethyl tert -butyloxycarbonylaminomethyl, methylcarbonylaminomethyl, ethylcarbonylaminomethyl, n-propylcarbonylaminomethyl, iso -propylcarbonylaminomethyl, 2- (methylamino) eth-1-yl, 2- (dieth-1-ylamino) eth-1-yl, 2- ( Diethylamino) eth-1-yl, 2- (ethylamino) eth-1-yl, 2- (iso -propylamino) eth-1-yl, 2- (cyclopropylamino) eth-1-yl, 2- (cyclobutylamino) ethane 1-yl, 2- (cyclopentylamino) eth-1-yl, 2- (cyclohexylamino) eth-1-yl,
  • R 5 and R 6 with the carbon atom to which they are attached, a fully saturated or
  • R 5 and R 6 with the carbon atom to which they are attached form a optionally substituted by R 81 and R 82 double bond, according to the following formula (G)
  • R 20 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, n-propyloxy, n-butyloxy, m is 0, 1, 2,
  • R 81 and R 82 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,
  • R 81 and R 82 with the carbon atom to which they are attached, a saturated or
  • Q is one of the groupings Q-1.l to Q-16.90 mentioned specifically below:
  • R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, amino, dimethylamino
  • R 2 is hydrogen, methyl, ethyl, n-propyl , iso-propyl,
  • R 3 is hydrogen, fluorine, chlorine, bromine, methoxy
  • R 4 is halogen, cyano, NO 2 , C (O) NH 2 , C (S) NH 2 , difluoromethyl, trifluoromethyl, ethynyl,
  • R 5 and R 6 independently of one another are hydrogen, fluorine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,
  • Trifluoromethoxymethyl trifluoromethoxyethyl, trifluoromethoxy-n-propyl, phenyl,
  • Methylcarbonylethyl hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, aminocarbonyl, methylaminocarbonyl,
  • Ethoxycarbonylmethyl n-propyloxycarbonylmethyl, iso-propyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl,
  • R 5 and R 6 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
  • R 5 and R 6 with the carbon atom to which they are attached form a optionally substituted by R 81 and R 82 double bond, according to the following formula (G)
  • R 20 is hydrogen, fluorine, chlorine, trifluoromethyl, m is 0, 1, 2,
  • R 81 and R 82 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-
  • R 81 and R 82 with the carbon atom to which they are attached, a saturated or
  • R 1 is methyl, ethyl, n-propyl, 1-methylethyl, amino, dimethylamino,
  • R 2 is hydrogen, methyl, ethyl
  • R 3 is hydrogen, fluorine, chlorine, bromine, methoxy
  • R 4 is fluorine, chlorine, bromine, cyano, NO 2 , C (O) NH 2 , C (S) NH 2 , difluoromethyl, trifluoromethyl,
  • R 5 and R 6 independently of one another are hydrogen, fluorine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1, 2-trimethylpropyl, 1, 2,2-
  • R 5 and R 6 with the carbon atom to which they are attached form a optionally substituted by R 81 and R 82 double bond, according to the following formula (G)
  • R 20 is hydrogen, fluorine, chlorine, trifluoromethyl, m is 0, 1, 2,
  • R 81 and R 82 independently of one another represent hydrogen, fluorine, chlorine, methyl, ethyl, n-
  • R 81 and R 82 with the carbon atom to which they are attached, a saturated or
  • the compounds of the general formula (1) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by formula (1). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be distinguished from those in the Preparation of resulting mixtures obtained by conventional separation methods.
  • the chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the preparation of test samples for the biological assay.
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (1), but are not specified with their specific stereoform, and mixtures thereof.
  • the purification can also by
  • Isolation, purification and stereoisomer separation methods of compounds of formula (1) can be any of the methods well known to those skilled in the art from analogous cases, e.g. through physical processes such as crystallization, chromatography, especially
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms for example (but not limited to) (C 1 -C 6 ) -alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl- propylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpent
  • heteroarylsulfonyl is optionally substituted pyridylsulfonyl
  • Heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (GG) - or (Ci-C i) -alkylthio, for example (but not limited to) (Ci- C 6 ) -Alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, Butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1- Ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethyl
  • Alkenylthio in the invention means an alkenyl radical bonded via a sulfur atom
  • Alkynylthio represents an alkynyl group bonded through a sulfur atom
  • cycloalkylthio represents a cycloalkyl group bonded through a sulfur atom
  • cycloalkenylthio represents an above
  • (C 1 -C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
  • Alkoxy means an alkyl radical bonded via an oxygen atom, e.g. (But not limited to) (C 1 -C 6 ) alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1, 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2 Methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, l Dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy , 1, 2,2-trimethylpropoxy, 1-
  • Alkenyloxy is an alkenyl radical bonded via an oxygen atom
  • alkynyloxy is an alkynyl radical bonded via an oxygen atom, such as (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) - ( C3-C6) - or (C3-C4) alkynoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom
  • the number of C atoms refers to the alkyl radical in the
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl
  • Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
  • heterocyclic radical contains at least one heterocyclic ring
  • heterocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P
  • N, O, S, P saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • optionally substituted heterocyclyl also become
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
  • Oxygen atoms are to be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
  • 3-membered ring and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 or 2 or
  • 6-yl 1, 4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1, 6-dihydropyriazine-1- or 3- or 4- or 5- or 6-yl;
  • 1,2-dithiolan-3 or 4-yl 1,2-dithiolan-3 or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2 or 4-yl; l, 3-dithiol-2- or 4-yl; 1, 2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3 or 4 or 5 or 6-yl; 3,6-dihydro-
  • 1,2-dithiin-3 or 4-yl 1,2-dithiin-3 or 4-yl; l, 2-dithiin-3 or 4-yl; l, 3-dithian-2 or 4 or 5-yl; 4H-l, 3-dithiin-2 or 4 or 5 or 6-yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, Halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group can also occur at the hetero ring atoms, which can exist in different oxidation states, for example at N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring.
  • N (O), S (O) (also SO for short) and S (O) 2 also short SO2
  • heteroaryl refers to heteroaromatic compounds, i. H.
  • heteroaryls are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
  • quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines eg isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline quinazoline
  • cinnoline l, 5-naphthyridine; l, 6-naphthyridine; l, 7-naphthyridine; l, 8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyrido
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H- Indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran; 5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophene-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazole
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated Hydrocarbon radical which is optionally mono- or polysubstituted and is referred to in the latter case as “substituted alkyl".
  • Preferred substituents are halogen, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo.
  • the prefix "bis” also includes the combination of different alkyl radicals, e.g. For example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, e.g. monohaloalkyl
  • ( Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHCICH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCl 3, CClF 2, CFC1 2 CF 2 CC1F 2, CF 2 CCIFCF3; Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3 ; The term perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, wherein the corresponding fluorine atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3 .
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated one
  • Hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, wherein all other optional halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4) -alkyl denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
  • Range for C atoms includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. B. "(Ci-C 6 ) alkyl”, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
  • the lower carbon skeletons for example with 1 to 6 C atoms or in unsaturated groups having 2 to 6 carbon atoms, are preferred.
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or
  • alkenyl in particular also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl means e.g.
  • Vinyl which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C 2 -C 6) -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl , 3-Butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4 Pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl , 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1,
  • alkynyl in particular also includes straight-chain or branched open-chain
  • C 2 -C 6) -alkynyl denotes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2 Butinyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl 3 -butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
  • alkylidene group such as methylidene
  • polycyclic aliphatic systems are also included, such as, for example, bicyclo [1,1.0] butan-1-yl, bicyclo [1,11] butan-2-yl, bicyclo [2.1.0] pentane-1-ol yl, bicyclo [1,11] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl,
  • 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl radical, for.
  • substituents having a double bond on the cycloalkenyl radical for.
  • an alkylidene group such as methylidene
  • substituted cycloalkyl the explanations for substituted cycloalkyl apply correspondingly.
  • alkylidene for. B. in the form of (Ci-Cio) alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical, via a double bond is bound.
  • Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom
  • arylalkyloxy means an arylalkyl radical bonded via an oxygen atom
  • Alkoxyalkyl means an alkoxy group attached via an alkyl group
  • alkoxyalkoxy means an alkoxyalkyl group bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded via an alkyl group
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl stands for an aryloxy radical bound via an alkyl group
  • Heteroaryloxyalkyl means a heteroaryloxy group bonded via an alkyl group.
  • Haloalkoxyalkyl means a haloalkoxy radical attached and "haloalkylthioalkyl” means a haloalkylthio radical attached via an alkyl group.
  • Arylalkyl means an aryl group attached via an alkyl group
  • heteroarylalkyl means a heteroaryl group bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl group bonded through an alkyl group.
  • Cycloalkylalkyl means a cycloalkyl group bonded via an alkyl group, e.g. B. (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.
  • Arylalkenyl is an aryl group bonded through an alkenyl group
  • heteroarylalkenyl means a heteroaryl group bonded via an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl group bonded via an alkenyl group
  • Arylalkynyl means an aryl group bonded through an alkynyl group
  • heteroarylalkynyl means a heteroaryl group bonded via an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl group bonded through an alkynyl group.
  • haloalkylthio in isolation or as part of a chemical group-stands for straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cs) -, (C ' iG,) - or (Ci-C4) -haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2 , 2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
  • Halocycloalkyl and “Halocycloalkenyl” mean by the same or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. Trifluoromethyl or difluoromethyl, partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • trialkylsilyl alone or as part of a chemical group - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as tri - [(Ci-C 8 ) -, (Ci-Cr,) - or (Ci-C i) -alkyl] silyl, for example (but not limited to) trimethylsilyl, triethylsilyl, tri- (n-) propyl) silyl, tri (isopropyl) silyl, tri (n-butyl) silyl, tri (1-methylprop-1-yl) silyl, tri (2-methylprop-1-yl) silyl, tri ( 1, 1-dimethyleth-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl.
  • Trialkylsilylalkinyl stands for a trialkylsilyl radical bonded via an alkynyl group.
  • the substituted thiophenyluracils of the general formula (1) according to the invention can be prepared starting from known processes.
  • the synthetic routes used and investigated are based on commercially available or easily prepared heteroaromatic amines and correspondingly substituted amino acids.
  • the groupings Q, W, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 20 of the general formula (1) in the following schemes have the meanings defined above, if not exemplary but not limiting, Definitions are made.
  • a suitable substituted aniline by way of example but not limitation, of 2-fluoro-4-chloroaniline, with a suitable reagent (eg triphosgene) in a suitable polar aprotic solvent (eg dichloromethane) in the corresponding isocyanate
  • a suitable reagent eg triphosgene
  • a suitable polar aprotic solvent eg dichloromethane
  • the next step is to implement it with a suitable aminoacrylic acid ester using a suitable base (e.g., sodium hydride or potassium tert -butylate) in a suitable polar aprotic solvent (e.g., N, N-dimethylformamide) in the corresponding optionally further substituted pyrimidine-2,4 -dione, by way of example but not limitation, 3- (4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (Scheme 1).
  • W is illustrative but not limiting of O
  • R 1 by way of example but not limitation of CH 3
  • R 2 by way of example but not limitation of hydrogen
  • R 3 is illustrative but not limiting of fluoro
  • R 4 is exemplified but not limiting for chlorine
  • R 20 by way of example but not limiting to fluorine.
  • the intermediary further substituted 5-mercaptophenyl-lH-pyrimidine-2,4-diones (11) can then be converted into the desired erfmdungsmeä on compounds of general formula (1) in two different ways (Scheme 4), (i) by reaction with a suitable optionally further substituted 2-haloacetamide (III) using a suitable base (eg., Potassium carbonate, cesium carbonate or sodium carbonate) in a suitable polar aprotic solvent or (ii) by reacting the intermediates (II) with a suitable optionally further substituted 2 Haloacetic acid into a corresponding thioacetic acid intermediate (IV) using a suitable base (e.g., potassium carbonate, cesium carbonate) and subsequent reaction of the corresponding intermediate (IV) with a suitable optionally further substituted amino acid using suitable coupling reagents (e.g.
  • HOBt 1-hydroxybenzotriazole
  • EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
  • HATU 0- (7-azabenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl, 3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide) and suitable bases (eg, diisopropylethylamine, triethylamine) in a suitable polar -aprot solvent (e.g. Dichloromethane, chloroform).
  • R 2 and R 6 are illustrative but not limiting of hydrogen
  • Q is exemplary but not limiting of the moieties Ql and Q-2.
  • reaction mixture was stirred for 1 h at room temperature, then cooled to a temperature of -30 ° C and 2-fluoro-4-chlorophenyl isocyanate (12.0 g, 70.0 mmol) was added.
  • the resulting reaction mixture was stirred after complete addition for 4 h at room temperature and then added to ice-water.
  • ethyl acetate and acidification with 1N hydrochloric acid the aqueous phase was extracted thoroughly with ethyl acetate.
  • the combined organic phases were washed with water, dried over sodium sulfate, filtered off and concentrated under reduced pressure.
  • reaction mixture was stirred for 1 h at a temperature of 50 ° C and after cooling to room temperature with water and dichloromethane and extracted thoroughly.
  • the aqueous phase was then made acidic with 10% hydrochloric acid and extracted again several times with dichloromethane.
  • the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.
  • the aqueous phase was then made acidic with 10% hydrochloric acid and extracted again several times with dichloromethane.
  • the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.
  • the crude product was then purified by column chromatography (gradient ethyl acetate / heptane), and 2 - ( ⁇ 2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine -l (2H) -yl] phenyl ⁇ sulfanyl) butanoic acid (2.0 g, 80% of theory) was obtained as a colorless solid.
  • Triethylamine (0.08 ml, 0.60 mmol) was added. The resulting reaction mixture was stirred for 6 hours at room temperature, then treated with water and dichloromethane and washed thoroughly with
  • the reaction mixture was stirred for 1 h at room temperature, then cooled to a temperature of -30 ° C and 2-fluoro-4-chlorophenyl isocyanate (12.0 g, 70.0 mmol) was added.
  • the resulting reaction mixture was stirred after complete addition for 4 h at room temperature and then added to ice-water.
  • the aqueous phase was extracted thoroughly with ethyl acetate.
  • the combined organic phases were washed with water, dried over sodium sulfate, filtered off and concentrated under reduced pressure.
  • reaction mixture was stirred for 1 h at a temperature of 50 ° C and after cooling to room temperature with water and dichloromethane and extracted thoroughly.
  • the aqueous phase was then made acidic with 10% hydrochloric acid and extracted again several times with dichloromethane.
  • the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.
  • Triethylamine (0.07 ml, 0.53 mmol) was added. The resulting reaction mixture was stirred for 6 hours at room temperature, then treated with water and dichloromethane and washed thoroughly with
  • reaction mixture was stirred for 1 h at -78 ° C, treated with 2,2,2-trifluoroethyl trifluoroacetate (147 g, 750 mmol) and finally stirred overnight at room temperature. After complete reaction was acidified with dil. Hydrochloric acid (1M) and extracted several times thoroughly with ethyl acetate.
  • N, N-dimethylformamide and ethyl (2Z) -3-amino-4,4,4-trifluoro-2-methylbut-2-enoate (14.2 g, 72.1 mmol) were added.
  • the reaction mixture was stirred for 1 h at room temperature, then cooled to a temperature of -30 ° C and 2-fluoro-4-chlorophenyl isocyanate (12.0 g, 70.0 mmol) was added.
  • the resulting reaction mixture was stirred after complete addition for 4 h at room temperature and then added to ice-water. After the addition of ethyl acetate and acidification with 1N hydrochloric acid, the aqueous phase was extracted thoroughly with ethyl acetate.
  • reaction mixture was stirred for 105 minutes at a temperature of 50 ° C and after cooling to room temperature with water and dichloromethane and extracted thoroughly.
  • the aqueous phase was then made acidic with 10% hydrochloric acid and extracted again several times with dichloromethane.
  • the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.
  • the aqueous phase was then made acidic with 10% hydrochloric acid and extracted again several times with dichloromethane.
  • the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.
  • the crude product was then purified by column chromatography (gradient ethyl acetate / heptane), and 2- ( ⁇ 2-chloro-5- [3,5-dimethyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H) -yl] -4-fluorophenyl ⁇ sulfanyl) propanoic acid (1.54 g, 86% of theory) was obtained as a colorless solid.
  • Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-965, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.1-1 to 1.1-965 of Table 1.1 are thus determined by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-965, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.1-1 to 1.1-965 of Table 1.1 are thus determined by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-965, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.1-1 to 1.1-965 of Table 1.1 are thus determined by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1 Preferred compounds of the formula (1.1) are the
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-965, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.2-1 to 1.2-965 of Table 1.2 are thus determined by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-965, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.3-1 to 1.3-965 of Table 1.3 are thus determined by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-965, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.4-1 to 1.4-965 of Table 1.4 are thus by the meaning of the respective entries no. 1 to 965 for Q the
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-965, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.5-1 to 1.5-965 of Table 1.5 are thus by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-965, in which Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.6-1 to 1.6-965 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 965 for Q the
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-965, in which Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.7-1 to 1.7-965 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-965, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.8-1 to 1.8-965 of Table 1.8 are thus characterized by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-965, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.9-1 to 1.9-965 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-965, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.10-1 to 1.10-965 of Table 1.10 are therefore distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1. 1 11
  • Table 1.11 Preferred compounds of the formula (1.1.1) are the compounds 1.11-1 to 1.11-965, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.11-1 to 1.11-965 of Table 1.11 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.12-1 to 1.12-965 of Table 1.12 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.13-1 to 1.13-965 of Table 1.13 are therefore distinguished by the meaning of the respective entries no. 1 to
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.14-1 to 1.14-965 of Table 1.14 are therefore distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.15-1 to 1.15-965 of Table 1.15 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-965, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-965, in which Q has the meanings of Table 1 given in the respective line. The connections
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.20-1 to 1.20-965 of Table 1.20 are therefore distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.21-1 to 1.21-965 of Table 1.21 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.22-1 to 1.22-965 of Table 1.22 are therefore distinguished by the meaning of the respective entries no. 1 to
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.23-1 to 1.23-965 of Table 1.23 are therefore distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-965, wherein Q has the meanings given in Table 1 of each line.
  • the compounds 1.24-1 to 1.24-965 of Table 1.24 are therefore distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.25-1 to 1.25-965 of Table 1.25 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.26-1 to 1.26-965 of Table 1.26 are thus characterized by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.27-1 to 1.27-965 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-965, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.28-1 to 1.28-965 of Table 1.28 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-965, in which Q has the meanings given in Table 1 of each line.
  • the compounds 1.29-1 to 1.29-965 of Table 1.29 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.30-1 to 1.30-965 of Table 1.30 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-965, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-965, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-965, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-965, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.34-1 to 1.34-965 of Table 1.34 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.35-1 to 1.35-965 of Table 1.35 are thus characterized by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.36-1 to 1.36-965 of Table 1.36 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-965, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.37-1 to 1.37-965 of Table 1.37 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.38-1 to 1.38-965 of Table 1.38 are therefore distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.39-1 to 1.39-965 of Table 1.39 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-965, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.40-1 to 1.40-965 of Table 1.40 are therefore distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-965, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.41-1 to 1.41-965 of Table 1.41 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.42-1 to 1.42-965 of Table 1.42 are thus distinguished by the meaning of the respective entries no. 1 to 965 are defined for Q of Table 1.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-965, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.43-1 to 1.43-965 of Table 1.43 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-965, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-965, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-965, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • NMR Peak List Method The H-NMR data of selected examples are noted in terms of H-NMR peak lists. For each signal peak, first the d-value in ppm and then the signal intensity listed in round brackets. The d-value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: di (intensity ⁇ ; 62 (intensity2);.; D;
  • the tetramethylsilane peak may occur in NMR peaks, but it does not have to.
  • connection signals may show, like classical H NMR expressing solvent signals, signals of stereoisomers of the target compounds, which are also subject of the invention, and / or peaks of impurities.
  • Solvent peaks for example peaks of DMSO in DM SO-Df, and the peak of water, which are usually of high intensity on average.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of each
  • Isolate target compounds optionally using additional intensity filters. This isolation would be similar to the peak picking in the classical 1H NMR interpretation. Further details on ⁇ -NMR peak lists can be found in Research Disclosure Database Number 564025.

Abstract

La présente invention concerne des thiophényluraciles substitués de formule générale (I) ou leurs sels, formule (I), les radicaux de la formule générale (I) étant tels que définis dans la description, ainsi que leur utilisation comme herbicides, en particulier pour lutter contre les plantes adventices et/ou les mauvaises herbes dans les cultures de plantes utiles et/ou comme régulateurs de croissance des plantes destinés à influencer la croissance des cultures de plantes utiles.
PCT/EP2018/085267 2017-12-19 2018-12-17 Thiophényluraciles substitués, leurs sels et leur utilisation comme agents herbicides WO2019121547A1 (fr)

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CN114401956A (zh) * 2019-07-22 2022-04-26 拜耳公司 取代的n-苯基尿嘧啶、其盐以及作为除草剂的用途

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EP0086750A2 (fr) 1982-02-17 1983-08-24 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0094349A2 (fr) 1982-05-07 1983-11-16 Ciba-Geigy Ag Utilisation de dérivés de quinoléine pour protéger des plantes cultivées
JPS6087254A (ja) 1983-10-19 1985-05-16 Japan Carlit Co Ltd:The 新規尿素化合物及びそれを含有する除草剤
EP0174562A2 (fr) 1984-09-11 1986-03-19 Hoechst Aktiengesellschaft Agents pour la protection de plantes basés sur des dérivés de 1,2,4- briazole ainsi que dérivés 1,2,4-triazole
EP0191736A2 (fr) 1985-02-14 1986-08-20 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0268554A2 (fr) 1986-10-22 1988-05-25 Ciba-Geigy Ag Dérivés d'acide diphényl-1,5-pyrazol-3-carbonique pour la protection de plantes de culture
EP0269806A1 (fr) 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
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EP0714602A1 (fr) 1994-12-02 1996-06-05 Nihon Bayer Agrochem K.K. Sulphonylaminophényluracile-herbicides pour rizières
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CN101838227A (zh) 2010-04-30 2010-09-22 孙德群 一种苯甲酰胺类除草剂的安全剂
KR20110110420A (ko) 2010-04-01 2011-10-07 한국화학연구원 제초성 우라실계 화합물 및 이를 포함하는 제초제
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KR101345394B1 (ko) 2012-07-13 2013-12-24 동부팜한농 주식회사 5-(3,6-다이하이드로-2,6-다이옥소-4-트리플루오로메틸-1(2ｈ)-피리미디닐)페닐싸이올 화합물의 제조방법

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