EP3606915A1 - Dérivés de 2-amino-5-oxyalkyl-pyrimidine et leur utilisation pour lutter contre la croissance de plantes adventices - Google Patents

Dérivés de 2-amino-5-oxyalkyl-pyrimidine et leur utilisation pour lutter contre la croissance de plantes adventices

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Publication number
EP3606915A1
EP3606915A1 EP18715613.8A EP18715613A EP3606915A1 EP 3606915 A1 EP3606915 A1 EP 3606915A1 EP 18715613 A EP18715613 A EP 18715613A EP 3606915 A1 EP3606915 A1 EP 3606915A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
haloalkyl
compounds
group
cycloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP18715613.8A
Other languages
German (de)
English (en)
Inventor
Harald Jakobi
ARSEQUELL Estella BUSCATO
Klemens Minn
Uwe Döller
Hansjörg Dietrich
Elmar Gatzweiler
Anu Bheemaiah MACHETTIRA
Christopher Hugh Rosinger
Dirk Schmutzler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Bayer CropScience AG
Original Assignee
Bayer AG
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG, Bayer CropScience AG filed Critical Bayer AG
Publication of EP3606915A1 publication Critical patent/EP3606915A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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

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 and in the
  • the invention relates to substituted 2-amino-5-oxyalkyl-pyrimidine derivatives, processes for their preparation and their use for controlling harmful plants.
  • the compounds of the formula (I) according to the invention have in the 5-position of the pyrimidine an oxyalkyl group and in the 2-position of the pyrimidine in the alpha position to the aromatic bound via an amine partially hydrogenated bicyclic substituent, wherein the pyrimidine in the 4 - Position and 6-position may also be substituted and the oxyalkyl group can form a ring via the alkyl radical together with the substituent in the adjacent position.
  • 2,4-diaminopyrimidines and their use in the field of crop protection are disclosed, for example, by the documents EP 0523533 A1, WO 2010/076009 Al and WO 2010/076010 Al.
  • 2.4- Diaminopyrimidines with bicyclic radical which are bridged and adjacent
  • Carbon atom have a (1R, 2S) configuration and at the same time are distinguished by a herbicidal activity, are known from US 2010/0167934 AI.
  • Thienocycloalkylamino-2-pyrimidine derivatives may have, in addition to the amino substituent in the 2-position, additional amino radicals in the 4-, 5-, or 6-position.
  • the subject matter of the present application differs from the compounds known from WO 2017/016914 Al by a fused phenyl ring. The from WO 2017/016914 Al
  • 2-amino-pyrimidine derivatives namely 2-amino-5-ketoxime-pyrimidine derivatives
  • This application is according to its disclosure in relation to the present application, a document acc. Art. 54 (3) EPC.
  • the object of the present invention is to provide alternative pyrimidine derivatives, which are used as herbicides or plant growth regulators, with a satisfactory herbicidal activity and a broad spectrum of activity against harmful plants and / or with a high
  • the alternative pyrimidine derivatives show a better property profile compared to the pyrimidine derivatives known from the prior art, in particular they show a better herbicidal activity against harmful plants, a broader spectrum against harmful plants and / or a higher selectivity in crops.
  • the object is achieved by specifically substituted 2-amino-5-oxyalkyl-pyrimidine derivatives of the formula (I) according to claim 1, which can be used advantageously as herbicides and also as plant growth regulators, in particular due to the substitution in the 5-position of the pyrimidine ring.
  • R la selected from the group consisting of hydrogen, cyano, C (0) OH, C (0) NH 2;
  • Pyridyl which may each be substituted by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • Thienyl which may each be substituted by halogen, (Ci-C6) -alkyl and / or (Ci-C6) -haloalkyl;
  • (C 6 -C 4 ) -aryl (C 1 -C 6) -alkyl which may each be substituted on the aryl part by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl; - aminocarbonyl- (C 1 -C 6) -alkyl;
  • (C6-C14) -aryl which may each be substituted on the aryl part by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • Pyridyl which may each be substituted by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • Thienyl which may each be substituted by halogen, (Ci-C6) -alkyl and / or (Ci-C6) -haloalkyl;
  • Aminocarbonyl (Ci-C6) alkyl; (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl;
  • (C3-Cg) -cycloalkyl which may be unsubstituted or monosubstituted or polysubstituted on the cycloalkyl radical by (Ci-C6) -alkyl and / or halogen; (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkyl;
  • R a and R are each independently selected from the group consisting of - hydrogen, halogen, hydroxy, cyano, C (O) OH, C (O) NH 2 ;
  • (C3-Cg) -cycloalkyl which is unsubstituted or monosubstituted or polysubstituted on the cycloalkyl radical by (Ci-C6) -alkyl and / or halogen; (C3-Cg) cycloalkoxy, (C3-Cg) cycloalkyl (Ci- C6) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C 6) -haloalkyl, (C 3 -C 8) - Cycloalkyl- (C 1 -C 6 ) -alkoxy, (C 3 -Cg) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 9) -cycloalkylcarbonyl, (C 3 -C 8) -cycloalkoxycarbonyl, (C 3 -C 8 ) -Cycloalkyl- (
  • (C6-C14) -arylcarbonyl which may each be substituted on the aryl part by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • (C6-C14) -arylsulfonyl which in each case may be substituted on the aryl part by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • (C6-C14) -aryl which may each be substituted on the aryl part by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • (C 2 -C 4) -Het-aryl which in each case can be substituted on the het-aryl moiety by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl; - (C 6 -C 14) -aryl (C 1 -C 6) -alkyl, which may each be substituted on the aryl part by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • Aminocarbonyl (Ci-C6) alkyl
  • (C3-Cg) -cycloalkyl which may be monosubstituted or polysubstituted on the cycloalkyl radical by (Ci-C6) -alkyl and / or halogen;
  • R 4 and R 5 are each independently selected from the group consisting of
  • R 6 and R 7 are each independently selected from the group consisting of
  • R 8 , R 9 , R 10 and R 11 are each independently selected from the group consisting of hydrogen, halogen, cyano, C (O) OH, C (O) NH 2 , (C 1 -C 6 ) alkyl , (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkyloxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, (C 1 -C 6 ) -di-alkylaminocarbonyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) - Alkoxy, (C 1 -C 6) -halogenoalkoxy, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl,
  • Heteroatom O or S is attached to the partially hydrogenated portion of the amine
  • R 12 and R 13 are each independently selected from the group consisting of
  • R 14 is selected from the group consisting of hydrogen, (C 1 -C 6) alkyl and (C 1 -C 6) haloalkyl.
  • the 2-amino-5-oxyalkyl-pyrimidine derivatives of the formula (I) according to the invention differ from the diamino-pyrimidine derivatives known from the prior art (for example those disclosed in EP 0523533 A1, WO 2010/076009 Al and WO 2010/076010 Al known herbicides with 2.4 diaminopyrimidine structure) in the number of directly connected to a ring atom of the pyrimidine ring amino groups.
  • the comparative data of Tables 1 and 2 below relate to the diamino-pyrimidine derivatives known from WO 2010/076010 Al.
  • the two radicals R a and R therefore do not represent an amino group, ie R 2a and R 2b do not have a nitrogen atom with the
  • the 2-amino-5-oxyalkyl-pyrimidines invention are substituted by only one amino group, said amino group, the pyrimidine ring and the bicyclic
  • the 2-amino-5-oxyalkyl-pyrimidines of the formula (I) of the present invention differ in that the amino group in 2 - Position, ie between the two nitrogen atoms belonging to the pyrimidine ring, and not in the 5-position.
  • Monoaminopyrimidines of the formula (I) a partially hydrogenated bicyclic substituent, wherein the partially hydrogenated bicyclic substituent is bonded in the alpha position to the aromatic to the amine.
  • the monoaminopyrimidines of the formula (I) according to the invention differ from the two abovementioned 2-amino-pyrimine derivatives in that they have no keto group (carbonyl group) or no ketooxime structural element in the 5-position. That is to say that the group of structural elements in the 5-position of the compounds according to the invention which comprises the radicals R 3 -O-C, R 1a and R 1b and together form an oxyalkyl group are characterized in that they contain no carbonyl and no ketooxime Feature structural element.
  • the comparative data of the following Tables 3 and 4 relate to the monoamino-pyrimidine derivatives known from WO 2016/001118 Al.
  • Table 2 Comparison of the herbicidal effect postemergence of compounds of the invention with compounds of WO 2010/076010 Al
  • the comparative compounds of the invention are either unsubstituted (4-H) in the 4-position of the pyrimidine or by a substituent other than amino, e.g. substituted by methyl (4-Me).
  • the compounds according to the invention are distinguished by a surprisingly good activity profile.
  • Table 3 a Comparison of the herbicidal action in the pre-emergence of compounds according to the invention with compounds from WO 2016/001118 A1
  • Table 3b Comparison of the herbicidal effect postemergence of compounds of the invention with compounds from WO 2016/001118 AI
  • the comparative compounds of the invention have in the 5-position of the pyrimidine one
  • the compounds according to the invention are distinguished by a surprisingly good activity profile.
  • the compounds of formula (I) are characterized, in addition to a good efficacy profile and / or a good crop tolerance, by their cost-effective production, since the
  • Substances of the invention can be prepared from inexpensive and easily accessible precursors by inexpensive processes. Therefore, the use of expensive and difficult to access intermediates can be dispensed with.
  • a first embodiment of the present invention comprises compounds of the general formula (I) in which
  • R la is preferably selected from the group consisting of hydrogen, cyano; - (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) - alkynyl, ( C2-C6) -haloalkynyl;
  • (C3-Cg) -cycloalkyl which may be unsubstituted or monosubstituted or polysubstituted on the cycloalkyl radical by (Ci-Ce) -alkyl and / or halogen;
  • R 1a is particularly preferably selected from the group consisting of - hydrogen
  • R 1a is most preferably hydrogen, CH 3 or CH 2 CH 3 .
  • a second embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 1b is preferably selected from the group consisting of cyano, C (O) OH, C (O) NH 2 ;
  • Pyridyl which may each be substituted by halogen, (C 1 -C 6) -alkyl and / or (C 1 -C 6) -haloalkyl;
  • Thienyl which may each be substituted by halogen, (Ci-C6) -alkyl and / or (Ci-C6) -haloalkyl;
  • R 1b is more preferably selected from the group consisting of cyano; - (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl;
  • Phenyl which may be substituted on the aryl moiety with halogen and / or methyl;
  • CH 2 is phenyl (benzyl) or cyclopropyl.
  • a third embodiment of the present invention comprises compounds of the general formula (I) in which
  • R la with R lb are preferably linked together via a bond, so that together with the carbon to which these two radicals are bonded, a saturated 3 to 6-membered carbocycle is formed which is unsubstituted or substituted is substituted by one or more substituents selected from the group consisting of methyl, trifluoromethyl, cyclopropyl;
  • R la with R lb are particularly preferably linked together by a bond, so that together with the carbon to which these two radicals are bonded, a saturated 3 to 6-membered carbocycle is formed which is unsubstituted or substituted is with one or more methyl groups, with an unsubstituted 3 to 6 membered carbocycle, in which the ring elements are each formed by CH 2 units, is particularly preferred;
  • R la with R lb are most preferably connected to one another via a bond, so that together with the carbon attached to these two radicals, a saturated 3-membered carbocycle is formed which is unsubstituted or with a methyl group is substituted;
  • R 1a with R 1b in the case where R 1a is other than hydrogen, most preferably linked together via a bond, so that together with the carbon to which these two radicals are bonded, a saturated 3-membered carbocycle is formed which is unsubstituted;
  • a fourth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 2a and R 2b are each independently, preferably selected from the group consisting of
  • R 2a and R 2b are each independently selected, more preferably selected from the group consisting of hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (Ci-C 3 ) alkoxy, (C1 -C 3) - alkoxy- (C 1 -C 3 ) -alkyl and (C 3 -C 6 ) -cycloalkyl;
  • R 2a and R 2b are each independently selected, most preferably selected from
  • R 2a and R 2b are most preferably each independently selected from the group consisting of hydrogen, CH 3 , CH (CH 3 ) F and CF 2 H; being the combination
  • R 2a is most preferably selected from the group consisting of hydrogen, CH 3 , CH (CH 3 ) F and CF 2 H and R 2b is hydrogen.
  • a fifth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 3 is preferably selected from the group consisting of
  • Phenylcarbonyl which may each be substituted on the aryl part by halogen, and / or methyl;
  • R 3 is particularly preferably selected from the group consisting of
  • R 3 is particularly preferably selected from the group consisting of
  • R 3 most preferably is selected from the group consisting of hydrogen
  • CH 2 C CH
  • CH 2 C CCH 3
  • R 3 in the aforementioned group is again particularly hydrogen or CH 3 , and R 3 is most preferably hydrogen.
  • a sixth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 4 and R 5 are each independently, preferably selected from the group consisting of
  • R 4 and R 5 are each independently selected, more preferably selected from the group consisting of hydrogen, (C 1 -C 6) -alkyl and (C 1 -C 6) -alkoxy;
  • R 4 and R 5 are each independently selected, very particularly preferably selected from
  • R 4 and R 5 are each independently, most preferably hydrogen or methyl.
  • R 4 and R 5 are hydrogen. That is, when in each case at least one of R 4 , or R 5 is hydrogen and the other radical R 4 , or R 5 is not hydrogen, namely in particular (Ci-C6) alkyl, preferably methyl (CH 3 ).
  • a seventh embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 6 and R 7 are independently of one another, preferably selected from the group consisting of
  • R 6 and R 7 are independently selected, more preferably selected from the group consisting of hydrogen, methyl and phenyl;
  • R 6 and R 7 are very particularly preferably each hydrogen or methyl
  • R 6 and R 7 are most preferably hydrogen.
  • An eighth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 8 is preferably selected from the group consisting of hydrogen, halogen, cyano, C (0) OH, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyloxycarbonyl, and (C 6 -C 4 ) -aryl;
  • R 8 is particularly preferably selected from the group consisting of hydrogen, halogen, cyano, C (0) OH, (C 1 -C 3 ) -alkyl, (C 1 -C 3 ) -alkoxy, (C 1 -C 3 ) -alkyloxycarbonyl and (C 6 -C 8 ) aryl;
  • R 8 is very particularly preferably selected from the group consisting of hydrogen, fluorine,
  • R 8 is most preferably hydrogen or CH 3.
  • a ninth embodiment of the present invention includes compounds of the general formula (I) in which
  • R 9 is preferably selected from the group consisting of hydrogen, halogen, (C 1 -C 6 ) -alkyl and (C 1 -C 6 ) -alkoxy;
  • R 9 is particularly preferably selected from the group consisting of hydrogen, chlorine, fluorine and (C 1 -C 3 ) -alkoxy;
  • R 9 is very particularly preferably selected from the group consisting of hydrogen, fluorine, chlorine and methoxy; R 9 is most preferably hydrogen.
  • a tenth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 10 is preferably selected from the group consisting of hydrogen, halogen, cyano,
  • R 10 is particularly preferably selected from the group consisting of hydrogen, fluorine, chlorine,
  • R 10 is most preferably hydrogen or CH 3 .
  • An eleventh embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 11 is preferably selected from the group consisting of hydrogen and (C 1 -C 6) -alkyl;
  • R 11 is more preferably selected from the group consisting of hydrogen and (C 1 -C 4) -alkyl;
  • R 11 is very particularly preferably hydrogen or methyl; R 11 is most preferably hydrogen.
  • a twelfth embodiment of the present invention comprises compounds of the general formula (I) in which
  • X is preferably selected from the group consisting of a chemical bond, CH 2 , O, S, Carbonyl, NH, CH (Ci-C 6 ) alkyl, N (Ci-C 6 ) alkyl, OCH 2 , and SCH 2 where in the latter two groups the carbon atom to the aromatic part and the heteroatom O or S to the partially hydrogenated part the amine is bound; is particularly preferably selected from the group consisting of a chemical bond, CH 2, O, S, CHCH 3, NCH 3, OCH 2, and SCH 2 where in the latter two groups the carbon atom to the aromatic part and the heteroatom O or S to the partially hydrogenated part of Amine is bound; and in which most preferably represents a chemical bond, CH 2 or O.
  • compounds of the general formula (I) are encompassed by the present invention, in which, for example, the substituent R la has a preferred meaning and the substituents R lb to R 14 have the general meaning or the substituent R 2a has a preferred meaning has, the substituent R 3 has a particularly preferred, or a very particularly preferred, meaning and the other substituents have a general meaning.
  • a thirteenth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R la is selected from the group consisting of hydrogen, (C 1 -C 3 ) -alkyl, (C 1 -C 3 ) -haloalkyl, (C 2 -C 3 ) -alkenyl and (C 2 -C 3 ) -alkynyl;
  • R 1b is selected from the group consisting of cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 3) -alkoxycarbonylmethyl, (C 2 -C 4) -alkenyl, (C 2 -C 4) -Haloalkenyl, (C 2 -C 4) -alkynyl, (C 2 -C 4) -haloalkynyl, phenyl which may be substituted on the aryl moiety by halogen and / or methyl, CE-phenyl (benzyl) which is substituted on the ary
  • R 2a and R 2b are each independently selected from the group consisting of
  • R 3 is selected from the group consisting of hydrogen, (C 1 -C 4 ) -alkylcarbonyl,
  • R 4 and R 5 are each independently selected from the group consisting of
  • R 6 and R 7 are independently selected from the group consisting of hydrogen
  • R 8 is selected from the group consisting of hydrogen, halogen, cyano, C (0) OH, (Ci-C 3) - alkyl, (Ci-C 3) alkoxy, (Ci-C 3) alkyloxycarbonyl and (C 6 -C 8 ) -aryl;
  • R 9 is selected from the group consisting of hydrogen, chlorine, fluorine and (C 1 -C 3 ) -alkoxy;
  • R 10 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, Methoxy (OCH 3) (Ci-C 3) alkyl, (Ci-C 3) -haloalkyl, (Ci-C 3) alkoxy, (C 2 -C 4) alkenyl, (C 2 -C 4) Alkynyl, (C 1 -C 3 ) -alkyl- (C 2 -C 4 ) -alkynyl, hydroxy- (C 1 -C 3 ) -alkyl- (C 2 -C 4 ) -alkynyl, (C 1 -C 3 ) - Alkoxy (C 2 -C 4 ) alkynyl and phenyl (C 2 -C 4 ) alkynyl;
  • R 11 is selected from the group consisting of hydrogen and (C 1 -C 4 ) -alkyl;
  • X is a chemical bond or O, S, carbonyl, CH 2 , NH, CHCH 3 , NCH 3 , C (CH 3 ) 2 , OCH 2 and SCH 2 , where in the latter two groups the carbon atom to the aromatic part and the heteroatom O or S is attached to the partially hydrogenated portion of the amine.
  • R lb is selected from the group consisting of cyano, CH 3 , CH 2 CH 3 , CH 2 CH (CH 3 ) 2 , CF 3 ,
  • R a and R are each independently selected, very particularly preferably selected from
  • R 4 and R 5 are each independently selected from the group consisting of
  • R 8 is selected from the group consisting of hydrogen, fluorine, chlorine, CH 3 , methoxycarbonyl, and phenyl;
  • R 9 is selected from the group consisting of hydrogen, fluoro, chloro and methoxy
  • X is a chemical bond or O, S, CH 2 , CHCH 3 , OCH 2 , SCH 2 and NCH 3 , where in the latter two groups the carbon atom on the aromatic part and the heteroatom O or S on the partially hydrogenated part of the amine is bound.
  • a fifteenth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R la is selected from the group consisting of hydrogen, CH 3 and CH 2 CH 3;
  • R 2a and R 2b are each independently selected from the group consisting of
  • R 3 is selected from the group consisting of hydrogen and CH 3;
  • R 4 and R 5 are each independently hydrogen or methyl
  • R 6 and R 7 are each hydrogen
  • R 8 is hydrogen or CH 3 ;
  • R 9 is hydrogen; R 10 is hydrogen or CH 3
  • R 11 is hydrogen; and X represents a chemical bond, CH 2 or O.
  • the compound of the general formula (I) also includes compounds which are characterized by a) protonation, b) alkylation or c) oxidation on a
  • Nitrogen atom are quaternized.
  • these include the corresponding N-oxides.
  • the compounds of formula (I) can form salts. Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom.
  • suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and 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 especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR'R "R"'] + , wherein R to R'"are each independently
  • the compounds of the formula (I) may be substituted by an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl Addition of a suitable inorganic or organic acid, such as, for example, mineral acids, such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, for example carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, such as for example, p-toluenesulfonic acid, to a basic group such as amino, alkylamino, dialkyla
  • Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
  • the compounds of the formula (I) and their salts are also referred to briefly as "compounds (I)" used according to the invention or according to the invention.
  • the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, alkylthio, haloalkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton may each be straight-chain or branched. Unless specifically stated, these residues are the lower ones Carbon skeletons, e.g. B.
  • Alkyl radicals including in the composite meanings 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-methylhexy 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, preferably a double bond or triple bond is included.
  • Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-ene-1 -yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl;
  • Alkynyl means, for example. Ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl.
  • Cycloalkyl groups are, for. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • the cycloalkyl groups can occur in bi- or tri-cyclic form.
  • Alkylene groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 10 carbon atoms, in particular 1 to 6 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples are methylene, ethylene, n- and i-propylene and n-, s-, i-, t-butylene.
  • Hydroxyalkyl groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the corresponding unsaturated and / or
  • substituted radicals in the carbon skeleton which may each be straight-chain or branched.
  • Examples of these are 1, 2-dihydroxyethyl and 3-hydroxypropyl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl, alkenyl and alkynyl are alkyl, alkenyl or alkynyl, for example, partially or completely substituted by halogen, preferably by fluorine, chlorine or bromine, in particular by fluorine and / or chlorine.
  • Monohaloalkyl (
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl;
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl or naphthyl, preferably phenyl.
  • compounds of the general formula (I) or their agrochemical salts or quaternary N derivatives of the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the aforementioned or mentioned below preferred meanings occur in combination.
  • this carbon atom can have both an (R) and an (S) configuration.
  • the present invention relates to compounds of the general formula (I) both with (S) - and also with (R) configuration, ie that the present invention covers the compounds of the general formula (I) in which the relevant carbon atom
  • the present invention particularly relates to compounds of the general formula (I *) in which the stereochemical configuration at the carbon atom marked with (*) having a stereochemical purity of 60 to 100%> (R), preferably 80 to 100%> (R ), in particular 90 to 100% (R), especially 95 to 100% (R).
  • the present invention relates in particular to compounds of the general formula (I) in which the stereochemical configuration at the carbon atom marked with (*) having a stereochemical purity of 60 to 100% (R, or analog-R), preferably 80 to 100 % (R, or analog-R), in particular 90 to 100% (R, or analog-R), very particularly 95 to 100% (R, or analog-R), is present.
  • the compounds of the general formula (I) according to the invention may have further chiral centers on the carbon atoms labeled with (**) and (3):
  • Corresponding stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, 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 are encompassed by the general formula (I) but are not specified with their specific stereoform and their mixtures.
  • the possible combinations of the various substituents of the general formula (I) are to be understood as including the general principles of the construction of chemical compounds, i. the formula (I) does not include compounds which the person skilled in the art knows are chemically impossible.
  • Another object of the present invention are methods for preparing corresponding compounds of general formula (I) and / or salts thereof and / or their agrochemically acceptable quaternized nitrogen derivatives
  • R la , R lb , R 2a , R 2b and R 3 have the above significance and Z 1 represents an exchangeable radical or a leaving group, with an amine of the general formula (III) or an acid addition salt of the amine of the general formula (III )
  • the exchangeable radical Z 1 or the leaving group Z 1 is fluorine, chlorine, bromine, iodine, a (C 1 -C 4 ) -alkylsulfanyl or a (C 1 -C 4 ) -alkylsulfinyl or a (C 1 -C 4 ) -alkylsulfonyl , an unsubstituted or a mono- or poly-substituted by fluorine, chlorine, bromine or (Ci-C 4) -alkyl or (Ci-C 4) alkoxy, phenyl (Ci-C 4) alkylsulfonyl or a (Ci-C 4 ) alkylphenyl-sulfonyl.
  • Particularly preferred exchangeable radicals Z 1 or leaving groups Z 1 are chlorine, methylsulfanyl, methylsulfiny
  • a radical Z 1 can be converted into another, more easily exchangeable group.
  • a (Ci-C4) alkylsulfanyl with an oxidizing agent such as m-chloroperbenzoic acid or Oxone ® in a (Ci-C4) alkylsulfinyl or a (Ci- C4) alkylsulfonyl or mixtures thereof and then reacted with an amine of general formula (III) or an acid addition salt using an auxiliary base such as triethylamine or potassium carbonate.
  • reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
  • the compounds of general formula (II) can be prepared by known methods, for example from the corresponding 5-keto-pyrimidines.
  • Such reactions of C nucleophiles to the CO double bond such as aldol addition, Grignard reaction or Reformatzki reaction, are well known to those skilled in the literature.
  • the compounds of the general formula (II) can also be prepared, for example, from the corresponding 5-halopyrimidines, particularly preferably from the corresponding 5-bromopyrimidines or 5-iodopyrimidines, by known processes.
  • the corresponding 5-halopyrimidines can be converted with ketones of the formula R 1a C (O) R 1b and an organolithium compound, for example n-butyllithium, into compounds of the general formula (II) in which R 3 is hydrogen ,
  • R 3 is hydrogen
  • the hydrogen atom can be converted, for example, by reactions of the type of alkylation or acylation into other molecules of formula (II).
  • R is hydrogen
  • the hydrogen atom can be converted into other molecules of the formula (I) by reactions of the alkylation or acylation type.
  • R 1b and R 2a and R 2b have the above meaning and Z 1 for a
  • the exchangeable radical Z 1 or the leaving group Z 1 is fluorine, chlorine, bromine, iodine, a (C 1 -C 4 ) -alkylsulfanyl or a (C 1 -C 4 ) -alkylsulfinyl or a (C 1 -C 4 ) -alkylsulfonyl , an unsubstituted or substituted phenyl- (C 1 -C 4 ) -alkylsulfonyl or a (C 1 -C 4 ) -alkylphenyl-sulfonyl.
  • Particularly preferred exchangeable radicals Z 1 or leaving groups Z 1 are chlorine, methylsulfanyl, methylsulfinyl or methylsulfonyl.
  • a radical Z 1 can be converted into another, more easily exchangeable group.
  • a (Ci-C4) alkylsulfanyl with an oxidizing agent such as m-chloroperbenzoic acid or Oxone ® in a (Ci-C4) alkylsulfinyl or a (Ci- C4) alkylsulfonyl or mixtures thereof and then reacted with an amine of general formula (III) or an acid addition salt using an auxiliary base such as triethylamine or potassium carbonate.
  • reaction can also be catalyzed by different excipients, such as by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special
  • Transition metal catalyst systems are commercially available or can be prepared by known methods, for example according to methods disclosed in document WO
  • amines of the general formula (III) or the acid addition salt thereof are commercially available or their synthesis is described in WO 2004/069814 Al.
  • aldehydes or ketones of the general formula (IIb) can also be used as starting materials for the preparation of compounds of the formula (I).
  • R la and R 2a and R 2b have the above significance and Z 1 for a
  • the exchangeable radical Z 1 or the leaving group Z 1 is fluorine, chlorine, bromine, iodine, a (C 1 -C 4 ) -alkylsulfanyl or a (C 1 -C 4 ) -alkylsulfinyl or a (C 1 -C 4 ) -alkylsulfonyl , an unsubstituted or substituted phenyl- (C 1 -C 4 ) -alkylsulfonyl or a (C 1 -C 4 ) -alkylphenyl-sulfonyl.
  • Particularly preferred exchangeable radicals Z 1 or leaving groups Z 1 are chlorine, methylsulfanyl, methylsulfinyl or methylsulfonyl.
  • a radical Z 1 can be converted into another, more easily exchangeable group.
  • a (Ci-C4) alkylsulfanyl with an oxidizing agent such as m-chloroperbenzoic acid or Oxone ® in a (Ci-C4) alkylsulfinyl or a (Ci- C4) alkylsulfonyl or mixtures thereof and then reacted with an amine of general formula (III) or an acid addition salt using an auxiliary base such as triethylamine or potassium carbonate.
  • reaction can also be catalyzed by different excipients, for example by the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special Transition metal catalyst systems.
  • the reagents potassium phosphate, copper (I) iodide and N, N-diethyl-2-hydroxybenzamide or in the sense of Buchwald-Hartwig coupling by special Transition metal catalyst systems.
  • Hydrogen atom ( R 3 ), for example, by reactions of the type of alkylation or acylation in other molecules of the formula (I), with R 3 other than hydrogen, are converted.
  • compounds of the general formula (I) according to a third process (c) can also be prepared by initially preparing a compound of the general formula (IIc)
  • R 2a and R 2b have the above meaning and Z 1 is an exchangeable or a leaving group, analogous to those under a. described method, with an amine of formula (III) or a
  • reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 3AZ, England or MultiPROBE Automated
  • Solid-phase assisted synthesis methods allow a number of protocols known from the literature, which in turn can be performed manually or automatically.
  • Both solid and liquid phases may require the performance of one or more
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • Another object of the invention is due to the herbicidal property of the compounds of general formula (I), the use of the compounds of general formula (I) according to the invention as herbicides for controlling harmful plants.
  • Herbicides are used in agricultural crops during various stages of cultivation. Thus, the application of some products already before or during the sowing. Others are applied before the crop is run up, i. before the seedling the earth's surface
  • Post-emergence herbicides breaks through (pre-emergence herbicides). Post-emergence herbicides are eventually used when the cultured plant either already the cotyledons or leaves are formed.
  • Pre-emergence treatment includes pre-sowing (ppi) pre-sowing treatment as well as treatment of sown, but not overgrown crop areas.
  • the compounds of the formula (I) according to the invention and their salts, also referred to below together as compounds of the formula (I), have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.
  • herbicidal activity in dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium are observed. Be the compounds of general formula (I) according to the invention before germination on the
  • the compounds of general formula (I) according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops such. As wheat, barley, rye, rice, corn, sugar beet, cotton, oilseed rape and soy only insignificant or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.
  • the substances of the general formula (I) according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to influence the metabolism
  • Plant ingredients and harvest relief such. B. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented.
  • the substances of the general formula (I) according to the invention can be used in combination with other active substances, plant growth regulators and / or safeners.
  • Acetolactate synthase acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase,
  • Photosystem I, photosystem II or protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and cited therein.
  • ISO International Organization for Standardization
  • all forms of application such as acids, salts, esters and all isomeric forms such as stereoisomers and optical isomers are always included, even if they are not explicitly mentioned.
  • Examples of such herbicidal mixture partners are:
  • methabenzothiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • met.zthiazuron methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro -4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiar
  • plant growth regulators as possible mixing partners are:
  • the safeners are preferably selected from the group consisting of:
  • nA is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (WA 1 ) to (W A 4 ),
  • niA is 0 or 1
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered one
  • Heterocycle having at least one N-atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom with the carbonyl group in (S l) and unsubstituted or by radicals from the group (Ci-C i ) Alkyl, (Ci-C i) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula ORA 3 , NHR A 4 or N (CH 3 ) 2, in particular of the formula ORA 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RA 4 is hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy (Ci-C 8 ) alkyl, cyano or COORA 9 , where RA 9 hydrogen, (Ci-C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) -alkyl,
  • RA 6 , RA 7 , RA 8 are identical or different hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 3 -C 12) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (Sl a ), preferably
  • Fenchlorazole ethyl ester
  • related compounds as described in EP -A-174,562 and EP-A-346,620;
  • R B 1 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, nitro or (Ci-C 4 ) haloalkyl;
  • n is a natural number of 0 to 5, preferably 0 to 3;
  • RB 2 is OR B 3 , SR b 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, the about the N-atom with the
  • Carbonyl group in (S2) is connected and unsubstituted or by radicals from the group (C
  • R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (Ci-C6) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;
  • TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C i) alkyl radicals or by [(Ci-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolinoxyacetic acid type (S2 a ), preferably
  • Rc 3 are identical or different hydrogen, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (Ci C 4) haloalkyl, (C 2 -C 4) haloalkenyl , (Ci-C 4) alkylcarbamoyl (Ci-C4) alkyl, (C 2 - C 4) Alkenylcarbamoyl- (Ci-C 4) alkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, Dioxolanyl- (C 1 -C 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thi
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • RD is CO-NRD 5 RD 6 or NHCO-RD 7 ;
  • D 2 is halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro, (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Ci C 4) alkylsulfonyl, (Ci- C 4 ) alkoxycarbonyl or (C 1 -C 4 ) alkylcarbonyl;
  • D 3 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • D 4 is halogen, nitro, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, (C 3 -C 6) cycloalkyl, phenyl, (Ci-C 4) alkoxy, cyano, (Ci-C 4) alkylthio, (Ci-C 4) Alkylsulfmyl, (Ci-C 4) alkylsulfonyl, (Ci-C 4) alkoxycarbonyl or (Ci-C 4) alkylcarbonyl;
  • D 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -
  • D 6 is hydrogen, (Ci-C6) alkyl, (C 2 -Ce) alkenyl or (C 2 -C 6) alkynyl, wherein the three
  • D 7 is hydrogen, (Ci-C 4 ) alkylamino, di (Ci-C 4 ) alkylamino, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, wherein the latter two radicals by VD substituents from the halogen, (Ci C 4) alkoxy, (Ci-C6) haloalkoxy and (Ci-C 4) alkylthio and in case of cyclic radicals, also (Ci- C4) alkyl and (Ci-C4) haloalkyl groups; is 0, 1 or 2; is 1 or 2; is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which are, for example, B. are known from WO-A-97/45016
  • Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744,
  • RD RD 8 and 9 are each independently hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C 3 C 6) alkenyl, (C3-C6) alkynyl,
  • RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 niD is 1 or 2; for example, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea ("metcamifen", S4-6),
  • N-phenylsulfonylterephthalamides of the formula (S4 d ) which are known, for example, from CN 101838227,
  • RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; niD 1 or 2;
  • RD 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl.
  • Carboxylic acid derivatives (S5) e.g.
  • RE 1 , RE 2 are each independently halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkyl,
  • a E is COORE 3 or COSR E 4 RE 3 , RE 4 are, independently of one another, hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6) -alkenyl,
  • Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).
  • RF 2 is hydrogen or (Ci-C 4 ) alkyl
  • RF 3 is hydrogen, (Ci-Cg) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, wherein each of the
  • said C-containing radicals unsubstituted or substituted by one or more, preferably up to three identical or different radicals selected from the group consisting of halogen and alkoxy; or their salts, preferably compounds wherein
  • nF is an integer from 0 to 2
  • RF 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, RF 2 is hydrogen or (Ci-C 4) alkyl,
  • RF 3 is hydrogen, (Ci-Cg) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, wherein each of the
  • RG 2 (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, RG 3 is hydrogen or (Ci-Ce) alkyl.
  • Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl 1 -1), which is known as millet safener for millet against damage by metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone 0- (1,3-dioxolan-2-ylmethyl) -oxime) (S l 1 -2), which was used as a Seed pickling safener for millet is known against damage from metolachlor, and
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l -3), which is known as a seed dressing safener for millet against damage by metolachlor.
  • Isothiochromanone (S 12) class agents such as Methyl [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121 -04-6) (S 12-1) and related compounds of WO-A -1998 / 13361.
  • Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
  • Fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as safener for pretilachlor in sown rice,
  • Cyanamide which is known as safener for maize against damage of imidazolinones
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
  • Active substances which, in addition to having a herbicidal action against harmful plants, also have safener action on cultivated plants such as rice, such as, for example, rice.
  • CSB (1-Bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Registry No. 54091-06-4), which is known as a safener against damage of some herbicides in rice.
  • RH 1 is a (Ci-C6) haloalkyl radical and RH 2 is hydrogen or halogen and
  • R 3 , R 4 independently of one another denote hydrogen, (C 1 -C 16) alkyl, (C 2 -C 6) alkenyl or (C 2 -C 6) alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one Hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C i) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylamino, di [(Ci-C 4 ) alkyl] -amino, [ (C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted
  • Preferred safeners are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, mecamifen, particularly preferred are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl, Mefenpyr diethyl and metcamifen.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • Other special properties may be in a tolerance or resistance to abiotic stressors z.
  • heat, cold, drought, salt and ultraviolet radiation Preference is given to the use of the compounds of the general formula (I) according to the invention or salts thereof in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • EP 0131624 For example, genetic modifications of crop plants have been described in several cases for the purpose of modifying the starch synthesized in the plants (eg WO 92/011376, WO 92/014827, WO 91/019806), - transgenic crop plants which are resistant to certain glufosinate-type herbicides (see eg.
  • EP 0242236, EP 0242246) or glyphosate (WO 92/000377) or the sulfonylureas are transgenic crops, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which Make plants resistant to certain pests (EP 0142924, EP 0193259), transgenic crops with modified fatty acid composition (WO 91/013972), genetically modified crops with new content or secondary substances z.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants can in principle be plants of any one
  • Plant species ie, both monocotyledonous and dicotyledonous plants.
  • the compounds of the general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth substances, such. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, are resistant.
  • the active compounds of the general formula (I) according to the invention in transgenic cultures which are resistant to growth substances, such. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group
  • crops often have effects that are specific for application in the respective transgenic culture, for example a modified or specially extended weed spectrum that can be controlled, altered application rates that are used for the application can, preferably good compatibility with the herbicides against which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds of the general formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, and elevator Adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers ", 2nd ed., Darland Books, Caldwell NJ, Hv Olphen,
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
  • Dispersant e.g. Example, polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent z.
  • organic solvent z As butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which may be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
  • Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as. B. sorbitan fatty acid esters or
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally added surfactants, such as. B. are already listed above in the other formulation types, are produced.
  • Emulsions for example oil-in-water emulsions (EW), can be prepared, for example, by stirring,
  • Granules can either by spraying the active ingredient on adsorptive, granulated
  • Inert material or by applying active substance concentrates by means of adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I).
  • the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • Active ingredient concentration about 1 to 90, preferably 5 to 80 wt .-% amount.
  • Formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of
  • Active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers and the like are present. be used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent agents, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and Viscosity-influencing agent.
  • the compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) with other pesticidal substances, such.
  • Growth regulators are used in combination, z. B. as a ready-made formulation or as
  • Tank mixes For use, the formulations present in commercially available form are optionally diluted in a customary manner, for. As in wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or
  • Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I) and their salts. It can vary within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha g / ha. This is true for both
  • Tetrahydrofuran was added at 0 ° C 0.260g (0.924 mmol) of 1- (2- ⁇ [(lR, 2S) -2,6-dimethyl-2,3-dihydro-lH-inden-l -yl] amino ⁇ pyrimidine -5-yl) ethanone in 4.5 ml of dry tetrahydrofuran and stirred for 1.5 h at 20 ° C under a nitrogen atmosphere. It was added dropwise to the mixture saturated aqueous
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity i); 82 (intensity2); ; ⁇ ; (Intensity;); ; ⁇ ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In broad
  • Signals can show multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum.
  • 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
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation.
  • ⁇ 8.3992 (0.6); 7.2657 (0.8); 7.2649 (0.9); 7.2641 (1.0); 7.2587 (88.9); 7.1005 (1.1); 7.0813 (1.8); 7.0543 (1.0); 7.0329 (1.4); 7.0127 (0.8); 6.9947 (0.5); 3.0900 (0.6); 3.0710 (0.7); 3.0513 (0.7); 3.0320 (0.7); 2.5613 (0.6); 2.5388 (0.7); 2.5004 (0.6); 2.3126 (0.7); 2.2965 (9.4); 2.2738 (0.5); 1.8843 (5.8); 1.6732 (16.0); 1.5391 (5.3); 1.2866 (7.1); 1.2697 (7.1); 0.8820 (0.6); 0.0079 (1.0); -0.0002 (33.4); -
  • ⁇ 8.3854 (6.3); 7.5179 (0.5); 7.2688 (0.6); 7.2681 (0.6); 7.2590 (95.9); 7.0996 (2.1); 7.0806 (3.2); 7.0329 (4.1); 7.0297 (4.1); 7.0085 (1.6); 6.9950 (0.6); 5.4067 (0.5); 5.2654 (1.3); 5.2436 (2.2); 5.2218 (1.0); 3.0824 (1.3); 3.0633 (1.4); 3.0440 (1.5); 3.0249 (1.6); 2.5965 (0.6); 2.5936 (0.6); 2.5597 (1.1); 2.5369 (1.2); 2.5218 (0.9); 2.4985 (2.4); 2.3287 (0.6); 2.3225 (0.6); 2.3063 (1.8); 2.2882 (16.0); 2.2721
  • ⁇ 8.3280 (1.8); 7.3384 (1.2); 7.3205 (1.5); 7.2594 (26.6); 7.2504 (1.6); 7.2464 (2.7); 7.2438 (2.7); 7.2296 (1.7); 7.2274 (1.5); 7.2117 (0.8); 7.2053 (1.2); 7.1998 (0.8); 7.1874 (1.1); 7.1827 (0.9); 5.6212 (0.9); 5.6015 (0.9); 5.0053 (0.9); 4.9892 (0.8); 4.1292 (0.5); 4.1114 (0.5); 2.9974 (0.7); 2.9885 (0.7); 2.9757 (0.7); 2.9669 (0.7); 2.9284 (0.5); 2.9079 (1.1); 2.8876 (0.8); 2.8687 (0.5); 2.6928 (0.7); 2.6839 (0.6); 2.6808 (0.5); 2.6720 (0.5); 2.6611 (0.7); 2.6522 (0.6); 2.4125 (16.0); 2.0424 (2.4); 1.8848 (0.9); 1.8826 (0.7); 1.8654 (0.6); 1.8632 (0.9); 1.8531 (0.8); 1.8509 (0.6);
  • ⁇ 8.3483 (1.6); 7.2592 (66.5); 7.1679 (2.7); 7.1578 (2.3); 7.0856 (1.7); 7.0663 (1.1); 5.5936 (0.9); 5.5739 (0.9); 5.0203 (0.8); 5.0111 (0.8); 5.0040 (0.8); 4.9949 (0.8); 2.9557 (0.7); 2.9471 (0.7); 2.9340 (0.7); 2.9257 (0.7); 2.8849 (0.5); 2.8647 (1.1); 2.8445 (0.8); 2.8250 (0.6); 2.8205 (0.6); 2.6948 (0.7); 2.6862 (0.7); 2.6822 (0.6); 2.6736 (0.6); 2.6632 (0.8); 2.6545 (0.8); 2.6439 (1.4); 2.6355 (0.6); 2.6248
  • ⁇ 7.5183 (0.5); 7.2594 (93.5); 7.0774 (0.9); 6.9953 (1.0); 6.9741 (0.6); 6.9686 (0.5); 6.7516 (1.4); 6.7308 (1.1); 4.2488 (0.8); 4.2419 (0.6); 4.2377 (0.5); 4.2213 (0.5); 2.6710 (2.7); 2.6593 (0.6); 2.2344 (6.4); 2.1697 (0.6); 1.6560 (16.0); 1.6143 (1.3); 1.5418 (0.8); 0.8819 (0.5); 0.0080 (1.2); -0.0002 (39.3);
  • ⁇ 8.4375 (7.4); 7.5178 (1.0); 7.2590 (178.9); 7.2450 (1.3); 7.2358 (1.7); 7.2304 (0.8); 7.2218 (1.3); 7.0993 (0.5); 7.0807 (3.4); 7.0755 (2.8); 7.0666 (7.6); 6.9950 (1.0); 5.3459 (0.6); 5.2648 (1.0); 5.2446 (0.6); 2.6897 (1.0); 2.6748 (0.5); 2.6535 (0.6); 2.6388 (1.0); 2.6219 (0.7); 2.2451 (16.0); 2.0688 (0.7); 2.0577 (0.9); 2.0432 (0.9); 1.9719 (0.6); 1.9574 (0.8); 1.9417 (1.1); 1.9321 (1.6); 1.9272 (1.5); 1.9152
  • ⁇ 8.4402 (0.6); 8.3765 (16.0); 7.5181 (1.2); 7.2754 (0.5); 7.2738 (0.7); 7.2731 (0.7); 7.2714 (0.8); 7.2706 (0.9); 7.2699 (1.0); 7.2691 (1.1); 7.2682 (1.2); 7.2674 (1.4); 7.2666 (1.6); 7.2658 (1.9); 7.2592 (206.0); 7.1016 (1.6); 7.0830 (2.7); 7.0481 (3.0); 7.0301 (2.2); 7.0111 (1.2); 6.9952 (1.2); 5.2661 (0.6); 5.2431 (1.6); 5.2237 (2.5); 5.0354 (1.9); 5.0331 (2.4); 5.0301 (2.4); 5.0278 (2.0); 4.8654 (1.8); 4.8618
  • ⁇ 8.3390 (0.9); 7.2594 (13.0); 7.1483 (0.7); 7.1285 (1.6); 7.1086 (1.0); 6.9975 (1.4); 6.9781 (1.1); 6.7452 (1.3); 6.7256 (1.2); 3.8310 (16.0); 2.7131 (0.6); 2.6470 (0.6); 2.0300 (0.6); 1.9051 (0.5); 1.8897 (0.6); 1.8822 (0.7); 1.8783 (0.6); 1.8737 (0.8); 1.8646 (1.0); 1.8540 (1.0); 1.8471 (0.6); 1.7498 (1.4);
  • ⁇ 8.4336 (1.0); 7.2659 (0.6); 7.2651 (0.6); 7.2643 (0.8); 7.2634 (0.9); 7.2626 (1.2); 7.2585 (67.0); 7.1628 (2.1); 7.1465 (4.8); 7.1453 (4.9); 7.0750 (2.2); 7.0733 (2.3); 7.0560 (1.4); 7.0539 (1.5); 5.6459 (0.6); 5.6267 (0.9); 5.5920 (0.9); 5.5738 (1.8); 5.5539 (1.4); 2.9710 (0.5); 2.9627 (0.8); 2.9538 (0.9); 2.9412 (0.8); 2.9323 (0.9); 2,800 (0.6); 2.8700 (1.3); 2.8504 (1.0); 2.8311 (0.7); 2.7109 (0.8); 2.7018 (0.8); 2.6929 (1.0); 2.6915 (1.0); 2.6838 (1.0); 2.6823 (0.9); 2.6791 (1.0); 2.6734 (0.9); 2.6699 (0.9); 2.6641 (0.8); 2.6612 (1.0); 2.6597 (1.0); 2.6520 (1.0); 2.6417 (0.7); 2.
  • ⁇ 8.3830 (5.7); 7.2673 (0.5); 7.2665 (0.6); 7.2657 (0.7); 7.2649 (0.9); 7.2641 (1.1); 7.2600 (50.7); 7.2568 (1.2); 7.2559 (0.8); 7.2551 (0.6); 7.1047 (0.7); 7.0857 (1.1); 7.0431 (1.4); 7.0343 (1.0); 7.0155 (0.5); 5.2985 (2.2); 5.2607 (0.5); 5.2395 (0.7); 3.8994 (7.4); 3.7401 (14.3); 3.0279 (0.5); 2.2989 (5.7);
  • ⁇ 8.3848 (4.4); 7.5184 (0.8); 7.2595 (145.6); 7.1057 (0.6); 7.0867 (1.0); 7.0447 (1.2); 7.0344 (0.9); 6.9955 (0.8); 5.2631 (0.5); 5.2439 (0.6); 3.9393 (3.8); 3.9332 (3.8); 2.3930 (0.9); 2.3870 (1.9); 2.3808 (0.9); 2.2980 (5.0); 1.5905 (14.6); 1.5374 (16.0); 1.2970 (4.4); 1.2802 (4.3); 0.0080 (1.6); -0.0002 (57.0);
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • talc as an inert material
  • Alkylphenolpolyglykolether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 ° C) and mixed in a ball mill to a fineness of less than 5 microns married.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight
  • a water-dispersible granule is also obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts,
  • Seeds of monocotyledonous or dicotyledonous weeds and crops are in plastic or
  • Wood fiber pots designed and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion with the addition of 0.5% of additive at a water application rate of 600 l / ha.
  • WP wettable powders
  • EC emulsion concentrates
  • ABUTH Abutilon theophrasti ALOMY: Alopecurus myosuroides
  • AMARE Amaranthus retroflexus AVEFA: Avena fatua
  • ECHCG Echinochloa crus-galli HORMU: Hordeum murinum
  • PHBPU Ipomoea purpurea
  • POLCO Polygonum convolvulus
  • VERPE Veronica persica VIOTR: Viola tricolor Table 6: Pre-emergence efficacy (herbicidal activity against [%])
  • the compounds according to the invention have a very good action in the pre-emergence process (80% to 100%) herbicidal action) against harmful plants such as, for example
  • graminaceous crops such as barley, wheat, rye, millet, corn or rice pre-emergence even with high doses of active ingredient undamaged.
  • some substances also protect dicotyledonous crops such as soya, cotton, rapeseed, sugar beet or potatoes.
  • Some of the compounds according to the invention show a high selectivity and are therefore suitable in the pre-emergence process for controlling undesired plant growth in agricultural crops. 2.
  • Seeds of monocotyledonous or dicotyledonous weeds or crops are in plastic or
  • the compounds according to the invention formulated as wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green plant parts as an aqueous suspension or emulsion with the addition of 0.5% of additive at a rate of 600 l / ha.
  • WP wettable powders
  • EC emulsion concentrates
  • the compounds according to the invention have a very good herbicidal action (80% to 100% herbicidal action) against harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora , Ipomoea purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor at an application rate of 0.32 kg of active ingredient or less per hectare.
  • harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora , Ipomoea purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media,
  • compounds according to the invention leave gramineous crops such as barley, wheat, rye, millet, maize or rice, post-emergence, virtually undamaged, even at high doses of active ingredient.
  • some substances also protect dicotyledonous crops such as soya, cotton, rapeseed, sugar beet or potatoes.
  • Some of the compounds according to the invention show a high selectivity and are therefore suitable postemergence for combating undesired plant growth in agricultural crops.

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Abstract

L'invention concerne des composés de formule générale (I) et leurs sels compatibles sur le plan agrochimique, ainsi que leur préparation et leur utilisation dans le domaine phytosanitaire.
EP18715613.8A 2017-04-05 2018-03-29 Dérivés de 2-amino-5-oxyalkyl-pyrimidine et leur utilisation pour lutter contre la croissance de plantes adventices Withdrawn EP3606915A1 (fr)

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US11477982B2 (en) 2022-10-25
US20200029565A1 (en) 2020-01-30
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