US20080269059A1 - Pyridinecarboxamides, useful-plant-protecting composition comprising them and processes for their prepartion and their use - Google Patents

Pyridinecarboxamides, useful-plant-protecting composition comprising them and processes for their prepartion and their use Download PDF

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US20080269059A1
US20080269059A1 US12/111,419 US11141908A US2008269059A1 US 20080269059 A1 US20080269059 A1 US 20080269059A1 US 11141908 A US11141908 A US 11141908A US 2008269059 A1 US2008269059 A1 US 2008269059A1
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alkyl
substituted
unsubstituted
alkoxy
haloalkoxy
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Frank Ziemer
Lothar Willms
Christopher Rosinger
Thomas Auler
Erwin Hacker
Udo Bickers
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Bayer CropScience AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D413/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to useful-plant-protecting compounds and compositions comprising specific compounds as safeners for reducing phytotoxic actions of agrochemicals, in particular of herbicides.
  • the invention relates in particular to pyridone derivatives as safeners and to processes for their preparation.
  • the useful plants When controlling unwanted organisms in crops of plants which are useful for agriculture or forestry by using pesticides, the useful plants are frequently also damaged to a greater or lesser extent, by the pesticides employed. This unwanted phytotoxic effect is encountered in particular with the use of a considerable number of herbicides in crops of useful plants such as, for example, corn, rice or cereals—and there primarily in the post-emergence application.
  • the useful plants can be protected against the phytotoxic properties of the pesticides by employing safeners or antidotes, without diminishing or substantially impairing the pesticidal activity against the harmful organisms. In some cases, even an improved pesticidal action against harmful organisms such as weeds was observed.
  • safeners belong to a large number of different chemical structure classes, their suitability as safeners generally also depending on the chemical structures of the pesticides and on the crops of useful plants.
  • Examples of such safeners are the safeners mefenpyr-diethyl and isoxadifen-ethyl, which are used in commercial products.
  • WO 2004/084631 discloses the use of hydroxyl-substituted aromatic carboxylic acid derivatives.
  • WO 2005/015994 (US 2005-037922) describes specific derivatives of salicylic acid as safeners. These compounds are suitable in particular for use as safeners in crops of corn and soybeans.
  • WO 2005/112630 discloses 1,2-dihydroquinoxalin-2-one derivatives as safeners.
  • WO 2001/055115 (U.S. Pat. No. 6,794,397) describes nicotinanilides as inductors of apoptosis, and US 2004/0116479 describes dialkylnicotinamides as inhibitors of angiogenesis.
  • EP-A-522392 (U.S. Pat. No. 5,232,060) describes 6-trifluoromethyl-substituted pyridonecarboxamides as precursors for the synthesis of herbicidally active sulfonylureas. Helv. Chim.
  • Acta 71 (1988) 596-601 and GB 2305174 mention 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide, 6-chloro(difluoro)methyl-1,2-dihydro-2-oxopyridine-3-carboxamide and 6-difluoromethyl-1,2-dihydro-2-oxo-pyridine-3-carboxamide as intermediates in the synthesis of pyranopyridines.
  • WO 2007/041052 mentions 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide as an intermediate in the synthesis of pharmacologically active spiropiperidines.
  • WO 2006/007981 (US 2007-265164) describes a method for identifying compounds which induce the defense of plants against pathogens, where the increase of the expression of plant-endogenous genes is considered to be an indication for the induction.
  • 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide is mentioned as part of a group of six compounds which may be referred to as safeners.
  • a safener action confirmed by biological tests on plants has hitherto not been disclosed for this compound, and is also not sufficiently disclosed by WO 2006/007981.
  • the invention provides the use of compounds of the formula (I) or salts thereof
  • the compounds of the formula (I) also include tautomers which can be formed by hydrogen shifts and whose structure is formally not embraced by the formula (I). These tautomers are nevertheless included in the definition of the compounds of the formula (I) according to the invention.
  • the definition of the compounds of the formula (I) includes in particular the tautomeric structures of the formula (Ia) (2-hydroxypyridine-3-carboxamides) or salts thereof
  • R 1 , R 2 , R 3 and R 4 are as defined in formula (I).
  • the invention does not intend to encompass within the scope of the invention any previously disclosed product, process of making the product or method of using the product, which meets the written description and enablement requirements of the USPTO (35 U.S.C. 112, first paragraph) or the EPO (Article 83 of the EPC), such that applicant(s) reserve the right and hereby disclose a disclaimer of any previously described product, method of making the product or process of using the product.
  • the invention also provides useful-plant-protecting compositions comprising compounds of the formula (I) or salts thereof and formulation auxiliaries.
  • the invention also provides useful-plant-protecting compositions comprising compounds of the formula (I) or salts thereof in combination with further agrochemicals, preferably pesticides, in particular herbicides, and, if appropriate, formulation auxiliaries.
  • the invention also provides compounds of the formula (I) or salts thereof
  • R 1 is (C 1 -C 3 )-alkyl which is substituted by one to three fluorine atoms
  • R 2 is hydrogen
  • R 3 is (C 1 -C 2 )-alkyl
  • R 4 is (C 1 -C 2 )-alkyl.
  • the compounds of the formula (I) may be present as stereoisomers. All possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are embraced by the formula (I).
  • stereoisomers can be obtained by customary separation methods, for example by chromatographic separation procedures, from the mixtures obtained in the preparation. It is also possible to selectively prepare stereoisomers by employing stereoselective reactions using optically active starting materials and/or auxiliaries.
  • the invention also relates to all stereoisomers embraced by the formula (I) but not shown in their specific stereoform and mixtures thereof.
  • (C 1 -C 4 )-alkyl is a short notation for open-chain alkyl having 1 to 4 carbon atoms corresponding to the stated range of carbon atoms, i.e. it includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl and tert-butyl.
  • general alkyl radicals having a wider stated range of carbon atoms for example “(C 1 -C 6 )-alkyl”, also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, i.e. in the example also the alkyl radicals having 5 and 6 carbon atoms.
  • the lower carbon skeletons for example those having 1 to 6 carbon atoms or, in the case of unsaturated groups, having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including in composite radicals.
  • Alkyl radicals including in the composite meanings, such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or isopropyl, n-, iso, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the possible unsaturated radicals which correspond to the alkyl radicals; alkenyl is, for example, vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl, preferably allyl, 1-methylprop-2-en-1-yl, 2-methyl
  • (C 2 -C 6 )-alkynyl is, for example, ethynyl, propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methylbut-3-yn-1-yl.
  • Alkylidene including, for example, in the form (C 1 -C 10 )-alkylidene, is the radical of a straight-chain or branched alkane which is attached via a double bond, where the position of the point of attachment has not yet been fixed.
  • the only possible positions in the case of a branched alkane are, of course, positions in which two hydrogen atoms may be replaced by the double bond; radicals are, for example, ⁇ CH 2 , ⁇ CH—CH 3 , ⁇ C(CH 3 )—CH 3 , ⁇ C(CH 3 )—C 2 H 5 or ⁇ C(C 2 H 5 )—C 2 H 5 .
  • Cycloalkyl is a carbocyclic saturated ring system having preferably 3-8 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Substituted cycloalkyl embraces cyclic systems having substituents, substituents having a double bond at the cycloalkyl radical, for example an alkylidene group, such as methylidene, also being included.
  • Substituted cycloalkyl also embraces polycyclic aliphatic systems, such as, for example, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[2,1,0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
  • Cycloalkenyl is a carbocyclic, non-aromatic, partially unsaturated ring system having preferably 4-8 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl.
  • substituted cycloalkyl apply correspondingly to substituted cycloalkenyl.
  • halogen denotes, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by identical or different halogen atoms, preferably from the group consisting of fluorine, chlorine and bromine, in particular from the group consisting of fluorine and chlorine, for example monohaloalkyl, such as CH 2 CH 2 Cl, CH 2 CH 2 F, CH 2 ClCH 3 , CH 2 FCH 3 , CH 2 Cl, CH 2 F; perhaloalkyl such as CCl 3 or CF 3 or CF 3 CF 2 ; polyhaloalkyl, such as CHF 2 , CH 2 F, CH 2 FCHCl, CHCl 2 , CF 2 CF 2 H, CH 2 CF 3 , CH 2 ClCH 3 , CH 2 FCH 3 ; haloalkoxy is, for
  • Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, benzyl, heterocyclyl and heteroaryl radical, are, for example, substituted radicals derived from an unsubstituted skeleton, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, alkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, trialkylsilyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted heterocyclyl, where each of the last mentioned cyclic groups may also be
  • substituted cyclic radicals having aliphatic moieties in the ring also embraces cyclic systems having substituents which are attached to the ring via a double bond, for example substituted by an alkylidene group, such as methylidene or ethylidene, or an oxo group, imino group or substituted imino group.
  • first substituent level can, if they contain hydrocarbon-containing moieties, be, if appropriate, substituted further in the moieties (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
  • second substituent level can, if appropriate, substituted further in the moieties, for example by one of the substituents as defined for the first substituent level.
  • substituent levels are possible.
  • substituted radical preferably embraces only one or two substituent levels.
  • Preferred substituents for the substituent levels are, for example,
  • radicals having carbon atoms preference is given to those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms.
  • substituents selected from the group consisting of halogen, for example fluorine and chlorine, (C 1 -C 4 )-alkyl, preferably methyl or ethyl, (C 1 -C 4 )-haloalkyl, preferably trifluoromethyl, (C 1 -C 4 )-alkoxy, preferably methoxy or ethoxy, (C 1 -C 4 )-haloalkoxy, nitro and cyano.
  • substituents methyl, methoxy, fluorine and chlorine.
  • Substituted amino such as mono- or disubstituted amino, denotes a radical from the group of the substituted amino radicals which are N-substituted, for example, by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and saturated N-heterocycles; here, preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; for acyl, the definition given further down applies, preference is given to (C 1 -C 4 )-alkanoyl. This applies correspondingly to substituted hydroxylamino or hydrazino.
  • Substituted amino also includes quaternary ammonium compounds (salts) with four organic substituents at the nitrogen atom.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4-trifluoromethyl- and -trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
  • Optionally substituted cycloalkyl is preferably cycloalkyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl and (C 1 -C 4 )-haloalkoxy, in particular by one or two (C 1 -C 4 )-alkyl radicals.
  • Optionally substituted heterocyclyl is preferably heterocyclyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, nitro and oxo, in particular mono- or polysubstituted by radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl and oxo, very particularly substituted by one or two (C 1 -C 4 )-alkyl radicals.
  • Acyl denotes a radical of an organic acid which, formally, is formed by removing a hydroxyl group from the acid function, it also being possible for the organic radical in the acid to be attached to the acid function via a heteroatom.
  • acyl are the radical —CO—R of a carboxylic acid HO—CO—R and radicals of acids derived therefrom, such as thiocarboxylic acid, unsubstituted or N-substituted iminocarboxylic acids or the radical of carbonic acid monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamido acids, phosphonic acids, phosphinic acids.
  • Acyl denotes, for example, formyl, alkylcarbonyl such as [(C 1 -C 4 )-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl, N-alkyl- and N,N-dialkylcarbamoyl and other radicals of organic acids.
  • alkylcarbonyl such as [(C 1 -C 4 )-alkyl]carbonyl
  • phenylcarbonyl alkyloxycarbonyl
  • phenyloxycarbonyl benzyloxycarbonyl
  • alkylsulfonyl alkylsulfinyl
  • N-alkyl-1-iminoalkyl N-alkyl- and N,N-dialkylcarbamoyl
  • radicals may in each case be substituted further in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents which have already been mentioned further above in a general manner for substituted phenyl.
  • Acyl denotes preferably an acyl radical in the narrower sense, i.e. a radical of an organic acid where the acid group is attached directly to the carbon atom of an organic radical, for example alkanoyl, such as formyl and acetyl, aroyl, such as phenylcarbonyl, and other radicals of saturated or unsaturated organic acids.
  • alkanoyl such as formyl and acetyl
  • aroyl such as phenylcarbonyl
  • Aroyl denotes an aryl radical as defined above which is attached via a carbonyl group, for example the benzoyl group.
  • heterocyclyl is preferably a heterocyclic 3- to 9-membered, in particular 5- or 6-membered, ring having 1 to 3 hetero ring atoms from the group consisting of N, O and S.
  • the compounds of the general formula (I) can be prepared, for example, by
  • the amide formations according to variant (a) can be carried out, for example, in an inert organic solvent in a temperature range between 0° C. and 150° C., preferably between 0° C. and 50° C.
  • Suitable organic solvents are, for example, polar protic or aprotic solvents, such as ethers, for example diethyl ether, tetrahydrofuran and dioxane, or nitriles, such as acetonitrile, or amides, such as dimethylformamide.
  • the amide formations according to variant (b) can be carried out, for example, in an inert organic solvent in a temperature range between 0° C. and 150° C., preferably between 50° C. and 100° C.
  • Suitable organic solvents are, for example, polar protic or aprotic solvents, such as ethers, for example tetrahydrofuran and dioxane, or nitriles, such as acetonitrile, or amides, such as dimethylformamide.
  • polar protic or aprotic solvents such as ethers, for example tetrahydrofuran and dioxane, or nitriles, such as acetonitrile, or amides, such as dimethylformamide.
  • the amide formations according to variant (c) can be carried out, for example, in the presence of an acid binder in an inert organic solvent in a temperature range between 0° C. and 150° C., preferably between 50° C. and 100° C.
  • Suitable organic solvents are, for example, polar protic or aprotic solvents, such as ethers, for example diethyl ether, tetrahydrofuran and dioxane, or nitriles, such as acetonitrile, or amides, such as dimethylformamide.
  • Acid binders are, for example, alkali metal or alkaline earth metal carbonates, such as, for example, sodium carbonate, potassium carbonate or calcium carbonate, alkali metal or alkaline earth metal hydroxides, such as sodium hydroxide, potassium hydroxide or calcium hydroxide, or alkali metal hydrides or amides, such as sodium hydride or potassium hydride or sodium amide or potassium amide, or else organic bases, such as triethylamine, pyridine, dimethylaminopyridine, DBU (1,8-diazabicyclo[5.4.0]-undec-7-ene), DBN (1,5-diazabicyclo[4.3.0]non-5-ene) and 1,4-diaza-bicyclo[2.2.2]octane.
  • alkali metal or alkaline earth metal carbonates such as, for example, sodium carbonate, potassium carbonate or calcium carbonate
  • alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, potassium
  • the amide formations according to variant (d) can be carried out analogously to the processes described in EP 522392 and Helv. Chim. Acta 71 (1988) 596-601 and GB 2305174.
  • the malonamide can be converted in an organic anhydrous polar protic or aprotic solvent, for example in an alcohol, with a strong base, such as an alkali metal, alkali metal hydride or alkali metal alkoxide, into a reactive salt, and then be reacted with the compound of the formula (VI).
  • the reaction with the compound (VI) can generally be carried out in a temperature range between 0° C. and the boiling point of the solvent (depending on the solvent up to about 150° C.).
  • the starting materials of the formula (VI) are either commercially available or can be prepared by known methods (for example Synthesis 2000, 738-742; J. Fluor. Chem., 107, 2001, 285-300; Organometallics 15, 1996, 5374-5379).
  • the compounds of the formula (IV) in which R 2 is a halogen atom can be prepared by customary halogenations from the compounds of the formula (IVa).
  • Suitable for use as halogenating agents for pyridine are, for example, chlorine (J. Org. Chem. 23, 1958, 1614), bromine (Synth. Commun. 19, 1989, 553-560; U.S. Pat. No. 2,532,055), iodine (Tetrahedron Lett. 45, 2004, 6633-6636), sodium hypochlorite (J. Org. Chem. 49, 1984, 4784-4786; J. Med. Chem. 36, 1993, 2676-2688, U.S. Pat. No.
  • the compounds of the formula (IV) can be prepared from the compounds of the formula (IVa) by successive nitration (for example J. Med. Chem. 36, 1993, 2676-2688; J. Heterocycl. Chem. 33, 1996, 287-294), reduction (for example J. Med. Chem. 33, 1990, 1859-1865), diazotation and subsequent reaction of the diazonium salts in a Sandmeyer or Schiemann reaction.
  • the compounds of the formula (I) in which R 3 and R 4 together with the directly attached nitrogen atom are the group —N ⁇ CR 5 —NR 6 R 7 can be prepared by reacting a compound of the formula (I) in which R 3 and R 4 are hydrogen with compounds of the formula (VIII) in which R 5 , R 6 and R 7 are as defined above
  • the invention also provides a method for protecting crop plants or useful plants against phytotoxic actions of agrochemicals, such as pesticides or, in particular, herbicides which cause damage to crop plants or useful plants, which method comprises using compounds of the formula (I) or salts thereof as safeners, preferably by applying an effective amount of the compounds of the formula (I) or salts thereof to the plants, to parts of plants or their seeds (or seed).
  • agrochemicals such as pesticides or, in particular, herbicides which cause damage to crop plants or useful plants
  • crops of economic importance such as cereals (wheat, barley, triticale, rye, rice, corn, millet), sugar beet, sugar cane, oilseed rape, cotton, sunflower, peas, beans and soybeans.
  • monocotyledonous crops such as cereals (wheat, barley, rye, triticale, sorghum), including corn and rice, and monocotyledonous vegetable crops, but also in dicotyledonous crops, such as, for example, soybean, oilseed rape, cotton, grape vines, vegetable plants, fruit plants and ornamental plants.
  • the herbicide/safener combinations with the safeners (I) are also suitable for controlling harmful plants in beds and plots of useful plants and ornamental plants, such as, for example, lawn plots with useful or ornamental lawn, especially lolium, meadow grass or Bermuda grass.
  • herbicide/safener combinations with safeners (I) are mutant crops which are completely or partially tolerant to certain pesticides or completely or partially tolerant transgenic crops, for example corn crops which are resistant to glufosinate or glyphosate, or soybean crops which are resistant to herbicidal imidazolinones.
  • the particular advantage of the safeners used in this novel way is their efficient action in crops which normally are insufficiently tolerant to the pesticides being applied.
  • the compounds of the formula (I) according to the invention can be applied simultaneously with the active compounds or in any order, and they are then capable of reducing or completely eliminating harmful side effects of these active compounds in crop plants, without negatively affecting or substantially reducing the activity of these active compounds against unwanted harmful organisms.
  • a plurality of pesticides for example a plurality of herbicides or herbicides in combination with insecticides or fungicides, can be reduced substantially or eliminated completely. In this manner, it is possible to extend the field of use of conventional pesticides considerably.
  • compositions according to the invention comprise pesticides
  • these compositions are, after appropriate dilution, applied either directly to the area under cultivation, to the already germinated harmful and/or useful plants or to the already emerged harmful and/or useful plants.
  • safener and pesticide are applied within a short time of one another, in particular when the safener is applied to the plants after the herbicide.
  • the advantageous actions of the compounds (I) according to the invention are observed when they are used together with the pesticides by the pre-emergence method or the post-emergence method, for example in the case of simultaneous application as a tank mix or a coformulation or in the case of a separate application, in parallel or in succession (split application). It is also possible to repeat the application a number of times. In some cases, it may be expedient to combine a pre-emergence application with a post-emergence application. In most cases, one option is a post-emergence application to the useful plant or crop plant together with a simultaneous or later application of the pesticide. Also possible is the use of the compounds (I) according to the invention for seed dressing, for (dip) treatment of seedlings (for example rice) or for the treatment of other propagation material (for example potato tubers).
  • seed dressing for (dip) treatment of seedlings (for example rice) or for the treatment of other propagation material (for example potato tubers).
  • compositions according to the invention may comprise one or more pesticides.
  • suitable pesticides are, for example, herbicides, insecticides, fungicides, acaricides and nematicides, which, when used on their own, would cause phytotoxic damage to the crop plants or would probably cause damage.
  • Suitable pesticides are, for example, herbicides, insecticides, fungicides, acaricides and nematicides, which, when used on their own, would cause phytotoxic damage to the crop plants or would probably cause damage.
  • Of particular interest are corresponding pesticidally active compounds from the groups of the herbicides, insecticides, acaricides, nematicides and fungicides, in particular herbicides.
  • the weight ratio of safener to pesticide can be varied within wide limits and is generally in the range from 1:100 to 100:1, preferably from 1:20 to 20:1, in particular from 1:10 to 10:1.
  • the optimum weight ratio of safener to pesticide depends both on the respective safener used and the respective pesticide, and on the type of useful plant or crop plant to be protected.
  • the required application rate of safener can, depending on the pesticide used and the type of useful plant to be protected, be varied within wide limits and is generally in the range from 0.001 to 10 kg, preferably from 0.01 to 1 kg, in particular from 0.05 to 0.5 kg, of safener per hectare.
  • the weight ratios and amounts required for a successful treatment can be determined by simple preliminary experiments.
  • seed dressing for example, from 0.005 to 20 g of safener per kilogram of seed, preferably from 0.01 to 10 g of safener per kilogram of seed, in particular from 0.05 to 5 g of safener per kilogram of seed, are used.
  • the suitable concentration is generally in the range from 1 to 10 000 ppm, preferably from 100 to 1000 ppm, based on the weight.
  • the weight ratios and amounts required for a successful treatment can be determined by simple preliminary experiments.
  • the safeners can be formulated in the customary manner, separately or together with the pesticides. Accordingly, the present invention also provides the useful-plant-protecting or crop-plant-protecting compositions.
  • Preferred is the joint application of safener and pesticide, in particular that of safener and herbicide as a readymix or the use by the tankmix method.
  • the compounds of the formula (I) or their salts, as such or in the form of their preparations (formulations), can be used in combination with other pesticidally active compounds, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example as finished formulation or as tank mixes.
  • pesticidally active compounds such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example as finished formulation or as tank mixes.
  • the combination formulations can be prepared based on the formulations mentioned above, taking into account the physical properties and stabilities of the active compounds to be combined.
  • Suitable as combination partners for the active compounds according to the invention in formulations of mixtures or in tank-mixes are, for example, known, preferably herbicidally active compounds whose action is based on the inhibition of, for example, acetolactate synthase, acetyl-coenzyme-A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate 3-phosphate synthetase.
  • herbicides known from the literature which may be combined with the compounds of the formula (I) are, for example, the following active compounds (note: the compounds are referred to either by the “common name” according to the International Organization for Standardization (ISO) or by the chemical name, if appropriate together with a customary code number):
  • acetochlor acibenzolar-5-methyl; acifluorfen(-sodium); aclonifen; AD-67; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]oxy]acetic acid and methyl [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate; alachlor; alloxydim(-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid; amitrol; AMS, i.e.
  • ammonium sulfamate ancimidol
  • anilofos asulam
  • atrazine aviglycine
  • azafenidin azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516H, i.e.
  • Insecticides which may cause damage to plants when used on their own or together with herbicides are, for example, the following:
  • Organophosphates for example terbufos (Counter®), fonofos (Dyfonate®), phorate (Thimet®), chlorpyriphos (Reldan®), carbamates, such as carbofuran (Furadan®), pyrethroid insecticides, such as tefluthrin (Force®), deltamethrin (Decis®) and tralomethrin (Scout®), and other insecticidal agents having a different mechanism of action.
  • Herbicides whose phytotoxic side effects on crop plants can be reduced using compounds of the formula (I) are, for example, herbicides from the group of the carbamates, thiocarbamates, haloacetanilides, substituted phenoxy-, naphthoxy- and phenoxyphenoxycarboxylic acid derivatives and heteroaryloxyphenoxyalkane-carboxylic acid derivatives, such as quinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy- and benzothiazolyloxyphenoxyalkanecarboxylic acid esters, cyclo-hexanedione oximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoyl-pyrazoles, imidazolinones, pyrimidinyloxypyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, sulfonylureas
  • phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts Preference is given here to phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, cyclohexanedione oximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles sulfonylureas, sulfonylaminocarbonyltriazolinones, imidazolinones and mixtures of the active compounds mentioned with one another and/or with active compounds used for broadening the activity spectrum of the herbicides, for example bentazone, cyanazine, atrazine, bromoxynil, dicamba and other leaf-acting herbicides.
  • Herbicides which are suitable for combination with the safeners according to the invention are, for example:
  • herbicides of the type of the phenoxyphenoxy- and heteroaryloxyphenoxy-carboxylic acid derivatives such as
  • the herbicides of groups A to W are known, for example, from the respective abovementioned publications and from “The Pesticide Manual”, The British Crop Protection Council, 14th Edition, 2006, or the e-Pesticide Manual, Version 4.0, British Crop Protection Council 2006 or else from the “Compendium of Pesticide Common Names”.
  • active compound formulations or coformulations When used as active compound formulations or coformulations, they generally comprise, if appropriate, the respective customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and colorants, antifoams, evaporation inhibitors and pH- and viscosity-modifying agents.
  • the compounds of the formula I and their combinations with one or more of the abovementioned pesticides can be formulated in various ways, depending on the prevailing physicochemical and biological parameters. Examples of suitable formulation types are:
  • the useful-plant-protecting compositions may comprise, if appropriate, customary tackifiers, wetting agents, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers, colorants, anti-foams, evaporation inhibitors and pH or viscosity regulators.
  • the useful-plant-protecting compositions generally comprise 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the formula I or a combination of safener and pesticide. Furthermore, they comprise 1 to 99.9, in particular 4 to 99.5,% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25,% by weight of a surfactant.
  • the concentration of active compound i.e. the concentration of safener and/or pesticide
  • Dusts usually comprise 1 to 30, preferably 5 to 20,% by weight of active compound.
  • the concentration of active compound is generally 10 to 90% by weight.
  • the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the formulations which are present in commercially available form, are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, with water. Preparations in the form of dusts, granules and sprayable solutions are usually not diluted with any further inert substances prior to use.
  • the required application rate of the safeners varies with the external conditions such as, inter alia, temperature, humidity and the type of herbicide used.
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I) and 90 parts by weight of talc as inert material and comminuting in a hammer mill.
  • a pesticide eg. herbicide
  • a safener of the formula (I) 90 parts by weight of talc as inert material and comminuting in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I), 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil and grinding in a ball mill to a fineness of below 5 microns.
  • a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil and grinding in a ball mill to a fineness of below 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) or of an active compound mixture of a pesticide (eg. herbicide) and a safener of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a pesticide eg. herbicide
  • cyclohexanone as solvent
  • 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • Water-dispersible granules are also obtained by homogenizing
  • Table 1 lists a number of compounds of the general formula (I) which can be obtained in a manner analogous to Examples A1 to A10 above and to the methods mentioned further above.
  • the number indices in the formula are not subscript but arranged in the same line height and font size as the symbols for the atoms.
  • the formula CF 3 in the table corresponds to the formula CF 3 according to the customary notation with subscript index
  • the formula CH 2 CH(CH 2 CH 3 ) 2 corresponds to the formula CH 2 CH(CH 2 CH 3 ) 2 with subscript indices.
  • the damage to the plants is scored visually using a scale of 0-100%, in comparison to control plants:
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous harmful plants and crop plants are placed in sandy loam soil in plastic pots, covered with soil and cultivated in the greenhouse under good growth conditions.
  • harmful plants encountered in paddy rice cultivation are cultivated in pots in which the surface of the soil is covered by up to 2 cm of water. Three weeks after sowing, the test plants are treated at the three-leaf stage.
  • the herbicide/safener active compound combinations according to the invention formulated as emulsion concentrates, and in parallel tests the individual active compounds formulated in a corresponding manner, are sprayed at various dosages at a water application rate of 300 l/ha (converted) onto the green parts of the plants, and, after the test plants were left to stand in the greenhouse for about 2 to 3 weeks under optimum growth conditions, the effect of the preparations is scored visually in comparison to untreated controls.
  • the active compounds are also added directly to the irrigation water (application analogously to the so-called granule application) or sprayed onto the plants and into the irrigation water.
  • a good safener action for the herbicide mesosulfuron-methyl could be achieved using the compounds Nos. 1, 2, 3, 5, 7, 9, 10, 13, 14, 22, 25, 26, 30, 34, 36, 40, 57, 64, 66, 79, 100, 101, 102, 105, 114, 115, 116, 117, 119, 123, 124, 128, 130, 134, 136, 138, 140, 146, 148, 153, 154, 155, 157, 163, 165, 168, 169, 171, 178, 193, 194, 214, 341, 342, 344, 345, 346, 382, 384, 392, 398, 405, 407, 455, 457, 489, 496, 498, 571, 909, 910, 911, 913, 943, 950, 960, 1023, 1026, 1029, 1030, 1201, 1481, 1487, 1598, 1599, 1600, 1636, 1907.
  • a good safener action for the herbicide tembotrione could be achieved using the following compounds from Table 1: 4, 6, 9, 10, 14, 24, 32, 34, 36, 43, 64, 66, 71, 75, 79, 105, 114, 118, 140, 146, 148, 153, 169, 178, 210, 214, 345, 51, 95, 341, 456, 457, 489, 496, 498, 909, 911, 913, 943, 960, 1026, 1139, 1368, 1371, 1485, 1488, 1596, 1597, 1598, 1599, 1600, 1604, 1619, 1625, 1629, 1636, 1638, 1646, 1758.
  • the following compounds from Table 1 achieved good safener action for fenoxaprop-P-ethyl and thiencarbazone or thiencarbazone-methyl: 1, 2, 3, 4, 9, 16, 20, 22, 34, 41, 47, 54, 57, 75, 76, 79, 80, 81, 101, 103, 105, 114, 115, 117, 118, 120, 127, 128, 130, 153, 154, 157, 162, 165, 169, 171, 178, 218, 271, 341, 342, 344, 345, 346, 350, 355, 392, 398, 405, 407, 456, 973, 1482, 1596, 1597, 1598, 1600, 1603, 1609, 1625, 1638, 1646, 1659.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants and crop plants were placed in sandy loam soil in plastic pots and covered with soil.
  • the herbicide/safener active compound combinations according to the invention, formulated as suspension emulsion concentrates, and in parallel tests the individual active compounds formulated in a corresponding manner, were then, at various dosages at a water application rate of 600 to 800 l/ha (converted), applied to the surface of the covering soil.
  • the pots were placed in the greenhouse and kept under good growth conditions for the weeds and the crop plants. Visual scoring of the plant damage or emergence damage was carried out after the test plants had emerged after a test period of 3 to 4 weeks, in comparison to untreated controls. The test results showed that the compounds according to the invention prevented or reduced herbicide damage to the crop plants without reducing, or reducing substantially, the herbicide action against the harmful plants.
  • example Nos. 2, 19, 39, 72, 104, 122, 155, 193, 194, 217, 232, 271, 341, 380, 392, 1368, 1597, 1625, 1636 of Table 1 showed in the test in combination with the herbicide isoxaflutol a good safener action in corn.
  • the herbicidal action of the herbicidally active compounds used was not adversely affected. Accordingly, in many cases, the safeners, combined with herbicides, are suitable for the selective control of hermful plants in the pre-emergence treatment of crops of useful plants.
  • Seeds of crop plants were mixed in bottles with the safeners according to the invention, formulated as suspension or emulsion concentrates, and water, and the mixture was shaken well so that the seeds were coated evenly with the formulation of the safener in question.
  • the seeds or the emerged plants were then tested with herbicides in the pre- or post-emergence method according to the tests of examples 3.3 and 3.2, respectively.

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