TREA

INSECTICIDAL COMPOSITIONS WITH IMPROVED ACTION

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Information

  • Patent Application
  • 20100173943
  • Publication Number
    20100173943
  • Date Filed
    May 28, 2008
    16 years ago
  • Date Published
    July 08, 2010
    14 years ago
Information
Abstract
The present invention relates to enhancement of the action of crop protection compositions comprising enaminocarbonyl compounds by the addition of ammonium salts and/or phosphonium salts or by the addition of ammonium or phosphonium salts and penetrants, to the corresponding compositions, to processes for their production and to their use in crop protection.
Description

The present invention relates to enhancement of the action of crop protection compositions comprising enaminocarbonyl compounds by the addition of ammonium salts or phosphonium salts or by the addition of ammonium or phosphonium salts and penetrants, to the corresponding compositions, to processes for their production and to their use in crop protection.


Enaminocarbonyl compounds are known, for example, from EP 0 539 588 and WO 2006/037475. The enhancement of action for individual enaminocarbonyl compounds is described in WO 2007/068355.


Inventive enaminocarbonyl compounds are described, for example, by formula (I):







in which

    • A is pyrid-2-yl or pyrid-4-yl, or is pyrid-3-yl which is optionally 6-substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy, or is pyridazin-3-yl, which is optionally 6-substituted by chlorine or methyl, or is pyrazin-3-yl or is 2-chloropyrazin-5-yl or is 1,3-thiazol-5-yl which is optionally 2-substituted by chlorine or methyl, or
    • A is a pyrimidyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolyl radical which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C3-alkylthio (which is optionally substituted by fluorine and/or chlorine) or C1-C3-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine),


or

    • A is a radical







in which

    • X is halogen, alkyl or haloalkyl,
    • Y is halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano,
    • B is oxygen, sulphur, ethylene or methylene,
    • R1 is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, halocycloalkyl, alkoxy or halocycloalkylalkyl,
    • R2 is hydrogen or halogen and
    • R3 is hydrogen or alkyl,
    • with the proviso that 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one and 4-{[(6-chloropyrid-3-yl)methyl]amino}furan-2(5H)-one are excluded.


Preferred, particularly preferred and very particularly preferred substituents or ranges of the radicals detailed in the formula (I) mentioned above are illustrated below.


A is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-methylpyrid-3-yl, 6-trifluoromethylpyrid-3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl or 2-methyl-1,3-thiazol-5-yl, 2-chloropyrimidin-5-yl, 2-trifluoromethylpyrimidin-5-yl, 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-iodo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-fluoro-6-iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl, 5-bromo-6-iodopyrid-3-yl, 5-methyl-6-fluoropyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-methyl-6-bromopyrid-3-yl, 5-methyl-6-iodopyrid-3-yl, 5-difluoromethyl-6-fluoropyrid-3-yl, 5-difluoromethyl-6-chloropyrid-3-yl, 5-difluoromethyl-6-bromopyrid-3-yl or 5-difluoromethyl-6-iodopyrid-3-yl.

    • B is preferably oxygen or methylene.
    • R1 is preferably optionally fluorine-substituted C1-C5-alkyl, C2-C5-alkenyl, C3-C5-cycloalkyl or C3-C5-cycloalkylalkyl.
    • R2 is preferably hydrogen or halogen.
    • R3 is preferably in each case hydrogen or methyl.
    • A is more preferably the 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl, 2-chloropyrimidin-5-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-chloro-6-iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl radiacl.
    • B is more preferably oxygen or methylene.
    • R1 is more preferably methyl, ethyl, propyl, vinyl, allyl, propargyl, cyclopropyl, 2-fluoroethyl, 2,2-difluoroethyl or 2-fluorocyclopropyl.
    • R2 is more preferably hydrogen, fluorine or chlorine.
    • R3 is more preferably hydrogen.
    • B is most preferably oxygen.
    • A is most preferably the 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, or 6-chloro-1,4-pyridazin-3-yl, 5-fluoro-6-chloropyrid-3-yl or 5-fluoro-6-bromopyrid-3-yl radical.
    • R1 is most preferably methyl, ethyl, n-propyl, n-prop-2-enyl, n-prop-2-ynyl, cyclopropyl, 2-fluoroethyl, or 2,2-difluoroethyl.
    • R2 is most preferably hydrogen.
    • R3 is most preferably hydrogen.


In a prominent group of compounds of the formula (I), A is 6-fluoropyrid-3-yl







In a prominent group of compounds of the formula (I), A is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I), A is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I), A is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I), A is 6-chloro-1,4-pyridazin-3-yl







In a further prominent group of compounds of the formula (I), A is 2-chloro-1,3-thiazol-5-yl







A further group of preferred compounds of the formula (I) is defined below, in which

    • A is pyrid-3-yl which is 6-substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl, or is 2-chloropyrazin-5-yl or is 2-chloro-1,3-thiazol-5-yl,
    • B is oxygen, sulphur or methylene,
    • R1 is halo-C1-3-alkyl, halo-C2-3-alkenyl, halocyclopropyl (where halogen is especially fluorine or chlorine),
    • R2 is hydrogen or halogen,
    • R3 is hydrogen or methyl,
    • A is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-chloropyrazin-5-yl or 2-chloro-1,3-thiazol-5-yl,
    • B is preferably nitrogen or methylene,
    • R1 is preferably difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 3-fluoro-n-propyl, 2-fluorovinyl, 3,3-difluoroprop-2-enyl or 3,3-dichloroprop-2-enyl,
    • R2 is preferably hydrogen or halogen (where halogen is especially fluorine or chlorine), R3 is preferably in each case hydrogen,
    • A is more preferably the 6-chloropyrid-3-yl or 6-bromopyrid-3-yl radical,
    • B is more preferably oxygen,
    • R1 is more preferably 2-fluoroethyl or 2,2-difluoroethyl,
    • R2 is more preferably hydrogen,
    • R3 is more preferably in each case hydrogen,
    • A is most preferably the 6-chloropyrid-3-yl or 6-bromopyrid-3-yl radical,
    • B is most preferably oxygen,
    • R1 is most preferably 2,2-difluoroethyl,
    • R2 is most preferably hydrogen,
    • R3 is most preferably in each case hydrogen,


In a further prominent group of compounds of the formula (I), R3 is hydrogen, B is oxygen and A is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I), R3 is hydrogen, B is oxygen and A is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I), R3 is hydrogen, B is oxygen and A is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I), R3 is hydrogen, B is oxygen and A is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I), R3 is hydrogen, B is oxygen and A is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is oxygen and A is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is oxygen and A is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is oxygen and A is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is oxygen and A is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is oxygen and A is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is methylene and A is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is methylene and A is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is methylene and A is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is methylene and A is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I), R2 and R3 are each hydrogen, B is methylene and A is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the fomula (I), R1 is difluoromethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I), R1 is 2-fluoroethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I), R1 is 2,2-difluoroethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I), R1 is difluoromethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I), R1 is 2-fluoroethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I), R1 is 2,2-difluoroethyl, R2 and R3 are each hydrogen and B is methylene.


The radical definitions and illustrations listed above in general or listed in preferred ranges can be combined with one another as desired, i.e. including between the particular preferred ranges.


Preference is given in accordance with the invention to compounds of the formula (I) in which a combination of the definitions listed above as preferred is present.


Particular preference is given in accordance with the invention to compounds of the formula (I) in which a combination of the definitions listed above as particularly preferred is present.


Very particular preference is given in accordance with the invention to compounds of the formula (I) in which a combination of the definitions listed above as very particularly preferred is present.


A preferred subgroup of the inventive enaminocarbonyl compounds is that of the formula (I-a)







in which

    • E is pyrid-2-yl or pyrid-4-yl or is pyrid-3-yl which is optionally 6-substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy, or is pyridazin-3-yl which is optionally 6-substituted by chlorine or methyl, or is pyrazin-3-yl or is 2-chloropyrazin-5-yl or is 1,3-thiazol-5-yl which is optionally 2-substituted by chlorine or methyl,
    • R4 is haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
    • and R2, R3 and B are each as defined above.


Preferred substituents and ranges of the radicals listed in the formula (I-a) mentioned above and below are illustrated below.

    • E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-methylpyrid-3-yl, 6-trifluoromethylpyrid-3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl or 2-methyl-1,3-thiazol-5-yl.
    • B is preferably oxygen or methylene.
    • R2 is preferably hydrogen or halogen (where halogen is especially fluorine or chlorine).
    • R3 is preferably in each case hydrogen or methyl.
    • R4 is preferably fluorine-substituted C3-C5-alkyl, C2-C5-alkenyl, C3-C5-cycloalkyl or C3-C5-cycloalkyalkyl.
    • E is more preferably the 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl radical.
    • B is more preferably oxygen or methylene.
    • R2 is more preferably hydrogen.
    • R3 is more preferably hydrogen.
    • R4 is more preferably 2-fluoroethyl, 2,2-difluoroethyl, 2-fluorocyclopropyl.
    • E is most preferably the 6-chloropyrid-3-yl, 6-bromopyrid-3-yl or 6-chloro-1,4-pyridazin-3-yl radical.
    • B is most preferably oxygen.
    • R2 is most preferably hydrogen.
    • R3 is most preferably hydrogen.
    • R4 is most preferably 2,2-difluoroethyl.


In a prominent group of compounds of the formula (I-a), E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-a), E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-a), E is 6-chloro-1,4-pyridazin-3-yl







In a further prominent group of compounds of the formula (I-a), E is 2-chloro-1,3-thiazol-5-yl







A further group of preferred compounds of the formula (I-a) is defined below, in which

    • E is pyrid-3-yl which is 6-substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl, or is 2-chloropyrazin-5-yl or is 2-chloro-1,3-thiazol-5-yl,
    • B is oxygen, sulphur or methylene,
    • R2 is hydrogen or halogen,
    • R3 is hydrogen or methyl,
    • R4 is halo-C1-3-alkyl, halo-C2-3-alkenyl, halocyclopropyl (where halogen is especially fluorine or chlorine),
    • E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-trifluoro-methylpyrid-3-yl, 2-chloropyrazin-5-yl or 2-chloro-1,3-thiazol-5-yl,
    • B is preferably oxygen or methylene,
    • R2 is preferably hydrogen or halogen (where halogen is especially fluorine or chlorine),
    • R3 is preferably in each case hydrogen,
    • R4 is preferably difluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 3-fluoro-n-propyl, 2-fluorovinyl, 3,3-difluoroprop-2-enyl or 3,3-dichloroprop-2-enyl,
    • E is more preferably the 6-chloropyrid-3-yl or 6-bromopyrid-3-yl radical,
    • B is more preferably oxygen,
    • R2 is more preferably hydrogen,
    • R3 is more preferably hydrogen,
    • R4 is more preferably 2-fluoroethyl or 2,2-difluoroethyl,
    • E is most preferably the 6-chloropyrid-3-yl or 6-bromopyrid-3-yl radical,
    • B is most preferably oxygen,
    • R2 is most preferably hydrogen,
    • R3 is most preferably hydrogen and
    • R4 is most preferably 2,2-difluoroethyl.


In a prominent group of compounds of the formula (I-a), R3 is hydrogen, B is oxygen and E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R3 is hydrogen, B is oxygen and E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R3 is hydrogen, B is oxygen and E is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R3 is hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R3 is hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is oxygen and E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is oxygen and E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is oxygen and E is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is methylene and E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is methylene and E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is methylene and E is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is methylene and E is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I-a), R2 and R3 are each hydrogen, B is methylene and E is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I-a), R4 is difluoromethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-a), R4 is 2-fluoroethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-a), R4 is 2,2-difluoroethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-a), R4 is difluoromethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I-a), R4 is 2-fluoroethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I-a), R4 is 2,2-difluoroethyl, R2 and R3 are each hydrogen and B is methylene.


A further preferred subgroup of inventive enaminocarbonyl compounds is that of those of the formula (I-b)







in which

    • D is a pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolyl radical which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C3-alkylthio (which is optionally substituted by fluorine and/or chlorine), or C1-C3-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine),


or

    • D is a radical







in which

    • X and Y are each as defined above,
    • R5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy,
    • and R2, R3 and B are each as defined above.


Preferred substituents and ranges of the radicals detailed in the formula (I-b) mentioned above and below are illustrated hereinafter.

    • D is preferably 2-chloropyrimidin-5-yl or 2-trifluoromethylpyrimidin-5-yl,


in addition,

    • D is preferably one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-iodo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-fluoro-6-iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl, 5-bromo-6-iodopyrid-3-yl, 5-methyl-6-fluoropyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-methyl-6-bromopyrid-3-yl, 5-methyl-6-iodopyrid-3-yl, 5-difluoromethyl-6-fluoropyrid-3-yl, 5-difluoromethyl-6-chloropyrid-3-yl, 5-difluoromethyl-6-bromopyrid-3-yl, 5-difluoromethyl-6-iodopyrid-3-yl.
    • B is preferably oxygen or methylene.
    • R2 is preferably hydrogen or halogen (where halogen is especially fluorine or chlorine).
    • R3 is preferably hydrogen.
    • R5 is preferably C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C4-cycloalkyl.
    • D is more preferably 2-chloropyrimidin-5-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-chloro-6-iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl.
    • B is more preferably oxygen.
    • R2 is more preferably hydrogen.
    • R3 is more preferably hydrogen.
    • D is most preferably 5-fluoro-6-chloropyrid-3-yl or 5-fluoro-6-bromopyrid-3-yl.
    • B is most preferably oxygen.
    • R2 is most preferably hydrogen.
    • R3 is most preferably hydrogen.
    • R5 is most preferably methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.


In a prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 2-chloropyrimidin-5-yl,







In a further prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,







In a further prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 5,6-dichloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 5-bromo-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 5-methyl-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 5-fluoro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 5-chloro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R3 is hydrogen, B is oxygen and D is 5-chloro-6-iodopyrid-3-yl







In a prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 2-chloropyrimidin-5-yl,







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 5,6-dichloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 5-bromo-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 5-methyl-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 5-fluoro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 5-chloro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is oxygen and D is 5-chloro-6-iodopyrid-3-yl







In a prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 2-chloropyrimidin-5-yl,







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 5-fluoro-6-chloropyrid-3-yl,







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 5,6-dichloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 5-bromo-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 5-methyl-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 5-fluoro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 5-chloro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R2 and R3 are each hydrogen, B is methylene and D is 5-chloro-6-iodopyrid-3-yl







In a further prominent group of compounds of the formula (I-b), R5 is methyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-b), R5 is ethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-b), R5 is cyclopropyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-b), R5 is methyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I-b), R5 is ethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I-b), R5 is cyclopropyl, R2 and R3 are each hydrogen and B is methylene.


A further preferred subgroup of the inventive enaminocarbonyl compounds is that of those of the formula (I-c)







in which

    • D is a pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolyl radical which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C3-alkylthio (which is optionally substituted by fluorine and/or chlorine), or C1-C3-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine),


or

    • D is a radical







in which

    • X and Y are each as defined above,
    • R4 is haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
    • and R2, R3 and B are each as defined above.


Preferred substituents and ranges of the radicals detailed in the formula (I-c) mentioned above and below are illustrated below.

    • D is preferably 2-chloropyrimidin-5-yl or 2-trifluoromethylpyrimidin-5-yl;


in addition,

    • D is preferably one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo-6-fluoropyrid-3-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-iodo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-fluoro-6-iodopyrid-3-yl, 5-chloro-6-iodopyrid-3-yl, 5-bromo-6-iodopyrid-3-yl, 5-methyl-6-fluoropyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-methyl-6-bromopyrid-3-yl, 5-methyl-6-iodopyrid-3-yl, 5-difluoromethyl-6-fluoropyrid-3-yl, 5-difluoromethyl-6-chloropyrid-3-yl, 5-difluoromethyl-6-bromopyrid-3-yl, 5-difluoromethyl-6-iodopyrid-3-yl.
    • B is preferably oxygen or methylene.
    • R2 is preferably hydrogen or halogen (where halogen is especially fluorine or chlorine).
    • R3 is preferably hydrogen.
    • R4 is preferably fluorine-substituted C1-C5-alkyl, C2-C5-alkenyl, C3-C5-cycloalkyl or C3-C5-cycloalkylalkyl.
    • D is more preferably 2-chloropyrimidin-5-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3yl, 5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-chloro-6-iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl.
    • B is more preferably oxygen.
    • R2 is more preferably hydrogen.
    • R3 is more preferably hydrogen.
    • R4 is more preferably 2-fluoroethyl, 2,2-difluoroethyl, 2-fluorocyclopropyl.
    • D is most preferably 5-fluoro-6-chloropyrid-3-yl or 5-fluoro-6-bromopyrid-3-yl.
    • B is most preferably oxygen.
    • R2 is most preferably hydrogen.
    • R3 is most preferably hydrogen.
    • R4 is most preferably 2,2-difluoroethyl.


In a prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 2-chloropyrimidin-5-yl,







In a further prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,







In a further prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 5,6-dichloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 5-bromo-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 5-methyl-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 5-fluoro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 5-chloro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R3 is hydrogen, B is oxygen and D is 5-chloro-6-iodopyrid-3-yl







In a prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 2-chloropyrimidin-5-yl,







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 5-fluoro-6-chloropyrid-3-yl,







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 5,6-dichloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 5-bromo-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 5-methyl-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 5-fluoro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 5-chloro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is oxygen and D is 5-chloro-6-iodopyrid-3-yl







In a prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 2-chloropyrimidin-5-yl,







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 5-fluoro-6-chloropyrid-3-yl,







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 5,6-dichloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 5-bromo-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 5-methyl-6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 5-fluoro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 5-chloro-6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R2 and R3 are each hydrogen, B is methylene and D is 5-chloro-6-iodopyrid-3-yl







In a further prominent group of compounds of the formula (I-c), R4 is difluoromethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-c), R4 is 2-fluoroethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-c), R4 is 2,2-difluoroethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-c), R4 is difluoromethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I-c), R4 is 2-fluoroethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I-c), R4 is 2,2-difluoroethyl, R2 and R3 are each hydrogen and B is methylene.


A preferred subgroup of the inventive enaminocarbonyl compounds is that of those of the formula (I-d)







in which

    • E is pyrid-2-yl or pyrid-4-yl or is pyrid-3-yl which is optionally 6-substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy, or is pyridazin-3-yl which is optionally 6-substituted by chlorine or methyl, or is pyrazin-3-yl or is 2-chloropyrazin-5-yl or is 1,3-thiazol-5-yl which is optionally 2-substituted by chlorine or methyl,
    • R5 is C2-C4-alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy,
    • and R2, R3 and B are each as defined above.


Preferred substituents and ranges of the radicals detailed in the formula (I-d) mentioned above and below are illustrated hereinafter.

    • E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-methylpyrid-3-yl, 6-trifluoromethylpyrid-3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl or 2-methyl-1,3-thiazol-5-yl.
    • B is preferably oxygen or methylene.
    • R2 is preferably hydrogen or halogen (where halogen is especially fluorine or chlorine).
    • R3 is preferably in each case hydrogen or methyl.
    • R5 is preferably C2-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C4-cycloalkyl.
    • E is more preferably the 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl radical.
    • B is more preferably oxygen or methylene.
    • R2 is more preferably hydrogen.
    • R3 is more preferably hydrogen.
    • R5 is more preferably ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.
    • E is most preferably the 6-chloropyrid-3-yl, 6-bromopyrid-3-yl or 6-chloro-1,4-pyridazin-3-yl radical.
    • B is most preferably oxygen.
    • R2 is most preferably hydrogen.
    • R3 is most preferably hydrogen.
    • R5 is most preferably ethyl or cyclopropyl.


In a prominent group of compounds of the formula (I-d), E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-d), E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-d), E is 6-chloro-1,4-pyridazin-3-yl







In a further prominent group of compounds of the formula (I-d), E is 2-chloro-1,3-thiazol-5-yl







A further group of preferred compounds of the formula (I-d) is defined below, in which

    • E is pyrid-3-yl which is 6-substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl, or is 2-chloropyrazin-5-yl or is 2-chloro-1,3-thiazol-5-yl,
    • B is oxygen, sulphur or methylene,
    • R2 is hydrogen or halogen,
    • R3 is hydrogen or methyl,
    • R5 is C2-C4-alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy,
    • E is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-trifluoro-methylpyrid-3-yl, 2-chloropyrazin-5-yl or 2-chloro-1,3-thiazol-5-yl,
    • B is preferably oxygen or methylene,
    • R2 is preferably hydrogen or halogen (where halogen is especially fluorine or chlorine),
    • R3 is preferably in each case hydrogen,
    • R5 is preferably C2-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C4-cycloalkyl,
    • E is more preferably the 6-chloropyrid-3-yl or 6-bromopyrid-3-yl radical,
    • B is more preferably oxygen,
    • R2 is more preferably hydrogen,
    • R3 is more preferably hydrogen,
    • R5 is more preferably ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl,
    • E is most preferably the 6-chloropyrid-3-yl or 6-bromopyrid-3-yl radical,
    • B is most preferably oxygen,
    • R2 is most preferably hydrogen,
    • R3 is most preferably hydrogen and
    • R5 is most preferably ethyl or cyclopropyl.


In a prominent group of compounds of the formula (I-d), R3 is hydrogen, B is oxygen and E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R3 is hydrogen, B is oxygen and E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R3 is hydrogen, B is oxygen and E is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R3 is hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R3 is hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is oxygen and E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is oxygen and E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is oxygen and E is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is oxygen and E is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is oxygen and E is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is methylene and E is 6-chloropyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is methylene and E is 6-bromopyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is methylene and E is 6-fluoropyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is methylene and E is 6-trifluoromethylpyrid-3-yl







In a further prominent group of compounds of the formula (I-d), R2 and R3 are each hydrogen, B is methylene and E is 2-chloro-1,3-thiazol-5-yl







In a further prominent group of compounds of the formula (I-d), R5 is ethyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-d), R5 is cyclopropyl, R2 and R3 are each hydrogen and B is oxygen.


In a further prominent group of compounds of the formula (I-d), R5 is ethyl, R2 and R3 are each hydrogen and B is methylene.


In a further prominent group of compounds of the formula (I-d), R5 is cyclopropyl, R2 and R3 are each hydrogen and B is methylene.


The following compounds of the general formula (I) are specified hereinafter, each of which is outstandingly suitable for the inventive uses and compositions:


Compound (I-1), 4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115644.


Compound (I-2), 4-{([(6-bromopyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115644.


Compound (I-3), 4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115644.


Compound (I-4), 4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115644


Compound (I-5), 3-chloro-4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115644.


Compound (I-6), 4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115644.


Compound (I-7), 4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115644.


Compound (I-8), 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115643.


Compound (I-9), 4-{[(5,6-dichloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115643


Compound (I-10), 4-{[(5,6-dichloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115643


Compound (I-11), 4-{[(6-bromo-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115643


Compound (I-12), 4-{[(6-bromo-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115643


Compound (I-13), 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115643.


Compound (I-14), 4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino }furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115646.


Compound (I-15), 4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115646.


Compound (I-16), 4-{[(6-bromo-5-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}-furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115646.


Compound (I-17), 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one, has the formula






and is known from International patent application WO 2007/115646.


Compound (I-18), 3-{[(6-chloropyrid-3-yl)methyl](methyl)amino}cyclopent-2-en-1-one, has the formula






and is known from EP 0 539 588.


Compound (I-19), 3-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}cyclopent-2-en-1-one, has the formula






and is known from EP 0 539 588.


Compound (I-20), 4-{[(2-chloro-2,3-dihydro-1,3-thiazol-5-yl)methyl](methyl)amino}furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-21), 4-[methyl(pyrid-3-ylmethyl)amino]furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-22), 4-{cyclopropyl[(6-fluoropyrid-3-yl)methyl]amino}furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-23), 4-(methyl {[6-(trifluoromethyl)pyrid-3-yl]methyl}amino)furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-24), 4-(cyclopropyl {[6-(trifluoromethyl)pyrid-3-yl]methyl}amino)furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-25), 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}-5-methylfuran-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-26), 4-{[(6-bromopyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-27), 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}thiophen-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-28), 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}-3-fluorofuran-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-29), 4-{[(6-chloropyrid-3-yl)methyl](methoxy)amino}furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-30), 4-{[(6-chloropyrid-3-yl)methyl](ethyl)amino}furan-2(5H)-one, has formula






and is known from EP 0 539 588.


Compound (I-31), 4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-32), 4-{allyl[(6-chloropyrid-3-yl)methyl]amino}furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-33), 4-{[(6-chloropyrid-3-yl)methyl](prop-2-yn-1-yl)amino}furan-2(5H)-one, has the formula






and is known from EP 0 539 588.


Compound (I-34), 3-{[(6-chloropyrid-3-yl)methyl](propyl)amino}cyclohex-2-en-1-one, has the formula






and is known from EP 0 539 588.


Compound (I-35), 3-{allyl[(6-chloropyrid-3-yl)methyl]amino}cyclohex-2-en-1-one, has the formula






and is known from EP 0 539 588.


Compound (I-36), 3-{[(6-chloropyrid-3-yl)methyl](prop-2-yn-1-yl)amino}cyclohex-2-en-1-one, has the formula






and is known from EP 0 539 588.


Compound (I-37), 3-{[(6-chloropyrid-3-yl)methyl]amino}cyclohex-2-en-1-one, has the formula






and is known from EP 0 539 588.


Compound (I-38), 3-{[(6-chloropyrid-3-yl)methyl](methyl)amino}cyclohex-2-en-1-one, has the formula






and is known from EP 0 539 588.


Compound (I-39), 3-{[(6-chloropyrid-3-yl)methyl](ethyl)amino}cyclohex-2-en-1-one, has the formula






and is known from EP 0 539 588.


Halogen-substituted radicals, e.g. haloalkyl, are mono- or polyhalogenated up to the maximum possible number of substituents. In the case of polyhalogenation, the halogen atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine.


Preference, particular preference or very particular preference is given to compounds which in each case bear the substituents specified under preferred, particularly preferred or very particularly preferred.


Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl may, also in conjunction with heteroatoms, for example in alkoxy, where possible, each be straight-chain or branched.


Optionally substituted radicals may be mono- or polysubstituted, where the substituents may be the same or different in the case of polysubstitutions.


The radical definitions and illustrations listed above in general terms or listed in preferred ranges can, however, also be combined with one another as desired, i.e. between the particular ranges and preferred ranges.


The active ingredients can be used in the inventive compositions within a wide concentration range. The concentration of the active ingredients in the formulation is typically 0.1-50% by weight.


In the literature, it has already been stated that the action of different active ingredients can be enhanced by adding ammonium or phosphonium salts. However, these are salts which act as a detergent (e.g. WO 95/017817) or salts with relatively long alkyl and/or aryl substituents which have permeabilizing action or increase the solubility of the active ingredient (for example


EP-A 0 453 086, EP-A 0 664 081, FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No. 5,462,912, U.S. Pat. No. 5,538,937, U.S. Pat. No. 03/0,224,939, U.S. Pat. No. 05/0,009,880, U.S. Pat. No. 05/0,096,386). In addition, the prior art describes the effect only for particular active ingredients and/or particular uses of the corresponding compositions. In other cases again, the salts are those of sulphonic acids in which the acids themselves have paralysing action on insects (U.S. Pat. No. 2,842,476). An enhancement of action by ammonium sulphate has been described for the herbicides glyphosate and phosphinothricin (U.S. Pat. No. 6,645,914, EP-A 0 036 106). A corresponding effect in the case of the inventive insecticides is neither disclosed nor suggested by this prior art.


The use of ammonium sulphate as a formulating assistant has also been described for particular active ingredients and uses (WO 92/16108), but it serves there to stabilize the formulation, not to enhance the action.


It has now been found that, completely surprisingly, the action of insecticidal enaminocarbonyl compounds can be enhanced significantly through the addition of ammonium and/or phosphonium salts to the use solution (tankmix application) or through the incorporation of these salts into a formulation comprising such insecticides. The present invention thus provides for the use of ammonium and/or phosphonium salts for enhancing the action of crop protection compositions which comprise insecticidally active enaminocarbonyl compounds. The invention likewise provides compositions which comprise such insecticides and action-enhancing ammonium and/or phosphonium salts, specifically both formulated active ingredients and ready-to-use compositions (spray liquors). The invention finally further provides for the use of these compositions for controlling harmful insects.


Ammonium and phosphonium salts which, in accordance with the invention, enhance the action of crop protection compositions comprising enaminocarbonyl compounds are defined by formula (II)







in which

    • G is nitrogen or phosphorus,
    • G is preferably nitrogen,
    • R6, R7, R8 and R9 are each independently hydrogen or in each case optionally substituted C1-C8-alkyl or mono- or polyunsaturated, optionally substituted C2-C8-alkylene, where the substituents may be selected from halogen, nitro and cyano,
    • R6, R7, R8 and R9 are preferably each independently hydrogen or in each case optionally substituted C1-C4-alkyl, where the substituents may be selected from halogen, nitro and cyano,
    • R6, R7, R8 and R9 are more preferably each independently hydrogen methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl,
    • R6, R7, R8 and R9 are most preferably each hydrogen,
    • R6, R7, R8 and R9 are additionally most preferably simultaneously methyl or simultaneously ethyl,
    • n is 1, 2, 3 or 4,
    • n is preferably 1 or 2,
    • R10 is an inorganic or organic anion,
    • R10 is preferably hydrogencarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate, oxalate, carbonate, pentaborate, sulphite, benzoate, hydrogenoxalate, hydrogencitrate, methylsulphate or tetrafluoroborate,
    • R10 is more preferably lactate, sulphate, nitrate, thiosulphate, thiocyanate, citrate, oxalate, formate, monohydrogenphosphate or dihydrogenphosphate, and
    • R10 is most preferably sulphate.


The ammonium and phosphonium salts of the formula (II) can be used within a wide concentration range to enhance the action of crop protection compositions comprising enaminocarbonyl compounds. In general, the ammonium or phosphonium salts are used in a ready-to-use crop protection composition in a concentration of 0.5 to 80 mmol/1, preferably 0.75 to 37.5 mmol/1, more preferably 1.5 to 25 mmol/1. In the case of a formulated product, the ammonium and/or phosphonium salt concentration in the formulation is selected such that, after dilution of the formulation to the desired active ingredient concentration, it is within these stated general, preferred or particularly preferred ranges. The concentration of the salt in the formulation is typically 1-50% by weight.


In a preferred embodiment of the invention, not only an ammonium and/or phosphonium salt but additionally a penetrant is added to the crop protection compositions to enhance the action. It can be described as completely surprising that, even in these cases, an even greater enhancement of action is observed. The present invention thus likewise provides for the use of a combination of penetrant and ammonium and/or phosphonium salts for enhancing the action of crop protection compositions which comprise insecticidally active enaminocarbonyl compounds as an active ingredient. The invention likewise provides compositions which comprise insecticidally active enaminocarbonyl compounds, penetrants and ammonium and/or phosphonium salts, both in the form of formulated active ingredients and of ready-to-use compositions (spray liquors). The invention finally further provides for the use of these compositions for controlling harmful insects.


Useful penetrants in the present context include all of those substances which are typically used in order to improve the penetration of active agrochemical ingredients into plants. In this connection, penetrants are defined such that they penetrate from the aqueous spray liquor and/or from the sprayed coating into the cuticle of the plant and thus increase the mobility of active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.


Useful penetrants include, for example, alkanol alkoxylates. Inventive penetrants are alkanol alkoxylates of the formula





R—O—(-AO)v—R′  (III)


in which

    • R is straight-chain or branched alkyl having from 4 to 20 carbon atoms,
    • R′ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,
    • AO is an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical, or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals, and
    • v is 2 to 30.


A preferred group of penetrants is that of alkanol alkoxylates of the formula





R—O—(-EO—)m—R′  (III-a)


in which

    • R is as defined above,
    • R′ is as defined above,
    • EO is —CH2—CH2—O— and
    • m is 2 to 20.


A further preferred group of penetrants is that of alkanol alkoxylates of the formula





R—O—(-EO—)p—(—PO—)q—R′  (III-b)


in which

    • R is as defined above,
    • R′ is as defined above,
    • EO is —CH2—CH2—O—,
    • PO is









    • p is 1 to 10 and

    • q is 1 to 10.





A further preferred group of penetrants is that of alkanol alkoxylates of the formula





R—O—(—PO—)r—(EO—)s—R′  (III-c)


in which

    • R is as defined above,
    • R′ is as defined above,
    • EO is —CH2—CH2—O—,
    • PO is









    • r is 1 to 10 and

    • s is 1 to 10.





A further preferred group of penetrants is that of alkanol alkoxylates of the formula





R—O—(-EO—)v—(—BO—)x—R′  (III-d)


in which

    • R and R′ are each as defined above,
    • EO is CH2—CH2—O—,
    • BO is









    • v is 1 to 10 and

    • x is 1 to 10.





A further preferred group of penetrants is that of alkanol alkoxylates of the formula





R—O—(—BO—)y—(-EO—)z—R′  (III-e)


in which

    • R and R′ are each as defined above,
    • BO is









    • EO is CH2—CH2—O—,

    • y is 1 to 10 and

    • z is 1 to 10.





A further preferred group of penetrants is that of alkanol alkoxylates of the formula





CH3—(CH2)t—CH2—O—(—CH2—CH2—O—)u—R′  (III-f)


in which

    • R′ is as defined above,
    • t is 8 to 13,
    • u is 6 to 17.


In the above-specified formulae,


R is preferably butyl, i-butyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethylhexyl, nonyl, i-nonyl, decyl, n-dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl, trimethylnonyl, palmityl, stearyl or eicosyl.


One example of an alkanol alkoxylate of the formula (III-c) is 2-ethylhexyl alkoxylate of the formula







in which

    • EO is —CH2—CH2—O—,







and


the numbers 8 and 6 are average values.


One example of an alkanol alkoxylate of the formula (III-d) is the formula





CH3—(CH2)10—O—(-EO—)6—BO—)2—CH3   (III-d-1)


in which

    • EO is CH2—CH2—O—,







and


the numbers 10, 6 and 2 are average values.


Particularly preferred alkanol alkoxylates of the formula (III-f) are compounds of this formula in which

    • t is 9 to 12 and
    • u is 7 to 9.


Very particular preference is given to alkanol alkoxylate of the formula (III-f-1)





CH3—(CH2)t—CH2—O—(—CH2—CH2—O—)u—H   (III-f-1)


in which

    • t is the average value of 10.5 and
    • u is the average value of 8.4.


The alkanol alkoxylates are defined in general by the above formulae. These substances are mixtures of substances of the type specified with different chain lengths. For the indices, average values which may also deviate from integer values are therefore calculated.


The alkanol alkoxylates of the formulae specified are known, and some of them are commercially available or can be prepared by known methods (cf. WO 98-35 553, WO 00-35 278 and EP-A 0 681 865).


Useful penetrants are, for example, also substances which promote the solubility of the compounds of the formula (I) in the spray covering. These include, for example, mineral or vegetable oils. Useful oils include all mineral or vegetable oils, optionally modified, which are typically useable in agrochemical compositions. Examples include sunflower oil, rapeseed oil, olive oil, castor oil, colza oil, maize kernel oil, cottonseed oil, and soybean oil, or the esters of the oils mentioned. Preference is given to rapeseed oil, sunflower oil, and their methyl or ethyl esters. Particular preference is given to rapeseed oil methyl ester.


The concentration of penetrants in the inventive compositions can vary within a wide range. In the case of a formulated crop protection composition, it is generally 1 to 95% by weight, preferably 1 to 55% by weight, more preferably 15-40% by weight. In the ready-to-use compositions (spray liquors), the concentration is generally between 0.1 and 10 g/l, preferably between 0.5 and 5 g/l.


Combinations of active ingredient, salt and penetrant which are prominent in accordance with the invention are listed in the table which follows, each individual combination being prominent on its own. “According to test” means that any compound which acts as a penetrant in the test for cuticle penetration is suitable (Baur et al., 1997, Pesticide Science 51, 131-152).















Number
Active ingredient
Salt
Penetrant


















1
(I-1)
Ammonium sulphate
According to test


2
(I-1)
Ammonium lactate
According to test


3
(I-1)
Ammonium nitrate
According to test


4
(I-1)
Ammonium thiosulphate
According to test


5
(I-1)
Ammonium thiocyanate
According to test


6
(I-1)
Ammonium citrate
According to test


7
(I-1)
Ammonium oxalate
According to test


8
(I-1)
Ammonium formate
According to test


9
(I-1)
Ammonium hydrogenphosphate
According to test


10
(I-1)
Ammonium dihydrogenphosphate
According to test


11
(I-1)
Ammonium carbonate
According to test


12
(I-1)
Ammonium sulphite
According to test


13
(I-1)
Ammonium benzoate
According to test


14
(I-1)
Ammonium hydrogenoxalate
According to test


15
(I-1)
Ammonium hydrogencitrate
According to test


16
(I-1)
Ammonium acetate
According to test


17
(I-1)
Tetramethylammonium sulphate
According to test


18
(I-1)
Tetramethylammonium lactate
According to test


19
(I-1)
Tetramethylammonium nitrate
According to test


20
(I-1)
Tetramethylammonium thiosulphate
According to test


21
(I-1)
Tetramethylammonium thiocyanate
According to test


22
(I-1)
Tetramethylammonium citrate
According to test


23
(I-1)
Tetramethylammonium oxalate
According to test


24
(I-1)
Tetramethylammonium formate
According to test


25
(I-1)
Tetramethylammonium hydrogenphosphate
According to test


26
(I-1)
Tetramethylammonium dihydrogenphosphate
According to test


27
(I-1)
Tetraethylammonium sulphate
According to test


28
(I-1)
Tetraethylammonium lactate
According to test


29
(I-1)
Tetraethylammonium nitrate
According to test


30
(I-1)
Tetraethylammonium thiosulphate
According to test


31
(I-1)
Tetraethylammonium thiocyanate
According to test


32
(I-1)
Tetraethylammonium citrate
According to test


33
(I-1)
Tetraethylammonium oxalate
According to test


34
(I-1)
Tetraethylammonium formate
According to test


35
(I-1)
Tetraethylammonium hydrogenphosphate
According to test


36
(I-1)
Tetraethylammonium dihydrogenphosphate
According to test


37
(I-2)
Ammonium sulphate
According to test


38
(I-2)
Ammonium lactate
According to test


39
(I-2)
Ammonium nitrate
According to test


40
(I-2)
Ammonium thiosulphate
According to test


41
(I-2)
Ammonium thiocyanate
According to test


42
(I-2)
Ammonium citrate
According to test


43
(I-2)
Ammonium oxalate
According to test


44
(I-2)
Ammonium formate
According to test


45
(I-2)
Ammonium hydrogenphosphate
According to test


46
(I-2)
Ammonium dihydrogenphosphate
According to test


47
(I-2)
Ammonium carbonate
According to test


48
(I-2)
Ammonium sulphite
According to test


49
(I-2)
Ammonium benzoate
According to test


50
(I-2)
Ammonium hydrogenoxalate
According to test


51
(I-2)
Ammonium hydrogencitrate
According to test


52
(I-2)
Ammonium acetate
According to test


53
(I-2)
Tetramethylammonium sulphate
According to test


54
(I-2)
Tetramethylammonium lactate
According to test


55
(I-2)
Tetramethylammonium nitrate
According to test


56
(I-2)
Tetramethylammonium thiosulphate
According to test


57
(I-2)
Tetramethylammonium thiocyanate
According to test


58
(I-2)
Tetramethylammonium citrate
According to test


59
(I-2)
Tetramethylammonium oxalate
According to test


60
(I-2)
Tetramethylammonium formate
According to test


61
(I-2)
Tetramethylammonium hydrogenphosphate
According to test


62
(I-2)
Tetramethylammonium dihydrogenphosphate
According to test


63
(I-2)
TetraethylAmmonium sulphate
According to test


64
(I-2)
Tetraethylammonium lactate
According to test


65
(I-2)
Tetraethylammonium nitrate
According to test


66
(I-2)
Tetraethylammonium thiosulphate
According to test


67
(I-2)
Tetraethylammonium thiocyanate
According to test


68
(I-2)
Tetraethylammonium citrate
According to test


69
(I-2)
Tetraethylammonium oxalate
According to test


70
(I-2)
Tetraethylammonium formate
According to test


71
(I-2)
Tetraethylammonium hydrogenphosphate
According to test


72
(I-2)
Tetraethylammonium dihydrogenphosphate
According to test


73
(I-3)
Ammonium sulphate
According to test


74
(I-3)
Ammonium lactate
According to test


75
(I-3)
Ammonium nitrate
According to test


76
(I-3)
Ammonium thiosulphate
According to test


77
(I-3)
Ammonium thiocyanate
According to test


78
(I-3)
Ammonium citrate
According to test


79
(I-3)
Ammonium oxalate
According to test


80
(I-3)
Ammonium formate
According to test


81
(I-3)
Ammonium hydrogenphosphate
According to test


82
(I-3)
Ammonium dihydrogenphosphate
According to test


83
(I-3)
Ammonium carbonate
According to test


84
(I-3)
Ammonium sulphite
According to test


85
(I-3)
Ammonium benzoate
According to test


86
(I-3)
Ammonium hydrogenoxalate
According to test


87
(I-3)
Ammonium hydrogencitrate
According to test


88
(I-3)
Ammonium acetate
According to test


89
(I-3)
Tetramethylammonium sulphate
According to test


90
(I-3)
Tetramethylammonium lactate
According to test


91
(I-3)
Tetramethylammonium nitrate
According to test


92
(I-3)
Tetramethylammonium thiosulphate
According to test


93
(I-3)
Tetramethylammonium thiocyanate
According to test


94
(I-3)
Tetramethylammonium citrate
According to test


95
(I-3)
Tetramethylammonium oxalate
According to test


96
(I-3)
Tetramethylammonium formate
According to test


97
(I-3)
Tetramethylammonium hydrogenphosphate
According to test


98
(I-3)
Tetramethylammonium dihydrogenphosphate
According to test


99
(I-3)
Tetraethylammonium sulphate
According to test


100
(I-3)
Tetraethylammonium lactate
According to test


101
(I-3)
Tetraethylammonium nitrate
According to test


102
(I-3)
Tetraethylammonium thiosulphate
According to test


103
(I-3)
Tetraethylammonium thiocyanate
According to test


104
(I-3)
Tetraethylammonium citrate
According to test


105
(I-3)
Tetraethylammonium oxalate
According to test


106
(I-3)
Tetraethylammonium formate
According to test


107
(I-3)
Tetraethylammonium hydrogenphosphate
According to test


108
(I-3)
Tetraethylammonium dihydrogenphosphate
According to test


109
(I-4)
Ammonium sulphate
According to test


110
(I-4)
Ammonium lactate
According to test


111
(I-4)
Ammonium nitrate
According to test


112
(I-4)
Ammonium thiosulphate
According to test


113
(I-4)
Ammonium thiocyanate
According to test


114
(I-4)
Ammonium citrate
According to test


115
(I-4)
Ammonium oxalate
According to test


116
(I-4)
Ammonium formate
According to test


117
(I-4)
Ammonium hydrogenphosphate
According to test


118
(I-4)
Ammonium dihydrogenphosphate
According to test


119
(I-4)
Ammonium carbonate
According to test


120
(I-4)
Ammonium sulphite
According to test


121
(I-4)
Ammonium benzoate
According to test


122
(I-4)
Ammonium hydrogenoxalate
According to test


123
(I-4)
Ammonium hydrogencitrate
According to test


124
(I-4)
Ammonium acetate
According to test


125
(I-4)
Tetramethylammonium sulphate
According to test


126
(I-4)
Tetramethylammonium lactate
According to test


127
(I-4)
Tetramethylammonium nitrate
According to test


128
(I-4)
Tetramethylammonium thiosulphate
According to test


129
(I-4)
Tetramethylammonium thiocyanate
According to test


130
(I-4)
Tetramethylammonium citrate
According to test


131
(I-4)
Tetramethylammonium oxalate
According to test


132
(I-4)
Tetramethylammonium formate
According to test


133
(I-4)
Tetramethylammonium hydrogenphosphate
According to test


134
(I-4)
Tetramethylammonium dihydrogenphosphate
According to test


135
(I-4)
Tetraethylammonium sulphate
According to test


136
(I-4)
Tetraethylammonium lactate
According to test


137
(I-4)
Tetraethylammonium nitrate
According to test


138
(I-4)
Tetraethylammonium thiosulphate
According to test


139
(I-4)
Tetraethylammonium thiocyanate
According to test


140
(I-4)
Tetraethylammonium citrate
According to test


141
(I-4)
Tetraethylammonium oxalate
According to test


142
(I-4)
Tetraethylammonium formate
According to test


143
(I-4)
Tetraethylammonium hydrogenphosphate
According to test


144
(I-4)
Tetraethylammonium dihydrogenphosphate
According to test


145
(I-5)
Ammonium sulphate
According to test


146
(I-5)
Ammonium lactate
According to test


147
(I-5)
Ammonium nitrate
According to test


148
(I-5)
Ammonium thiosulphate
According to test


149
(I-5)
Ammonium thiocyanate
According to test


150
(I-5)
Ammonium citrate
According to test


151
(I-5)
Ammonium oxalate
According to test


152
(I-5)
Ammonium formate
According to test


153
(I-5)
Ammonium hydrogenphosphate
According to test


154
(I-5)
Ammonium dihydrogenphosphate
According to test


155
(I-5)
Ammonium carbonate
According to test


156
(I-5)
Ammonium sulphite
According to test


157
(I-5)
Ammonium benzoate
According to test


158
(I-5)
Ammonium hydrogenoxalate
According to test


159
(I-5)
Ammonium hydrogencitrate
According to test


160
(I-5)
Ammonium acetate
According to test


161
(I-5)
Tetramethylammonium sulphate
According to test


162
(I-5)
Tetramethylammonium lactate
According to test


163
(I-5)
Tetramethylammonium nitrate
According to test


164
(I-5)
Tetramethylammonium thiosulphate
According to test


165
(I-5)
Tetramethylammonium thiocyanate
According to test


166
(I-5)
Tetramethylammonium citrate
According to test


167
(I-5)
Tetramethylammonium oxalate
According to test


168
(I-5)
Tetramethylammonium formate
According to test


169
(I-5)
Tetramethylammonium hydrogenphosphate
According to test


170
(I-5)
Tetramethylammonium dihydrogenphosphate
According to test


171
(I-5)
Tetraethylammonium sulphate
According to test


172
(I-5)
Tetraethylammonium lactate
According to test


173
(I-5)
Tetraethylammonium nitrate
According to test


174
(I-5)
Tetraethylammonium thiosulphate
According to test


175
(I-5)
Tetraethylammonium thiocyanate
According to test


176
(I-5)
Tetraethylammonium citrate
According to test


177
(I-5)
Tetraethylammonium oxalate
According to test


178
(I-5)
Tetraethylammonium formate
According to test


179
(I-5)
Tetraethylammonium hydrogenphosphate
According to test


180
(I-5)
Tetraethylammonium dihydrogenphosphate
According to test


181
(I-6)
Ammonium sulphate
According to test


182
(I-6)
Ammonium lactate
According to test


183
(I-6)
Ammonium nitrate
According to test


184
(I-6)
Ammonium thiosulphate
According to test


185
(I-6)
Ammonium thiocyanate
According to test


186
(I-6)
Ammonium citrate
According to test


187
(I-6)
Ammonium oxalate
According to test


188
(I-6)
Ammonium formate
According to test


189
(I-6)
Ammonium hydrogenphosphate
According to test


190
(I-6)
Ammonium dihydrogenphosphate
According to test


191
(I-6)
Ammonium carbonate
According to test


192
(I-6)
Ammonium sulphite
According to test


193
(I-6)
Ammonium benzoate
According to test


194
(I-6)
Ammonium hydrogenoxalate
According to test


195
(I-6)
Ammonium hydrogencitrate
According to test


196
(I-6)
Ammonium acetate
According to test


197
(I-6)
Tetramethylammonium sulphate
According to test


198
(I-6)
Tetramethylammonium lactate
According to test


199
(I-6)
Tetramethylammonium nitrate
According to test


200
(I-6)
Tetramethylammonium thiosulphate
According to test


201
(I-6)
Tetramethylammonium thiocyanate
According to test


202
(I-6)
Tetramethylammonium citrate
According to test


203
(I-6)
Tetramethylammonium oxalate
According to test


204
(I-6)
Tetramethylammonium formate
According to test


205
(I-6)
Tetramethylammonium hydrogenphosphate
According to test


206
(I-6)
Tetramethylammonium dihydrogenphosphate
According to test


207
(I-6)
Tetraethylammonium sulphate
According to test


208
(I-6)
Tetraethylammonium lactate
According to test


209
(I-6)
Tetraethylammonium nitrate
According to test


210
(I-6)
Tetraethylammonium thiosulphate
According to test


211
(I-6)
Tetraethylammonium thiocyanate
According to test


212
(I-6)
Tetraethylammonium citrate
According to test


213
(I-6)
Tetraethylammonium oxalate
According to test


214
(I-6)
Tetraethylammonium formate
According to test


215
(I-6)
Tetraethylammonium hydrogenphosphate
According to test


216
(I-6)
Tetraethylammonium dihydrogenphosphate
According to test


217
(I-7)
Ammonium sulphate
According to test


218
(I-7)
Ammonium lactate
According to test


219
(I-7)
Ammonium nitrate
According to test


220
(I-7)
Ammonium thiosulphate
According to test


221
(I-7)
Ammonium thiocyanate
According to test


222
(I-7)
Ammonium citrate
According to test


223
(I-7)
Ammonium oxalate
According to test


224
(I-7)
Ammonium formate
According to test


225
(I-7)
Ammonium hydrogenphosphate
According to test


226
(I-7)
Ammonium dihydrogenphosphate
According to test


227
(I-7)
Ammonium carbonate
According to test


228
(I-7)
Ammonium sulphite
According to test


229
(I-7)
Ammonium benzoate
According to test


230
(I-7)
Ammonium hydrogenoxalate
According to test


231
(I-7)
Ammonium hydrogencitrate
According to test


232
(I-7)
Ammonium acetate
According to test


233
(I-7)
Tetramethylammonium sulphate
According to test


234
(I-7)
Tetramethylammonium lactate
According to test


235
(I-7)
Tetramethylammonium nitrate
According to test


236
(I-7)
Tetramethylammonium thiosulphate
According to test


237
(I-7)
Tetramethylammonium thiocyanate
According to test


238
(I-7)
Tetramethylammonium citrate
According to test


239
(I-7)
Tetramethylammonium oxalate
According to test


240
(I-7)
Tetramethylammonium formate
According to test


241
(I-7)
Tetramethylammonium hydrogenphosphate
According to test


242
(I-7)
Tetramethylammonium dihydrogenphosphate
According to test


243
(I-7)
Tetraethylammonium sulphate
According to test


244
(I-7)
Tetraethylammonium lactate
According to test


245
(I-7)
Tetraethylammonium nitrate
According to test


246
(I-7)
Tetraethylammonium thiosulphate
According to test


247
(I-7)
Tetraethylammonium thiocyanate
According to test


248
(I-7)
Tetraethylammonium citrate
According to test


249
(I-7)
Tetraethylammonium oxalate
According to test


250
(I-7)
Tetraethylammonium formate
According to test


251
(I-7)
Tetraethylammonium hydrogenphosphate
According to test


252
(I-7)
Tetraethylammonium dihydrogenphosphate
According to test


253
(I-8)
Ammonium sulphate
According to test


254
(I-8)
Ammonium lactate
According to test


255
(I-8)
Ammonium nitrate
According to test


256
(I-8)
Ammonium thiosulphate
According to test


257
(I-8)
Ammonium thiocyanate
According to test


258
(I-8)
Ammonium citrate
According to test


259
(I-8)
Ammonium oxalate
According to test


260
(I-8)
Ammonium formate
According to test


261
(I-8)
Ammonium hydrogenphosphate
According to test


262
(I-8)
Ammonium dihydrogenphosphate
According to test


263
(I-8)
Ammonium carbonate
According to test


264
(I-8)
Ammonium sulphite
According to test


265
(I-8)
Ammonium benzoate
According to test


266
(I-8)
Ammonium hydrogenoxalate
According to test


267
(I-8)
Ammonium hydrogencitrate
According to test


268
(I-8)
Ammonium acetate
According to test


269
(I-8)
Tetramethylammonium sulphate
According to test


270
(I-8)
Tetramethylammonium lactate
According to test


271
(I-8)
Tetramethylammonium nitrate
According to test


272
(I-8)
Tetramethylammonium thiosulphate
According to test


273
(I-8)
Tetramethylammonium thiocyanate
According to test


274
(I-8)
Tetramethylammonium citrate
According to test


275
(I-8)
Tetramethylammonium oxalate
According to test


276
(I-8)
Tetramethylammonium formate
According to test


277
(I-8)
Tetramethylammonium hydrogenphosphate
According to test


278
(I-8)
Tetramethylammonium dihydrogenphosphate
According to test


279
(I-8)
Tetraethylammonium sulphate
According to test


280
(I-8)
Tetraethylammonium lactate
According to test


281
(I-8)
Tetraethylammonium nitrate
According to test


282
(I-8)
Tetraethylammonium thiosulphate
According to test


283
(I-8)
Tetraethylammonium thiocyanate
According to test


284
(I-8)
Tetraethylammonium citrate
According to test


285
(I-8)
Tetraethylammonium oxalate
According to test


286
(I-8)
Tetraethylammonium formate
According to test


287
(I-8)
Tetraethylammonium hydrogenphosphate
According to test


288
(I-8)
Tetraethylammonium dihydrogenphosphate
According to test


289
(I-9)
Ammonium sulphate
According to test


290
(I-9)
Ammonium lactate
According to test


291
(I-9)
Ammonium nitrate
According to test


292
(I-9)
Ammonium thiosulphate
According to test


293
(I-9)
Ammonium thiocyanate
According to test


294
(I-9)
Ammonium citrate
According to test


295
(I-9)
Ammonium oxalate
According to test


296
(I-9)
Ammonium formate
According to test


297
(I-9)
Ammonium hydrogenphosphate
According to test


298
(I-9)
Ammonium dihydrogenphosphate
According to test


299
(I-9)
Ammonium carbonate
According to test


300
(I-9)
Ammonium sulphite
According to test


301
(I-9)
Ammonium benzoate
According to test


302
(I-9)
Ammonium hydrogenoxalate
According to test


303
(I-9)
Ammonium hydrogencitrate
According to test


304
(I-9)
Ammonium acetate
According to test


305
(I-9)
Tetramethylammonium sulphate
According to test


306
(I-9)
Tetramethylammonium lactate
According to test


307
(I-9)
Tetramethylammonium nitrate
According to test


308
(I-9)
Tetramethylammonium thiosulphate
According to test


309
(I-9)
Tetramethylammonium thiocyanate
According to test


310
(I-9)
Tetramethylammonium citrate
According to test


311
(I-9)
Tetramethylammonium oxalate
According to test


312
(I-9)
Tetramethylammonium formate
According to test


313
(I-9)
Tetramethylammonium hydrogenphosphate
According to test


314
(I-9)
Tetramethylammonium dihydrogenphosphate
According to test


315
(I-9)
Tetraethylammonium sulphate
According to test


316
(I-9)
Tetraethylammonium lactate
According to test


317
(I-9)
Tetraethylammonium nitrate
According to test


318
(I-9)
Tetraethylammonium thiosulphate
According to test


319
(I-9)
Tetraethylammonium thiocyanate
According to test


320
(I-9)
Tetraethylammonium citrate
According to test


321
(I-9)
Tetraethylammonium oxalate
According to test


322
(I-9)
Tetraethylammonium formate
According to test


323
(I-9)
Tetraethylammonium hydrogenphosphate
According to test


324
(I-9)
Tetraethylammonium dihydrogenphosphate
According to test


325
(I-10)
Ammonium sulphate
According to test


326
(I-10)
Ammonium lactate
According to test


327
(I-10)
Ammonium nitrate
According to test


328
(I-10)
Ammonium thiosulphate
According to test


329
(I-10)
Ammonium thiocyanate
According to test


330
(I-10)
Ammonium citrate
According to test


331
(I-10)
Ammonium oxalate
According to test


332
(I-10)
Ammonium formate
According to test


333
(I-10)
Ammonium hydrogenphosphate
According to test


334
(I-10)
Ammonium dihydrogenphosphate
According to test


335
(I-10)
Ammonium carbonate
According to test


336
(I-10)
Ammonium sulphite
According to test


337
(I-10)
Ammonium benzoate
According to test


338
(I-10)
Ammonium hydrogenoxalate
According to test


339
(I-10)
Ammonium hydrogencitrate
According to test


340
(I-10)
Ammonium acetate
According to test


341
(I-10)
Tetramethylammonium sulphate
According to test


342
(I-10)
Tetramethylammonium lactate
According to test


343
(I-10)
Tetramethylammonium nitrate
According to test


344
(I-10)
Tetramethylammonium thiosulphate
According to test


345
(I-10)
Tetramethylammonium thiocyanate
According to test


346
(I-10)
Tetramethylammonium citrate
According to test


347
(I-10)
Tetramethylammonium oxalate
According to test


348
(I-10)
Tetramethylammonium formate
According to test


349
(I-10)
Tetramethylammonium hydrogenphosphate
According to test


350
(I-10)
Tetramethylammonium dihydrogenphosphate
According to test


351
(I-10)
Tetraethylammonium sulphate
According to test


352
(I-10)
Tetraethylammonium lactate
According to test


353
(I-10)
Tetraethylammonium nitrate
According to test


354
(I-10)
Tetraethylammonium thiosulphate
According to test


355
(I-10)
Tetraethylammonium thiocyanate
According to test


356
(I-10)
Tetraethylammonium citrate
According to test


357
(I-10)
Tetraethylammonium oxalate
According to test


358
(I-10)
Tetraethylammonium formate
According to test


359
(I-10)
Tetraethylammonium hydrogenphosphate
According to test


360
(I-10)
Tetraethylammonium dihydrogenphosphate
According to test


361
(I-11)
Ammonium sulphate
According to test


362
(I-11)
Ammonium lactate
According to test


363
(I-11)
Ammonium nitrate
According to test


364
(I-11)
Ammonium thiosulphate
According to test


365
(I-11)
Ammonium thiocyanate
According to test


366
(I-11)
Ammonium citrate
According to test


367
(I-11)
Ammonium oxalate
According to test


368
(I-11)
Ammonium formate
According to test


369
(I-11)
Ammonium hydrogenphosphate
According to test


370
(I-11)
Ammonium dihydrogenphosphate
According to test


371
(I-11)
Ammonium carbonate
According to test


372
(I-11)
Ammonium sulphite
According to test


373
(I-11)
Ammonium benzoate
According to test


374
(I-11)
Ammonium hydrogenoxalate
According to test


375
(I-11)
Ammonium hydrogencitrate
According to test


376
(I-11)
Ammonium acetate
According to test


377
(I-11)
Tetramethylammonium sulphate
According to test


378
(I-11)
Tetramethylammonium lactate
According to test


379
(I-11)
Tetramethylammonium nitrate
According to test


380
(I-11)
Tetramethylammonium thiosulphate
According to test


381
(I-11)
Tetramethylammonium thiocyanate
According to test


382
(I-11)
Tetramethylammonium citrate
According to test


383
(I-11)
Tetramethylammonium oxalate
According to test


384
(I-11)
Tetramethylammonium formate
According to test


385
(I-11)
Tetramethylammonium hydrogenphosphate
According to test


386
(I-11)
Tetramethylammonium dihydrogenphosphate
According to test


387
(I-11)
Tetraethylammonium sulphate
According to test


388
(I-11)
Tetraethylammonium lactate
According to test


389
(I-11)
Tetraethylammonium nitrate
According to test


390
(I-11)
Tetraethylammonium thiosulphate
According to test


391
(I-11)
Tetraethylammonium thiocyanate
According to test


392
(I-11)
Tetraethylammonium citrate
According to test


393
(I-11)
Tetraethylammonium oxalate
According to test


394
(I-11)
Tetraethylammonium formate
According to test


395
(I-11)
Tetraethylammonium hydrogenphosphate
According to test


396
(I-11)
Tetraethylammonium dihydrogenphosphate
According to test


397
(I-12)
Ammonium sulphate
According to test


398
(I-12)
Ammonium lactate
According to test


399
(I-12)
Ammonium nitrate
According to test


400
(I-12)
Ammonium thiosulphate
According to test


401
(I-12)
Ammonium thiocyanate
According to test


402
(I-12)
Ammonium citrate
According to test


403
(I-12)
Ammonium oxalate
According to test


404
(I-12)
Ammonium formate
According to test


405
(I-12)
Ammonium hydrogenphosphate
According to test


406
(I-12)
Ammonium dihydrogenphosphate
According to test


407
(I-12)
Ammonium carbonate
According to test


408
(I-12)
Ammonium sulphite
According to test


409
(I-12)
Ammonium benzoate
According to test


410
(I-12)
Ammonium hydrogenoxalate
According to test


411
(I-12)
Ammonium hydrogencitrate
According to test


412
(I-12)
Ammonium acetate
According to test


413
(I-12)
Tetramethylammonium sulphate
According to test


414
(I-12)
Tetramethylammonium lactate
According to test


415
(I-12)
Tetramethylammonium nitrate
According to test


416
(I-12)
Tetramethylammonium thiosulphate
According to test


417
(I-12)
Tetramethylammonium thiocyanate
According to test


418
(I-12)
Tetramethylammonium citrate
According to test


419
(I-12)
Tetramethylammonium oxalate
According to test


420
(I-12)
Tetramethylammonium formate
According to test


421
(I-12)
Tetramethylammonium hydrogenphosphate
According to test


422
(I-12)
Tetramethylammonium dihydrogenphosphate
According to test


423
(I-12)
Tetraethylammonium sulphate
According to test


424
(I-12)
Tetraethylammonium lactate
According to test


425
(I-12)
Tetraethylammonium nitrate
According to test


426
(I-12)
Tetraethylammonium thiosulphate
According to test


427
(I-12)
Tetraethylammonium thiocyanate
According to test


428
(I-12)
Tetraethylammonium citrate
According to test


429
(I-12)
Tetraethylammonium oxalate
According to test


430
(I-12)
Tetraethylammonium formate
According to test


431
(I-12)
Tetraethylammonium hydrogenphosphate
According to test


432
(I-12)
Tetraethylammonium dihydrogenphosphate
According to test


433
(I-13)
Ammonium sulphate
According to test


434
(I-13)
Ammonium lactate
According to test


435
(I-13)
Ammonium nitrate
According to test


436
(I-13)
Ammonium thiosulphate
According to test


437
(I-13)
Ammonium thiocyanate
According to test


438
(I-13)
Ammonium citrate
According to test


439
(I-13)
Ammonium oxalate
According to test


440
(I-13)
Ammonium formate
According to test


441
(I-13)
Ammonium hydrogenphosphate
According to test


442
(I-13)
Ammonium dihydrogenphosphate
According to test


443
(I-13)
Ammonium carbonate
According to test


444
(I-13)
Ammonium sulphite
According to test


445
(I-13)
Ammonium benzoate
According to test


446
(I-13)
Ammonium hydrogenoxalate
According to test


447
(I-13)
Ammonium hydrogencitrate
According to test


448
(I-13)
Ammonium acetate
According to test


449
(I-13)
Tetramethylammonium sulphate
According to test


450
(I-13)
Tetramethylammonium lactate
According to test


451
(I-13)
Tetramethylammonium nitrate
According to test


452
(I-13)
Tetramethylammonium thiosulphate
According to test


453
(I-13)
Tetramethylammonium thiocyanate
According to test


454
(I-13)
Tetramethylammonium citrate
According to test


455
(I-13)
Tetramethylammonium oxalate
According to test


456
(I-13)
Tetramethylammonium formate
According to test


457
(I-13)
Tetramethylammonium hydrogenphosphate
According to test


458
(I-13)
Tetramethylammonium dihydrogenphosphate
According to test


459
(I-13)
Tetraethylammonium sulphate
According to test


460
(I-13)
Tetraethylammonium lactate
According to test


461
(I-13)
Tetraethylammonium nitrate
According to test


462
(I-13)
Tetraethylammonium thiosulphate
According to test


463
(I-13)
Tetraethylammonium thiocyanate
According to test


464
(I-13)
Tetraethylammonium citrate
According to test


465
(I-13)
Tetraethylammonium oxalate
According to test


466
(I-13)
Tetraethylammonium formate
According to test


467
(I-13)
Tetraethylammonium hydrogenphosphate
According to test


468
(I-13)
Tetraethylammonium dihydrogenphosphate
According to test


469
(I-14)
Ammonium sulphate
According to test


470
(I-14)
Ammonium lactate
According to test


471
(I-14)
Ammonium nitrate
According to test


472
(I-14)
Ammonium thiosulphate
According to test


473
(I-14)
Ammonium thiocyanate
According to test


474
(I-14)
Ammonium citrate
According to test


475
(I-14)
Ammonium oxalate
According to test


476
(I-14)
Ammonium formate
According to test


477
(I-14)
Ammonium hydrogenphosphate
According to test


478
(I-14)
Ammonium dihydrogenphosphate
According to test


479
(I-14)
Ammonium carbonate
According to test


480
(I-14)
Ammonium sulphite
According to test


481
(I-14)
Ammonium benzoate
According to test


482
(I-14)
Ammonium hydrogenoxalate
According to test


483
(I-14)
Ammonium hydrogencitrate
According to test


484
(I-14)
Ammonium acetate
According to test


485
(I-14)
Tetramethylammonium sulphate
According to test


486
(I-14)
Tetramethylammonium lactate
According to test


487
(I-14)
Tetramethylammonium nitrate
According to test


488
(I-14)
Tetramethylammonium thiosulphate
According to test


489
(I-14)
Tetramethylammonium thiocyanate
According to test


490
(I-14)
Tetramethylammonium citrate
According to test


491
(I-14)
Tetramethylammonium oxalate
According to test


492
(I-14)
Tetramethylammonium formate
According to test


493
(I-14)
Tetramethylammonium hydrogenphosphate
According to test


494
(I-14)
Tetramethylammonium dihydrogenphosphate
According to test


495
(I-14)
Tetraethylammonium sulphate
According to test


496
(I-14)
Tetraethylammonium lactate
According to test


497
(I-14)
Tetraethylammonium nitrate
According to test


498
(I-14)
Tetraethylammonium thiosulphate
According to test


499
(I-14)
Tetraethylammonium thiocyanate
According to test


500
(I-14)
Tetraethylammonium citrate
According to test


501
(I-14)
Tetraethylammonium oxalate
According to test


502
(I-14)
Tetraethylammonium formate
According to test


503
(I-14)
Tetraethylammonium hydrogenphosphate
According to test


504
(I-14)
Tetraethylammonium dihydrogenphosphate
According to test


505
(I-15)
Ammonium sulphate
According to test


506
(I-15)
Ammonium lactate
According to test


507
(I-15)
Ammonium nitrate
According to test


508
(I-15)
Ammonium thiosulphate
According to test


509
(I-15)
Ammonium thiocyanate
According to test


510
(I-15)
Ammonium citrate
According to test


511
(I-15)
Ammonium oxalate
According to test


512
(I-15)
Ammonium formate
According to test


513
(I-15)
Ammonium hydrogenphosphate
According to test


514
(I-15)
Ammonium dihydrogenphosphate
According to test


515
(I-15)
Ammonium carbonate
According to test


516
(I-15)
Ammonium sulphite
According to test


517
(I-15)
Ammonium benzoate
According to test


518
(I-15)
Ammonium hydrogenoxalate
According to test


519
(I-15)
Ammonium hydrogencitrate
According to test


520
(I-15)
Ammonium acetate
According to test


521
(I-15)
Tetramethylammonium sulphate
According to test


522
(I-15)
Tetramethylammonium lactate
According to test


523
(I-15)
Tetramethylammonium nitrate
According to test


524
(I-15)
Tetramethylammonium thiosulphate
According to test


525
(I-15)
Tetramethylammonium thiocyanate
According to test


526
(I-15)
Tetramethylammonium citrate
According to test


527
(I-15)
Tetramethylammonium oxalate
According to test


528
(I-15)
Tetramethylammonium formate
According to test


529
(I-15)
Tetramethylammonium hydrogenphosphate
According to test


530
(I-15)
Tetramethylammonium dihydrogenphosphate
According to test


531
(I-15)
Tetraethylammonium sulphate
According to test


532
(I-15)
Tetraethylammonium lactate
According to test


533
(I-15)
Tetraethylammonium nitrate
According to test


534
(I-15)
Tetraethylammonium thiosulphate
According to test


535
(I-15)
Tetraethylammonium thiocyanate
According to test


536
(I-15)
Tetraethylammonium citrate
According to test


537
(I-15)
Tetraethylammonium oxalate
According to test


538
(I-15)
Tetraethylammonium formate
According to test


539
(I-15)
Tetraethylammonium hydrogenphosphate
According to test


540
(I-15)
Tetraethylammonium dihydrogenphosphate
According to test


541
(I-16)
Ammonium sulphate
According to test


542
(I-16)
Ammonium lactate
According to test


543
(I-16)
Ammonium nitrate
According to test


544
(I-16)
Ammonium thiosulphate
According to test


545
(I-16)
Ammonium thiocyanate
According to test


546
(I-16)
Ammonium citrate
According to test


547
(I-16)
Ammonium oxalate
According to test


548
(I-16)
Ammonium formate
According to test


549
(I-16)
Ammonium hydrogenphosphate
According to test


550
(I-16)
Ammonium dihydrogenphosphate
According to test


551
(I-16)
Ammonium carbonate
According to test


552
(I-16)
Ammonium sulphite
According to test


553
(I-16)
Ammonium benzoate
According to test


554
(I-16)
Ammonium hydrogenoxalate
According to test


555
(I-16)
Ammonium hydrogencitrate
According to test


556
(I-16)
Ammonium acetate
According to test


557
(I-16)
Tetramethylammonium sulphate
According to test


558
(I-16)
Tetramethylammonium lactate
According to test


559
(I-16)
Tetramethylammonium nitrate
According to test


560
(I-16)
Tetramethylammonium thiosulphate
According to test


561
(I-16)
Tetramethylammonium thiocyanate
According to test


562
(I-16)
Tetramethylammonium citrate
According to test


563
(I-16)
Tetramethylammonium oxalate
According to test


564
(I-16)
Tetramethylammonium formate
According to test


565
(I-16)
Tetramethylammonium hydrogenphosphate
According to test


566
(I-16)
Tetramethylammonium dihydrogenphosphate
According to test


567
(I-16)
Tetraethylammonium sulphate
According to test


568
(I-16)
Tetraethylammonium lactate
According to test


569
(I-16)
Tetraethylammonium nitrate
According to test


570
(I-16)
Tetraethylammonium thiosulphate
According to test


571
(I-16)
Tetraethylammonium thiocyanate
According to test


572
(I-16)
Tetraethylammonium citrate
According to test


573
(I-16)
Tetraethylammonium oxalate
According to test


574
(I-16)
Tetraethylammonium formate
According to test


575
(I-16)
Tetraethylammonium hydrogenphosphate
According to test


576
(I-16)
Tetraethylammonium dihydrogenphosphate
According to test


577
(I-17)
Ammonium sulphate
According to test


578
(I-17)
Ammonium lactate
According to test


579
(I-17)
Ammonium nitrate
According to test


580
(I-17)
Ammonium thiosulphate
According to test


581
(I-17)
Ammonium thiocyanate
According to test


582
(I-17)
Ammonium citrate
According to test


583
(I-17)
Ammonium oxalate
According to test


584
(I-17)
Ammonium formate
According to test


585
(I-17)
Ammonium hydrogenphosphate
According to test


586
(I-17)
Ammonium dihydrogenphosphate
According to test


587
(I-17)
Ammonium carbonate
According to test


588
(I-17)
Ammonium sulphite
According to test


589
(I-17)
Ammonium benzoate
According to test


590
(I-17)
Ammonium hydrogenoxalate
According to test


591
(I-17)
Ammonium hydrogencitrate
According to test


592
(I-17)
Ammonium acetate
According to test


593
(I-17)
Tetramethylammonium sulphate
According to test


594
(I-17)
Tetramethylammonium lactate
According to test


595
(I-17)
Tetramethylammonium nitrate
According to test


596
(I-17)
Tetramethylammonium thiosulphate
According to test


597
(I-17)
Tetramethylammonium thiocyanate
According to test


598
(I-17)
Tetramethylammonium citrate
According to test


599
(I-17)
Tetramethylammonium oxalate
According to test


600
(I-17)
Tetramethylammonium formate
According to test


601
(I-17)
Tetramethylammonium hydrogenphosphate
According to test


602
(I-17)
Tetramethylammonium dihydrogenphosphate
According to test


603
(I-17)
Tetraethylammonium sulphate
According to test


604
(I-17)
Tetraethylammonium lactate
According to test


605
(I-17)
Tetraethylammonium nitrate
According to test


606
(I-17)
Tetraethylammonium thiosulphate
According to test


607
(I-17)
Tetraethylammonium thiocyanate
According to test


608
(I-17)
Tetraethylammonium citrate
According to test


609
(I-17)
Tetraethylammonium oxalate
According to test


610
(I-17)
Tetraethylammonium formate
According to test


611
(I-17)
Tetraethylammonium hydrogenphosphate
According to test


612
(I-17)
Tetraethylammonium dihydrogenphosphate
According to test


613
(I-18)
Ammonium sulphate
According to test


614
(I-18)
Ammonium lactate
According to test


615
(I-18)
Ammonium nitrate
According to test


616
(I-18)
Ammonium thiosulphate
According to test


617
(I-18)
Ammonium thiocyanate
According to test


618
(I-18)
Ammonium citrate
According to test


619
(I-18)
Ammonium oxalate
According to test


620
(I-18)
Ammonium formate
According to test


621
(I-18)
Ammonium hydrogenphosphate
According to test


622
(I-18)
Ammonium dihydrogenphosphate
According to test


623
(I-18)
Ammonium carbonate
According to test


624
(I-18)
Ammonium sulphite
According to test


625
(I-18)
Ammonium benzoate
According to test


626
(I-18)
Ammonium hydrogenoxalate
According to test


627
(I-18)
Ammonium hydrogencitrate
According to test


628
(I-18)
Ammonium acetate
According to test


629
(I-18)
Tetramethylammonium sulphate
According to test


630
(I-18)
Tetramethylammonium lactate
According to test


631
(I-18)
Tetramethylammonium nitrate
According to test


632
(I-18)
Tetramethylammonium thiosulphate
According to test


633
(I-18)
Tetramethylammonium thiocyanate
According to test


634
(I-18)
Tetramethylammonium citrate
According to test


635
(I-18)
Tetramethylammonium oxalate
According to test


636
(I-18)
Tetramethylammonium formate
According to test


637
(I-18)
Tetramethylammonium hydrogenphosphate
According to test


638
(I-18)
Tetramethylammonium dihydrogenphosphate
According to test


639
(I-18)
Tetraethylammonium sulphate
According to test


640
(I-18)
Tetraethylammonium lactate
According to test


641
(I-18)
Tetraethylammonium nitrate
According to test


642
(I-18)
Tetraethylammonium thiosulphate
According to test


643
(I-18)
Tetraethylammonium thiocyanate
According to test


644
(I-18)
Tetraethylammonium citrate
According to test


645
(I-18)
Tetraethylammonium oxalate
According to test


646
(I-18)
Tetraethylammonium formate
According to test


647
(I-18)
Tetraethylammonium hydrogenphosphate
According to test


648
(I-18)
Tetraethylammonium dihydrogenphosphate
According to test


649
(I-19)
Ammonium sulphate
According to test


650
(I-19)
Ammonium lactate
According to test


651
(I-19)
Ammonium nitrate
According to test


652
(I-19)
Ammonium thiosulphate
According to test


653
(I-19)
Ammonium thiocyanate
According to test


654
(I-19)
Ammonium citrate
According to test


655
(I-19)
Ammonium oxalate
According to test


656
(I-19)
Ammonium formate
According to test


657
(I-19)
Ammonium hydrogenphosphate
According to test


658
(I-19)
Ammonium dihydrogenphosphate
According to test


659
(I-19)
Ammonium carbonate
According to test


660
(I-19)
Ammonium sulphite
According to test


661
(I-19)
Ammonium benzoate
According to test


662
(I-19)
Ammonium hydrogenoxalate
According to test


663
(I-19)
Ammonium hydrogencitrate
According to test


664
(I-19)
Ammonium acetate
According to test


665
(I-19)
Tetramethylammonium sulphate
According to test


666
(I-19)
Tetramethylammonium lactate
According to test


667
(I-19)
Tetramethylammonium nitrate
According to test


668
(I-19)
Tetramethylammonium thiosulphate
According to test


669
(I-19)
Tetramethylammonium thiocyanate
According to test


670
(I-19)
Tetramethylammonium citrate
According to test


671
(I-19)
Tetramethylammonium oxalate
According to test


672
(I-19)
Tetramethylammonium formate
According to test


673
(I-19)
Tetramethylammonium hydrogenphosphate
According to test


674
(I-19)
Tetramethylammonium dihydrogenphosphate
According to test


675
(I-19)
Tetraethylammonium sulphate
According to test


676
(I-19)
Tetraethylammonium lactate
According to test


677
(I-19)
Tetraethylammonium nitrate
According to test


678
(I-19)
Tetraethylammonium thiosulphate
According to test


679
(I-19)
Tetraethylammonium thiocyanate
According to test


680
(I-19)
Tetraethylammonium citrate
According to test


681
(I-19)
Tetraethylammonium oxalate
According to test


682
(I-19)
Tetraethylammonium formate
According to test


683
(I-19)
Tetraethylammonium hydrogenphosphate
According to test


684
(I-19)
Tetraethylammonium dihydrogenphosphate
According to test


685
(I-20)
Ammonium sulphate
According to test


686
(I-20)
Ammonium lactate
According to test


687
(I-20)
Ammonium nitrate
According to test


688
(I-20)
Ammonium thiosulphate
According to test


689
(I-20)
Ammonium thiocyanate
According to test


690
(I-20)
Ammonium citrate
According to test


691
(I-20)
Ammonium oxalate
According to test


692
(I-20)
Ammonium formate
According to test


693
(I-20)
Ammonium hydrogenphosphate
According to test


694
(I-20)
Ammonium dihydrogenphosphate
According to test


695
(I-20)
Ammonium carbonate
According to test


696
(I-20)
Ammonium sulphite
According to test


697
(I-20)
Ammonium benzoate
According to test


698
(I-20)
Ammonium hydrogenoxalate
According to test


699
(I-20)
Ammonium hydrogencitrate
According to test


700
(I-20)
Ammonium acetate
According to test


701
(I-20)
Tetramethylammonium sulphate
According to test


702
(I-20)
Tetramethylammonium lactate
According to test


703
(I-20)
Tetramethylammonium nitrate
According to test


704
(I-20)
Tetramethylammonium thiosulphate
According to test


705
(I-20)
Tetramethylammonium thiocyanate
According to test


706
(I-20)
Tetramethylammonium citrate
According to test


707
(I-20)
Tetramethylammonium oxalate
According to test


708
(I-20)
Tetramethylammonium formate
According to test


709
(I-20)
Tetramethylammonium hydrogenphosphate
According to test


710
(I-20)
Tetramethylammonium dihydrogenphosphate
According to test


711
(I-20)
Tetraethylammonium sulphate
According to test


712
(I-20)
Tetraethylammonium lactate
According to test


713
(I-20)
Tetraethylammonium nitrate
According to test


714
(I-20)
Tetraethylammonium thiosulphate
According to test


715
(I-20)
Tetraethylammonium thiocyanate
According to test


716
(I-20)
Tetraethylammonium citrate
According to test


717
(I-20)
Tetraethylammonium oxalate
According to test


718
(I-20)
Tetraethylammonium formate
According to test


719
(I-20)
Tetraethylammonium hydrogenphosphate
According to test


720
(I-20)
Tetraethylammonium dihydrogenphosphate
According to test


721
(I-21)
Ammonium sulphate
According to test


722
(I-21)
Ammonium lactate
According to test


723
(I-21)
Ammonium nitrate
According to test


724
(I-21)
Ammonium thiosulphate
According to test


725
(I-21)
Ammonium thiocyanate
According to test


726
(I-21)
Ammonium citrate
According to test


727
(I-21)
Ammonium oxalate
According to test


728
(I-21)
Ammonium formate
According to test


729
(I-21)
Ammonium hydrogenphosphate
According to test


730
(I-21)
Ammonium dihydrogenphosphate
According to test


731
(I-21)
Ammonium carbonate
According to test


732
(I-21)
Ammonium sulphite
According to test


733
(I-21)
Ammonium benzoate
According to test


734
(I-21)
Ammonium hydrogenoxalate
According to test


735
(I-21)
Ammonium hydrogencitrate
According to test


736
(I-21)
Ammonium acetate
According to test


737
(I-21)
Tetramethylammonium sulphate
According to test


738
(I-21)
Tetramethylammonium lactate
According to test


739
(I-21)
Tetramethylammonium nitrate
According to test


740
(I-21)
Tetramethylammonium thiosulphate
According to test


741
(I-21)
Tetramethylammonium thiocyanate
According to test


742
(I-21)
Tetramethylammonium citrate
According to test


743
(I-21)
Tetramethylammonium oxalate
According to test


744
(I-21)
Tetramethylammonium formate
According to test


745
(I-21)
Tetramethylammonium hydrogenphosphate
According to test


746
(I-21)
Tetramethylammonium dihydrogenphosphate
According to test


747
(I-21)
Tetraethylammonium sulphate
According to test


748
(I-21)
Tetraethylammonium lactate
According to test


749
(I-21)
Tetraethylammonium nitrate
According to test


750
(I-21)
Tetraethylammonium thiosulphate
According to test


751
(I-21)
Tetraethylammonium thiocyanate
According to test


752
(I-21)
Tetraethylammonium citrate
According to test


753
(I-21)
Tetraethylammonium oxalate
According to test


754
(I-21)
Tetraethylammonium formate
According to test


755
(I-21)
Tetraethylammonium hydrogenphosphate
According to test


756
(I-21)
Tetraethylammonium dihydrogenphosphate
According to test


757
(I-22)
Ammonium sulphate
According to test


758
(I-22)
Ammonium lactate
According to test


759
(I-22)
Ammonium nitrate
According to test


760
(I-22)
Ammonium thiosulphate
According to test


761
(I-22)
Ammonium thiocyanate
According to test


762
(I-22)
Ammonium citrate
According to test


763
(I-22)
Ammonium oxalate
According to test


764
(I-22)
Ammonium formate
According to test


765
(I-22)
Ammonium hydrogenphosphate
According to test


766
(I-22)
Ammonium dihydrogenphosphate
According to test


767
(I-22)
Ammonium carbonate
According to test


768
(I-22)
Ammonium sulphite
According to test


769
(I-22)
Ammonium benzoate
According to test


770
(I-22)
Ammonium hydrogenoxalate
According to test


771
(I-22)
Ammonium hydrogencitrate
According to test


772
(I-22)
Ammonium acetate
According to test


773
(I-22)
Tetramethylammonium sulphate
According to test


774
(I-22)
Tetramethylammonium lactate
According to test


775
(I-22)
Tetramethylammonium nitrate
According to test


776
(I-22)
Tetramethylammonium thiosulphate
According to test


777
(I-22)
Tetramethylammonium thiocyanate
According to test


778
(I-22)
Tetramethylammonium citrate
According to test


779
(I-22)
Tetramethylammonium oxalate
According to test


780
(I-22)
Tetramethylammonium formate
According to test


781
(I-22)
Tetramethylammonium hydrogenphosphate
According to test


782
(I-22)
Tetramethylammonium dihydrogenphosphate
According to test


783
(I-22)
Tetraethylammonium sulphate
According to test


784
(I-22)
Tetraethylammonium lactate
According to test


785
(I-22)
Tetraethylammonium nitrate
According to test


786
(I-22)
Tetraethylammonium thiosulphate
According to test


787
(I-22)
Tetraethylammonium thiocyanate
According to test


788
(I-22)
Tetraethylammonium citrate
According to test


789
(I-22)
Tetraethylammonium oxalate
According to test


790
(I-22)
Tetraethylammonium formate
According to test


791
(I-22)
Tetraethylammonium hydrogenphosphate
According to test


792
(I-22)
Tetraethylammonium dihydrogenphosphate
According to test


793
(I-23)
Ammonium sulphate
According to test


794
(I-23)
Ammonium lactate
According to test


795
(I-23)
Ammonium nitrate
According to test


796
(I-23)
Ammonium thiosulphate
According to test


797
(I-23)
Ammonium thiocyanate
According to test


798
(I-23)
Ammonium citrate
According to test


799
(I-23)
Ammonium oxalate
According to test


800
(I-23)
Ammonium formate
According to test


801
(I-23)
Ammonium hydrogenphosphate
According to test


802
(I-23)
Ammonium dihydrogenphosphate
According to test


803
(I-23)
Ammonium carbonate
According to test


804
(I-23)
Ammonium sulphite
According to test


805
(I-23)
Ammonium benzoate
According to test


806
(I-23)
Ammonium hydrogenoxalate
According to test


807
(I-23)
Ammonium hydrogencitrate
According to test


808
(I-23)
Ammonium acetate
According to test


809
(I-23)
Tetramethylammonium sulphate
According to test


810
(I-23)
Tetramethylammonium lactate
According to test


811
(I-23)
Tetramethylammonium nitrate
According to test


812
(I-23)
Tetramethylammonium thiosulphate
According to test


813
(I-23)
Tetramethylammonium thiocyanate
According to test


814
(I-23)
Tetramethylammonium citrate
According to test


815
(I-23)
Tetramethylammonium oxalate
According to test


816
(I-23)
Tetramethylammonium formate
According to test


817
(I-23)
Tetramethylammonium hydrogenphosphate
According to test


818
(I-23)
Tetramethylammonium dihydrogenphosphate
According to test


819
(I-23)
Tetraethylammonium sulphate
According to test


820
(I-23)
Tetraethylammonium lactate
According to test


821
(I-23)
Tetraethylammonium nitrate
According to test


822
(I-23)
Tetraethylammonium thiosulphate
According to test


823
(I-23)
Tetraethylammonium thiocyanate
According to test


824
(I-23)
Tetraethylammonium citrate
According to test


825
(I-23)
Tetraethylammonium oxalate
According to test


826
(I-23)
Tetraethylammonium formate
According to test


827
(I-23)
Tetraethylammonium hydrogenphosphate
According to test


828
(I-23)
Tetraethylammonium dihydrogenphosphate
According to test


829
(I-24)
Ammonium sulphate
According to test


830
(I-24)
Ammonium lactate
According to test


831
(I-24)
Ammonium nitrate
According to test


832
(I-24)
Ammonium thiosulphate
According to test


833
(I-24)
Ammonium thiocyanate
According to test


834
(I-24)
Ammonium citrate
According to test


835
(I-24)
Ammonium oxalate
According to test


836
(I-24)
Ammonium formate
According to test


837
(I-24)
Ammonium hydrogenphosphate
According to test


838
(I-24)
Ammonium dihydrogenphosphate
According to test


839
(I-24)
Ammonium carbonate
According to test


840
(I-24)
Ammonium sulphite
According to test


841
(I-24)
Ammonium benzoate
According to test


842
(I-24)
Ammonium hydrogenoxalate
According to test


843
(I-24)
Ammonium hydrogencitrate
According to test


844
(I-24)
Ammonium acetate
According to test


845
(I-24)
Tetramethylammonium sulphate
According to test


846
(I-24)
Tetramethylammonium lactate
According to test


847
(I-24)
Tetramethylammonium nitrate
According to test


848
(I-24)
Tetramethylammonium thiosulphate
According to test


849
(I-24)
Tetramethylammonium thiocyanate
According to test


850
(I-24)
Tetramethylammonium citrate
According to test


851
(I-24)
Tetramethylammonium oxalate
According to test


852
(I-24)
Tetramethylammonium formate
According to test


853
(I-24)
Tetramethylammonium hydrogenphosphate
According to test


854
(I-24)
Tetramethylammonium dihydrogenphosphate
According to test


855
(I-24)
Tetraethylammonium sulphate
According to test


856
(I-24)
Tetraethylammonium lactate
According to test


857
(I-24)
Tetraethylammonium nitrate
According to test


858
(I-24)
Tetraethylammonium thiosulphate
According to test


859
(I-24)
Tetraethylammonium thiocyanate
According to test


860
(I-24)
Tetraethylammonium citrate
According to test


861
(I-24)
Tetraethylammonium oxalate
According to test


862
(I-24)
Tetraethylammonium formate
According to test


863
(I-24)
Tetraethylammonium hydrogenphosphate
According to test


864
(I-24)
Tetraethylammonium dihydrogenphosphate
According to test


865
(I-25)
Ammonium sulphate
According to test


866
(I-25)
Ammonium lactate
According to test


867
(I-25)
Ammonium nitrate
According to test


868
(I-25)
Ammonium thiosulphate
According to test


869
(I-25)
Ammonium thiocyanate
According to test


870
(I-25)
Ammonium citrate
According to test


871
(I-25)
Ammonium oxalate
According to test


872
(I-25)
Ammonium formate
According to test


873
(I-25)
Ammonium hydrogenphosphate
According to test


874
(I-25)
Ammonium dihydrogenphosphate
According to test


875
(I-25)
Ammonium carbonate
According to test


876
(I-25)
Ammonium sulphite
According to test


877
(I-25)
Ammonium benzoate
According to test


878
(I-25)
Ammonium hydrogenoxalate
According to test


879
(I-25)
Ammonium hydrogencitrate
According to test


880
(I-25)
Ammonium acetate
According to test


881
(I-25)
Tetramethylammonium sulphate
According to test


882
(I-25)
Tetramethylammonium lactate
According to test


883
(I-25)
Tetramethylammonium nitrate
According to test


884
(I-25)
Tetramethylammonium thiosulphate
According to test


885
(I-25)
Tetramethylammonium thiocyanate
According to test


886
(I-25)
Tetramethylammonium citrate
According to test


887
(I-25)
Tetramethylammonium oxalate
According to test


888
(I-25)
Tetramethylammonium formate
According to test


889
(I-25)
Tetramethylammonium hydrogenphosphate
According to test


890
(I-25)
Tetramethylammonium dihydrogenphosphate
According to test


891
(I-25)
Tetraethylammonium sulphate
According to test


892
(I-25)
Tetraethylammonium lactate
According to test


893
(I-25)
Tetraethylammonium nitrate
According to test


894
(I-25)
Tetraethylammonium thiosulphate
According to test


895
(I-25)
Tetraethylammonium thiocyanate
According to test


896
(I-25)
Tetraethylammonium citrate
According to test


897
(I-25)
Tetraethylammonium oxalate
According to test


898
(I-25)
Tetraethylammonium formate
According to test


899
(I-25)
Tetraethylammonium hydrogenphosphate
According to test


900
(I-25)
Tetraethylammonium dihydrogenphosphate
According to test


901
(I-26)
Ammonium sulphate
According to test


902
(I-26)
Ammonium lactate
According to test


903
(I-26)
Ammonium nitrate
According to test


904
(I-26)
Ammonium thiosulphate
According to test


905
(I-26)
Ammonium thiocyanate
According to test


906
(I-26)
Ammonium citrate
According to test


907
(I-26)
Ammonium oxalate
According to test


908
(I-26)
Ammonium formate
According to test


909
(I-26)
Ammonium hydrogenphosphate
According to test


910
(I-26)
Ammonium dihydrogenphosphate
According to test


911
(I-26)
Ammonium carbonate
According to test


912
(I-26)
Ammonium sulphite
According to test


913
(I-26)
Ammonium benzoate
According to test


914
(I-26)
Ammonium hydrogenoxalate
According to test


915
(I-26)
Ammonium hydrogencitrate
According to test


916
(I-26)
Ammonium acetate
According to test


917
(I-26)
Tetramethylammonium sulphate
According to test


918
(I-26)
Tetramethylammonium lactate
According to test


919
(I-26)
Tetramethylammonium nitrate
According to test


920
(I-26)
Tetramethylammonium thiosulphate
According to test


921
(I-26)
Tetramethylammonium thiocyanate
According to test


922
(I-26)
Tetramethylammonium citrate
According to test


923
(I-26)
Tetramethylammonium oxalate
According to test


924
(I-26)
Tetramethylammonium formate
According to test


925
(I-26)
Tetramethylammonium hydrogenphosphate
According to test


926
(I-26)
Tetramethylammonium dihydrogenphosphate
According to test


927
(I-26)
Tetraethylammonium sulphate
According to test


928
(I-26)
Tetraethylammonium lactate
According to test


929
(I-26)
Tetraethylammonium nitrate
According to test


930
(I-26)
Tetraethylammonium thiosulphate
According to test


931
(I-26)
Tetraethylammonium thiocyanate
According to test


932
(I-26)
Tetraethylammonium citrate
According to test


933
(I-26)
Tetraethylammonium oxalate
According to test


934
(I-26)
Tetraethylammonium formate
According to test


935
(I-26)
Tetraethylammonium hydrogenphosphate
According to test


936
(I-26)
Tetraethylammonium dihydrogenphosphate
According to test


937
(I-27)
Ammonium sulphate
According to test


938
(I-27)
Ammonium lactate
According to test


939
(I-27)
Ammonium nitrate
According to test


940
(I-27)
Ammonium thiosulphate
According to test


941
(I-27)
Ammonium thiocyanate
According to test


942
(I-27)
Ammonium citrate
According to test


943
(I-27)
Ammonium oxalate
According to test


944
(I-27)
Ammonium formate
According to test


945
(I-27)
Ammonium hydrogenphosphate
According to test


946
(I-27)
Ammonium dihydrogenphosphate
According to test


947
(I-27)
Ammonium carbonate
According to test


948
(I-27)
Ammonium sulphite
According to test


949
(I-27)
Ammonium benzoate
According to test


950
(I-27)
Ammonium hydrogenoxalate
According to test


951
(I-27)
Ammonium hydrogencitrate
According to test


952
(I-27)
Ammonium acetate
According to test


953
(I-27)
Tetramethylammonium sulphate
According to test


954
(I-27)
Tetramethylammonium lactate
According to test


955
(I-27)
Tetramethylammonium nitrate
According to test


956
(I-27)
Tetramethylammonium thiosulphate
According to test


957
(I-27)
Tetramethylammonium thiocyanate
According to test


958
(I-27)
Tetramethylammonium citrate
According to test


959
(I-27)
Tetramethylammonium oxalate
According to test


960
(I-27)
Tetramethylammonium formate
According to test


961
(I-27)
Tetramethylammonium hydrogenphosphate
According to test


962
(I-27)
Tetramethylammonium dihydrogenphosphate
According to test


963
(I-27)
Tetraethylammonium sulphate
According to test


964
(I-27)
Tetraethylammonium lactate
According to test


965
(I-27)
Tetraethylammonium nitrate
According to test


966
(I-27)
Tetraethylammonium thiosulphate
According to test


967
(I-27)
Tetraethylammonium thiocyanate
According to test


968
(I-27)
Tetraethylammonium citrate
According to test


969
(I-27)
Tetraethylammonium oxalate
According to test


970
(I-27)
Tetraethylammonium formate
According to test


971
(I-27)
Tetraethylammonium hydrogenphosphate
According to test


972
(I-27)
Tetraethylammonium dihydrogenphosphate
According to test


973
(I-28)
Ammonium sulphate
According to test


974
(I-28)
Ammonium lactate
According to test


975
(I-28)
Ammonium nitrate
According to test


976
(I-28)
Ammonium thiosulphate
According to test


977
(I-28)
Ammonium thiocyanate
According to test


978
(I-28)
Ammonium citrate
According to test


979
(I-28)
Ammonium oxalate
According to test


980
(I-28)
Ammonium formate
According to test


981
(I-28)
Ammonium hydrogenphosphate
According to test


982
(I-28)
Ammonium dihydrogenphosphate
According to test


983
(I-28)
Ammonium carbonate
According to test


984
(I-28)
Ammonium sulphite
According to test


985
(I-28)
Ammonium benzoate
According to test


986
(I-28)
Ammonium hydrogenoxalate
According to test


987
(I-28)
Ammonium hydrogencitrate
According to test


988
(I-28)
Ammonium acetate
According to test


989
(I-28)
Tetramethylammonium sulphate
According to test


990
(I-28)
Tetramethylammonium lactate
According to test


991
(I-28)
Tetramethylammonium nitrate
According to test


992
(I-28)
Tetramethylammonium thiosulphate
According to test


993
(I-28)
Tetramethylammonium thiocyanate
According to test


994
(I-28)
Tetramethylammonium citrate
According to test


995
(I-28)
Tetramethylammonium oxalate
According to test


996
(I-28)
Tetramethylammonium formate
According to test


997
(I-28)
Tetramethylammonium hydrogenphosphate
According to test


998
(I-28)
Tetramethylammonium dihydrogenphosphate
According to test


999
(I-28)
Tetraethylammonium sulphate
According to test


1000
(I-28)
Tetraethylammonium lactate
According to test


1001
(I-28)
Tetraethylammonium nitrate
According to test


1002
(I-28)
Tetraethylammonium thiosulphate
According to test


1003
(I-28)
Tetraethylammonium thiocyanate
According to test


1004
(I-28)
Tetraethylammonium citrate
According to test


1005
(I-28)
Tetraethylammonium oxalate
According to test


1006
(I-28)
Tetraethylammonium formate
According to test


1007
(I-28)
Tetraethylammonium hydrogenphosphate
According to test


1008
(I-28)
Tetraethylammonium dihydrogenphosphate
According to test


1009
(I-29)
Ammonium sulphate
According to test


1010
(I-29)
Ammonium lactate
According to test


1011
(I-29)
Ammonium nitrate
According to test


1012
(I-29)
Ammonium thiosulphate
According to test


1013
(I-29)
Ammonium thiocyanate
According to test


1014
(I-29)
Ammonium citrate
According to test


1015
(I-29)
Ammonium oxalate
According to test


1016
(I-29)
Ammonium formate
According to test


1017
(I-29)
Ammonium hydrogenphosphate
According to test


1018
(I-29)
Ammonium dihydrogenphosphate
According to test


1019
(I-29)
Ammonium carbonate
According to test


1020
(I-29)
Ammonium sulphite
According to test


1021
(I-29)
Ammonium benzoate
According to test


1022
(I-29)
Ammonium hydrogenoxalate
According to test


1023
(I-29)
Ammonium hydrogencitrate
According to test


1024
(I-29)
Ammonium acetate
According to test


1025
(I-29)
Tetramethylammonium sulphate
According to test


1026
(I-29)
Tetramethylammonium lactate
According to test


1027
(I-29)
Tetramethylammonium nitrate
According to test


1028
(I-29)
Tetramethylammonium thiosulphate
According to test


1029
(I-29)
Tetramethylammonium thiocyanate
According to test


1030
(I-29)
Tetramethylammonium citrate
According to test


1031
(I-29)
Tetramethylammonium oxalate
According to test


1032
(I-29)
Tetramethylammonium formate
According to test


1033
(I-29)
Tetramethylammonium hydrogenphosphate
According to test


1034
(I-29)
Tetramethylammonium dihydrogenphosphate
According to test


1035
(I-29)
Tetraethylammonium sulphate
According to test


1036
(I-29)
Tetraethylammonium lactate
According to test


1037
(I-29)
Tetraethylammonium nitrate
According to test


1038
(I-29)
Tetraethylammonium thiosulphate
According to test


1039
(I-29)
Tetraethylammonium thiocyanate
According to test


1040
(I-29)
Tetraethylammonium citrate
According to test


1041
(I-29)
Tetraethylammonium oxalate
According to test


1042
(I-29)
Tetraethylammonium formate
According to test


1043
(I-29)
Tetraethylammonium hydrogenphosphate
According to test


1044
(I-29)
Tetraethylammonium dihydrogenphosphate
According to test


1045
(I-30)
Ammonium sulphate
According to test


1046
(I-30)
Ammonium lactate
According to test


1047
(I-30)
Ammonium nitrate
According to test


1048
(I-30)
Ammonium thiosulphate
According to test


1049
(I-30)
Ammonium thiocyanate
According to test


1050
(I-30)
Ammonium citrate
According to test


1051
(I-30)
Ammonium oxalate
According to test


1052
(I-30)
Ammonium formate
According to test


1053
(I-30)
Ammonium hydrogenphosphate
According to test


1054
(I-30)
Ammonium dihydrogenphosphate
According to test


1055
(I-30)
Ammonium carbonate
According to test


1056
(I-30)
Ammonium sulphite
According to test


1057
(I-30)
Ammonium benzoate
According to test


1058
(I-30)
Ammonium hydrogenoxalate
According to test


1059
(I-30)
Ammonium hydrogencitrate
According to test


1060
(I-30)
Ammonium acetate
According to test


1061
(I-30)
Tetramethylammonium sulphate
According to test


1062
(I-30)
Tetramethylammonium lactate
According to test


1063
(I-30)
Tetramethylammonium nitrate
According to test


1064
(I-30)
Tetramethylammonium thiosulphate
According to test


1065
(I-30)
Tetramethylammonium thiocyanate
According to test


1066
(I-30)
Tetramethylammonium citrate
According to test


1067
(I-30)
Tetramethylammonium oxalate
According to test


1068
(I-30)
Tetramethylammonium formate
According to test


1069
(I-30)
Tetramethylammonium hydrogenphosphate
According to test


1070
(I-30)
Tetramethylammonium dihydrogenphosphate
According to test


1071
(I-30)
Tetraethylammonium sulphate
According to test


1072
(I-30)
Tetraethylammonium lactate
According to test


1073
(I-30)
Tetraethylammonium nitrate
According to test


1074
(I-30)
Tetraethylammonium thiosulphate
According to test


1075
(I-30)
Tetraethylammonium thiocyanate
According to test


1076
(I-30)
Tetraethylammonium citrate
According to test


1077
(I-30)
Tetraethylammonium oxalate
According to test


1078
(I-30)
Tetraethylammonium formate
According to test


1079
(I-30)
Tetraethylammonium hydrogenphosphate
According to test


1080
(I-30)
Tetraethylammonium dihydrogenphosphate
According to test


1081
(I-31)
Ammonium sulphate
According to test


1082
(I-31)
Ammonium lactate
According to test


1083
(I-31)
Ammonium nitrate
According to test


1084
(I-31)
Ammonium thiosulphate
According to test


1085
(I-31)
Ammonium thiocyanate
According to test


1086
(I-31)
Ammonium citrate
According to test


1087
(I-31)
Ammonium oxalate
According to test


1088
(I-31)
Ammonium formate
According to test


1089
(I-31)
Ammonium hydrogenphosphate
According to test


1090
(I-31)
Ammonium dihydrogenphosphate
According to test


1091
(I-31)
Ammonium carbonate
According to test


1092
(I-31)
Ammonium sulphite
According to test


1093
(I-31)
Ammonium benzoate
According to test


1094
(I-31)
Ammonium hydrogenoxalate
According to test


1095
(I-31)
Ammonium hydrogencitrate
According to test


1096
(I-31)
Ammonium acetate
According to test


1097
(I-31)
Tetramethylammonium sulphate
According to test


1098
(I-31)
Tetramethylammonium lactate
According to test


1099
(I-31)
Tetramethylammonium nitrate
According to test


1100
(I-31)
Tetramethylammonium thiosulphate
According to test


1101
(I-31)
Tetramethylammonium thiocyanate
According to test


1102
(I-31)
Tetramethylammonium citrate
According to test


1103
(I-31)
Tetramethylammonium oxalate
According to test


1104
(I-31)
Tetramethylammonium formate
According to test


1105
(I-31)
Tetramethylammonium hydrogenphosphate
According to test


1106
(I-31)
Tetramethylammonium dihydrogenphosphate
According to test


1107
(I-31)
Tetraethylammonium sulphate
According to test


1108
(I-31)
Tetraethylammonium lactate
According to test


1109
(I-31)
Tetraethylammonium nitrate
According to test


1110
(I-31)
Tetraethylammonium thiosulphate
According to test


1111
(I-31)
Tetraethylammonium thiocyanate
According to test


1112
(I-31)
Tetraethylammonium citrate
According to test


1113
(I-31)
Tetraethylammonium oxalate
According to test


1114
(I-31)
Tetraethylammonium formate
According to test


1115
(I-31)
Tetraethylammonium hydrogenphosphate
According to test


1116
(I-31)
Tetraethylammonium dihydrogenphosphate
According to test


1117
(I-32)
Ammonium sulphate
According to test


1118
(I-32)
Ammonium lactate
According to test


1119
(I-32)
Ammonium nitrate
According to test


1120
(I-32)
Ammonium thiosulphate
According to test


1121
(I-32)
Ammonium thiocyanate
According to test


1122
(I-32)
Ammonium citrate
According to test


1123
(I-32)
Ammonium oxalate
According to test


1124
(I-32)
Ammonium formate
According to test


1125
(I-32)
Ammonium hydrogenphosphate
According to test


1126
(I-32)
Ammonium dihydrogenphosphate
According to test


1127
(I-32)
Ammonium carbonate
According to test


1128
(I-32)
Ammonium sulphite
According to test


1129
(I-32)
Ammonium benzoate
According to test


1130
(I-32)
Ammonium hydrogenoxalate
According to test


1131
(I-32)
Ammonium hydrogencitrate
According to test


1132
(I-32)
Ammonium acetate
According to test


1133
(I-32)
Tetramethylammonium sulphate
According to test


1134
(I-32)
Tetramethylammonium lactate
According to test


1135
(I-32)
Tetramethylammonium nitrate
According to test


1136
(I-32)
Tetramethylammonium thiosulphate
According to test


1137
(I-32)
Tetramethylammonium thiocyanate
According to test


1138
(I-32)
Tetramethylammonium citrate
According to test


1139
(I-32)
Tetramethylammonium oxalate
According to test


1140
(I-32)
Tetramethylammonium formate
According to test


1141
(I-32)
Tetramethylammonium hydrogenphosphate
According to test


1142
(I-32)
Tetramethylammonium dihydrogenphosphate
According to test


1143
(I-32)
Tetraethylammonium sulphate
According to test


1144
(I-32)
Tetraethylammonium lactate
According to test


1145
(I-32)
Tetraethylammonium nitrate
According to test


1146
(I-32)
Tetraethylammonium thiosulphate
According to test


1147
(I-32)
Tetraethylammonium thiocyanate
According to test


1148
(I-32)
Tetraethylammonium citrate
According to test


1149
(I-32)
Tetraethylammonium oxalate
According to test


1150
(I-32)
Tetraethylammonium formate
According to test


1151
(I-32)
Tetraethylammonium hydrogenphosphate
According to test


1152
(I-32)
Tetraethylammonium dihydrogenphosphate
According to test


1153
(I-33)
Ammonium sulphate
According to test


1154
(I-33)
Ammonium lactate
According to test


1155
(I-33)
Ammonium nitrate
According to test


1156
(I-33)
Ammonium thiosulphate
According to test


1157
(I-33)
Ammonium thiocyanate
According to test


1158
(I-33)
Ammonium citrate
According to test


1159
(I-33)
Ammonium oxalate
According to test


1160
(I-33)
Ammonium formate
According to test


1161
(I-33)
Ammonium hydrogenphosphate
According to test


1162
(I-33)
Ammonium dihydrogenphosphate
According to test


1163
(I-33)
Ammonium carbonate
According to test


1164
(I-33)
Ammonium sulphite
According to test


1165
(I-33)
Ammonium benzoate
According to test


1166
(I-33)
Ammonium hydrogenoxalate
According to test


1167
(I-33)
Ammonium hydrogencitrate
According to test


1168
(I-33)
Ammonium acetate
According to test


1169
(I-33)
Tetramethylammonium sulphate
According to test


1170
(I-33)
Tetramethylammonium lactate
According to test


1171
(I-33)
Tetramethylammonium nitrate
According to test


1172
(I-33)
Tetramethylammonium thiosulphate
According to test


1173
(I-33)
Tetramethylammonium thiocyanate
According to test


1174
(I-33)
Tetramethylammonium citrate
According to test


1175
(I-33)
Tetramethylammonium oxalate
According to test


1176
(I-33)
Tetramethylammonium formate
According to test


1177
(I-33)
Tetramethylammonium hydrogenphosphate
According to test


1178
(I-33)
Tetramethylammonium dihydrogenphosphate
According to test


1179
(I-33)
Tetraethylammonium sulphate
According to test


1180
(I-33)
Tetraethylammonium lactate
According to test


1181
(I-33)
Tetraethylammonium nitrate
According to test


1182
(I-33)
Tetraethylammonium thiosulphate
According to test


1183
(I-33)
Tetraethylammonium thiocyanate
According to test


1184
(I-33)
Tetraethylammonium citrate
According to test


1185
(I-33)
Tetraethylammonium oxalate
According to test


1186
(I-33)
Tetraethylammonium formate
According to test


1187
(I-33)
Tetraethylammonium hydrogenphosphate
According to test


1188
(I-33)
Tetraethylammonium dihydrogenphosphate
According to test


1189
(I-34)
Ammonium sulphate
According to test


1190
(I-34)
Ammonium lactate
According to test


1191
(I-34)
Ammonium nitrate
According to test


1192
(I-34)
Ammonium thiosulphate
According to test


1193
(I-34)
Ammonium thiocyanate
According to test


1194
(I-34)
Ammonium citrate
According to test


1195
(I-34)
Ammonium oxalate
According to test


1196
(I-34)
Ammonium formate
According to test


1197
(I-34)
Ammonium hydrogenphosphate
According to test


1198
(I-34)
Ammonium dihydrogenphosphate
According to test


1199
(I-34)
Ammonium carbonate
According to test


1200
(I-34)
Ammonium sulphite
According to test


1201
(I-34)
Ammonium benzoate
According to test


1202
(I-34)
Ammonium hydrogenoxalate
According to test


1203
(I-34)
Ammonium hydrogencitrate
According to test


1204
(I-34)
Ammonium acetate
According to test


1205
(I-34)
Tetramethylammonium sulphate
According to test


1206
(I-34)
Tetramethylammonium lactate
According to test


1207
(I-34)
Tetramethylammonium nitrate
According to test


1208
(I-34)
Tetramethylammonium thiosulphate
According to test


1209
(I-34)
Tetramethylammonium thiocyanate
According to test


1210
(I-34)
Tetramethylammonium citrate
According to test


1211
(I-34)
Tetramethylammonium oxalate
According to test


1212
(I-34)
Tetramethylammonium formate
According to test


1213
(I-34)
Tetramethylammonium hydrogenphosphate
According to test


1214
(I-34)
Tetramethylammonium dihydrogenphosphate
According to test


1215
(I-34)
Tetraethylammonium sulphate
According to test


1216
(I-34)
Tetraethylammonium lactate
According to test


1217
(I-34)
Tetraethylammonium nitrate
According to test


1218
(I-34)
Tetraethylammonium thiosulphate
According to test


1219
(I-34)
Tetraethylammonium thiocyanate
According to test


1220
(I-34)
Tetraethylammonium citrate
According to test


1221
(I-34)
Tetraethylammonium oxalate
According to test


1222
(I-34)
Tetraethylammonium formate
According to test


1223
(I-34)
Tetraethylammonium hydrogenphosphate
According to test


1224
(I-34)
Tetraethylammonium dihydrogenphosphate
According to test


1225
(I-35)
Ammonium sulphate
According to test


1226
(I-35)
Ammonium lactate
According to test


1227
(I-35)
Ammonium nitrate
According to test


1228
(I-35)
Ammonium thiosulphate
According to test


1229
(I-35)
Ammonium thiocyanate
According to test


1230
(I-35)
Ammonium citrate
According to test


1231
(I-35)
Ammonium oxalate
According to test


1232
(I-35)
Ammonium formate
According to test


1233
(I-35)
Ammonium hydrogenphosphate
According to test


1234
(I-35)
Ammonium dihydrogenphosphate
According to test


1235
(I-35)
Ammonium carbonate
According to test


1236
(I-35)
Ammonium sulphite
According to test


1237
(I-35)
Ammonium benzoate
According to test


1238
(I-35)
Ammonium hydrogenoxalate
According to test


1239
(I-35)
Ammonium hydrogencitrate
According to test


1240
(I-35)
Ammonium acetate
According to test


1241
(I-35)
Tetramethylammonium sulphate
According to test


1242
(I-35)
Tetramethylammonium lactate
According to test


1243
(I-35)
Tetramethylammonium nitrate
According to test


1244
(I-35)
Tetramethylammonium thiosulphate
According to test


1245
(I-35)
Tetramethylammonium thiocyanate
According to test


1246
(I-35)
Tetramethylammonium citrate
According to test


1247
(I-35)
Tetramethylammonium oxalate
According to test


1248
(I-35)
Tetramethylammonium formate
According to test


1249
(I-35)
Tetramethylammonium hydrogenphosphate
According to test


1250
(I-35)
Tetramethylammonium dihydrogenphosphate
According to test


1251
(I-35)
Tetraethylammonium sulphate
According to test


1252
(I-35)
Tetraethylammonium lactate
According to test


1253
(I-35)
Tetraethylammonium nitrate
According to test


1254
(I-35)
Tetraethylammonium thiosulphate
According to test


1255
(I-35)
Tetraethylammonium thiocyanate
According to test


1256
(I-35)
Tetraethylammonium citrate
According to test


1257
(I-35)
Tetraethylammonium oxalate
According to test


1258
(I-35)
Tetraethylammonium formate
According to test


1259
(I-35)
Tetraethylammonium hydrogenphosphate
According to test


1260
(I-35)
Tetraethylammonium dihydrogenphosphate
According to test


1261
(I-36)
Ammonium sulphate
According to test


1262
(I-36)
Ammonium lactate
According to test


1263
(I-36)
Ammonium nitrate
According to test


1264
(I-36)
Ammonium thiosulphate
According to test


1265
(I-36)
Ammonium thiocyanate
According to test


1266
(I-36)
Ammonium citrate
According to test


1267
(I-36)
Ammonium oxalate
According to test


1268
(I-36)
Ammonium formate
According to test


1269
(I-36)
Ammonium hydrogenphosphate
According to test


1270
(I-36)
Ammonium dihydrogenphosphate
According to test


1271
(I-36)
Ammonium carbonate
According to test


1272
(I-36)
Ammonium sulphite
According to test


1273
(I-36)
Ammonium benzoate
According to test


1274
(I-36)
Ammonium hydrogenoxalate
According to test


1275
(I-36)
Ammonium hydrogencitrate
According to test


1276
(I-36)
Ammonium acetate
According to test


1277
(I-36)
Tetramethylammonium sulphate
According to test


1278
(I-36)
Tetramethylammonium lactate
According to test


1279
(I-36)
Tetramethylammonium nitrate
According to test


1280
(I-36)
Tetramethylammonium thiosulphate
According to test


1281
(I-36)
Tetramethylammonium thiocyanate
According to test


1282
(I-36)
Tetramethylammonium citrate
According to test


1283
(I-36)
Tetramethylammonium oxalate
According to test


1284
(I-36)
Tetramethylammonium formate
According to test


1285
(I-36)
Tetramethylammonium hydrogenphosphate
According to test


1286
(I-36)
Tetramethylammonium dihydrogenphosphate
According to test


1287
(I-36)
Tetraethylammonium sulphate
According to test


1288
(I-36)
Tetraethylammonium lactate
According to test


1289
(I-36)
Tetraethylammonium nitrate
According to test


1290
(I-36)
Tetraethylammonium thiosulphate
According to test


1291
(I-36)
Tetraethylammonium thiocyanate
According to test


1292
(I-36)
Tetraethylammonium citrate
According to test


1293
(I-36)
Tetraethylammonium oxalate
According to test


1294
(I-36)
Tetraethylammonium formate
According to test


1295
(I-36)
Tetraethylammonium hydrogenphosphate
According to test


1296
(I-36)
Tetraethylammonium dihydrogenphosphate
According to test


1297
(I-37)
Ammonium sulphate
According to test


1298
(I-37)
Ammonium lactate
According to test


1299
(I-37)
Ammonium nitrate
According to test


1300
(I-37)
Ammonium thiosulphate
According to test


1301
(I-37)
Ammonium thiocyanate
According to test


1302
(I-37)
Ammonium citrate
According to test


1303
(I-37)
Ammonium oxalate
According to test


1304
(I-37)
Ammonium formate
According to test


1305
(I-37)
Ammonium hydrogenphosphate
According to test


1306
(I-37)
Ammonium dihydrogenphosphate
According to test


1307
(I-37)
Ammonium carbonate
According to test


1308
(I-37)
Ammonium sulphite
According to test


1309
(I-37)
Ammonium benzoate
According to test


1310
(I-37)
Ammonium hydrogenoxalate
According to test


1311
(I-37)
Ammonium hydrogencitrate
According to test


1312
(I-37)
Ammonium acetate
According to test


1313
(I-37)
Tetramethylammonium sulphate
According to test


1314
(I-37)
Tetramethylammonium lactate
According to test


1315
(I-37)
Tetramethylammonium nitrate
According to test


1316
(I-37)
Tetramethylammonium thiosulphate
According to test


1317
(I-37)
Tetramethylammonium thiocyanate
According to test


1318
(I-37)
Tetramethylammonium citrate
According to test


1319
(I-37)
Tetramethylammonium oxalate
According to test


1320
(I-37)
Tetramethylammonium formate
According to test


1321
(I-37)
Tetramethylammonium hydrogenphosphate
According to test


1322
(I-37)
Tetramethylammonium dihydrogenphosphate
According to test


1323
(I-37)
Tetraethylammonium sulphate
According to test


1324
(I-37)
Tetraethylammonium lactate
According to test


1325
(I-37)
Tetraethylammonium nitrate
According to test


1326
(I-37)
Tetraethylammonium thiosulphate
According to test


1327
(I-37)
Tetraethylammonium thiocyanate
According to test


1328
(I-37)
Tetraethylammonium citrate
According to test


1329
(I-37)
Tetraethylammonium oxalate
According to test


1330
(I-37)
Tetraethylammonium formate
According to test


1331
(I-37)
Tetraethylammonium hydrogenphosphate
According to test


1332
(I-37)
Tetraethylammonium dihydrogenphosphate
According to test


1333
(I-38)
Ammonium sulphate
According to test


1334
(I-38)
Ammonium lactate
According to test


1335
(I-38)
Ammonium nitrate
According to test


1336
(I-38)
Ammonium thiosulphate
According to test


1337
(I-38)
Ammonium thiocyanate
According to test


1338
(I-38)
Ammonium citrate
According to test


1339
(I-38)
Ammonium oxalate
According to test


1340
(I-38)
Ammonium formate
According to test


1341
(I-38)
Ammonium hydrogenphosphate
According to test


1342
(I-38)
Ammonium dihydrogenphosphate
According to test


1343
(I-38)
Ammonium carbonate
According to test


1344
(I-38)
Ammonium sulphite
According to test


1345
(I-38)
Ammonium benzoate
According to test


1346
(I-38)
Ammonium hydrogenoxalate
According to test


1347
(I-38)
Ammonium hydrogencitrate
According to test


1348
(I-38)
Ammonium acetate
According to test


1349
(I-38)
Tetramethylammonium sulphate
According to test


1350
(I-38)
Tetramethylammonium lactate
According to test


1351
(I-38)
Tetramethylammonium nitrate
According to test


1352
(I-38)
Tetramethylammonium thiosulphate
According to test


1353
(I-38)
Tetramethylammonium thiocyanate
According to test


1354
(I-38)
Tetramethylammonium citrate
According to test


1355
(I-38)
Tetramethylammonium oxalate
According to test


1356
(I-38)
Tetramethylammonium formate
According to test


1357
(I-38)
Tetramethylammonium hydrogenphosphate
According to test


1358
(I-38)
Tetramethylammonium dihydrogenphosphate
According to test


1359
(I-38)
Tetraethylammonium sulphate
According to test


1360
(I-38)
Tetraethylammonium lactate
According to test


1361
(I-38)
Tetraethylammonium nitrate
According to test


1362
(I-38)
Tetraethylammonium thiosulphate
According to test


1363
(I-38)
Tetraethylammonium thiocyanate
According to test


1364
(I-38)
Tetraethylammonium citrate
According to test


1365
(I-38)
Tetraethylammonium oxalate
According to test


1366
(I-38)
Tetraethylammonium formate
According to test


1367
(I-38)
Tetraethylammonium hydrogenphosphate
According to test


1368
(I-38)
Tetraethylammonium dihydrogenphosphate
According to test


1369
(I-39)
Ammonium sulphate
According to test


1370
(I-39)
Ammonium lactate
According to test


1371
(I-39)
Ammonium nitrate
According to test


1372
(I-39)
Ammonium thiosulphate
According to test


1373
(I-39)
Ammonium thiocyanate
According to test


1374
(I-39)
Ammonium citrate
According to test


1375
(I-39)
Ammonium oxalate
According to test


1376
(I-39)
Ammonium formate
According to test


1377
(I-39)
Ammonium hydrogenphosphate
According to test


1378
(I-39)
Ammonium dihydrogenphosphate
According to test


1379
(I-39)
Ammonium carbonate
According to test


1380
(I-39)
Ammonium sulphite
According to test


1381
(I-39)
Ammonium benzoate
According to test


1382
(I-39)
Ammonium hydrogenoxalate
According to test


1383
(I-39)
Ammonium hydrogencitrate
According to test


1384
(I-39)
Ammonium acetate
According to test


1385
(I-39)
Tetramethylammonium sulphate
According to test


1386
(I-39)
Tetramethylammonium lactate
According to test


1387
(I-39)
Tetramethylammonium nitrate
According to test


1388
(I-39)
Tetramethylammonium thiosulphate
According to test


1389
(I-39)
Tetramethylammonium thiocyanate
According to test


1390
(I-39)
Tetramethylammonium citrate
According to test


1391
(I-39)
Tetramethylammonium oxalate
According to test


1392
(I-39)
Tetramethylammonium formate
According to test


1393
(I-39)
Tetramethylammonium hydrogenphosphate
According to test


1394
(I-39)
Tetramethylammonium dihydrogenphosphate
According to test


1395
(I-39)
Tetraethylammonium sulphate
According to test


1396
(I-39)
Tetraethylammonium lactate
According to test


1397
(I-39)
Tetraethylammonium nitrate
According to test


1398
(I-39)
Tetraethylammonium thiosulphate
According to test


1399
(I-39)
Tetraethylammonium thiocyanate
According to test


1400
(I-39)
Tetraethylammonium citrate
According to test


1401
(I-39)
Tetraethylammonium oxalate
According to test


1402
(I-39)
Tetraethylammonium formate
According to test


1403
(I-39)
Tetraethylammonium hydrogenphosphate
According to test


1404
(I-39)
Tetraethylammonium dihydrogenphosphate
According to test









Inventive crop protection compositions may also comprise further components, for example surfactants or dispersion aids or emulsifiers.


Useful nonionic surfactants or dispersion aids include all substances of this type typically useable in agrochemical formulations. Preference is given to polyethylene oxide-polypropylene oxide block copolymers polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and/or propylene oxide, and also polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone, and also copolymers of (meth)acrylic acid and (meth)acrylic esters, and also alkyl ethoxylates and alkylaryl ethoxylates, which may optionally have been phosphated and may optionally have been neutralized with bases, the examples including sorbitol ethoxylates, and also polyalkylenamine derivatives.


Useful anionic surfactants include all substances of this type which are typically used in agrochemical formulations. Preference is given to alkali metal and alkaline earth metal salts of alkylsulphonic acids or alkylarylsulphonic acids.


A further preferred group of anionic surfactants or dispersion aids is that of salts, each of which is of low solubility in vegetable oil, of polystyrenesulphonic acids, those of polyvinylsulphonic acids, those of naphthalenesulphonic acid-formaldehyde condensation products, those of condensation products of naphthalenesulphonic acid, phenol and formaldehyde, and those of lignosulphonic acid.


Useful additives which may be present in the inventive formulations include emulsifiers, foam inhibitors, preservatives, antioxidants, dyes and inert filler materials.


Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and/or propylene oxide, ethoxylated arylalkylphenols, and also ethoxylated and propoxylated arylalkylphenols, and also sulphated or phosphated arylalkyl ethoxylates or ethoxypropoxylates, examples including sorbitan derivatives such as polyethylene oxide-sorbitan fatty acid esters and sorbitan fatty acid esters.


The examples which follow serve to illustrate the invention and should in no way be interpreted as restrictive.







EXAMPLE 1


Aphis gossypii Test (APHIGO Spray Treatment)


Solvent: 7 parts by weight of dimethylformamide


Emulsifier: 2 parts by weight of alkylaryl polyglycol ether


To prepare a ready-to-use active ingredient formulation, 1 part by weight of active ingredient is mixed with the specified amounts of solvent and emulsifier and the concentrate is diluted with emulsifier-containing water to the desired concentration. In the case that addition of ammonium salts, penetrants, or ammonium salts and penetrants is required, they are pipetted in each case into the finished preparation solution after dilution in a concentration of 1000 ppm each.


Cotton leaves (Gossypium hirsutum) highly infested by the cotton aphid (Aphis gossypii) are sprayed with an active ingredient formulation with the desired concentration.


After the desired period, the kill rate in % is determined. 100% means that all aphids have been killed; 0% means that no aphids have been killed.


In this test, for example, the following compounds of the preparation examples exhibit good activity:














Active
Concentration
Kill in % after 6 days












ingredient
in ppm
a.i.
+AMS
+RME
+AMS + RME















I-1
0.8
25
20
50
95


I-2
0.8
15
98
90
15


I-3
0.8
0
15
35
90


I-4
4
20
20
65
85


I-5
0.8
0
5
15
85


I-6
0.8
45
55
80
70



0.16
0
0
25
40


I-7
0.8
60
60
70
80


I-8
0.8
20
30
60
75


I-9
0.8
0
0
15
30


I-10
4
65
99
85
99


I-11
0.8
15
55
95
99


I-12
4
55
80
85
75



0.8
0
5
10
25


I-13
4
80
65
75
75



0.8
0
5
5
20


I-14
0.8
0
5
40
70


I-15
4
60
85
98
98


I-16
4
80
95
98
90



0.8
0
10
10
5


I-17
0.8
0
20
40
40


I-18
0.8
65
50
75
90


I-19
4
15
40
85
80



0.8
0
0
40
50


I-20
4
40
40
85
60


I-21
4
10
5
50
45


I-22
4
60
70
55
65



0.8
25
20
30
45


I-23
0.8
10
15
50
25


I-24
20
50
85
85
90


I-25
4
65
60
75
100


I-26
0.8
90
70
98
98


I-28
20
55
90
95
95



4
50
60
75
80


I-29
4
50
65
50
75


I-30
20
80
100
100
95


I-31
0.8
50
65
80
80



0.16
0
30
15
60


I-32
20
0
100
100
100


I-33
4
30
25
65
15


I-34
100
15
20
40
45


I-35
100
60
75
85
75


I-36
100
55
98
80
99



20
30
15
45
65


I-37
20
55
45
40
65


I-38
100
45
90
70
55


I-39
100
45
45
60
60





AMS = Ammonium sulphate


RME = Rapeseed oil methyl ester (formulated for use as 500 EW)






EXAMPLE 2


Myzus persicae Test (MYZUPE)


Solvent: 7 parts by weight of dimethylformamide


Emulsifier: 2 parts by weight of alkylaryl polyglycol ether


To prepare an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the given amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. In the case that addition of ammonium salts, penetrants, or ammonium salts and penetrants is required, they are pippetted in each case into the finished preparation solution after dilution in a concentration of 1000 ppm each.


Pepper plants (Capsicum annuum) highly infested by the green peach aphid (Myzus persicaei) are treated by spraying with the active ingredient formulation in the desired concentration.


After the desired time, the kill rate in % is determined. 100% means that all animals have been killed; 0% means that no animals have been killed.


In this test, for example, the following compounds of the preparation examples exhibit good activity:














Active
Concentration
Kill in % after 6 days












ingredient
in ppm
a.i.
+AMS
+RME
+AMS + RME















I-1
4
35
95
99
99



0.8
0
0
25
35


I-2
0.8
0
50
98
30


I-3
4
0
80
85
100


I-4
4
15
80
90
100


I-5
0.8
0
0
5
70


I-6
4
60
85
100
100


I-7
0.8
55
45
80
90


I-8
0.8
40
50
95
95


I-9
4
0
15
60
70


I-10
0.8
0
0
90
99


I-11
0.8
85
95
99
99



0.16
0
0
0
90


I-12
4
85
95
100
95



0.8
5
0
10
45


I-13
0.8
5
5
35
90


I-14
4
25
60
95
95


I-15
0.8
0
0
80
0


I-16
4
95
99
98
100



0.8
5
0
10
10


I-17
4
95
99
100
100



0.8
0
5
35
25


I-18
4
80
95
100
100



0.8
25
0
98
70


I-19
20
80
80
98
100


I-20
20
40
85
98
95



4
15
35
85
55


I-21
100
50
70
90
65


I-22
20
65
80
85
90



4
5
0
70
80


I-23
0.8
35
10
75
80


I-24
20
75
90
95
98



4
15
20
85
75


I-25
4
0
50
80
55


I-26
0.8
65
55
100
95


I-28
4
50
15
90
95


I-29
0.8
0
0
30
50


I-30
0.8
5
25
95
45


I-31
0.8
50
80
100
95


I-32
20
15
100
98
100



4
0
60
70
80


I-33
100
40
45
95
95


I-34
100
40
50
85
85


I-35
100
75
75
98
95


I-36
20
40
25
85
85


I-37
20
20
35
90
95


I-38
4
5
5
65
70


I-39
100
85
90
95
95



20
20
25
80
30





AMS = Ammonium sulphate


RME = Rapeseed oil methyl ester (formulated for use as 500 EW)





Claims
  • 1. Composition comprising at least one active insecticidal ingredient of the formula (I)
  • 2. Composition according to claim 1, characterized in that the active ingredient content is between 0.5 and 50% by weight.
  • 3. Composition according to claim 1 or 2, characterized in that G is nitrogen.
  • 4. Composition according to any one of claims 1 to 3, characterized in that R10 is hydrogencarbonate, tetrafluoroborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate, oxalate, carbonate, pentaborate, sulphite, benzoate, hydrogenoxalate, hydrogencitrate, methylsulphate or tetrafluoroborate.
  • 5. Composition according to claim 4, characterized in that R10 is lactate, sulphate, nitrate, thiosulphate, thiocyanate, citrate, oxalate or formate.
  • 6. Composition according to claim 5, characterized in that R10 is sulphate.
  • 7. Composition according to claim 6, characterized in that the salt of the formula (II) is ammonium sulphate.
  • 8. Composition according to any one of claims 1 to 7, characterized in that it comprises at least one penetrant.
  • 9. Composition according to claim 8, characterized in that the penetrant comprises a fatty alcohol alkoxylate of the formula (III) R—O-(-AO)v—R′  (III)
  • 10. Composition according to claim 8, characterized in that the penetrant is an ester of a vegetable oil.
  • 11. Composition according to claim 8, characterized in that the penetrant is rapeseed oil methyl ester.
  • 12. Composition according to any one of claims 8 to 11, characterized in that the content of penetrant is 1 to 95% by weight.
  • 13. Process for controlling harmful insects, characterized in that a composition according to one or more of claims 1 to 12 is applied to insects or their habitat undiluted or diluted in such an amount that an effective amount of the active insecticidal ingredients present acts on the insects or their habitat.
  • 14. Process for enhancing the action of crop protection compositions comprising an active ingredient of the formula (I) according to claim 1, characterized in that the ready-to-used composition (spray liquor) is prepared using a salt of the formula (II) according to claim 1.
  • 15. Process according to claim 13 or 14, characterized in that the spray liquor is prepared using a penetrant.
  • 16. Process according to any one of claims 13 to 15, characterized in that the salt of the formula (II) is present in the spray liquor in an end concentration of 0.5 to 80 mmol/l.
  • 17. Process according to claim 15, characterized in that the penetrant is present in the spray liquor in an end concentration of 0.1 to 10 g/l.
  • 18. Process according to claim 17, characterized in that the penetrant is present in an end concentration of 0.1 to 10 g/l and the salt of the formula (II) in an end concentration of 0.5 to 80 mmol/l.
  • 19. Use of a salt of the formula (II) according to claim 1 for enhancing the action of a crop protection composition comprising an active ingredient of the formula (I) according to claim 1, characterized in that the salt is used in the preparation of a ready-to-use crop protection composition (spray liquor).
  • 20. Use according to claim 19, characterized in that the salt of the formula (II) is present in the ready-to-use crop protection composition in a concentration of 0.5 to 80 mmol/l.
  • 21. Use according to claim 19 or 20, characterized in that the salt is used in the preparation of a ready-to-use crop protection composition (spray liquor) which further comprises a penetrant.
Priority Claims (1)
Number Date Country Kind
07109732.3 Jun 2007 EP regional
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/EP08/04217 5/28/2008 WO 00 11/25/2009