WO2018054723A1 - Pyridine compounds for controlling phytopathogenic harmful fungi - Google Patents

Pyridine compounds for controlling phytopathogenic harmful fungi Download PDF

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WO2018054723A1
WO2018054723A1 PCT/EP2017/072897 EP2017072897W WO2018054723A1 WO 2018054723 A1 WO2018054723 A1 WO 2018054723A1 EP 2017072897 W EP2017072897 W EP 2017072897W WO 2018054723 A1 WO2018054723 A1 WO 2018054723A1
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alkyl
compounds
halogen
alkoxy
cycloalkyl
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PCT/EP2017/072897
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French (fr)
Inventor
Bernd Mueller
Erica CAMBEIS
Jan Klaas Lohmann
Ana Escribano Cuesta
Nadine RIEDIGER
Marcus Fehr
Antje Wolf
Christian Winter
Violeta TERTERYAN-SEISER
Wassilios Grammenos
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

Abstract

The present invention relates to compounds of formula (I) wherein the variables are defined as given in the description and claims. The invention further relates to uses and composition for compounds of formula I.

Description

PYRIDINE COMPOUNDS FOR CONTROLLING PHYTOPATHOGENIC HARMFUL FUNGI
Description
The present invention relates to pyridine compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates to processes for preparing these compounds, intermediates, processes for preparing such intermediates, and to compositions comprising at least one compound I.
In many cases, in particular at low application rates, the fungicidal activity of the known fungi- cidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.
Surprisingly, this object is achieved by the use of the inventive pyridine compounds of formula I having favorable fungicidal activity against phytopathogenic fungi.
Accordingly, the present invention relates to the com ounds of formula I
Figure imgf000002_0001
is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted by groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted by groups R1 b which independently of one another are selected from:
R1 b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R2 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R2 are unsubstituted or substituted by groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or
substituted by groups R2b which independently of one another are selected from:
R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3;
R4 is Ci-C6-alkyl, which is substituted by a five-, six- or ten-membered heteroaryl, wherein the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S;
wherein the alkyl moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R4a halogen, OH, CN, N02, SH, NH2, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogenalkoxy; and
wherein one or two CH2 groups of alkyl moieties of R4 may be replaced by a group independently selected from C(=0), (=CH2) or form a three- four- five or six-membered carbocyle which han include optionally one O as ring member; and
wherein the heteroaryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from:
R halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4- alkyl), N(C(=0)d-C4-alkyl)2, NH-S02-Rx, C C4-alkyl, C C4-alkoxy, C C4-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx is as defined above;
n is 0, 1 , 2 or
R5 is H;
R6 is H;
A is selected from below group:
Figure imgf000004_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon at- oms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I .; wherein
Y is in each case independently selected from H, F, CI, Br, I , OH, CN, NO2, Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- Ce-alkoxy, Ci-C6-halogenalkoxy, ORY, S(0)zRY, NHRY, N(RY)2, C(=0)RY, C(=0)ORY, NH(C(=0)RY, N(C(=0)RY)2, NH-S02-Rx, C(RY)=NO(RY),
RY is in each case independently selected from Ci-C6-alkyl, Ci-C6-halogenalkyl, C2- C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cy- cloalkyl, C3-C6-halogencycloalkyl and phenyl; wherein the phenyl group is unsub- stituted or substituted from the group consisting of halogen, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
z is 0, 1 or 2;
wherein the acyclic moieties of Y are unsubstituted or substituted by groups Ya which independently of one another are selected from:
Ya halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents RY1a selected from the group consisting of halogen, OH, CN, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocyclic and phenyl moieties of Y are unsubstituted or substituted by groups Yb which independently of one another are selected from:
Yb halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
Rx is as defined above;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl),
N(CrC4-alkyl)2, NH(C(=0)d-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy,
Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein Rx is defined above; wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-al- kyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl and phenyl; and
wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which independently of one another are selected from: R78a halogen, OH , CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;
is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C4-alkyl), N(Ci-C4-alkyl)2, N H (C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4-alkynyl)2, N H(C3-C6-cycloalkyl), N (C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4- alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, Ci-C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H (Ci- Ce-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3- C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S; wherein
Rx is as defined above;
RY is as defined above;
wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH , CN , d-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or
substituted by groups R9b which independently of one another are selected from:
R9b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from the substituents as defined for R9, wherein the possible substituents for R10 are R10a and R10b , respectively, which correspond to R9a and R9b, respectively; R9, R10 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and SC>2Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m, wherein m is 0, 1 , 2, 3 or 4;
R11 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N,
O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R11 are unsubstituted or substituted with identical or different groups R11a which independently of one another are selected from:
R11a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R11 unsubstituted or substituted with identical or different groups R11b which independently of one another are selected from:
R11b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; with the provisio that if A is phenyl,
R1 is H;
and the N-oxides and the agriculturally acceptable salts thereof.
Compounds of formula I can be accessed e.g. starting from alcohols of type II with nitriles of type III in the presence of an acid in an organic solvent (see for example US 2008/0275242 or WO2005/070917). Preferably, sulfuric acid or a sulfonic acid, in particular triflic acid, are used as acid. Most suitable solvents are hydrocarbons, preferably benzene or dichloromethane. In the following schemes, the optionally substituted phenyl or heteroaryl formed by W together with the partially substituted pyridine ring to which it is attached is sketched by a semicircle named "A":
Figure imgf000008_0001
I
Depending on the nature of the starting materials, the reaction is performed at a temperature from -40°C to 200°C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room or ambient temperature (about 23°C) to 80°C.
Nitriles of type III are either commercially available or can be prepared by a skilled person from the corresponding halides following literature precedures (see, for example Journal of Organic Chemistry, 76(2), 665-668; 201 1 ; Angewandte Chemie, International Edition, 52(38), 10035- 10039; 2013; WO2004/013094).
Alcohols of type II can be prepared as described below. A skilled person will realize that compounds of type lllb can be reacted with organometallic reagents, preferably alkyl Grignard or al- kyi-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type II.
Figure imgf000008_0002
lllb
Alternatively, alcohols of type II can be prepared from epoxydes Ilia and compounds VI (see below):
"metallation"
Figure imgf000008_0003
The metallation reaction may preferably be carried out using Lithium-organic compounds, such as for example n-butyl lithium, sec-butyl lithium or tert-butyl lithium to result in an exchange of halogen by lithium. Also suitable is the reaction with magnesium resulting in the formation of the respective Grignard reagents. A further possibility is the use of other Grignard reagents such as isopropyl-magnesium-bromide instead of Mg.
A typical preparation of compounds of type lllb can be achieved by reacting compounds of type IV with organometallic reagents, preferably alkyl Grignard or alkyl-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type III as previously reported (see for example WO2012051036; WO201 1042918).
Figure imgf000009_0001
Compounds of type IV can be accessed by reacting a carbonyl compound of type V, preferably a carboxylic acid (X = OH) or an acid chloride (X = CI), with NH(OR')R", wherein R' and R" are selected from (Ci-C4)-alkyl, most preferably being methyl, in an organic solvent, preferably THF or dichloromethane. Typically the reaction is performed in a range between 0 °C and ambient temperature in the presence of an organic base, preferably N(C2Hs)3 or pyridine (see e.g. US 20130324506; Tetrahedron: Asymmetry, 17(4), 508-51 1 ; 2006). If X = OH, the addition of an activating reagent, preferably a carbodiimide, may be preferred (see for example ChemMedChem, 7(12), 2101 -21 12; 2012; 201 1038204; Journal of Organic Chemistry, 76(1 ), 164-169; 201 1 ).
Figure imgf000009_0002
If required, compounds of type V can be prepared from the corresponding aryl halides of type VI (Hal is halogen, preferably Br or I). As described (Tetrahedron, 68(9), 21 13-2120; 2012; Chemical Communications (Cambridge, United Kingdom), 49(60), 6767-6769; 2013), aryl halides will react with compounds of type VII in the presence of a transition metal catalyst, preferably a cop- per(l) salt, in an organic solvent, preferably DMF or DMSO, at elevated temperatures. Typically a base, preferably potassium phosphate, is added.
Figure imgf000009_0003
If appropriate, compounds of type II can be prepared as follows. A known or commercially available compound of type VIII can be reacted with an organometallic reagent of type IX, preferably a Grignard or an organolithium reagent, readily prepared by a skilled person. Preferably, the reaction is performed in a temperature range from -78 °C to room temperature under inert conditions in an ethereal solvent.
Figure imgf000009_0004
Alternatively compounds I in which R5 stands for hydrogen can be accessed by reacting a ni- trile III with an olefin ll# under acidic conditions as described elsewhere (US 7632783, B2, page 60, method A).
Figure imgf000010_0001
I
Alternatively compounds I can be prepared via intramolecular reaction of amide X when A is an electron-rich carbon- or heterocycle. The intramolecular cyclization will take place in the presence of a dehydrating agent in an organic solvent (WO 2008143263, Synthetic Communications 2007, 37, 1331 -1338.). Preferably, phosphoryl chloride (POCI3), POCI3/P2O5, H3PO4/P2O5, SnCU or BF3 are used as dehydrating agent. Most suitable solvents are hydrocarbons, prefera- bly benzene, toluene or acetonitrile. Alternatively halogenated solvents can be used, for example dichloromethane, chloroform or chlorobenzene.
Figure imgf000010_0002
Depending on the nature of starting materials, the reaction is performed at temperature from - 40°c to 200 °C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room temperature to 100°C.
Amides of type X can accessed by reacting a carbonyl of type XI, preferably a carboxylic acid (X = OH) or an acid chloride (X = CI), with an amines of type XII in an organic solvent, preferably THF or dichloromethane. Typically the reaction is performed in a range between 0°C and room temperature in the presence of an organic base, preferably N(C2Hs)3 or pyridine (see e.g. WO 8303968). If X = OH, the addition of an activating agent, preferably a carbodiimide or acid chloride, may be preferred (see e.g Bioorganic & Medicinal Chemistry, 2010, 18, 3088-31 15).
Figure imgf000010_0003
If required, compounds of type XII can be synthesized from the correspond nitriles. As de- scribed Synlett. 2007, 4 652-654 or Tetrahedron 2012, 68, 2696-2703, nitriles will react with or- ganometallic agents, preferably Grignard or Lithium reagent, in ethereal solvents, preferably THF at low temperature and under inert conditions to furnish compounds of type XII. The synthesis of compounds of type XII can take place in two steps or one pot.
Figure imgf000011_0001
In addtion, compound I can also be prepare by nucleophilic substitution on compound IA. Different^ nucleophiles can be used from N-nucleophiles, such as imidazole or pyridines to organo- metallic species, such as Grignard (see for example, Tetrahedron Letters, 2010, 51 (1 1 ), 1451- 1454; Faming Zhuanli Shenqing, 2013, 103373982). The reaction takes places in an organic solvent, most suitable solvents are hydrocarbons, preferably THF, benzene or dichloromethane. The reaction is performed at temperature from -40°c to 200 °C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C.
Figure imgf000011_0002
Alternatively, compound IB can be easily transformed into compound I by a skilled person. For example,
-Tetrazol can be obtaines via reaction with azides (for example HN3 TMSN3, or NaN3). Sometimes in the presence of a metal catalyst, such as ZnC , Bu2SnO, etc. The reaction takes plaxes with or without an organic solvent, such as toluene, THF, DMF, MeOH, BuOH, ether, etc in the presence of a base, for examples Et3N. The reaction is performed at temperature from 0 ° C to 200 °C (see for example, Synthesis, 2013, 45(8), 1051-1059; Tetrahedron Letters, 1989, 30(10), 1229-1232)
-2-Pyridines can be obtained via reactions with acytelene in the presence of a methal catalyst. The reaction takes plaxes with or without an organic solvent, such as toluene. Typical methal catalyst are from Co or Rh. The reaction is performed at temperature from 0 °C to 200 °C See for example, Synthesis, 1976, (1 ), 26-28; Angewandte Chemie, International Edition, 2009, 48(10), 1810-1813)
Figure imgf000012_0001
IB
The N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxi- dizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981 ) or ox- one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ). The oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
In the following, the intermediate compounds are further described. A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.
The intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X: The intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X:
Figure imgf000012_0002
The compounds of formula X have fungicidal activity and the details below referring to the pounds I also apply to compounds X.
Particular embodiments of the compounds X are the following compounds
Figure imgf000013_0001
Xm Xn Xo Xp
If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.
In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term "Cn-Cm" indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
The term "halogen" refers to fluorine, chlorine, bromine and iodine.
The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime- thylpropyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl- butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri- methylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methylpropyl. Likewise, the term "C2-C4-alkyl" refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (iso-butyl), 1 ,1-dimethylethyl (tert.-butyl).
The term "Ci-C6-halogenalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "Ci-C2-halogenalkyl" groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlor- ofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-
2.2- difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.
The term "Ci-C6-hydroxyalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by OH groups.
The term "Ci-C4-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above). Likewise, the term "CrC6-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above).
The term "C2-C6-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position. Examples are "C2-C4-alkenyl" groups, such as ethenyl, 1 -propenyl, 2-propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.
The term "C2-C6-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4-al- kynyl" groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-
3- ynyl, 1 -methyl-prop-2-ynyl.
The term "Ci-C6-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group. Examples are "C1-C4- alkoxy" groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1 -methyhprop- oxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.
The term "Ci-C6-halogenalkoxy" refers to a Ci-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "CrC4-halogenalkoxy" groups, such as OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro- ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,
2.3- difluoro-"propoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -fluo- romethyl-2-fluoroethoxy, 1 -chloromethyl-2-chloroethoxy, 1 -bromomethyl-2-bromoethoxy,
4- fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
The term "C2-C6-alkenyloxy" refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are "C2-C4-alkenyloxy" groups.
The term "C2-C6-alkynyloxy" refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are "C2-C4-alkynyloxy" groups.
The term "C3-C6-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C3-Cio-cycloalkyl".
The term "C3-C6-cycloalkenyl" refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-mem- bered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cy- clopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four- , five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloal- kenyl".
The term "C3-C8-cycloalkyl-CrC4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
The term "Ci-Ce-alkylthio" as used herein refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term "Ci- C6-halogenalkylthio" as used herein refers to straight-chain or branched halogenalkyi group hav- ing 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the halogenalkyi group.
The term "C(=0)-CrC6-alkyl" refers to a radical which is attached through the carbon atom of the group C(=0) as indicated by the number valence of the carbon atom. The number of valence of carbon is 4, that of nitrogen is 3. Likewise the following terms are to be construed: NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, C(=0)-NH(Ci-C6- alkyl), C(=0)-N(Ci-C6-alkyl)2.
The term "saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S" is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S. For example:
a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azet- idine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isox- azolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazoli- dinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5- yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxa- zolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5- yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4- yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyra- zol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropy- razol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydro- pyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihy- dropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidi- nyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tet- rahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hex- ahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4- hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; and
a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroaze- pinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahy- dro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-,-4-,-5- ,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4-oxa- zepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals.
The term "substituted" refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.
The term "5-or 6-membered heteroaryl" or "5-or 6-membered heteroaromatic" refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,
a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl; or
a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyri- dazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl. Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammo- nium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
Depending on the substitution pattern, the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure di- astereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or dia- stereomers and their mixtures are subject matter of the present invention.
In the following, particular embodiments of the inventive compounds are described. Therein, specific meanings of the respective substituents are further detained, wherein the meanings are in each case on their own but also in any combination with one another, particular embodiments of the present invention.
Furthermore, in respect of the variables, generally, the embodiments of the compounds I also apply to the intermediates.
R1 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(C C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted with identical or different groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted with identical or different groups R1b which independently of one another are selected from:
R1b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R1 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring.
According to one embodiment of formula I, R1 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another embodiment of formula I, R1 is hydrogen.
According to still another embodiment of formula I, R1 is halogen, in particular Br, F or CI, more specifically F or CI.
According to another embodiment of formula I, R1 is F
According to another embodiment of formula I, R1 is CI
According to another embodiment of formula I, R1 is Br.
According to still another embodiment of formula I, R1 is OH.
According to still another embodiment of formula I, R1 is CN.
According to still another embodiment of formula I, R1 is NO2.
According to still another embodiment of formula I, R1 is SH.
According to still another embodiment of formula I R1 is NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-RX, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy.
According to still another embodiment of formula I, R1 is Ci-C6-alkyl, in particular Ci-C4-alkyl,
Figure imgf000018_0001
According to still another embodiment of formula I, R1 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF2CHF2.
According to still another embodiment of formula I, R1 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH3)=CH2, CH=CCI2, CH=CF2, CCI=CCI2, CF=CF2, CH=CH2, CH2CH=CCI2, CH2CH=CF2, CH2CCI=CCI2, CH2CF=CF2, CCI2CH=CCI2, CF2CH=CF2, CCI2CCI=CCI2, CF2CF=CF2.
According to still another embodiment of formula I, R1 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C3-C4-alkynyl or C3-C4-halogenalkynyl, such as C≡CH, C≡CCI, C≡CF, CH2C≡CH, CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I, R1 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R1 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to still another embodiment of formula I R1 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I , R1 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R1 b as defined and preferably herein.
According to still another embodiment of formula I , R1 is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I , R1 is unsubstituted aryl or aryl that is substituted by one, two, three or four R1 b, as defined herein. In particular, R1 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R1 b, as defined herein.
According to still another embodiment of formula I , R1 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R1 is 5- or 6-membered heteroaryl that is substituted by one, two or three R1 b, as defined herein.
According to still another embodiment of formula l ,R1 is in each case independently selected from hydrogen, halogen, OH , CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R1 are not further substituted or carry one, two, three, four or five identical or differ- ent groups R1a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1 b as defined below.
According to still another embodiment of formula I , R1 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particu- lar independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
R1a are the possible substituents for the acyclic moieties of R1.
R1a according to the invention is independently selected from halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R11 a selected from the group consisting of halogen, OH , Ci-C4-alkyl, CrC4-halogenalkyl, CrC4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
In to one embodiment R1a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R1a is
independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R1a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I , R1a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R1a is independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
R1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R1.
R1b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R1b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy. Specifically, R1b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R1b is independently selected from halogen, CN, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, CHF2, OCHF2, OCF3, OCH3, C3-C6-cycloalkyl, C3- C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R1b is independently selected from halogen, OH, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-C - cyclopropyl, OCH F2 and OCF3.
Rx in the substituent NH-S02-RX is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted by one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy. In particular, Rx is in each case independently selected from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted by one, two or three Rx1 independently selected from Ci-C2-alkyl, more specifically Rx is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted by one CH3., more specifically S02-Rx is the tosyl group ("Ts").
Particularly preferred embodiments of R1 according to the invention are in Table P1 below, wherein each line of lines P1 -1 to P1-16 corresponds to one particular embodiment of the invention. Thereby, for every R1 that is present in the inventive compounds, these specific
embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring:
Table P1 :
"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.
Figure imgf000020_0001
Figure imgf000021_0001
R2 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R2 are unsubstituted or substituted with identical or different groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or substituted with identical or different groups R2b which independently of one another are selected from:
R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalky, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R2 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of the other R2 that may be present in the ring.
According to one embodiment of formula I , R2 is H, halogen or Ci-C6-alkyl, in particular H , CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another of formula I , R2 is halogen, in particular Br, F or CI, more specifically F or CI.
According to still another embodiment of formula I , R2 is hydrogen.
According to another embodiment of formula I , R2 is F
According to another embodiment of formula I , R2 is CI
According to another embodiment of formula I , R2 is Br.
According to still another embodiment of formula I , R2 is OH.
According to still another embodiment of formula I , R2 is CN. According to still another embodiment of formula I, R2 is NO2.
According to still another embodiment of formula I, R2 is SH.
In a further specific embodiment R2 is NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-Rx, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or CrC4-halogenalkoxy.
According to still another embodiment of formula I, R2 is Ci-C6-alkyl, in particular CrC4-alkyl, such as CH3 or CH2CH3.
According to still another embodiment of formula I, R2 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF2CHF2.
According to still a further embodiment, R2 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, CH=CCI2, CH=CF2, CCI=CCI2, CF=CF2, CH=CH2, CH2CH=CCI2, CH2CH=CF2, CH2CCI=CCI2, CH2CF=CF2, CCI2CH=CCI2, CF2CH=CF2, CCI2CCI=CCI2, or CF2CF=CF2.
According to still a further embodiment, R2 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH2C≡CH, CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I, R2 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R2 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
In a further specific embodiment R2 is C3-C6-cycloalkyl, in particular cyclopropyl.
In a further specific embodiment, R2 is C3-C6-cycloalkyl, for example cyclopropyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R2b as defined and preferably herein.
According to still another embodiment of formula I, R2 is C3-C6-halogencycloalkyl. In a special embodiment R2 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R2 is unsubstituted aryl or aryl that is substituted by one, two, three or four R2b, as defined herein. In particular, R2 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R2b, as defined herein.
According to still another embodiment of formula I, R2 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R2 is 5- or 6-membered heteroaryl that is substituted by one, two or three R2b, as defined herein.
According to still another embodiment of formula I, R2 is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R2 are not further substituted or carry one, two, three, four or five identical or different groups R2a as defined below and wherein the cycloalkyl moieties of R2 are not further substituted or carry one, two, three, four or five identical or different groups R2b as defined below.
According to still another embodiment of formula I, R2 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
R2a are the possible substituents for the acyclic moieties of R2.
R2a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br. According to one embodiment R2a is independently selected from halogen, OH, CN, C1-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R2a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R2a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R2a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R2a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
R2b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R2.
R2b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R2b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R2b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R2b is independently selected from halogen, C-i- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R2b is independently selected from halogen, CN, OH, CH3, OCH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl 1 ,1-F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl , OCHF2 and OCF3.
Particularly preferred embodiments of R2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-16 corresponds to one particular embodiment of the inven- tion. Thereby, for every R2 that is present in the inventive compounds, these specific embodiments and preferences apply independently of the meaning of any other R2 that may be present in the ring:
Table P2:
"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.
Figure imgf000024_0001
Figure imgf000024_0002
Figure imgf000024_0003
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3.
According to one embodiment R3 is CH3.
According to another embodiment R3 is CH2F.
According to still another embodiment R3 is CHF2.
According to another embodiment R3 is CF3.
R4 is CrC6-alkyl, which is substituted by a five-, six- or ten-membered heteroaryl, wherein the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S;
wherein the alkyl moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R4a halogen, OH, CN, N02, SH, NH2, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogenalkoxy; and
wherein one or two CH2 groups of alkyl moieties of R4 may be replaced by a group independently selected from C(=0), (=CH2) or form a three- four- five or six-membered carbocyle which han include optionally one O as ring member; and
wherein the heteroaryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from: R4b halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4- alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, Ci-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx is as defined above;
n is 0, 1 , 2.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains one N as ring member.
According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains two N as ring members.
According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains three N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b. According to one specific embodiment thereof, said 5-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains one S as ring member.
According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains one S and one N as ring mem- bers. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains one S and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I, it is substituted by R4b.
According to a further specific embodiment of formula I, R4 is Ci-C6-alkyl, especially CH2 subsitited by a 5-membered saturated heteroaryl which contains one oxygen and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one oxygen and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially CH2 subsitited by a 6-membered saturated heteroaryl which one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially CH2 subsitited by a 10-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b. According to one specific embodiment thereof, said 10-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) N.
According to a further specific embodiment of formula I , R4 is Ci-C6-alkyl, especially CH2 subsitited by a 10-membered saturated heteroaryl which one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R4b. According to still another embodiment of formula I , it is substituted by R4b.
According to still another embodiment of formula I , R4 is Chb substituted by a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl- 1-yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4- thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl.
According to still another embodiment of formula I , R4 is CH2 substituted by a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2- yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
Particularly preferred embodiments of R4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-51 corresponds to one particular embodiment of the invention, wherein P4-1 to P4-51 are also in any combination with one another a preferred embodi- ment of the present invention. The connection point to the carbon atom, to which R4 is bound is marked with "#" in the drawings.
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Particularly preferred embodiments of combinations of R3 and R4 according to the invention are in Table P34 below, wherein each line of lines P34-1 to P34-204 corresponds to one particular embodiment of the invention, wherein P34-1 to P34-204 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R3 and R4 are bound is marked with * in the drawings.
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
R4a are the possible substituents for the the acyclic moieties of R4 and the R4a are in each case independently selected from halogen, OH , CN , NO2, SH , N H2, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogen- alkoxy;
wherein one or two CH2 groups of alkyl moieties of R4 may be replaced by a group independently selected from C(=0), (=CH2) or form a three- four- five or six-membered carbocyle which han include optionally one O as ring member; and
According to still another embodiment of formula I, one or two CH2 groups of alkyl moieties of R4 may be replaced by a group independently selected from C(=0), (=CH2) or form a three- four- five or six-membered carbocyle which han include optionally one O as ring member.
According to still another embodiment of formula I, one or two CH2 groups of alkyl moieties of R4 may be replaced by C(=0). According to still another embodiment of formula I, one or two CH2 groups of alkyl moieties of R4 may be replaced by (=CH2).
According to still another embodiment of formula I, one or two CH2 groups of alkyl moieties of R4 may form a three- four- five or six-membered carbocyle which han include optionally one O as ring member.
According to still another embodiment of formula I, one or two CH2 groups of alkyl moieties of R4 are substituted by R4a which is halogen such as F or CI, most preferably F.
R4b are the possible substituents for the heteroaryl moieties, which are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, CrC4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and CrC4-halogenalkoxy.
According to one preferred embodiment, R4b is in each case independently selected from halogen, OH, CN, SH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C1-C6- alkylthio and S(0)n-Ci-C6-alkyl. According to one further preferred embodiment, R4b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkyl, Ci-C6-halogen- alkoxy and S(0)n-Ci-C6-alkyl. According to one further particular embodiment, R4b is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl. According to one further particular embodiment, R4b is in each case independently selected from halogen, such as F, CI and Br. According to one further particular embodiment, R4b is in each case independently selected from Ci-C6-alkoxy, such as OCH3. According to one further particular embodiment, R4b is in each case independently selected from Ci-C4-halogenalkoxy, such as OCHF2 and OCF3. According to one further particular embodiment, R4b is in each case independently selected from S(0)n-Ci-C6-alkyl. such as SO2CH3.
R5 is H.
R6 is H.
A is selected from below group:
Figure imgf000040_0001
Figure imgf000041_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.
According to one preferred embodiment, A is
Figure imgf000041_0002
According to one preferred embodiment, A is
Figure imgf000041_0003
According to one preferred embodiment, A is
Figure imgf000041_0004
According to one preferred embodiment, A is
Figure imgf000041_0005
Y is in each case independently selected from H, F, CI, Br, I , OH, CN, NO2, Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- Ce-alkoxy, Ci-C6-halogenalkoxy, ORY, S(0)zRY, NHRY, N(RY)2, C(=0)RY, C(=0)ORY, NH(C(=0)RY, N(C(=0)RY)2, NH-S02-Rx, C(RY)=NO(RY),
RY is in each case independently selected from Ci-C6-alkyl, Ci-C6-halogenalkyl, C2- C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cy- cloalkyl, C3-C6-halogencycloalkyl, and phenyl; wherein the phenyl group is unsub- stituted or substituted from the group consisting of halogen, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of Y are unsubstituted or substituted by groups Ya which independently of one another are selected from:
Ya halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents RY1a selected from the group consisting of halogen, OH, CN, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocyclic and phenyl moieties of Y are unsubstituted or substituted by groups Yb which independently of one another are selected from:
Yb halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl,
C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
Rx is as defined above;
z is 0, 1 , 2 or
According to one embodiment of formula I , Y is hydrogen.
According to one embodiment of formula I , Y is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I , Y is F.
According to still another embodiment of formula I , Y is CI.
According to still another embodiment of formula I , Y is Br.
According to still another embodiment of formula I , Y is OH.
According to still another embodiment of formula I , Y is CN .
According to still another embodiment of formula I , Y is NO2.
According to still another embodiment of formula I , Y is SH.
According to still another embodiment of formula I , Y is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3.
According to still another embodiment of formula I , Y is CH3.
According to still another embodiment of formula I , Y is C2H5. According to still another embodiment of formula I, Y is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, Y is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2, C(CH3)=CH2 or CH2 CH=CH2.
According to a further specific embodiment of formula I, Y is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2. CH2CF=CF2, CH2CCI=CCI2. CF2CF=CF2 or CCI2CCI=CCI2.
According to still another embodiment of formula I Y is C3-C6-cycloalkenyl, in particular cyclopro- penyl.
According to still a further embodiment of formula I, Y is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2C≡CH, C≡CCI, C≡CF CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I Y is C3-C6-cycloalkynyl, in particular cyclo- propynyl.
According to still another embodiment of formula I Y is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, Y is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to one embodiment, Y is C3-C6-cycloalkyl, such as a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent Yb. According to still another embodiment of formula I, it is substituted by Yb.
According to one embodiment, Y is C3-C6-cycloalkyl, such as a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent Yb. According to still another embodiment of formula I, it is substituted by Yb.
According to one embodiment, Y is C3-C6-cycloalkyl, such as a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent Yb. According to still another embodiment of formula I, it is substituted by Yb. According to a further specific embodiment of formula I, Y is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3, OCH2CH3, or CH2OCH3.
According to a further specific embodiment of formula I, Y is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, Y is ORY, such as C2-C6-alkenyloxy, in particular C2-C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2,
OCH2CH=CH2.
In still another embodiment of formula I, Y is ORY, wherein RY is Ci-C6-halogenalkenyl, in particular CrC4-halogenalkenyl, more specifically Ci-C3-halogenalkenyl, such as OCH=CHF, OCH=CHCI, OCH=CF2, OCH=CCI2, OCH2CH=CHF, OCH2CH=CHCI, OCH2CH=CF2,
OCH2CH=CCI2. OCH2CF=CF2, OCH2CCI=CCI2. OCF2CF=CF2 or OCCI2CCI=CCI2. According to a further specific embodiment of formula I, Y is ORY, such as C2-C6-alkynyloxy, in particular C2-C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH or OCH2OCH.
In still another embodiment of formula I, Y is ORY, wherein RY Ci-C6-halogenalkynyl, in particular Ci-C4-halogenalkynyl, more specifically Ci-C3-halogenalkynyl, such as OC≡CCI or OCH2O CCI.
In still another embodiment of formula I, Y is ORY, wherein RY is C3-C6-cycloalkyl, in particular C3-C4-cycloalky, more specifically cyclopropyl such as OcPr or OCH2cPr.
In still another embodiment of formula I, Y is ORY, wherein RY is C3-C6-halogencycloalkyl, in particular C3-C4-halogencycloalkyl. In a special embodiment RY is in each case independently se- lected from fully or partially halogenated cyclopropyl.
In still another embodiment of formula I Y is S(0)z(RY) such as S(0)z-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
In still another embodiment of formula I, Y is NHRY such as NH2.
In still another embodiment of formula I, Y is NHRY such as NH(CrC4-alkyl), in particular NH(CH3), NH(C2H5).
In still another embodiment of formula I, Y is N(RY)2, such as, N(Ci-C4-alkyl)2, in particular NH(CH3)2, NH(C2H5)2.
In still another embodiment of formula I, Y is NHRY such as, NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
In still another embodiment of formula I, Y is N(RY)2,) such as N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
In a further specific embodiment of formula I, Y is NH-S02-Rx such as NH-SO2-CH3, NH-SO2- CH2-CH3, NH-SO2-CF3 or NH-SOz-Ts.
In a further specific embodiment of formula I, Y is CO(RY) such as CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl) or C(=0)N(Ci-C6-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
In a further specific embodiment of formula I, Y is C(RY)=NO(RY),such as C(CH3)=NOCH3, C(CH3)=NOCH2CH3 or C(CH3)=NOCF3.
According to still another embodiment of formula I, Y is in each case independently selected from H, halogen, CN, CrC6-alkyl,C2-C6-alkenyl, C2-C6-alkynyl, and Ci-C6-alkoxy, wherein the acyclic moieties of Y are unsubstituted or substituted by halogen.
Ya are the possible substituents for the acyclic moieties of Y. Ya is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents RY1a selected from the group consisting of halogen, OH, CN, C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
Yb are the possible substituents for the carbocyclic and phenyl moieties of Y. Yb is
independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio; Particularly preferred embodiments of Y according to the invention are in Table PY below, wherein each line of lines PY-1 to PY-57 corresponds to one particular embodiment of the invention, wherein PY-1 to PY-57 are also in any combination with one another a preferred embodiment of the present invention:
Figure imgf000045_0002
Figure imgf000045_0001
Figure imgf000046_0001
o is 0, 1 , 2 or 3; and
According to still another embodiment of formula l ,o is 0.
According to still another embodiment of formula I , o is 1.
According to still another embodiment of formula I , o is 2 or 3. According to one specific embodiment thereof, o is 2. According to still another embodiment of formula I, o is 3.
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six- membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(CrC4-alkyl), N(C C4-alkyl)2, NH-S02-Rx, d-C6-alkyl, C C6-halo- genalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci- C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or
wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which independently of one another are selected from:
R78a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the het- eroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubsti- tuted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH, CN, C C4-alkyl, C C4-alkoxy, C C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio.
For every R78 that is present in the compounds of formula I, the following embodiments and preferences apply independently of the meaning of any other R78 that may be present in the ring. Furthermore, the particular embodiments and preferences given herein for R78 apply independently for each of o=1 , o=2 and o=3.
According to one embodiment of formula I, R78 is selected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy.
According to one embodiment of formula I, R78 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I , R78 is F.
According to still another embodiment of formula I , R78 is CI.
According to still another embodiment of formula I , R78 is Br.
According to still another embodiment of formula I , R78 is OH.
According to still another embodiment of formula I , R78 is CN.
According to still another embodiment of formula I , R78 is N02.
According to still another embodiment of formula I , R78 is SH.
According to still another embodiment of formula I , R78 is NH2.
According to still another embodiment of formula I , R78 is , NH(C
NH(CH3), NH(C2H5).
According to still another embodiment of formula I , R78 is , N(Ci-
NH(CH3)2, NH(C2H5)2.
According to still another embodiment of formula R78 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula R78 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I, R78 is NH-S02-RX such as NH-S02-CH3, NH-S02-CH2-CH3, NH-S02-CF3 or NH-S02-Ts.
According to a further specific embodiment of formula I, R78 is CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n- butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl. According to a further specific embodiment of formula I, R78 is CR'=NOR" such as C(CH3)=NOCH3, C(CH3)=NOCH2CH3 or C(CH3)=NOCF3.
According to still another embodiment of formula I, R78 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3.
According to still another embodiment of formula I, R78 is CH2CH3.
According to still another embodiment of formula I, R78 is CrC6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, R78 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2 or CH2 CH=CH2.
According to a further specific embodiment of formula I, R78 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2. CH2CF=CF2, CH2CCI=CCI2. CF2CF=CF2 or CCI2CCI=CCI2.
According to still a further embodiment of formula I, R78 is C2-C6-alkynyl or C2-C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2C=CH, C CCI, CH2C≡CCI, or CCI2C≡CCI.
According to a further specific embodiment of formula I, R78 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I, R78 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R78 is C2-C6-alkenyloxy, in particular C2- C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2, OCH2CH=CH2.
According to a further specific embodiment of formula I, R78 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH or OCH2C=CH
According to still another embodiment of formula I R78 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R78 is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to one embodiment, R78 is C3-C6-cycloalkyl, such as a 4-membered saturated carbo- cycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by
R78b.
According to one embodiment, R78 is C3-C6-cycloalkyl, such as a 5-membered saturated carbo- cycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by
R78b
According to one embodiment, R78 is a C3-C6-cycloalkyl, such as 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by
R78b
According to still another embodiment of formula I R78 is C3-C6-cycloalkenyl, in particular cyclo- propenyl.
According to still another embodiment of formula I R78 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I, R78 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, R78 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, in the embodiments of R78 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
According to one embodiment, R78 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by R78b.
According to still another embodiment of formula I, R78 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroa- torn. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by
R78b.
According to still another embodiment of formula I, R78 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by R78b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R78b. According to still another embodiment of formula I, it is substituted by R78b. According to still another embodiment of formula I, R78 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R78b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, CF3 OCHF2, and OCF3.
According to still another embodiment of formula I, R78 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R78b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, CHF2, OCH3, OCHF2, CF3 and OCF3. According to one embodiment, R78 is unsubstituted phenyl. According to another embodiment, R78 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R78 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R78 is a 6-membered heteroaryl, such as pyr- idin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I, R78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the carbo- and het- erocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a as defined and preferably defined herein, and wherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted with identical or different groups R78b as defined and preferably defined herein.
According to still another embodiment of formula I, R78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered satu- rated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a as defined and preferably defined herein, and wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted with identical or different groups R78b as defined and preferably defined herein. Accordingto one specific embodiment, the acyclic and cyclic moieties of R78 are unsubstituted, according to another embodiment, the acyclic moieties of R78 substituted with identical or different groups R78a as defined and preferably defined herein. According to still another embodiment of formula I , R78 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy and C3-C6-cycloalkyl, wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R78 are unsubstituted or substituted with identical or different groups R78b as defined and preferably defined herein.
According to still another embodiment of formula I , R78 is in each case independently selected from halogen, Ci-C6-alkyl and Ci-C6-alkoxy, wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a defined and preferably defined herein. According to still another embodiment of formula I , R78 is in each case independently selected from halogen, Ci-C6-alkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, wherein the acyclic moieties of R78 are unsubstituted or substituted with identical or different groups R78a defined and preferably defined herein. According to one specific embodiment, the acyclic and cyclic moieties of R78 are not further substituted, according to another embodiment, the acyclic moieties of R78 carry one, two, three or four identical or different groups R78a as defined and preferably defined herein.
R78a are the possible substituents for the acyclic moieties of R78. R78a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogengenalkoxy, Ci-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R78a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy.
According to one preferred embodiment, R78a is in each case independently selected from Ci- Ce-alkoxy, Ci-C6-halogenalkoxy, such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to one preferred embodiment, R78a is in each case independently selected from C3- C6-cycloalkyl, C3-C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cy- clopropyl.
According to still another embodiment of formula I , R78a is a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyra- zol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxa- zol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4- yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1-yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I , R78a is a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to one preferred embodiment, R78a is in each case independently selected from aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH3, CHF2, OCH3, OCHF3, CN or SO2CH3. According to one embodiment R78a is independently selected from halogen, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R78a is independently selected from CN, F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl , 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R78a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
R78b are the possible substituents for the C3-C6-cycloalkyl, heterocyclyl, heteroaryl and phenyl moieties of R78. R78b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment thereof R78b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R78b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of the A ring, optionally substituted by (R78)0, according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-40 corresponds to one particular embodiment of the invention, wherein P78-1 to P78-40 are also in any combination with one another a preferred embodiment of the present invention. Thereby, the positions of the pheny marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I:
Figure imgf000052_0001
wherein A is selected from below group:
Figure imgf000052_0002
Figure imgf000053_0001
Table P78: No. (R78)o No. (R78)o
P78-14 1 '-CN P78-28 3'-F
P78-15 2'-F P78-29 3 -CI
P78-16 2 -CI P78-30 3'-Br
P78-17 2'-Br P78-31 3'-CH3
P78-18 2'-CH3 P78-32 3 -C2H5
P78-19 2'-C2H5 P78-33 3'-CH2F
P78-20 2'-CH2F P78-34 3'-CHF2
P78-21 2'-CHF2 P78-35 3'-CF3
P78-22 2'-CF3 3'-OCH3
P78-36
P78-23 2'-OCH3
P78-24 2'-OCH2F
P78-37 3'-OCH2F
P78-25 2'-OCHF2
P78-38 3'-OCHF2
P78-26 2'-OCF3
P78-39 3'-OCF3
Figure imgf000053_0002
P78-27 2'-CN
P78-40 3'-CN
R9 is in each case independently selected from H, halogen, OH, CN, N02, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-al- kynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-al- kyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4- alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), NH(C(=0)Ci-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-C6-cycloalkylthio, S(0)n-C2- Ce-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6- alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci-C6-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6- alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cycloalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, 0RY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S;
wherein
Rx is as defined above;
RY is as defined above;
wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH, CN, Ci-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocycle, heteroaryl and aryl moieties of R9 are unsubstituted or
substituted by groups R9b which independently of one another are selected from:
R9b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Ce-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
According to one embodiment of formula I, R9 is selected from the group consisting of H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, Cs-Ce-halogencycloalkyl, and ORY.
According to one embodiment of formula I, R9 is H.
According to still another embodiment of formula I, R9 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I, R9 is F.
According to still another embodiment of formula I, R9 is CI.
According to still another embodiment of formula I, R9 is Br.
According to still another embodiment of formula I, R9 is OH.
According to still another embodiment of formula I, R9 is CN.
According to still another embodiment of formula I, R9 is N02.
According to still another embodiment of formula I, R9 is SH.
According to still another embodiment of formula I, R9 is NH2.
According to still another embodiment of formula I, R9 is , NH(Ci-C4-alkyl), in particular NH(CHs), NH(C2H5).
According to still another embodiment of formula I, R9 is , N(Ci-C4-alkyl)2, in particular NH(CHs)2, NH(C2H5)2.
According to still another embodiment of formula I, R9 is , NH(C2-C4-alkenyl), in particular NH(CH=CH2), NH(CH2CH=CH2).
According to still another embodiment of formula I, R9 is , N(C2-C4--alkenyl)2, in particular N(CH=CH2)2, N(CH2CH=CH2)2.
According to still another embodiment of formula I, R9 is , NH(C2-C4-alkynyl), in particular NH(C= CH), NH(CH2C≡CH).
According to still another embodiment of formula I, R9 is , N(C2-C4-alkynyl)2, in particular N(C= CH)2, N(CH2C≡CH)2.
According to still another embodiment of formula I, R9 is , NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H9).
According to still another embodiment of formula I, R9 is , N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H9)2.
According to still another embodiment of formula I, R9 is N(CrC4-alkyl)(C2-C4-alkenyl), in particular N(CH3)(CH=CH2), N(CH3)(CH2CH=CH2), N(C2H5)(CH=CH2), N(C2H5)(CH2CH=CH2).
According to still another embodiment of formula I, R9 is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).
According to still another embodiment of formula I, R9 is N(Ci-C4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H9), N(C2H5)(C3H7), N(CH3)(C4H9).
According to still another embodiment of formula I, R9 is N(C2-C4-alkenyl) (C2-C4-alkynyl), in particular N(CH=CH2)(C≡CH), N(CH2CH=CH2)(CH2C≡CH), N(CH=CH2)(C≡CH),
N(CH2CH=CH2)(CH2C≡CH).
According to still another embodiment of formula I, R9 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9), N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9). According to still another embodiment of formula I, R9 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9).
According to still another embodiment of formula I, R9 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula I, R9 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I, R9 is NH-S02-Rx such as NH-S02-CH3, NH-S02-CH2-CH3, NH-S02-CF3, NH-S02-Ts.
According to still another embodiment of formula I, R9 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I, R9 is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0)2phenyl. According to still another embodiment of formula I, R9 is S(0)n-C2-C6-alkenyl such as
SCH=CH2, S(=0)CH=CH2, S(0)2CH=CH2, SCH2CH=CH2, S(=0)CH2CH=CH2,
S(0)2CH2CH=CH2 .
According to still another embodiment of formula I, R9 is S(0)n-C2-C6-alkynyl such as SC CH, S(=0)C≡CH, S(0)2C≡CH, SCH2C≡CH, S(=0)CH2C≡CH, S(0)2CH2C≡CH.
According to a further specific embodiment of formula I, R9 is CH(=0).
According to a further specific embodiment of formula I, R9 is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R9 is C(=0)C2-C6-alkenyl, C(=0)0(C2- Ce-alkenyl) or C(=0)NH(C2-C6-alkenyl), wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R9 is C(=0)C2-C6-alkynyl, C(=0)0(C2- Ce-alkynyl) or C(=0)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I, R9 is C(=0)C3-C6-cycloalkyl,
C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I, R9 is CH(=S).
According to a further specific embodiment of formula I, R9 is C(=S)Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R9 is C(=S)C2-C6-alkenyl, wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R9 is C(=S)C2-C6-alkynyl, wherein alkynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I, R9 is C(=S)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C H9).
According to a further specific embodiment of formula I, R9 is C(=S)NHCi-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R9 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
According to still another embodiment of formula I, R9 is Ci-C6-halogenalkyl, in particular Ci-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, R9 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R9 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.
According to still a further embodiment of formula I, R9 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, Ch C CH, C CCI,
CH2C≡CCI, or CCI2C≡CCI.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY is in each case independently selected from Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogen- alkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.
According to a further specific embodiment of formula I , R9 is ORY wherein RY is in each case independently selected from Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically C1-C2- alkoxy. R9 is such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY is in each case independently selected from Ci-C6-halogenalkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl. R9 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCb.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R9 is such as OCH=CH2,
OCH2CH=CH2.
According to a further specific embodiment of formula I , R9 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R9 is such as OC≡CH, , OC≡CCI, OCH2C≡CCI, or OCCI2C≡CCI.
According to still another embodiment of formula I R9 is ORY, wherein RY is in each case inde- pendently selected from C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I , R9 is ORY, wherein RY is in each case independently selected from C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I , R9 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.
According to still another embodiment of formula I , R9 is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I , R9 is C3-C6-halogencycloalkyl. In a special embodiment R9b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl .
According to still another embodiment of formula I , R9 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R9b which independently of one another are selected from halogen, CN, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, CN, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R9 is unsubstituted phenyl. According to another embodiment, R9 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I , R9 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R9 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I, R9 is in each case independently selected from H, halogen, CN, d-Ce-alkyl, d-Ce-halogenalkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl wherein the acyclic moieties of R9 are unsubstituted or substituted with identical or different groups R9a as defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R9 are unsubstituted or substituted with identical or different groups R9b as defined and preferably defined herein.
According to still another embodiment of formula I, R9 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R9 are unsubstituted or substituted with iden- tical or different groups R9a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R9 are unsubstituted or substituted with identical or different groups R9b as defined and preferably defined herein.
R9a are the possible substituents for the acyclic moieties of R9.
According to one embodiment R9a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
According to one embodiment R9a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyi, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R9a is independently selected from F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1 -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R9a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
R9b are the possible substituents for the cycloalkyi, heteroaryl and phenyl moieties of R9. R9b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
According to one embodiment thereof R9b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R9b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of R9 according to the invention are in Table P13 below, wherein each line of lines P13-1 to P3-43 corresponds to one particular embodiment of the invention, wherein P13-1 to P3-43 are also in any combination with one another a preferred em- bodiment of the present invention. The connection point to the carbon atom, to which R9 is bound is marked with "#" in the drawings.
Table P13:
Figure imgf000059_0002
Figure imgf000059_0001
Figure imgf000060_0001
R10 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-al- kynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-al- kyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4- alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), NH(C(=0)Ci-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-Ce-cycloalkylthio, S(0)n-C2- Ce-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6- alkynyl, C(=0)C3-C6-cyclpalkyl, C(=0)NH(CrC6-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6- alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cyclpalkyl, C(=S)NH(CrC6-alkyl), CrC6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S;
wherein
Rx is as defined above;
RY is as defined above;
wherein the acyclic moieties of R10 are unsubstituted or substituted by groups R10a which independently of one another are selected from:
R10a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C
C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R101a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R10 are unsubstituted or
substituted by groups R10b which independently of one another are selected from:
R10b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, C C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, CrC4-halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment of formula I, R10 is in each case independently selected from hal- ogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4- alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4-alkyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cy- cloalkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)C C6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cyclpalkyl, C(=0)NH(C C6-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cyclpalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein
is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl;
wherein the acyclic moieties of R10 are unsubstituted or substituted by groups R10a which independently of one another are selected from:
R10a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-
C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R101a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R10 are unsubstituted or
substituted by groups R10b which independently of one another are selected from:
R10b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R10 is secected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2- C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-hal- ogenalkoxy and ORY.
According to still another embodiment of formula I, R10 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I , R10 is F.
According to still another embodiment of formula I , R10 is CI.
According to still another embodiment of formula I , R10 is Br.
According to still another embodiment of formula I , R10 is OH.
According to still another embodiment of formula I , R10 is CN.
According to still another embodiment of formula I , R10 is N02.
According to still another embodiment of formula I , R10 is SH.
According to still another embodiment of formula I , R10 is NH2.
According to still another embodiment of formula I , R10 is , NH(C
NH(CH3), NH(C2H5).
According to still another embodiment of formula R10 is , N(Ci-C4-alkyl)2, in particular
NH(CH3)2, NH(C2H5)2.
According to still another embodiment of formula R10 is , NH(C2-C4-alkenyl), in particular NH(CH=CH2), NH(CH2CH=CH2). According to still another embodiment of formula I , R10 is , N(C2-C4--alkenyl)2, in particular N(CH=CH2)2, N(CH2CH=CH2)2.
According to still another embodiment of formula I , R10 is , NH(C2-C4-alkynyl), in particular NH(C ≡CH), NH(CH2C≡CH).
According to still another embodiment of formula I , R10 is , N(C2-C4-alkynyl)2, in particular N(C= CH)2, N(CH2C≡CH)2.
According to still another embodiment of formula I , R10 is , NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H9).
According to still another embodiment of formula I , R10 is , N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H9)2.
According to still another embodiment of formula I , R10 is N(Ci-C4-alkyl)(C2-C4-alkenyl), in particular N(CH3)(CH=CH2), N(CH3)(CH2CH=CH2), N(C2H5)(CH=CH2), N(C2H5)(CH2CH=CH2).
According to still another embodiment of formula I , R10 is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).
According to still another embodiment of formula I , R10 is N(Ci-C4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H9), N(C2H5)(C3H7), N(CH3)(C4H9).
According to still another embodiment of formula I , R10 is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH=CH2)(C≡CH), N(CH2CH=CH2)(CH2C≡CH), N(CH=CH2)(C≡CH),
N(CH2CH=CH2)(CH2C≡CH).
According to still another embodiment of formula I , R10 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9), N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9).
According to still another embodiment of formula I , R10 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9).
According to still another embodiment of formula I , R10 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula I , R10 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I , R10 is NH-S02-RX such as NH-SO2- CH3, NH-S02-CH2-CH3, NH-S02-CF3, NH-S02-Ts.
According to still another embodiment of formula I , R10 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I , R10 is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0)2phenyl.
According to still another embodiment of formula I , R10 is S(0)n-C2-C6-alkenyl such as
SCH=CH2, S(=0)CH=CH2, S(0)2CH=CH2, SCH2CH=CH2, S(=0)CH2CH=CH2,
S(0)2CH2CH=CH2 .
According to still another embodiment of formula I , R10 is S(0)n-C2-C6-alkynyl such as SC CH, S(=0)C≡CH, S(0)2C≡CH, SCH2C≡CH, S(=0)CH2C≡CH , S(0)2CH2C≡CH. According to a further specific embodiment of formula I, R10 is CH(=0).
According to a further specific embodiment of formula I, R10 is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R10 is C(=0)C2-C6-alkenyl, C(=0)0(C2- Ce-alkenyl) or C(=0)NH(C2-C6-alkenyl), wherein alkenyl is CH=CH2, C(CH3)=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R10 is C(=0)C2-C6-alkynyl, C(=0)0(C2- Ce-alkynyl) or C(=0)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH, C≡CCI,
CH2C≡CCI, or CCI2C≡CCI.
According to a further specific embodiment of formula I, R10 is C(=0)C3-C6-cycloalkyl,
C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyi is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I, R10 is CH(=S).
According to a further specific embodiment of formula I, R10 is C(=S)CrC6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R10 is C(=S)C2-C6-alkenyl, wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R10 is C(=S)C2-C6-alkynyl, wherein alkynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I, R10 is C(=S)C3-C6-cycloalkyl, wherein cycloalkyi is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I, R10 is C(=S)NHCrC6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R10 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
According to still another embodiment of formula I, R10 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, R10 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2.
According to a further specific embodiment of formula I, R10 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.
According to still a further embodiment of formula I, R10 is C2-C6-alkynyl or C2-C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2 C CH.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY is in each case independently selected from Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogen- alkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl. According to a further specific embodiment of formula I, R10 is ORY, wherein RY is in each case independently selected from Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically C1-C2- alkoxy. R10 is such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY is in each case independently selected from Ci-C6-halogenalkyl, in particular Ci-C4-halogenalkyl, more specifically C C2-halogenalkyl. R10 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R10 is such as OCH=CH2,
OCH2CH=CH2.
According to a further specific embodiment of formula I, R10 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R10 is such as OC≡CH, OC≡CCI, OCH2C≡CCI, or OCCI2C≡CCI.
According to still another embodiment of formula I R10 is ORY wherein RY is in each case inde- pendently selected from C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I, R10 is ORY, wherein RY is in each case independently selected from C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R10 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.
According to still another embodiment of formula I, R10 is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I, R10 is C3-C6-halogencycloalkyl. In a special embodiment R10b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl
According to still another embodiment of formula I, R10 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R10b which independently of one another are selected from halogen, CN, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CN, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R10 is unsubstituted phenyl. According to another embodiment, R10 is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R10 is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl. According to still another embodiment of formula I , R10 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I , R10 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy,C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl wherein the acyclic moieties of R10 are unsubstituted or substituted with identical or different groups R10a as defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R10 are unsubstituted or substituted with identical or different groups R10b as defined and preferably defined herein.
According to still another embodiment of formula I , R10 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R10 are unsubstituted or substituted with iden- tical or different groups R10a as defined and preferably defined herein, and wherein the cycloal- kyl moieties of R10 are unsubstituted or substituted with identical or different groups R10b as defined and preferably defined herein.
R10a are the possible substituents for the acyclic moieties of R9.
According to one embodiment R10a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R10a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
According to one embodiment R10a is independently selected from halogen, Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R10a is
independently selected from F, CI, Br, I , Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I , R10a is independently halogen, in particular selected from F, CI, Br and I , more specifically F, CI and Br.
R10b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R10. R10b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
According to one embodiment thereof R10b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R10b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of R10 according to the invention are in Table P14 below, wherein each line of lines P14-1 to P14-43 corresponds to one particular embodiment of the in- vention, wherein P14-1 to P14-43 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R10 is bound is marked with "#" in the drawings.
Table P14:
Figure imgf000066_0001
Figure imgf000066_0002
According to still another embodiment of formula I, R9, R10 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaro- matic ring; wherein the heterocyclic or heteroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci- C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m , wherein m is 0, 1 , 2, 3 or 4;
RN is the substituent of the heteroatom NRN that is contained in the heterocycle formed by R9 and R10 in some of the inventive compounds. RN is selected from Ci-C4-alkyl, Ci-C4-halogen- alkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from Ci-C4-alkyl. In one preferred embodiment, RN is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl substituents. In one particular embod- iment, RN is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, RN is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl.
According to still another embodiment of formula I, R9 and R10 together with the carbon atoms to which they are bound form a saturated or partially unsaturated five-, six-or seven -membered carbo- and heterocycle that is unsubstituted or substituted.
According to one embodiment, R9 and R10 form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 3-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11.
According to one embodiment, R9 and R10 form a 4-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R11. According to still another embodiment of formula I, it is substituted by R11. According to one embodiment, R9 and R10 form a 5-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R1 1. According to still another embodiment of formula I, it is substituted by R1 1.
According to one embodiment, R9 and R10 form a 6-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R1 1. According to still another embodiment of formula I, it is substituted by R1 1.
According to one embodiment, R9 and R10 form a 7-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R1 1. According to still another embodiment of formula I, it is substituted by R1 1.
According to one embodiment, R9 and R10 form a 5-membered saturated heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R1 1. According to still another embodiment of formula I, it is substituted by R1 1.
According to one embodiment, R9 and R10 form a 6-membered heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R1 1 . According to still another embodiment of formula I, it is substituted by R1 1 .
R1 1 according to the invention is in each case independently selected from hydrogen, halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains one, two or three heteroatoms selected from N , O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents Rx1 1 independently selected from Ci-C4-alkyl, halogen, OH , CN , Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 1 are unsubstituted or substituted with identical or different groups R1 1 a which independently of one another are selected from:
R1 1 a halogen, OH , CN , d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C4-halo- genalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R1 1 1 a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN , C3-C6-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl of R11 are unsubstituted or substituted with identical or different groups R1 1 b which independently of one another are selected from:
R1 1 b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R1 1 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R1 1 that may be present in the ring.
According to one embodiment of formula I, wherein m is 0, 1 , 2, 3 or 4. According to still another embodiment of formula l,m is 0.
According to still another embodiment of formula I , m is 1 .
According to still another embodiment of formula I , m is 2 or 3. According to one specific embodiment thereof, m is 2. According to still another embodiment of formula I , m is 3.
According to one embodiment of formula I , R11 is H, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, d-Ce-alkoxy or , C C6-halogenalkoxy, in particular H, CH3, Et, CHF2, OCH3, OCHF2, OCF3, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another embodiment of formula I , R11 is hydrogen.
According to still another embodiment of formula I , R11 is halogen, in particular Br, F or CI, more specifically F or CI.
According to still another embodiment of formula I , R11 is OH .
According to still another embodiment of formula I , R11 is CN.
According to still another embodiment of formula I R11 is Nhb, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-SC>2-RX, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is sub- stituted by one, two, three, four or five substituents Rx1 1 independently selected from Ci-C4-al- kyl.
According to still another embodiment of formula I , R11 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3.
According to still another embodiment of formula I , R11 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2 or CH2CI.
According to still another embodiment of formula I , R11 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH3)=CH2,
CH2CH=CH2, CH=CH F, CH=CHCI, CH=CF2, CH=CCI2, CF=CF2, CCI=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CH2CF=CF2, CH2CCI=CCI2, CF2CF=CF2 or
CCI2CCI=CCI2.
According to still another embodiment of formula I , R11 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2C≡CH, CH2C≡CH, C≡C-CI, C≡C-CH3, CH2C≡CH, CH2C≡CCI or CH2C≡C-CH3.
According to still another embodiment of formula I , R11 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I , R11 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to still another embodiment of formula I R11 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I , R11 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R11 b as defined and preferably herein. According to still another embodiment of formula I, R11 is C3-C6-halogencycloalkyl. In a special embodiment R11 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R11 is unsubstituted aryl or aryl that is substituted by one, two, three or four R11b, as defined herein. In particular, R11 is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R11 b, as defined herein.
According to still another embodiment of formula I, R11 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R11 is 5- or 6-membered heteroaryl that is substituted by one, two or three R11b, as defined herein.
According to still another embodiment of formula I, R11 is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R11 are not further substituted or carry one, two, three, four or five identical or different groups R11a as defined below and wherein the carbocyclic, heterocyclic and heteroaryl moieties of R11 are not further substituted or carry one, two, three, four or five identical or different groups R11b as defined below.
According to still another embodiment of formula I, R11 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
R11a are the possible substituents for the acyclic moieties of R11.
R11a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4- halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio.
R11a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, Ci-C2- alkoxy, Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
In to one embodiment R11a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R11a is
independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-CI2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R11a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R11a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R11a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy. R11 b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of R11.
R11 b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R11 b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy. Specifically, R11 b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 , 1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R11 b is independently selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogen- alkoxy. Specifically, R11 b is independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F- cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 - Cl-cyclopropyl, 1 , 1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl cyclopropyl and OCHF2.
Particularly preferred embodiments of combinations of R9 and R10 according to the invention are in Table P35 below, wherein each line of lines P35-1 to P35-305 corresponds to one particular embodiment of the invention, wherein P35-1 to P35-305 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R9 bound is marked with * in the drawings and the carbon atom, to which R10 is bound is marked with # in the drawings. cPr stands for cyclopropyl. Table P35:
Figure imgf000071_0001
line R9 R10 line R9 R10
P35-23 F CH2CH3 P35-53 Br F
P35-24 F CH2F P35-54 Br CI
P35-25 F CHF2 P35-55 Br Br
P35-26 F CFs P35-56 Br CHs
P35-27 F OCH3 P35-57 Br CH2CH3
P35-28 F OCH2F P35-58 Br CH2F
P35-29 F OCHF2 P35-59 Br CHF2
P35-30 F OCF3 P35-60 Br CFs
P35-31 F cPr P35-61 Br OCHs
P35-32 F C≡CH P35-62 Br OCH2F
P35-33 F CN P35-63 Br OCHF2
P35-34 F S-CHs P35-64 Br OCFs
P35-35 CI H P35-65 Br cPr
P35-36 CI F P35-66 Br C≡CH
P35-37 CI CI P35-67 Br CN
P35-38 CI Br P35-68 Br S-CHs
P35-39 CI CH3 P35-69 CHs H
P35-40 CI CH2CH3 P35-70 CHs F
P35-41 CI CH2F P35-71 CHs CI
P35-42 CI CHF2 P35-72 CHs Br
P35-43 CI CF3 P35-73 CHs CHs
P35-44 CI OCHs P35-74 CHs CH2CH3
P35-45 CI OCH2F P35-75 CHs CH2F
P35-46 CI OCHF2 P35-76 CHs CHF2
P35-47 CI OCF3 P35-77 CHs CFs
P35-48 CI cPr P35-78 CHs OCHs
P35-49 CI C≡CH P35-79 CHs OCH2F
P35-50 CI CN P35-80 CHs OCHF2
P35-51 CI S-CHs P35-81 CHs OCFs
P35-52 Br H P35-82 CHs cPr line R9 R10 line R9 R10
P35-83 CHs C≡CH P35-1 13 CH2F OCH2F
P35-84 CHs CN P35-1 14 CH2F OCHF2
P35-85 CHs S-CHs P35-1 15 CH2F OCFs
P35-86 CH2CH3 H P35-1 16 CH2F cPr
P35-87 CH2CH3 F P35-1 17 CH2F C≡CH
P35-88 CH2CH3 CI P35-1 18 CH2F CN
P35-89 CH2CH3 Br P35-1 19 CH2F S-CHs
P35-90 CH2CH3 CHs P35-120 CHF2 H
P35-91 CH2CH3 CH2CH3 P35-121 CHF2 F
P35-92 CH2CH3 CH2F P35-122 CHF2 CI
P35-93 CH2CH3 CHF2 P35-123 CHF2 Br
P35-94 CH2CH3 CFs P35-124 CHF2 CHs
P35-95 CH2CH3 OCHs P35-125 CHF2 CH2CH3
P35-96 CH2CH3 OCH2F P35-126 CHF2 CH2F
P35-97 CH2CH3 OCHF2 P35-127 CHF2 CHF2
P35-98 CH2CH3 OCFs P35-128 CHF2 CFs
P35-99 CH2CH3 cPr P35-129 CHF2 OCHs
P35-100 CH2CH3 C≡CH P35-130 CHF2 OCH2F
P35-101 CH2CH3 CN P35-131 CHF2 OCHF2
P35-102 CH2CH3 S-CHs P35-132 CHF2 OCFs
P35-103 CH2F H P35-133 CHF2 cPr
P35-104 CH2F F P35-134 CHF2 C≡CH
P35-105 CH2F CI P35-135 CHF2 CN
P35-106 CH2F Br P35-136 CHF2 S-CHs
P35-107 CH2F CHs P35-137 CFs H
P35-108 CH2F CH2CH3 P35-138 CFs F
P35-109 CH2F CH2F P35-139 CFs CI
P35-1 10 CH2F CHF2 P35-140 CFs Br
P35-1 1 1 CH2F CFs P35-141 CFs CHs
P35-1 12 CH2F OCHs P35-142 CFs CH2CH3 line R9 R10 line R9 R10
P35-143 CFs CH2F P35-173 OCH2F CI
P35-144 CFs CHF2 P35-174 OCH2F Br
P35-145 CFs CFs P35-175 OCH2F CHs
P35-146 CFs OCHs P35-176 OCH2F CH2CH3
P35-147 CFs OCH2F P35-177 OCH2F CH2F
P35-148 CFs OCHF2 P35-178 OCH2F CHF2
P35-149 CFs OCFs P35-179 OCH2F CFs
P35-150 CFs cPr P35-180 OCH2F OCHs
P35-151 CFs C≡CH P35-181 OCH2F OCH2F
P35-152 CFs CN P35-182 OCH2F OCHF2
P35-153 CFs S-CHs P35-183 OCH2F OCFs
P35-154 OCHs H P35-184 OCH2F cPr
P35-155 OCHs F P35-185 OCH2F C≡CH
P35-156 OCHs CI P35-186 OCH2F CN
P35-157 OCHs Br P35-187 OCH2F S-CHs
P35-158 OCHs CHs P35-188 OCHF2 H
P35-159 OCHs CH2CH3 P35-189 OCHF2 F
P35-160 OCHs CH2F P35-190 OCHF2 CI
P35-161 OCHs CHF2 P35-191 OCHF2 Br
P35-162 OCHs CFs P35-192 OCHF2 CHs
P35-163 OCHs OCHs P35-193 OCHF2 CH2CH3
P35-164 OCHs OCH2F P35-194 OCHF2 CH2F
P35-165 OCHs OCHF2 P35-195 OCHF2 CHF2
P35-166 OCHs OCFs P35-196 OCHF2 CFs
P35-167 OCHs cPr P35-197 OCHF2 OCHs
P35-168 OCHs C≡CH P35-198 OCHF2 OCH2F
P35-169 OCHs CN P35-199 OCHF2 OCHF2
P35-170 OCHs S-CHs P35-200 OCHF2 OCFs
P35-171 OCH2F H P35-201 OCHF2 cPr
P35-172 OCH2F F P35-202 OCHF2 C≡CH line R9 R10 line R9 R10
P35-203 OCHF2 CN P35-233 cPr OCHF2
P35-204 OCHF2 S-CH3 P35-234 cPr OCF3
P35-205 OCF3 H P35-235 cPr cPr
P35-206 OCF3 F P35-236 cPr C≡CH
P35-207 OCF3 CI P35-237 cPr CN
P35-208 OCF3 Br P35-238 cPr S-CH3
P35-209 OCF3 CH3 P35-239 C≡CH H
P35-210 OCF3 CH2CH3 P35-240 C≡CH F
P35-21 1 OCF3 CH2F P35-241 C≡CH CI
P35-212 OCF3 CHF2 P35-242 C≡CH Br
P35-213 OCF3 CF3 P35-243 C≡CH CH3
P35-214 OCF3 OCH3 P35-244 C≡CH CH2CH3
P35-215 OCF3 OCH2F P35-245 C≡CH CH2F
P35-216 OCF3 OCHF2 P35-246 C≡CH CHF2
P35-217 OCF3 OCF3 P35-247 C≡CH CF3
P35-218 OCF3 cPr P35-248 C≡CH OCH3
P35-219 OCF3 C≡CH P35-249 C≡CH OCH2F
P35-220 OCF3 CN P35-250 C≡CH OCH F2
P35-221 OCF3 S-CH3 P35-251 C≡CH OCF3
P35-222 cPr H P35-252 C≡CH cPr
P35-223 cPr F P35-253 C≡CH C≡CH
P35-224 cPr CI P35-254 C≡CH CN
P35-225 cPr Br P35-255 C≡CH S-CH3
P35-226 cPr CH3 P35-256 CN H
P35-227 cPr CH2CH3 P35-257 CN F
P35-228 cPr CH2F P35-258 CN CI
P35-229 cPr CHF2 P35-259 CN Br
P35-230 cPr CF3 P35-260 CN CH3
P35-231 cPr OCH3 P35-261 CN CH2CH3
P35-232 cPr OCH2F P35-262 CN CH2F
Figure imgf000076_0001
Figure imgf000077_0001
Particular embodiments of the compounds I are the following compounds: 1-1.A, 1-1. B, 1-1. C, I- 1.D, 1-1. E, 1-1 . F; I-2.A, I-2.B, I-2.C, I-2.D, I-2.E, I-2.F; I-3.A, I-3.B, I-3.C, I-3.D, I-3.E, I-3.F; I-4.A, I- 4.B, I-4.C, I-4.D, I-4.E, I-4.F that are compiled in the Tables 1-1 to 1 -8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Figure imgf000077_0002
1-1.A 1-1 . B 1-1. C
Figure imgf000077_0003
1-1. D 1-1. E 1-1. F
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000079_0002
Table 1-1 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds I-1 .A.1-1.A-1 to I-1 .A.1 -1.A-2304, compounds I-2.A.1 -
1. A-1 to I-2.A.1 -1.A-2304, compounds I-3.A.1 -1 .A-1 to I-3.A.1-1 .A-2304 compounds I-4.A.1-1 .A- 1 to I-4.A.1 -1.A-2304).
Table 1-2 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-2.A-1 to 1-1 .A.1 -2.A-2304, compounds I-2.A.1 -
2. A-1 to I-2.A.1 -2.A-2304, compounds I-3.A.1 -2.A-1 to I-3.A.1-2.A-2304 compounds I-4.A.1-2.A- 1 to I-4.A.1 -2.A-2304).
Table 1-3 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-3.A-1 to 1-1 .A.1 -3.A-2304, compounds I-2.A.1 -
3. A-1 to I-2.A.1 -3.A-2304, compounds I-3.A.1 -3.A-1 to I-3.A.1-3.A-2304 compounds I-4.A.1-3.A- 1 to I-4.A.1 -3.A-2304).
Table 1-4 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is Br and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -4.A-1 to 1-1 .A.1-4.A-2304, compounds I-2.A.1-4.A-1 to I-2.A.1-4.A-2304, compounds I-3.A.1 -4.A-1 to I-3.A.1-4.A-2304 compounds I-4.A.1 -4.A-1 to I-
4. A.1-4.A-2304).
Table 1-5 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-5.A-1 to 1-1 .A.1 -5.A-2304, compounds I-2.A.1 -
5. A-1 to I-2.A.1 -5.A-2304, compounds I-3.A.1 -5.A-1 to I-3.A.1-5.A-2304 compounds I-4.A.1-5.A- 1 to I-4.A.1 -5.A-2304). Table 1-6 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-6.A-1 to I-1.A.1 -6.A-2304, compounds I- 2.A.1-6.A-1 to I-2.A.1-6.A-2304, compounds I-3.A.1-6.A-1 to I-3.A.1-6.A-2304 compounds I- 4.A.1-6.A-1 to I-4.A.1-6.A-2304).
Table 1-7 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R9 is H and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -7.A-1 to 1-1 .A.1-7.A-2304, compounds I-2.A.1-7.A-1 to I-2.A.1-7.A-2304, compounds I-3.A.1 -7.A-1 to I-3.A.1-7.A-2304 compounds I-4.A.1 -7.A-1 to I- 4.A.1-7.A-2304).
Table 1-8 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-8.A-1 to 1-1 .A.1 -8.A-2304, compounds I-2.A.1 - 8.A-1 to I-2.A.1 -8.A-2304, compounds I-3.A.1 -8.A-1 to I-3.A.1-8.A-2304 compounds I-4.A.1-8.A- 1 to I-4.A.1 -8.A-2304).
Table 2-1 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-1.A-1 to 1-1 .B.2-1.A-2304, compounds I-2.B.2- 1.A-1 to I-2.B.2-1.A-2304, compounds I-3.B.2-1 .A-1 to I-3. B.2-1 .A-2304 compounds I-4. B.2-1 .A- 1 to I-4.B.2-1.A-2304).
Table 2-2 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-2.A-1 to 1-1 .B.2-2.A-2304, compounds I-2.B.2- 2.A-1 to I-2.B.2-2.A-2304, compounds I-3.B.2-2.A-1 to I-3.B.2-2.A-2304 compounds I-4.B.2-2.A- 1 to I-4.B.2-2.A-2304).
Table 2-3 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-3.A-1 to 1-1 .B.2-3.A-2304, compounds I-2.B.2- 3.A-1 to I-2.B.2-3.A-2304, compounds I-3.B.2-3.A-1 to I-3.B.2-3.A-2304 compounds I-4.B.2-3.A- 1 to I-4.B.2-3.A-2304).
Table 2-4 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is Br and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.B.2-4.A-1 to 1-1 .B.2-4.A-2304, compounds I-2.B.2-4.A-1 to I-2.B.2-4.A-2304, compounds I-3.B.2-4.A-1 to I-3.B.2-4.A-2304 compounds I-4.B.2-4.A-1 to I- 4.B.2-4.A-2304).
Table 2-5 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-5.A-1 to 1-1 .B.2-5.A-2304, compounds I-2.B.2- 5.A-1 to I-2.B.2-5.A-2304, compounds I-3.B.2-5.A-1 to I-3.B.2-5.A-2304 compounds I-4.B.2-5.A- 1 to I-4.B.2-5.A-2304). Table 2-6 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-6.A-1 to 1-1.B.2-6.A-2304, compounds I- 2.B.2-6.A-1 to I-2.B.2-6.A-2304, compounds I-3.B.2-6.A-1 to I-3.B.2-6.A-2304 compounds I- 4.B.2-6.A-1 to I-4.B.2-6.A-2304).
Table 2-7 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is H and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.B.2-7.A-1 to 1-1 .B.2-7.A-2304, compounds I-2.B.2-7.A-1 to I-2.B.2-7.A-2304, compounds I-3.B.2-7.A-1 to I-3.B.2-7.A-2304 compounds I-4.B.2-7.A-1 to I- 4.B.2-7.A-2304).
Table 2-8 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-8.A-1 to 1-1 .B.2-8.A-2304, compounds I-2.B.2- 8.A-1 to I-2.B.2-8.A-2304, compounds I-3.B.2-8.A-1 to I-3.B.2-8.A-2304 compounds I-4.B.2-8.A- 1 to I-4.B.2-8.A-2304).
Table 3-1 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-1 .A-1 to 1-1.C.3-1.A-2304, compounds I-2.C.3- 1.A-1 to I-2. C.3-1.A-2304, compounds I-3. C.3-1 .A-1 to I-3. C.3-1 .A-2304 compounds I-4.C.3-
1. A-1 to I-4.C.3-1. A-2304).
Table 3-2 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-2.A-1 to 1-1.C.3-2.A-2304, compounds I-2.C.3- 2.A-1 to I-2.C.3-2.A-2304, compounds I-3.C.3-2.A-1 to I-3.C.3-2.A-2304 compounds I-4.C.3-
2. A-1 to I-4.C.3-2.A-2304).
Table 3-3 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-3.A-1 to 1-1.C.3-3.A-2304, compounds I-2.C.3- 3.A-1 to I-2.C.3-3.A-2304, compounds I-3.C.3-3.A-1 to I-3.C.3-3.A-2304 compounds I-4.C.3-
3. A-1 to I-4.C.3-3.A-2304).
Table 3-4 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is Br and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.C.3-4.A-1 to I-1.C.3-4.A-2304, compounds I-2.C.3-4.A-1 to I-2.C.3-4.A-2304, compounds I-3.C.3-4.A-1 to I-3.C.3-4.A-2304 compounds I-4.C.3-4.A-1 to I-
4. C.3-4.A-2304).
Table 3-5 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-5.A-1 to 1-1.C.3-5.A-2304, compounds I-2.C.3- 5.A-1 to I-2.C.3-5.A-2304, compounds I-3.C.3-5.A-1 to I-3.C.3-5.A-2304 compounds I-4.C.3-
5. A-1 to I-4.C.3-5.A-2304). Table 3-6 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-6.A-1 to 1-1.C.3-6.A-2304, compounds I- 2.C.3-6.A-1 to I-2.C.3-6.A-2304, compounds I-3.C.3-6.A-1 to I-3.C.3-6.A-2304 compounds I- 4.C.3-6.A-1 to I-4.C.3-6.A-2304).
Table 3-7 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is H and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.C.3-7.A-1 to I-1.C.3-7.A-2304, compounds I-2.C.3-7.A-1 to I-2.C.3-7.A-2304, compounds I-3.C.3-7.A-1 to I-3.C.3-7.A-2304 compounds I-4.C.3-7.A-1 to I- 4.C.3-7.A-2304).
Table 3-8 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-8.A-1 to 1-1.C.3-8.A-2304, compounds I-2.C.3- 8.A-1 to I-2.C.3-8.A-2304, compounds I-3.C.3-8.A-1 to I-3.C.3-8.A-2304 compounds I-4.C.3- 8.A-1 to I-4.C.3-8.A-2304).
Table 4-1 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-1 .A-1 to 1-1.D.4-1.A-2304, compounds I-2.D.4- 1.A-1 to I-2.D.4-1.A-2304, compounds I-3. D.4-1 .A-1 to I-3. D.4-1 .A-2304 compounds I-4.D.4-
1. A-1 to I-4.D.4-1. A-2304).
Table 4-2 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-2.A-1 to 1-1.D.4-2.A-2304, compounds I-2.D.4- 2.A-1 to I-2.D.4-2.A-2304, compounds I-3.D.4-2.A-1 to I-3.D.4-2.A-2304 compounds I-4.D.4-
2. A-1 to I-4.D.4-2.A-2304).
Table 4-3 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-3.A-1 to 1-1.D.4-3.A-2304, compounds I-2.D.4- 3.A-1 to I-2.D.4-3.A-2304, compounds I-3.D.4-3.A-1 to I-3.D.4-3.A-2304 compounds I-4.D.4-
3. A-1 to I-4.D.4-3.A-2304).
Table 4-4 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is Br and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.D.4-4.A-1 to I-1.D.4-4.A-2304, compounds I-2.D.4-4.A-1 to I-2.D.4-4.A-2304, compounds I-3.D.4-4.A-1 to I-3.D.4-4.A-2304 compounds I-4.D.4-4.A-1 to I-
4. D.4-4.A-2304).
Table 4-5 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-5.A-1 to 1-1.D.4-5.A-2304, compounds I-2.D.4- 5.A-1 to I-2.D.4-5.A-2304, compounds I-3.D.4-5.A-1 to I-3.D.4-5.A-2304 compounds I-4.D.4-
5. A-1 to I-4.D.4-5.A-2304). Table 4-6 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-6.A-1 to 1-1.D.4-6.A-2304, compounds I- 2.D.4-6.A-1 to I-2.D.4-6.A-2304, compounds I-3.D.4-6.A-1 to I-3.D.4-6.A-2304 compounds I- 4.D.4-6.A-1 to I-4.D.4-6.A-2304).
Table 4-7 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is H and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.D.4-7.A-1 to I-1.D.4-7.A-2304, compounds I-2.D.4-7.A-1 to I-2.D.4-7.A-2304, compounds I-3.D.4-7.A-1 to I-3.D.4-7.A-2304 compounds I-4.D.4-7.A-1 to I- 4.D.4-7.A-2304).
Table 4-8 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-8.A-1 to 1-1.D.4-8.A-2304, compounds I-2.D.4- 8.A-1 to I-2.D.4-8.A-2304, compounds I-3.D.4-8.A-1 to I-3.D.4-8.A-2304 compounds I-4.D.4- 8.A-1 to I-4.D.4-8.A-2304).
Table 5-1 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-1.A-1 to 1-1 .E.5-1.A-2304, compounds I-2.E.5- 1.A-1 to I-2.E.5-1.A-2304, compounds I-3.E.5-1 .A-1 to I-3. E.5-1 .A-2304 compounds I-4. E.5-1 .A- 1 to I-4.E.5-1.A-2304).
Table 5-2 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-2.A-1 to 1-1 .E.5-2.A-2304, compounds I-2.E.5- 2.A-1 to I-2.E.5-2.A-2304, compounds I-3.E.5-2.A-1 to I-3.E.5-2.A-2304 compounds I-4.E.5-2.A- 1 to I-4.E.5-2.A-2304).
Table 5-3 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-3.A-1 to 1-1 .E.5-3.A-2304, compounds I-2.E.5- 3.A-1 to I-2.E.5-3.A-2304, compounds I-3.E.5-3.A-1 to I-3.E.5-3.A-2304 compounds I-4.E.5-3.A- 1 to I-4.E.5-3.A-2304).
Table 5-4 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is Br and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.E.5-4.A-1 to 1-1 .E.5-4.A-2304, compounds I-2.E.5-4.A-1 to I-2.E.5-4.A-2304, compounds I-3.E.5-4.A-1 to I-3.E.5-4.A-2304 compounds I-4.E.5-4.A-1 to I- 4.E.5-4.A-2304).
Table 5-5 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-5.A-1 to 1-1 .E.5-5.A-2304, compounds I-2.E.5- 5.A-1 to I-2.E.5-5.A-2304, compounds I-3.E.5-5.A-1 to I-3.E.5-5.A-2304 compounds I-4.E.5-5.A- 1 to I-4.E.5-5.A-2304). Table 5-6 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-6.A-1 to 1-1.E.5-6.A-2304, compounds I- 2.E.5-6.A-1 to I-2.E.5-6.A-2304, compounds I-3.E.5-6.A-1 to I-3.E.5-6.A-2304 compounds I- 4.E.5-6.A-1 to I-4.E.5-6.A-2304).
Table 5-7 Compounds of the formula 1-1. E, I-2.E, I-3.E, I-4.E in which R9 is H and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.E.5-7.A-1 to 1-1 .E.5-7.A-2304, compounds I-2.E.5-7.A-1 to I-2.E.5-7.A-2304, compounds I-3.E.5-7.A-1 to I-3.E.5-7.A-2304 compounds I-4.E.5-7.A-1 to I- 4.E.5-7.A-2304).
Table 5-8 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-8.A-1 to 1-1 .E.5-8.A-2304, compounds I-2.E.5- 8.A-1 to I-2.E.5-8.A-2304, compounds I-3.E.5-8.A-1 to I-3.E.5-8.A-2304 compounds I-4.E.5-8.A- 1 to I-4.E.5-8.A-2304).
Table 6-1 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is CH3 and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds 1-1.F.6-1.A-1 to 1-1.F.6-1.A-2304, compounds I-2.F.6-1.A-1 to I-2.F.6-1 .A-2304, compounds I-3.F.6-1.A-1 to I-3.F.6-1.A-2304 compounds I-4.F.6-1 .A-1 to I- 4.F.6-1 .A-2304).
Table 6-2 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.F.6-2.A-1 to 1-1 .F.6-2.A-2304, compounds I-2.F.6- 2.A-1 to I-2.F.6-2.A-2304, compounds I-3.F.6-2.A-1 to I-3.F.6-2.A-2304 compounds I-4.F.6-2.A- 1 to I-4.F.6-2.A-2304).
Table 6-3 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.F.6-3.A-1 to 1-1 .F.6-3.A-2304, compounds I-2.F.6- 3.A-1 to I-2.F.6-3.A-2304, compounds I-3.F.6-3.A-1 to I-3.F.6-3.A-2304 compounds I-4.F.6-3.A- 1 to I-4.F.6-3.A-2304).
Table 6-4 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is Br and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.6-4.A-1 to I-1.F.6-4.A-2304, compounds I-2.F.6-4.A-1 to I-2.F.6-4.A-2304, compounds I-3.F.6-4.A-1 to I-3.F.6-4.A-2304 compounds I-4.F.6-4.A-1 to I- 4.F.6-4.A-2304).
Table 6-5 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1.F.6-5.A-1 to 1-1 .F.6-5.A-2304, compounds I-2.F.6- 5.A-1 to I-2.F.6-5.A-2304, compounds I-3.F.6-5.A-1 to I-3.F.6-5.A-2304 compounds I-4.F.6-5.A- 1 to I-4.F.6-5.A-2304). Table 6-6 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.6-6.A-1 to I-1.F.6-6.A-2304, compounds I- 2.F.6-6.A-1 to I-2.F.6-6.A-2304, compounds I-3.F.6-6.A-1 to I-3.F.6-6.A-2304 compounds I- 4.F.6-6.A-1 to I-4.F.6-6.A-2304).
Table 6-7 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is H and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .F.6-7.A-1 to 1-1 .F.6-7.A-2304, compounds I-2.F.6-7.A-1 to I- 2.F.6-7.A-2304, compounds I-3.F.6-7.A-1 to I-3.F.6-7.A-2304 compounds I-4.F.6-7.A-1 to I- 4.F.6-7.A-2304).
Table 6-8 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R9 is CF3 and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.6-8.A-1 to I-1.F.6-8.A-2304, compounds I-2.F.6-8.A-1 to I-2.F.6-8.A-2304, compounds I-3.F.6-8.A-1 to I-3.F.6-8.A-2304 compounds I-4.F.6-8.A-1 to I- 4.F.6-8.A-2304).
Particular embodiments of the compounds I are the following compounds: X-1.A, X-1.B, X-1 .C, X-1 .D, X-1.E, X-1 .F; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F; X-3.A, X-3.B, X-3.C, X-3.D, X- 3
Figure imgf000085_0001
X-1.D X-1.E X-1.F
Figure imgf000086_0001
X-2.A X-2.B X-2.C
Figure imgf000086_0002
X-3.A X-3.B X-3.C
Figure imgf000086_0003
X-3.D X-3.E X-3.F
Figure imgf000087_0001
Figure imgf000087_0002
X- -D X-4.E X4.F
Particular embodiments of the compounds I are the following compounds: X-1 .A, X-1 .B, X-1.C, X-1 .D, X-1 .E, X-1.F; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F; X-3.A, X-3.B, X-3.C, X-3.D, X-3.E, X-3.F; X-4.A, X-4.B, X-4.C, X-4.D, X-4.E, X-4.F that are compiled in the Tables 1-1 to 1 -8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Table 1-1 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 . A.1-1. A- 1 to X-1.A.1 -1 .A-2304, compounds X-
2.A.1-1.A-1 to X-2.A.1 -1.A-2304, compounds X-3.A.1 -1.A-1 to X-3.A.1-1.A-2304 compounds X- 4.A.1-1.A-1 to X-4.A.1 -1.A-2304).
Table 1-2 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-2.A-1 to X-1.A.1 -2.A-2304, compounds X-
2.A.1-2.A-1 to X-2.A.1 -2.A-2304, compounds X-3.A.1 -2.A-1 to X-3.A.1-2.A-2304 compounds X- 4.A.1-2.A-1 to X-4.A.1 -2.A-2304).
Table 1-3 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-3.A-1 to X-1.A.1 -3.A-2304, compounds X-
2.A.1-3.A-1 to X-2.A.1 -3.A-2304, compounds X-3.A.1 -3.A-1 to X-3.A.1-3.A-2304 compounds X- 4.A.1-3.A-1 to X-4.A.1 -3.A-2304).
Table 1-4 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is Br and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 . A.1-4.A-1 to X-1.A.1 -4.A-2304, compounds X-
2.A.1-4.A-1 to X-2.A.1 -4.A-2304, compounds X-3.A.1 -4.A-1 to X-3.A.1-4.A-2304 compounds X- 4.A.1-4.A-1 to X-4.A.1 -4.A-2304).
Table 1-5 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-5.A-1 to X-1.A.1 -5.A-2304, compounds X- 2.A.1-5.A-1 to X-2.A.1 -5.A-2304, compounds X-3.A.1 -5.A-1 to X-3.A.1-5.A-2304 compounds X- 4.A.1-5.A-1 to X-4.A.1 -5.A-2304).
Table 1-6 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-6.A-1 to X-1.A.1 -6.A-2304, compounds X-2.A.1-6.A-1 to X-2.A.1 -6.A-2304, compounds X-3.A.1 -6.A-1 to X-3.A.1 -6.A-2304 compounds X-4.A.1-6.A-1 to X-4.A.1 -6.A-2304).
Table 1-7 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is H and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-7.A-1 to X-1.A.1 -7.A-2304, compounds X- 2.A.1-7.A-1 to X-2.A.1 -7.A-2304, compounds X-3.A.1 -7.A-1 to X-3.A.1-7.A-2304 compounds X- 4.A.1-7.A-1 to X-4.A.1 -7.A-2304).
Table 1-8 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-8.A-1 to X-1.A.1 -8.A-2304, compounds X- 2.A.1-8.A-1 to X-2.A.1 -8.A-2304, compounds X-3.A.1 -8.A-1 to X-3.A.1-8.A-2304 compounds X- 4.A.1-8.A-1 to X-4.A.1 -8.A-2304).
Table 2-1 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .B.2-1.A-1 to X-1.B.2-1 .A-2304, compounds X- 2.B.2-1.A-1 to X-2.B.2-1.A-2304, compounds X-3.B.2-1.A-1 to X-3. B.2-1. A-2304 compounds X- 4.B.2-1.A-1 to X-4.B.2-1.A-2304).
Table 2-2 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .B.2-2.A-1 to X-1.B.2-2.A-2304, compounds X- 2.B.2-2.A-1 to X-2.B.2-2.A-2304, compounds X-3.B.2-2.A-1 to X-3.B.2-2.A-2304 compounds X- 4.B.2-2.A-1 to X-4.B.2-2.A-2304).
Table 2-3 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .B.2-3.A-1 to X-1.B.2-3.A-2304, compounds X- 2.B.2-3.A-1 to X-2.B.2-3.A-2304, compounds X-3.B.2-3.A-1 to X-3.B.2-3.A-2304 compounds X- 4.B.2-3.A-1 to X-4.B.2-3.A-2304).
Table 2-4 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is Br and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .B.2-4.A-1 to X-1.B.2-4.A-2304, compounds X- 2.B.2-4.A-1 to X-2.B.2-4.A-2304, compounds X-3.B.2-4.A-1 to X-3.B.2-4.A-2304 compounds X- 4.B.2-4.A-1 to X-4.B.2-4.A-2304).
Table 2-5 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .B.2-5.A-1 to X-1.B.2-5.A-2304, compounds X- 2.B.2-5.A-1 to X-2.B.2-5.A-2304, compounds X-3.B.2-5.A-1 to X-3.B.2-5.A-2304 compounds X- 4.B.2-5.A-1 to X-4.B.2-5.A-2304).
Table 2-6 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-6.A-1 to X-1.B.2-6.A-2304, compounds X-2.B.2-6.A-1 to X-2.B.2-6.A-2304, compounds X-3.B.2-6.A-1 to X-3.B.2-6.A-2304 compounds X-4.B.2-6.A-1 to X-4.B.2-6.A-2304).
Table 2-7 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is H and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .B.2-7.A-1 to X-1.B.2-7.A-2304, compounds X- 2.B.2-7.A-1 to X-2.B.2-7.A-2304, compounds X-3.B.2-7.A-1 to X-3.B.2-7.A-2304 compounds X- 4.B.2-7.A-1 to X-4.B.2-7.A-2304).
Table 2-8 Compounds of the formula X-1 .B, X-2.B, X-3.B, X-4.B in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .B.2-8.A-1 to X-1.B.2-8.A-2304, compounds X- 2.B.2-8.A-1 to X-2.B.2-8.A-2304, compounds X-3.B.2-8.A-1 to X-3.B.2-8.A-2304 compounds X- 4.B.2-8.A-1 to X-4.B.2-8.A-2304).
Table 3-1 Compounds of the formula X-1 .C, X-2.C, X-3.C, X-4.C in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .C.3-1.A-1 to X-1.C.3-1 .A-2304, compounds X- 2.C.3-1 .A-1 to X-2.C.3-1.A-2304, compounds X-3.C.3-1 .A-1 to X-3. C.3-1. A-2304 compounds X- 4.C.3-1 .A-1 to X-4.C.3-1.A-2304).
Table 3-2 Compounds of the formula X-1 .C, X-2.C, X-3.C, X-4.C in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .C.3-2.A-1 to X-1.C.3-2.A-2304, compounds X- 2.C.3-2.A-1 to X-2.C.3-2.A-2304, compounds X-3.C.3-2.A-1 to X-3.C.3-2.A-2304 compounds X- 4.C.3-2.A-1 to X-4.C.3-2.A-2304).
Table 3-3 Compounds of the formula X-1 .C, X-2.C, X-3.C, X-4.C in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .C.3-3.A-1 to X-1.C.3-3.A-2304, compounds X- 2.C.3-3.A-1 to X-2.C.3-3.A-2304, compounds X-3.C.3-3.A-1 to X-3.C.3-3.A-2304 compounds X- 4.C.3-3.A-1 to X-4.C.3-3.A-2304).
Table 3-4 Compounds of the formula X-1 .C, X-2.C, X-3.C, X-4.C in which R9 is Br and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .C.3-4.A-1 to X-1.C.3-4.A-2304, compounds X- 2.C.3-4.A-1 to X-2.C.3-4.A-2304, compounds X-3.C.3-4.A-1 to X-3.C.3-4.A-2304 compounds X- 4.C.3-4.A-1 to X-4.C.3-4.A-2304).
Table 3-5 Compounds of the formula X-1 .C, X-2.C, X-3.C, X-4.C in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-5.A-1 to X-1.C.3-5.A-2304, compounds X- 2.C.3-5.A-1 to X-2.C.3-5.A-2304, compounds X-3.C.3-5.A-1 to X-3.C.3-5.A-2304 compounds X- 4.C.3-5.A-1 to X-4.C.3-5.A-2304).
Table 3-6 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-6.A-1 to X-1.C.3-6.A-2304, compounds X-2.C.3-6.A-1 to X-2.C.3-6.A-2304, compounds X-3.C.3-6.A-1 to X-3.C.3-6.A-2304 compounds X-4.C.3-6.A-1 to X-4.C.3-6.A-2304).
Table 3-7 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is H and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-7.A-1 to X-1.C.3-7.A-2304, compounds X- 2.C.3-7.A-1 to X-2.C.3-7.A-2304, compounds X-3.C.3-7.A-1 to X-3.C.3-7.A-2304 compounds X- 4.C.3-7.A-1 to X-4.C.3-7.A-2304).
Table 3-8 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R9 is CF3 and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-8.A-1 to X-1.C.3-8.A-2304, compounds X- 2.C.3-8.A-1 to X-2.C.3-8.A-2304, compounds X-3.C.3-8.A-1 to X-3.C.3-8.A-2304 compounds X- 4.C.3-8.A-1 to X-4.C.3-8.A-2304).
Table 4-1 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-1.A-1 to X-1.D.4-1.A-2304, compounds X- 2.D.4-1.A-1 to X-2. D.4-1.A-2304, compounds X-3.D.4-1.A-1 to X-3. D.4-1. A-2304 compounds X- 4.D.4-1.A-1 to X-4. D.4-1.A-2304).
Table 4-2 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-2.A-1 to X-1.D.4-2.A-2304, compounds X- 2.D.4-2.A-1 to X-2.D.4-2.A-2304, compounds X-3.D.4-2.A-1 to X-3.D.4-2.A-2304 compounds X- 4.D.4-2.A-1 to X-4.D.4-2.A-2304).
Table 4-3 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-3.A-1 to X-1.D.4-3.A-2304, compounds X- 2.D.4-3.A-1 to X-2.D.4-3.A-2304, compounds X-3.D.4-3.A-1 to X-3.D.4-3.A-2304 compounds X- 4.D.4-3.A-1 to X-4.D.4-3.A-2304).
Table 4-4 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is Br and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-4.A-1 to X-1.D.4-4.A-2304, compounds X- 2.D.4-4.A-1 to X-2.D.4-4.A-2304, compounds X-3.D.4-4.A-1 to X-3.D.4-4.A-2304 compounds X- 4.D.4-4.A-1 to X-4.D.4-4.A-2304).
Table 4-5 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .D.4-5.A-1 to X-1.D.4-5.A-2304, compounds X- 2.D.4-5.A-1 to X-2.D.4-5.A-2304, compounds X-3.D.4-5.A-1 to X-3.D.4-5.A-2304 compounds X- 4.D.4-5.A-1 to X-4.D.4-5.A-2304).
Table 4-6 Compounds of the formula X-1 .D, X-2.D, X-3.D, X-4.D in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-6.A-1 to X-1 .D.4-6.A-2304, compounds X-2.D.4-6.A-1 to X-2.D.4-6.A-2304, compounds X-3.D.4-6.A-1 to X-3.D.4-6.A-2304 compounds X-4.D.4-6.A-1 to X-4.D.4-6.A-2304).
Table 4-7 Compounds of the formula X-1 .D, X-2.D, X-3.D, X-4.D in which R9 is H and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .D.4-7.A-1 to X-1.D.4-7.A-2304, compounds X- 2.D.4-7.A-1 to X-2.D.4-7.A-2304, compounds X-3.D.4-7.A-1 to X-3.D.4-7.A-2304 compounds X- 4.D.4-7.A-1 to X-4.D.4-7.A-2304).
Table 4-8 Compounds of the formula X-1 .D, X-2.D, X-3.D, X-4.D in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .D.4-8.A-1 to X-1.D.4-8.A-2304, compounds X- 2.D.4-8.A-1 to X-2.D.4-8.A-2304, compounds X-3.D.4-8.A-1 to X-3.D.4-8.A-2304 compounds X- 4.D.4-8.A-1 to X-4.D.4-8.A-2304).
Table 5-1 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .E.5-1.A-1 to X-1.E.5-1 .A-2304, compounds X- 2.E.5-1.A-1 to X-2.E.5-1.A-2304, compounds X-3.E.5-1.A-1 to X-3. E.5-1.A-2304 compounds X- 4.E.5-1.A-1 to X-4.E.5-1.A-2304).
Table 5-2 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .E.5-2.A-1 to X-1.E.5-2.A-2304, compounds X- 2.E.5-2.A-1 to X-2.E.5-2.A-2304, compounds X-3.E.5-2.A-1 to X-3.E.5-2.A-2304 compounds X- 4.E.5-2.A-1 to X-4.E.5-2.A-2304).
Table 5-3 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .E.5-3.A-1 to X-1.E.5-3.A-2304, compounds X- 2.E.5-3.A-1 to X-2.E.5-3.A-2304, compounds X-3.E.5-3.A-1 to X-3.E.5-3.A-2304 compounds X- 4.E.5-3.A-1 to X-4.E.5-3.A-2304).
Table 5-4 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is Br and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .E.5-4.A-1 to X-1.E.5-4.A-2304, compounds X- 2.E.5-4.A-1 to X-2.E.5-4.A-2304, compounds X-3.E.5-4.A-1 to X-3.E.5-4.A-2304 compounds X- 4.E.5-4.A-1 to X-4.E.5-4.A-2304).
Table 5-5 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .E.5-5.A-1 to X-1.E.5-5.A-2304, compounds X- 2.E.5-5.A-1 to X-2.E.5-5.A-2304, compounds X-3.E.5-5.A-1 to X-3.E.5-5.A-2304 compounds X- 4.E.5-5.A-1 to X-4.E.5-5.A-2304).
Table 5-6 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-6.A-1 to X-1.E.5-6.A-2304, compounds X-2.E.5-6.A-1 to X-2.E.5-6.A-2304, compounds X-3.E.5-6.A-1 to X-3.E.5-6.A-2304 compounds X-4.E.5-6.A-1 to X-4.E.5-6.A-2304).
Table 5-7 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is H and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .E.5-7.A-1 to X-1.E.5-7.A-2304, compounds X- 2.E.5-7.A-1 to X-2.E.5-7.A-2304, compounds X-3.E.5-7.A-1 to X-3.E.5-7.A-2304 compounds X- 4.E.5-7.A-1 to X-4.E.5-7.A-2304).
Table 5-8 Compounds of the formula X-1 .E, X-2.E, X-3.E, X-4.E in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .E.5-8.A-1 to X-1.E.5-8.A-2304, compounds X- 2.E.5-8.A-1 to X-2.E.5-8.A-2304, compounds X-3.E.5-8.A-1 to X-3.E.5-8.A-2304 compounds X- 4.E.5-8.A-1 to X-4.E.5-8.A-2304).
Table 6-1 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is CH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .F.1 -1.A-1 to X-1 .F.1 -1 .A-2304, compounds X- 2.F.1 -1 .A-1 to X-2.F.1 -1.A-2304, compounds X-3.F.1-1 .A-1 to X-3.F.1-1 .A-2304 compounds X- 4.F.1 -1 .A-1 to X-4. F.1 -1.A-2304).
Table 6-2 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is CHF2 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .F.1 -2.A-1 to X-1 .F.1 -2.A-2304, compounds X- 2.F.1 -2.A-1 to X-2.F.1 -2.A-2304, compounds X-3.F.1-2.A-1 to X-3.F.1-2. A-2304 compounds X- 4.F.1 -2.A-1 to X-4.F.1 -2.A-2304).
Table 6-3 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is C≡CH and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .F.1 -3.A-1 to X-1 .F.1 -3.A-2304, compounds X- 2.F.1 -3.A-1 to X-2.F.1 -3.A-2304, compounds X-3.F.1-3.A-1 to X-3.F.1-3. A-2304 compounds X- 4.F.1 -3.A-1 to X-4.F.1 -3.A-2304).
Table 6-4 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is Br and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .F.1 -4.A-1 to X-1 .F.1 -4.A-2304, compounds X- 2.F.1 -4.A-1 to X-2.F.1 -4.A-2304, compounds X-3.F.1-4.A-1 to X-3.F.1-4. A-2304 compounds X- 4.F.1 -4.A-1 to X-4.F.1 -4.A-2304).
Table 6-5 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is OCH3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .F.1 -5.A-1 to X-1 .F.1 -5.A-2304, compounds X- 2.F.1 -5.A-1 to X-2.F.1 -5.A-2304, compounds X-3.F.1-5.A-1 to X-3.F.1-5.A-2304 compounds X- 4.F.1 -5.A-1 to X-4.F.1 -5.A-2304).
Table 6-6 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is cyclopropyl and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-6.A-1 to X-1 .F.1 -6.A-2304, compounds X-2.F.1 -6.A-1 to X-2.F.1-6.A-2304, compounds X-3.F.1 -6.A-1 to X-3.F.1-6.A-2304 compounds X-4.F.1 -6.A-1 to X-4.F.1-6.A-2304).
Table 6-7 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is H and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .F.1 -7.A-1 to X-1 .F.1 -7.A-2304, compounds X- 2.F.1 -7.A-1 to X-2.F.1 -7.A-2304, compounds X-3.F.1-7.A-1 to X-3.F.1-7.A-2304 compounds X- 4.F.1 -7.A-1 to X-4.F.1 -7.A-2304).
Table 6-8 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R9 is CF3 and the meaning for the combination of Y, R4 and R10 for each individual compound corresponds in each case to one line of Table A (compounds X-1 .F.1 -8.A-1 to X-1 .F.1 -8.A-2304, compounds X- 2.F.1 -8.A-1 to X-2.F.1 -8.A-2304, compounds X-3.F.1-8.A-1 to X-3.F.1-8.A-2304 compounds X- 4.F.1 -8.A-1 to X-4.F.1 -8.A-2304).
Table A
Please note that following R4 structure are in the Table A named as follows:
Figure imgf000093_0001
Figure imgf000094_0001
Figure imgf000095_0001
line Y R4 R10 line Y R4 R10
A-1 H R4-1 H A-26 F R4-2 H
A-2 H R4-2 H A-27 F R4-3 H
A-3 H R4-3 H A-28 F R4-4 H
A-4 H R4-4 H A-29 F R4-5 H
A-5 H R4-5 H A-30 F R4-6 H
A-6 H R4-6 H A-31 F R4-7 H
A-7 H R4-7 H A-32 F R4-8 H
A-8 H R4-8 H A-33 F R4-9 H
A-9 H R4-9 H A-34 F R4-10 H
A-10 H R4-10 H A-35 F R4-1 1 H
A-1 1 H R4-1 1 H A-36 F R4-12 H
A-12 H R4-12 H A-37 F R4-13 H
A-13 H R4-13 H A-38 F R4-14 H
A-14 H R4-14 H A-39 F R4-15 H
A-15 H R4-15 H A-40 F R4-16 H
A-16 H R4-16 H A-41 F R4-17 H
A-17 H R4-17 H A-42 F R4-18 H
A-18 H R4-18 H A-43 F R4-19 H
A-19 H R4-19 H A-44 F R4-20 H
A-20 H R4-20 H A-45 F R4-21 H
A-21 H R4-21 H A-46 F R4-22 H
A-22 H R4-22 H A-47 F R4-23 H
A-23 H R4-23 H A-48 F R4-24 H
A-24 H R4-24 H A-49 CI R4-1 H
A-25 F R4-1 H A-50 CI R4-2 H line Y R4 R10 line Y R4 R10
A-51 CI R4-3 H A-93 Br R4-21 H
A-52 CI R4-4 H A-94 Br R4-22 H
A-53 CI R4-5 H A-95 Br R4-23 H
A-54 CI R4-6 H A-96 Br R4-24 H
A-55 CI R4-7 H A-97 CHs R4-1 H
A-56 CI R4-8 H A-98 CHs R4-2 H
A-57 CI R4-9 H A-99 CHs R4-3 H
A-58 CI R4-10 H A-100 CHs R4-4 H
A-59 CI R4-1 1 H A-101 CHs R4-5 H
A-60 CI R4-12 H A-102 CHs R4-6 H
A-61 CI R4-13 H A-103 CHs R4-7 H
A-62 CI R4-14 H A-104 CHs R4-8 H
A-63 CI R4-15 H A-105 CHs R4-9 H
A-64 CI R4-16 H A-106 CHs R4-10 H
A-65 CI R4-17 H A-107 CHs R4-1 1 H
A-66 CI R4-18 H A-108 CHs R4-12 H
A-67 CI R4-19 H A-109 CHs R4-13 H
A-68 CI R4-20 H A-1 10 CHs R4-14 H
A-69 CI R4-21 H A-1 1 1 CHs R4-15 H
A-70 CI R4-22 H A-1 12 CHs R4-16 H
A-71 CI R4-23 H A-1 13 CHs R4-17 H
A-72 CI R4-24 H A-1 14 CHs R4-18 H
A-73 Br R4-1 H A-1 15 CHs R4-19 H
A-74 Br R4-2 H A-1 16 CHs R4-20 H
A-75 Br R4-3 H A-1 17 CHs R4-21 H
A-76 Br R4-4 H A-1 18 CHs R4-22 H
A-77 Br R4-5 H A-1 19 CHs R4-23 H
A-78 Br R4-6 H A-120 CHs R4-24 H
A-79 Br R4-7 H A-121 CHF2 R4-1 H
A-80 Br R4-8 H A-122 CHF2 R4-2 H
A-81 Br R4-9 H A-123 CHF2 R4-3 H
A-82 Br R4-10 H A-124 CHF2 R4-4 H
A-83 Br R4-1 1 H A-125 CHF2 R4-5 H
A-84 Br R4-12 H A-126 CHF2 R4-6 H
A-85 Br R4-13 H A-127 CHF2 R4-7 H
A-86 Br R4-14 H A-128 CHF2 R4-8 H
A-87 Br R4-15 H A-129 CHF2 R4-9 H
A-88 Br R4-16 H A-130 CHF2 R4-10 H
A-89 Br R4-17 H A-131 CHF2 R4-1 1 H
A-90 Br R4-18 H A-132 CHF2 R4-12 H
A-91 Br R4-19 H A-133 CHF2 R4-13 H
A-92 Br R4-20 H A-134 CHF2 R4-14 H line Y R4 R10 line Y R4 R10
A-135 CHF2 R4-15 H A-177 OCHF2 R4-9 H
A-136 CHF2 R4-16 H A-178 OCHF2 R4-10 H
A-137 CHF2 R4-17 H A-179 OCHF2 R4-1 1 H
A-138 CHF2 R4-18 H A-180 OCHF2 R4-12 H
A-139 CHF2 R4-19 H A-181 OCHF2 R4-13 H
A-140 CHF2 R4-20 H A-182 OCHF2 R4-14 H
A-141 CHF2 R4-21 H A-183 OCHF2 R4-15 H
A-142 CHF2 R4-22 H A-184 OCHF2 R4-16 H
A-143 CHF2 R4-23 H A-185 OCHF2 R4-17 H
A-144 CHF2 R4-24 H A-186 OCHF2 R4-18 H
A-145 OCHs R4-1 H A-187 OCHF2 R4-19 H
A-146 OCH3 R4-2 H A-188 OCHF2 R4-20 H
A-147 OCHs R4-3 H A-189 OCHF2 R4-21 H
A-148 OCHs R4-4 H A-190 OCHF2 R4-22 H
A-149 OCH3 R4-5 H A-191 OCHF2 R4-23 H
A-150 OCH3 R4-6 H A-192 OCHF2 R4-24 H
A-151 OCH3 R4-7 H A-193 OCF3 R4-1 H
A-152 OCH3 R4-8 H A-194 OCF3 R4-2 H
A-153 OCH3 R4-9 H A-195 OCF3 R4-3 H
A-154 OCH3 R4-10 H A-196 OCF3 R4-4 H
A-155 OCH3 R4-1 1 H A-197 OCF3 R4-5 H
A-156 OCH3 R4-12 H A-198 OCF3 R4-6 H
A-157 OCH3 R4-13 H A-199 OCF3 R4-7 H
A-158 OCH3 R4-14 H A-200 OCF3 R4-8 H
A-159 OCH3 R4-15 H A-201 OCF3 R4-9 H
A-160 OCH3 R4-16 H A-202 OCF3 R4-10 H
A-161 OCH3 R4-17 H A-203 OCF3 R4-1 1 H
A-162 OCH3 R4-18 H A-204 OCF3 R4-12 H
A-163 OCH3 R4-19 H A-205 OCF3 R4-13 H
A-164 OCH3 R4-20 H A-206 OCF3 R4-14 H
A-165 OCH3 R4-21 H A-207 OCF3 R4-15 H
A-166 OCH3 R4-22 H A-208 OCF3 R4-16 H
A-167 OCH3 R4-23 H A-209 OCF3 R4-17 H
A-168 OCH3 R4-24 H A-210 OCF3 R4-18 H
A-169 OCHF2 R4-1 H A-21 1 OCF3 R4-19 H
A-170 OCHF2 R4-2 H A-212 OCF3 R4-20 H
A-171 OCHF2 R4-3 H A-213 OCF3 R4-21 H
A-172 OCHF2 R4-4 H A-214 OCF3 R4-22 H
A-173 OCHF2 R4-5 H A-215 OCF3 R4-23 H
A-174 OCHF2 R4-6 H A-216 OCF3 R4-24 H
A-175 OCHF2 R4-7 H A-217 CF3 R4-1 H
A-176 OCHF2 R4-8 H A-218 CF3 R4-2 H line Y R4 R10 line Y R4 R10
A-219 CFs R4-3 H A-257 R4-17 H
A-220 CFs R4-4 H A-258 R4-18 H
A-221 CFs R4-5 H
A-259 R4-19 H
A-222 CFs R4-6 H
A-260 R4-20 H
A-223 CFs R4-7 H
A-224 CFs R4-8 H A-261 R4-21 H
A-225 CFs R4-9 H A-262 R4-22 H
A-226 CFs R4-10 H A-263 R4-23 H
A-227 CFs R4-1 1 H
A-264 R4-24 H
A-228 CFs R4-12 H
A-265 cPr R4-1 H
A-229 CFs R4-13 H
A-266 cPr R4-2 H
A-230 CFs R4-14 H
A-267 cPr R4-3 H
A-231 CFs R4-15 H
A-268 cPr R4-4 H
A-232 CFs R4-16 H
A-269 cPr R4-5 H
A-233 CFs R4-17 H
A-270 cPr R4-6 H
A-234 CFs R4-18 H
A-271 cPr R4-7 H
A-235 CFs R4-19 H
A-272 cPr R4-8 H
A-236 CFs R4-20 H
A-273 cPr R4-9 H
A-237 CFs R4-21 H
A-274 cPr R4-10 H
A-238 CFs R4-22 H
A-275 cPr R4-1 1 H
A-239 CFs R4-23 H
A-276 cPr R4-12 H
A-240 CFs R4-24 H
A-277 cPr R4-13 H
A-241 R4-1 H
A-278 cPr R4-14 H
A-242 R4-2 H
A-279 cPr R4-15 H
A-243 R4-3 H A-280 cPr R4-16 H
A-244 R4-4 H A-281 cPr R4-17 H
A-245 R4-5 H A-282 cPr R4-18 H
A-283 cPr R4-19 H
A-246 R4-6 H
A-284 cPr R4-20 H
A-247 R4-7 H
A-285 cPr R4-21 H
A-248 R4-8 H A-286 cPr R4-22 H
A-249 R4-9 H A-287 cPr R4-23 H
A-250 R4-10 H A-288 cPr R4-24 H
A-289 H R4-1 Br
A-251 R4-1 1 H
A-290 H R4-2 Br
A-252 R4-12 H
A-291 H R4-3 Br
A-253 R4-13 H A-292 H R4-4 Br
A-254 R4-14 H A-293 H R4-5 Br
A-255 R4-15 H A-294 H R4-6 Br
A-295 H R4-7 Br
A-256 R4-16 H
A-296 H R4-8 Br line Y R4 R10 line Y R4 R10
A-297 H R4-9 Br A-339 CI R4-3 Br
A-298 H R4-10 Br A-340 CI R4-4 Br
A-299 H R4-1 1 Br A-341 CI R4-5 Br
A-300 H R4-12 Br A-342 CI R4-6 Br
A-301 H R4-13 Br A-343 CI R4-7 Br
A-302 H R4-14 Br A-344 CI R4-8 Br
A-303 H R4-15 Br A-345 CI R4-9 Br
A-304 H R4-16 Br A-346 CI R4-10 Br
A-305 H R4-17 Br A-347 CI R4-1 1 Br
A-306 H R4-18 Br A-348 CI R4-12 Br
A-307 H R4-19 Br A-349 CI R4-13 Br
A-308 H R4-20 Br A-350 CI R4-14 Br
A-309 H R4-21 Br A-351 CI R4-15 Br
A-310 H R4-22 Br A-352 CI R4-16 Br
A-31 1 H R4-23 Br A-353 CI R4-17 Br
A-312 H R4-24 Br A-354 CI R4-18 Br
A-313 F R4-1 Br A-355 CI R4-19 Br
A-314 F R4-2 Br A-356 CI R4-20 Br
A-315 F R4-3 Br A-357 CI R4-21 Br
A-316 F R4-4 Br A-358 CI R4-22 Br
A-317 F R4-5 Br A-359 CI R4-23 Br
A-318 F R4-6 Br A-360 CI R4-24 Br
A-319 F R4-7 Br A-361 Br R4-1 Br
A-320 F R4-8 Br A-362 Br R4-2 Br
A-321 F R4-9 Br A-363 Br R4-3 Br
A-322 F R4-10 Br A-364 Br R4-4 Br
A-323 F R4-1 1 Br A-365 Br R4-5 Br
A-324 F R4-12 Br A-366 Br R4-6 Br
A-325 F R4-13 Br A-367 Br R4-7 Br
A-326 F R4-14 Br A-368 Br R4-8 Br
A-327 F R4-15 Br A-369 Br R4-9 Br
A-328 F R4-16 Br A-370 Br R4-10 Br
A-329 F R4-17 Br A-371 Br R4-1 1 Br
A-330 F R4-18 Br A-372 Br R4-12 Br
A-331 F R4-19 Br A-373 Br R4-13 Br
A-332 F R4-20 Br A-374 Br R4-14 Br
A-333 F R4-21 Br A-375 Br R4-15 Br
A-334 F R4-22 Br A-376 Br R4-16 Br
A-335 F R4-23 Br A-377 Br R4-17 Br
A-336 F R4-24 Br A-378 Br R4-18 Br
A-337 CI R4-1 Br A-379 Br R4-19 Br
A-338 CI R4-2 Br A-380 Br R4-20 Br line Y R4 R10 line Y R4 R10
A-381 Br R4-21 Br A-423 CHF2 R4-15 Br
A-382 Br R4-22 Br A-424 CHF2 R4-16 Br
A-383 Br R4-23 Br A-425 CHF2 R4-17 Br
A-384 Br R4-24 Br A-426 CHF2 R4-18 Br
A-385 CHs R4-1 Br A-427 CHF2 R4-19 Br
A-386 CHs R4-2 Br A-428 CHF2 R4-20 Br
A-387 CHs R4-3 Br A-429 CHF2 R4-21 Br
A-388 CHs R4-4 Br A-430 CHF2 R4-22 Br
A-389 CHs R4-5 Br A-431 CHF2 R4-23 Br
A-390 CHs R4-6 Br A-432 CHF2 R4-24 Br
A-391 CHs R4-7 Br A-433 OCHs R4-1 Br
A-392 CHs R4-8 Br A-434 OCHs R4-2 Br
A-393 CHs R4-9 Br A-435 OCHs R4-3 Br
A-394 CHs R4-10 Br A-436 OCHs R4-4 Br
A-395 CHs R4-1 1 Br A-437 OCHs R4-5 Br
A-396 CHs R4-12 Br A-438 OCHs R4-6 Br
A-397 CHs R4-13 Br A-439 OCHs R4-7 Br
A-398 CHs R4-14 Br A-440 OCHs R4-8 Br
A-399 CHs R4-15 Br A-441 OCHs R4-9 Br
A-400 CHs R4-16 Br A-442 OCHs R4-10 Br
A-401 CHs R4-17 Br A-443 OCHs R4-1 1 Br
A-402 CHs R4-18 Br A-444 OCHs R4-12 Br
A-403 CHs R4-19 Br A-445 OCHs R4-13 Br
A-404 CHs R4-20 Br A-446 OCHs R4-14 Br
A-405 CHs R4-21 Br A-447 OCHs R4-15 Br
A-406 CHs R4-22 Br A-448 OCHs R4-16 Br
A-407 CHs R4-23 Br A-449 OCHs R4-17 Br
A-408 CHs R4-24 Br A-450 OCHs R4-18 Br
A-409 CHF2 R4-1 Br A-451 OCHs R4-19 Br
A-410 CHF2 R4-2 Br A-452 OCHs R4-20 Br
A-41 1 CHF2 R4-3 Br A-453 OCHs R4-21 Br
A-412 CHF2 R4-4 Br A-454 OCHs R4-22 Br
A-413 CHF2 R4-5 Br A-455 OCHs R4-23 Br
A-414 CHF2 R4-6 Br A-456 OCHs R4-24 Br
A-415 CHF2 R4-7 Br A-457 OCHF2 R4-1 Br
A-416 CHF2 R4-8 Br A-458 OCHF2 R4-2 Br
A-417 CHF2 R4-9 Br A-459 OCHF2 R4-3 Br
A-418 CHF2 R4-10 Br A-460 OCHF2 R4-4 Br
A-419 CHF2 R4-1 1 Br A-461 OCHF2 R4-5 Br
A-420 CHF2 R4-12 Br A-462 OCHF2 R4-6 Br
A-421 CHF2 R4-13 Br A-463 OCHF2 R4-7 Br
A-422 CHF2 R4-14 Br A-464 OCHF2 R4-8 Br
Figure imgf000101_0001
line Y R4 R10 line Y R4 R10
A-545 R4-17 Br A-585 H R4-9 CHs
A-546 R4-18 Br A-586 H R4-10 CHs
A-587 H R4-1 1 CHs
A-547 R4-19 Br
A-588 H R4-12 CHs
A-548 R4-20 Br
A-589 H R4-13 CHs
A-549 R4-21 Br A-590 H R4-14 CHs
A-550 R4-22 Br A-591 H R4-15 CHs
A-551 R4-23 Br A-592 H R4-16 CHs
A-593 H R4-17 CHs
A-552 R4-24 Br
A-594 H R4-18 CHs
A-553 cPr R4-1 Br
A-595 H R4-19 CHs
A-554 cPr R4-2 Br
A-596 H R4-20 CHs
A-555 cPr R4-3 Br
A-597 H R4-21 CHs
A-556 cPr R4-4 Br
A-598 H R4-22 CHs
A-557 cPr R4-5 Br
A-599 H R4-23 CHs
A-558 cPr R4-6 Br
A-600 H R4-24 CHs
A-559 cPr R4-7 Br
A-601 F R4-1 CHs
A-560 cPr R4-8 Br
A-602 F R4-2 CHs
A-561 cPr R4-9 Br
A-603 F R4-3 CHs
A-562 cPr R4-10 Br
A-604 F R4-4 CHs
A-563 cPr R4-1 1 Br
A-605 F R4-5 CHs
A-564 cPr R4-12 Br
A-606 F R4-6 CHs
A-565 cPr R4-13 Br
A-607 F R4-7 CHs
A-566 cPr R4-14 Br
A-608 F R4-8 CHs
A-567 cPr R4-15 Br
A-609 F R4-9 CHs
A-568 cPr R4-16 Br
A-610 F R4-10 CHs
A-569 cPr R4-17 Br
A-61 1 F R4-1 1 CHs
A-570 cPr R4-18 Br
A-612 F R4-12 CHs
A-571 cPr R4-19 Br
A-613 F R4-13 CHs
A-572 cPr R4-20 Br
A-614 F R4-14 CHs
A-573 cPr R4-21 Br
A-615 F R4-15 CHs
A-574 cPr R4-22 Br
A-616 F R4-16 CHs
A-575 cPr R4-23 Br
A-617 F R4-17 CHs
A-576 cPr R4-24 Br
A-618 F R4-18 CHs
A-577 H R4-1 CHs
A-619 F R4-19 CHs
A-578 H R4-2 CHs
A-620 F R4-20 CHs
A-579 H R4-3 CHs
A-621 F R4-21 CHs
A-580 H R4-4 CHs
A-622 F R4-22 CHs
A-581 H R4-5 CHs
A-623 F R4-23 CHs
A-582 H R4-6 CHs
A-624 F R4-24 CHs
A-583 H R4-7 CHs
A-625 CI R4-1 CHs
A-584 H R4-8 CHs
A-626 CI R4-2 CHs line Y R4 R10 line Y R4 R10
A-627 CI R4-3 CHs A-669 Br R4-21 CHs
A-628 CI R4-4 CHs A-670 Br R4-22 CHs
A-629 CI R4-5 CHs A-671 Br R4-23 CHs
A-630 CI R4-6 CHs A-672 Br R4-24 CHs
A-631 CI R4-7 CHs A-673 CHs R4-1 CHs
A-632 CI R4-8 CHs A-674 CHs R4-2 CHs
A-633 CI R4-9 CHs A-675 CHs R4-3 CHs
A-634 CI R4-10 CHs A-676 CHs R4-4 CHs
A-635 CI R4-1 1 CHs A-677 CHs R4-5 CHs
A-636 CI R4-12 CHs A-678 CHs R4-6 CHs
A-637 CI R4-13 CHs A-679 CHs R4-7 CHs
A-638 CI R4-14 CHs A-680 CHs R4-8 CHs
A-639 CI R4-15 CHs A-681 CHs R4-9 CHs
A-640 CI R4-16 CHs A-682 CHs R4-10 CHs
A-641 CI R4-17 CHs A-683 CHs R4-1 1 CHs
A-642 CI R4-18 CHs A-684 CHs R4-12 CHs
A-643 CI R4-19 CHs A-685 CHs R4-13 CHs
A-644 CI R4-20 CHs A-686 CHs R4-14 CHs
A-645 CI R4-21 CHs A-687 CHs R4-15 CHs
A-646 CI R4-22 CHs A-688 CHs R4-16 CHs
A-647 CI R4-23 CHs A-689 CHs R4-17 CHs
A-648 CI R4-24 CHs A-690 CHs R4-18 CHs
A-649 Br R4-1 CHs A-691 CHs R4-19 CHs
A-650 Br R4-2 CHs A-692 CHs R4-20 CHs
A-651 Br R4-3 CHs A-693 CHs R4-21 CHs
A-652 Br R4-4 CHs A-694 CHs R4-22 CHs
A-653 Br R4-5 CHs A-695 CHs R4-23 CHs
A-654 Br R4-6 CHs A-696 CHs R4-24 CHs
A-655 Br R4-7 CHs A-697 CHF2 R4-1 CHs
A-656 Br R4-8 CHs A-698 CHF2 R4-2 CHs
A-657 Br R4-9 CHs A-699 CHF2 R4-3 CHs
A-658 Br R4-10 CHs A-700 CHF2 R4-4 CHs
A-659 Br R4-1 1 CHs A-701 CHF2 R4-5 CHs
A-660 Br R4-12 CHs A-702 CHF2 R4-6 CHs
A-661 Br R4-13 CHs A-703 CHF2 R4-7 CHs
A-662 Br R4-14 CHs A-704 CHF2 R4-8 CHs
A-663 Br R4-15 CHs A-705 CHF2 R4-9 CHs
A-664 Br R4-16 CHs A-706 CHF2 R4-10 CHs
A-665 Br R4-17 CHs A-707 CHF2 R4-1 1 CHs
A-666 Br R4-18 CHs A-708 CHF2 R4-12 CHs
A-667 Br R4-19 CHs A-709 CHF2 R4-13 CHs
A-668 Br R4-20 CHs A-710 CHF2 R4-14 CHs line Y R4 R10 line Y R4 R10
A-71 1 CHF2 R4-15 CH3 A-753 OCHF2 R4-9 CH3
A-712 CHF2 R4-16 CH3 A-754 OCHF2 R4-10 CH3
A-713 CHF2 R4-17 CH3 A-755 OCHF2 R4-1 1 CH3
A-714 CHF2 R4-18 CH3 A-756 OCHF2 R4-12 CH3
A-715 CHF2 R4-19 CH3 A-757 OCHF2 R4-13 CH3
A-716 CHF2 R4-20 CH3 A-758 OCHF2 R4-14 CH3
A-717 CHF2 R4-21 CH3 A-759 OCHF2 R4-15 CH3
A-718 CHF2 R4-22 CH3 A-760 OCHF2 R4-16 CH3
A-719 CHF2 R4-23 CH3 A-761 OCHF2 R4-17 CH3
A-720 CHF2 R4-24 CH3 A-762 OCHF2 R4-18 CH3
A-721 OCHs R4-1 CH3 A-763 OCHF2 R4-19 CH3
A-722 OCH3 R4-2 CH3 A-764 OCHF2 R4-20 CH3
A-723 OCHs R4-3 CH3 A-765 OCHF2 R4-21 CH3
A-724 OCHs R4-4 CH3 A-766 OCHF2 R4-22 CH3
A-725 OCH3 R4-5 CH3 A-767 OCHF2 R4-23 CH3
A-726 OCH3 R4-6 CH3 A-768 OCHF2 R4-24 CH3
A-727 OCH3 R4-7 CH3 A-769 OCF3 R4-1 CH3
A-728 OCH3 R4-8 CH3 A-770 OCF3 R4-2 CH3
A-729 OCH3 R4-9 CH3 A-771 OCF3 R4-3 CH3
A-730 OCH3 R4-10 CH3 A-772 OCF3 R4-4 CH3
A-731 OCH3 R4-1 1 CH3 A-773 OCF3 R4-5 CH3
A-732 OCH3 R4-12 CH3 A-774 OCF3 R4-6 CH3
A-733 OCH3 R4-13 CH3 A-775 OCF3 R4-7 CH3
A-734 OCH3 R4-14 CH3 A-776 OCF3 R4-8 CH3
A-735 OCH3 R4-15 CH3 A-777 OCF3 R4-9 CH3
A-736 OCH3 R4-16 CH3 A-778 OCF3 R4-10 CH3
A-737 OCH3 R4-17 CH3 A-779 OCF3 R4-1 1 CH3
A-738 OCH3 R4-18 CH3 A-780 OCF3 R4-12 CH3
A-739 OCH3 R4-19 CH3 A-781 OCF3 R4-13 CH3
A-740 OCH3 R4-20 CH3 A-782 OCF3 R4-14 CH3
A-741 OCH3 R4-21 CH3 A-783 OCF3 R4-15 CH3
A-742 OCH3 R4-22 CH3 A-784 OCF3 R4-16 CH3
A-743 OCH3 R4-23 CH3 A-785 OCF3 R4-17 CH3
A-744 OCH3 R4-24 CH3 A-786 OCF3 R4-18 CH3
A-745 OCHF2 R4-1 CH3 A-787 OCF3 R4-19 CH3
A-746 OCHF2 R4-2 CH3 A-788 OCF3 R4-20 CH3
A-747 OCHF2 R4-3 CH3 A-789 OCF3 R4-21 CH3
A-748 OCHF2 R4-4 CH3 A-790 OCF3 R4-22 CH3
A-749 OCHF2 R4-5 CH3 A-791 OCF3 R4-23 CH3
A-750 OCHF2 R4-6 CH3 A-792 OCF3 R4-24 CH3
A-751 OCHF2 R4-7 CH3 A-793 CF3 R4-1 CH3
A-752 OCHF2 R4-8 CH3 A-794 CF3 R4-2 CH3 line Y R4 R10 line Y R4 R10
A-795 CFs R4-3 CHs A-833 R4-17 CHs
A-796 CFs R4-4 CHs A-834 R4-18 CHs
A-797 CFs R4-5 CHs
A-835 R4-19 CHs
A-798 CFs R4-6 CHs
A-836 R4-20 CHs
A-799 CFs R4-7 CHs
A-800 CFs R4-8 CHs A-837 R4-21 CHs
A-801 CFs R4-9 CHs A-838 R4-22 CHs
A-802 CFs R4-10 CHs A-839 R4-23 CHs
A-803 CFs R4-1 1 CHs
A-840 R4-24 CHs
A-804 CFs R4-12 CHs
A-841 cPr R4-1 CHs
A-805 CFs R4-13 CHs
A-842 cPr R4-2 CHs
A-806 CFs R4-14 CHs
A-843 cPr R4-3 CHs
A-807 CFs R4-15 CHs
A-844 cPr R4-4 CHs
A-808 CFs R4-16 CHs
A-845 cPr R4-5 CHs
A-809 CFs R4-17 CHs
A-846 cPr R4-6 CHs
A-810 CFs R4-18 CHs
A-847 cPr R4-7 CHs
A-81 1 CFs R4-19 CHs
A-848 cPr R4-8 CHs
A-812 CFs R4-20 CHs
A-849 cPr R4-9 CHs
A-813 CFs R4-21 CHs
A-850 cPr R4-10 CHs
A-814 CFs R4-22 CHs
A-851 cPr R4-1 1 CHs
A-815 CFs R4-23 CHs
A-852 cPr R4-12 CHs
A-816 CFs R4-24 CHs
A-853 cPr R4-13 CHs
A-817 R4-1 CHs
A-854 cPr R4-14 CHs
A-818 R4-2 CHs
A-855 cPr R4-15 CHs
A-819 R4-3 CHs A-856 cPr R4-16 CHs
A-820 R4-4 CHs A-857 cPr R4-17 CHs
A-821 R4-5 CHs A-858 cPr R4-18 CHs
A-859 cPr R4-19 CHs
A-822 R4-6 CHs
A-860 cPr R4-20 CHs
A-823 R4-7 CHs
A-861 cPr R4-21 CHs
A-824 R4-8 CHs A-862 cPr R4-22 CHs
A-825 R4-9 CHs A-863 cPr R4-23 CHs
A-826 R4-10 CHs A-864 cPr R4-24 CHs
A-865 H R4-1 CHF2
A-827 R4-1 1 CHs
A-866 H R4-2 CHF2
A-828 R4-12 CHs
A-867 H R4-3 CHF2
A-829 R4-13 CHs A-868 H R4-4 CHF2
A-830 R4-14 CHs A-869 H R4-5 CHF2
A-831 R4-15 CHs A-870 H R4-6 CHF2
A-871 H R4-7 CHF2
A-832 R4-16 CHs
A-872 H R4-8 CHF2 line Y R4 R10 line Y R4 R10
A-873 H R4-9 CHF2 A-915 CI R4-3 CHF2
A-874 H R4-10 CHF2 A-916 CI R4-4 CHF2
A-875 H R4-1 1 CHF2 A-917 CI R4-5 CHF2
A-876 H R4-12 CHF2 A-918 CI R4-6 CHF2
A-877 H R4-13 CHF2 A-919 CI R4-7 CHF2
A-878 H R4-14 CHF2 A-920 CI R4-8 CHF2
A-879 H R4-15 CHF2 A-921 CI R4-9 CHF2
A-880 H R4-16 CHF2 A-922 CI R4-10 CHF2
A-881 H R4-17 CHF2 A-923 CI R4-1 1 CHF2
A-882 H R4-18 CHF2 A-924 CI R4-12 CHF2
A-883 H R4-19 CHF2 A-925 CI R4-13 CHF2
A-884 H R4-20 CHF2 A-926 CI R4-14 CHF2
A-885 H R4-21 CHF2 A-927 CI R4-15 CHF2
A-886 H R4-22 CHF2 A-928 CI R4-16 CHF2
A-887 H R4-23 CHF2 A-929 CI R4-17 CHF2
A-888 H R4-24 CHF2 A-930 CI R4-18 CHF2
A-889 F R4-1 CHF2 A-931 CI R4-19 CHF2
A-890 F R4-2 CHF2 A-932 CI R4-20 CHF2
A-891 F R4-3 CHF2 A-933 CI R4-21 CHF2
A-892 F R4-4 CHF2 A-934 CI R4-22 CHF2
A-893 F R4-5 CHF2 A-935 CI R4-23 CHF2
A-894 F R4-6 CHF2 A-936 CI R4-24 CHF2
A-895 F R4-7 CHF2 A-937 Br R4-1 CHF2
A-896 F R4-8 CHF2 A-938 Br R4-2 CHF2
A-897 F R4-9 CHF2 A-939 Br R4-3 CHF2
A-898 F R4-10 CHF2 A-940 Br R4-4 CHF2
A-899 F R4-1 1 CHF2 A-941 Br R4-5 CHF2
A-900 F R4-12 CHF2 A-942 Br R4-6 CHF2
A-901 F R4-13 CHF2 A-943 Br R4-7 CHF2
A-902 F R4-14 CHF2 A-944 Br R4-8 CHF2
A-903 F R4-15 CHF2 A-945 Br R4-9 CHF2
A-904 F R4-16 CHF2 A-946 Br R4-10 CHF2
A-905 F R4-17 CHF2 A-947 Br R4-1 1 CHF2
A-906 F R4-18 CHF2 A-948 Br R4-12 CHF2
A-907 F R4-19 CHF2 A-949 Br R4-13 CHF2
A-908 F R4-20 CHF2 A-950 Br R4-14 CHF2
A-909 F R4-21 CHF2 A-951 Br R4-15 CHF2
A-910 F R4-22 CHF2 A-952 Br R4-16 CHF2
A-91 1 F R4-23 CHF2 A-953 Br R4-17 CHF2
A-912 F R4-24 CHF2 A-954 Br R4-18 CHF2
A-913 CI R4-1 CHF2 A-955 Br R4-19 CHF2
A-914 CI R4-2 CHF2 A-956 Br R4-20 CHF2 line Y R4 R10 line Y R4 R10
A-957 Br R4-21 CHF2 A-999 CHF2 R4-15 CHF2
A-958 Br R4-22 CHF2 A- 1000 CHF2 R4-16 CHF2
A-959 Br R4-23 CHF2 A-1001 CHF2 R4-17 CHF2
A-960 Br R4-24 CHF2 A- 1002 CHF2 R4-18 CHF2
A-961 CHs R4-1 CHF2 A- 1003 CHF2 R4-19 CHF2
A-962 CHs R4-2 CHF2 A- 1004 CHF2 R4-20 CHF2
A-963 CHs R4-3 CHF2 A- 1005 CHF2 R4-21 CHF2
A-964 CHs R4-4 CHF2 A- 1006 CHF2 R4-22 CHF2
A-965 CHs R4-5 CHF2 A- 1007 CHF2 R4-23 CHF2
A-966 CHs R4-6 CHF2 A- 1008 CHF2 R4-24 CHF2
A-967 CHs R4-7 CHF2 A- 1009 OCHs R4-1 CHF2
A-968 CHs R4-8 CHF2 A-1010 OCHs R4-2 CHF2
A-969 CHs R4-9 CHF2 A-1011 OCHs R4-3 CHF2
A-970 CHs R4-10 CHF2 A-1012 OCHs R4-4 CHF2
A-971 CHs R4-11 CHF2 A-1013 OCHs R4-5 CHF2
A-972 CHs R4-12 CHF2 A-1014 OCHs R4-6 CHF2
A-973 CHs R4-13 CHF2 A-1015 OCHs R4-7 CHF2
A-974 CHs R4-14 CHF2 A-1016 OCHs R4-8 CHF2
A-975 CHs R4-15 CHF2 A-1017 OCHs R4-9 CHF2
A-976 CHs R4-16 CHF2 A-1018 OCHs R4-10 CHF2
A-977 CHs R4-17 CHF2 A-1019 OCHs R4-11 CHF2
A-978 CHs R4-18 CHF2 A- 1020 OCHs R4-12 CHF2
A-979 CHs R4-19 CHF2 A-1021 OCHs R4-13 CHF2
A-980 CHs R4-20 CHF2 A- 1022 OCHs R4-14 CHF2
A-981 CHs R4-21 CHF2 A- 1023 OCHs R4-15 CHF2
A-982 CHs R4-22 CHF2 A- 1024 OCHs R4-16 CHF2
A-983 CHs R4-23 CHF2 A- 1025 OCHs R4-17 CHF2
A-984 CHs R4-24 CHF2 A- 1026 OCHs R4-18 CHF2
A-985 CHF2 R4-1 CHF2 A- 1027 OCHs R4-19 CHF2
A-986 CHF2 R4-2 CHF2 A- 1028 OCHs R4-20 CHF2
A-987 CHF2 R4-3 CHF2 A- 1029 OCHs R4-21 CHF2
A-988 CHF2 R4-4 CHF2 A- 1030 OCHs R4-22 CHF2
A-989 CHF2 R4-5 CHF2 A-1031 OCHs R4-23 CHF2
A-990 CHF2 R4-6 CHF2 A- 1032 OCHs R4-24 CHF2
A-991 CHF2 R4-7 CHF2 A- 1033 OCHF2 R4-1 CHF2
A-992 CHF2 R4-8 CHF2 A- 1034 OCHF2 R4-2 CHF2
A-993 CHF2 R4-9 CHF2 A- 1035 OCHF2 R4-3 CHF2
A-994 CHF2 R4-10 CHF2 A- 1036 OCHF2 R4-4 CHF2
A-995 CHF2 R4-11 CHF2 A- 1037 OCHF2 R4-5 CHF2
A-996 CHF2 R4-12 CHF2 A- 1038 OCHF2 R4-6 CHF2
A-997 CHF2 R4-13 CHF2 A- 1039 OCHF2 R4-7 CHF2
A-998 CHF2 R4-14 CHF2 A- 1040 OCHF2 R4-8 CHF2
Figure imgf000108_0001
Figure imgf000109_0001
line Y R4 R10 line Y R4 R10
A-1203 CI R4-3 CFs A- 1245 Br R4-21 CFs
A-1204 CI R4-4 CFs A- 1246 Br R4-22 CFs
A-1205 CI R4-5 CFs A- 1247 Br R4-23 CFs
A-1206 CI R4-6 CFs A- 1248 Br R4-24 CFs
A-1207 CI R4-7 CFs A- 1249 CHs R4-1 CFs
A-1208 CI R4-8 CFs A- 1250 CHs R4-2 CFs
A-1209 CI R4-9 CFs A-1251 CHs R4-3 CFs
A-1210 CI R4-10 CFs A- 1252 CHs R4-4 CFs
A-121 1 CI R4-1 1 CFs A- 1253 CHs R4-5 CFs
A-1212 CI R4-12 CFs A- 1254 CHs R4-6 CFs
A-1213 CI R4-13 CFs A- 1255 CHs R4-7 CFs
A-1214 CI R4-14 CFs A- 1256 CHs R4-8 CFs
A-1215 CI R4-15 CFs A- 1257 CHs R4-9 CFs
A-1216 CI R4-16 CFs A- 1258 CHs R4-10 CFs
A-1217 CI R4-17 CFs A- 1259 CHs R4-1 1 CFs
A-1218 CI R4-18 CFs A- 1260 CHs R4-12 CFs
A-1219 CI R4-19 CFs A-1261 CHs R4-13 CFs
A-1220 CI R4-20 CFs A- 1262 CHs R4-14 CFs
A-1221 CI R4-21 CFs A- 1263 CHs R4-15 CFs
A-1222 CI R4-22 CFs A- 1264 CHs R4-16 CFs
A-1223 CI R4-23 CFs A- 1265 CHs R4-17 CFs
A-1224 CI R4-24 CFs A- 1266 CHs R4-18 CFs
A-1225 Br R4-1 CFs A- 1267 CHs R4-19 CFs
A-1226 Br R4-2 CFs A- 1268 CHs R4-20 CFs
A-1227 Br R4-3 CFs A- 1269 CHs R4-21 CFs
A-1228 Br R4-4 CFs A- 1270 CHs R4-22 CFs
A-1229 Br R4-5 CFs A-1271 CHs R4-23 CFs
A-1230 Br R4-6 CFs A- 1272 CHs R4-24 CFs
A-1231 Br R4-7 CFs A- 1273 CHF2 R4-1 CFs
A-1232 Br R4-8 CFs A- 1274 CHF2 R4-2 CFs
A-1233 Br R4-9 CFs A- 1275 CHF2 R4-3 CFs
A-1234 Br R4-10 CFs A- 1276 CHF2 R4-4 CFs
A-1235 Br R4-1 1 CFs A- 1277 CHF2 R4-5 CFs
A-1236 Br R4-12 CFs A- 1278 CHF2 R4-6 CFs
A-1237 Br R4-13 CFs A- 1279 CHF2 R4-7 CFs
A-1238 Br R4-14 CFs A- 1280 CHF2 R4-8 CFs
A-1239 Br R4-15 CFs A-1281 CHF2 R4-9 CFs
A-1240 Br R4-16 CFs A- 1282 CHF2 R4-10 CFs
A-1241 Br R4-17 CFs A- 1283 CHF2 R4-1 1 CFs
A-1242 Br R4-18 CFs A- 1284 CHF2 R4-12 CFs
A-1243 Br R4-19 CFs A- 1285 CHF2 R4-13 CFs
A-1244 Br R4-20 CFs A- 1286 CHF2 R4-14 CFs line Y R4 R10 line Y R4 R10
A-1287 CHF2 R4-15 CF3 A- 1329 OCHF2 R4-9 CF3
A-1288 CHF2 R4-16 CF3 A- 1330 OCHF2 R4-10 CF3
A-1289 CHF2 R4-17 CF3 A-1331 OCHF2 R4-1 1 CF3
A-1290 CHF2 R4-18 CF3 A- 1332 OCHF2 R4-12 CF3
A-1291 CHF2 R4-19 CF3 A- 1333 OCHF2 R4-13 CF3
A-1292 CHF2 R4-20 CF3 A- 1334 OCHF2 R4-14 CF3
A-1293 CHF2 R4-21 CF3 A- 1335 OCHF2 R4-15 CF3
A-1294 CHF2 R4-22 CF3 A- 1336 OCHF2 R4-16 CF3
A-1295 CHF2 R4-23 CF3 A- 1337 OCHF2 R4-17 CF3
A-1296 CHF2 R4-24 CF3 A- 1338 OCHF2 R4-18 CF3
A-1297 OCHs R4-1 CF3 A- 1339 OCHF2 R4-19 CF3
A-1298 OCH3 R4-2 CF3 A- 1340 OCHF2 R4-20 CF3
A-1299 OCHs R4-3 CF3 A-1341 OCHF2 R4-21 CF3
A-1300 OCHs R4-4 CF3 A- 1342 OCHF2 R4-22 CF3
A-1301 OCH3 R4-5 CF3 A- 1343 OCHF2 R4-23 CF3
A-1302 OCH3 R4-6 CF3 A- 1344 OCHF2 R4-24 CF3
A-1303 OCH3 R4-7 CF3 A- 1345 OCF3 R4-1 CF3
A-1304 OCH3 R4-8 CF3 A- 1346 OCF3 R4-2 CF3
A-1305 OCH3 R4-9 CF3 A- 1347 OCF3 R4-3 CF3
A-1306 OCH3 R4-10 CF3 A- 1348 OCF3 R4-4 CF3
A-1307 OCH3 R4-1 1 CF3 A- 1349 OCF3 R4-5 CF3
A-1308 OCH3 R4-12 CF3 A- 1350 OCF3 R4-6 CF3
A-1309 OCH3 R4-13 CF3 A-1351 OCF3 R4-7 CF3
A-1310 OCH3 R4-14 CF3 A- 1352 OCF3 R4-8 CF3
A-131 1 OCH3 R4-15 CF3 A- 1353 OCF3 R4-9 CF3
A-1312 OCH3 R4-16 CF3 A- 1354 OCF3 R4-10 CF3
A-1313 OCH3 R4-17 CF3 A- 1355 OCF3 R4-1 1 CF3
A-1314 OCH3 R4-18 CF3 A- 1356 OCF3 R4-12 CF3
A-1315 OCH3 R4-19 CF3 A- 1357 OCF3 R4-13 CF3
A-1316 OCH3 R4-20 CF3 A- 1358 OCF3 R4-14 CF3
A-1317 OCH3 R4-21 CF3 A- 1359 OCF3 R4-15 CF3
A-1318 OCH3 R4-22 CF3 A- 1360 OCF3 R4-16 CF3
A-1319 OCH3 R4-23 CF3 A-1361 OCF3 R4-17 CF3
A-1320 OCH3 R4-24 CF3 A- 1362 OCF3 R4-18 CF3
A-1321 OCHF2 R4-1 CF3 A- 1363 OCF3 R4-19 CF3
A-1322 OCHF2 R4-2 CF3 A- 1364 OCF3 R4-20 CF3
A-1323 OCHF2 R4-3 CF3 A- 1365 OCF3 R4-21 CF3
A-1324 OCHF2 R4-4 CF3 A- 1366 OCF3 R4-22 CF3
A-1325 OCHF2 R4-5 CF3 A- 1367 OCF3 R4-23 CF3
A-1326 OCHF2 R4-6 CF3 A- 1368 OCF3 R4-24 CF3
A-1327 OCHF2 R4-7 CF3 A- 1369 CF3 R4-1 CF3
A-1328 OCHF2 R4-8 CF3 A- 1370 CF3 R4-2 CF3
Figure imgf000112_0001
line Y R4 R10 line Y R4 R10
A-1449 H R4-9 OCH3 A-1491 CI R4-3 OCH3
A-1450 H R4-10 OCH3 A- 1492 CI R4-4 OCH3
A-1451 H R4-1 1 OCH3 A- 1493 CI R4-5 OCH3
A-1452 H R4-12 OCH3 A- 1494 CI R4-6 OCH3
A-1453 H R4-13 OCH3 A- 1495 CI R4-7 OCH3
A-1454 H R4-14 OCH3 A- 1496 CI R4-8 OCH3
A-1455 H R4-15 OCH3 A- 1497 CI R4-9 OCH3
A-1456 H R4-16 OCH3 A- 1498 CI R4-10 OCH3
A-1457 H R4-17 OCH3 A- 1499 CI R4-1 1 OCH3
A-1458 H R4-18 OCH3 A- 1500 CI R4-12 OCH3
A-1459 H R4-19 OCH3 A-1501 CI R4-13 OCH3
A-1460 H R4-20 OCH3 A- 1502 CI R4-14 OCH3
A-1461 H R4-21 OCH3 A- 1503 CI R4-15 OCH3
A-1462 H R4-22 OCH3 A- 1504 CI R4-16 OCH3
A-1463 H R4-23 OCH3 A- 1505 CI R4-17 OCH3
A-1464 H R4-24 OCH3 A- 1506 CI R4-18 OCH3
A-1465 F R4-1 OCH3 A- 1507 CI R4-19 OCH3
A-1466 F R4-2 OCH3 A- 1508 CI R4-20 OCH3
A-1467 F R4-3 OCH3 A- 1509 CI R4-21 OCH3
A-1468 F R4-4 OCH3 A-1510 CI R4-22 OCH3
A-1469 F R4-5 OCH3 A-151 1 CI R4-23 OCH3
A-1470 F R4-6 OCH3 A-1512 CI R4-24 OCH3
A-1471 F R4-7 OCH3 A-1513 Br R4-1 OCH3
A-1472 F R4-8 OCH3 A-1514 Br R4-2 OCH3
A-1473 F R4-9 OCH3 A-1515 Br R4-3 OCH3
A-1474 F R4-10 OCH3 A-1516 Br R4-4 OCH3
A-1475 F R4-1 1 OCH3 A-1517 Br R4-5 OCH3
A-1476 F R4-12 OCH3 A-1518 Br R4-6 OCH3
A-1477 F R4-13 OCH3 A-1519 Br R4-7 OCH3
A-1478 F R4-14 OCH3 A- 1520 Br R4-8 OCH3
A-1479 F R4-15 OCH3 A-1521 Br R4-9 OCH3
A-1480 F R4-16 OCH3 A- 1522 Br R4-10 OCH3
A-1481 F R4-17 OCH3 A- 1523 Br R4-1 1 OCH3
A-1482 F R4-18 OCH3 A- 1524 Br R4-12 OCH3
A-1483 F R4-19 OCH3 A- 1525 Br R4-13 OCH3
A-1484 F R4-20 OCH3 A- 1526 Br R4-14 OCH3
A-1485 F R4-21 OCH3 A- 1527 Br R4-15 OCH3
A-1486 F R4-22 OCH3 A- 1528 Br R4-16 OCH3
A-1487 F R4-23 OCH3 A- 1529 Br R4-17 OCH3
A-1488 F R4-24 OCH3 A- 1530 Br R4-18 OCH3
A-1489 CI R4-1 OCH3 A-1531 Br R4-19 OCH3
A-1490 CI R4-2 OCH3 A- 1532 Br R4-20 OCH3 line Y R4 R10 line Y R4 R10
A-1533 Br R4-21 OCHs A- 1575 CH F2 R4-15 OCHs
A-1534 Br R4-22 OCHs A- 1576 CH F2 R4-16 OCHs
A-1535 Br R4-23 OCHs A- 1577 CH F2 R4-17 OCHs
A-1536 Br R4-24 OCHs A- 1578 CH F2 R4-18 OCHs
A-1537 CHs R4-1 OCHs A- 1579 CH F2 R4-19 OCHs
A-1538 CHs R4-2 OCHs A- 1580 CH F2 R4-20 OCHs
A-1539 CHs R4-3 OCHs A-1581 CH F2 R4-21 OCHs
A-1540 CHs R4-4 OCHs A- 1582 CH F2 R4-22 OCHs
A-1541 CHs R4-5 OCHs A- 1583 CH F2 R4-23 OCHs
A-1542 CHs R4-6 OCHs A- 1584 CH F2 R4-24 OCHs
A-1543 CHs R4-7 OCHs A- 1585 OCHs R4-1 OCHs
A-1544 CHs R4-8 OCHs A- 1586 OCHs R4-2 OCHs
A-1545 CHs R4-9 OCHs A- 1587 OCHs R4-3 OCHs
A-1546 CHs R4-10 OCHs A- 1588 OCHs R4-4 OCHs
A-1547 CHs R4-1 1 OCHs A- 1589 OCHs R4-5 OCHs
A-1548 CHs R4-12 OCHs A- 1590 OCHs R4-6 OCHs
A-1549 CHs R4-13 OCHs A-1591 OCHs R4-7 OCHs
A-1550 CHs R4-14 OCHs A- 1592 OCHs R4-8 OCHs
A-1551 CHs R4-15 OCHs A- 1593 OCHs R4-9 OCHs
A-1552 CHs R4-16 OCHs A- 1594 OCHs R4-10 OCHs
A-1553 CHs R4-17 OCHs A- 1595 OCHs R4-1 1 OCHs
A- 1554 CHs R4-18 OCHs A- 1596 OCHs R4-12 OCHs
A-1555 CHs R4-19 OCHs A- 1597 OCHs R4-13 OCHs
A-1556 CHs R4-20 OCHs A- 1598 OCHs R4-14 OCHs
A-1557 CHs R4-21 OCHs A- 1599 OCHs R4-15 OCHs
A-1558 CHs R4-22 OCHs A- 1600 OCHs R4-16 OCHs
A-1559 CHs R4-23 OCHs A-1601 OCHs R4-17 OCHs
A-1560 CHs R4-24 OCHs A- 1602 OCHs R4-18 OCHs
A-1561 CH F2 R4-1 OCHs A- 1603 OCHs R4-19 OCHs
A-1562 CH F2 R4-2 OCHs A- 1604 OCHs R4-20 OCHs
A-1563 CH F2 R4-3 OCHs A- 1605 OCHs R4-21 OCHs
A-1564 CH F2 R4-4 OCHs A- 1606 OCHs R4-22 OCHs
A-1565 CH F2 R4-5 OCHs A- 1607 OCHs R4-23 OCHs
A-1566 CH F2 R4-6 OCHs A- 1608 OCHs R4-24 OCHs
A-1567 CH F2 R4-7 OCHs A- 1609 OCHF2 R4-1 OCHs
A-1568 CH F2 R4-8 OCHs A-1610 OCH F2 R4-2 OCHs
A-1569 CH F2 R4-9 OCHs A-161 1 OCH F2 R4-3 OCHs
A-1570 CH F2 R4-10 OCHs A-1612 OCH F2 R4-4 OCHs
A-1571 CH F2 R4-1 1 OCHs A-1613 OCH F2 R4-5 OCHs
A-1572 CH F2 R4-12 OCHs A-1614 OCH F2 R4-6 OCHs
A-1573 CH F2 R4-13 OCHs A-1615 OCH F2 R4-7 OCHs
A-1574 CH F2 R4-14 OCHs A-1616 OCH F2 R4-8 OCHs
Figure imgf000115_0001
Figure imgf000116_0001
line Y R4 R10 line Y R4 R10
A-1779 CI R4-3 C≡CH A-1821 Br R4-21 C≡CH
A-1780 CI R4-4 C≡CH A- 1822 Br R4-22 C≡CH
A-1781 CI R4-5 C≡CH A- 1823 Br R4-23 C≡CH
A-1782 CI R4-6 C≡CH A- 1824 Br R4-24 C≡CH
A-1783 CI R4-7 C≡CH A- 1825 CHs R4-1 C≡CH
A-1784 CI R4-8 C≡CH A- 1826 CHs R4-2 C≡CH
A-1785 CI R4-9 C≡CH A- 1827 CHs R4-3 C≡CH
A-1786 CI R4-10 C≡CH A- 1828 CHs R4-4 C≡CH
A-1787 CI R4-1 1 C≡CH A- 1829 CHs R4-5 C≡CH
A-1788 CI R4-12 C≡CH A- 1830 CHs R4-6 C≡CH
A-1789 CI R4-13 C≡CH A-1831 CHs R4-7 C≡CH
A-1790 CI R4-14 C≡CH A- 1832 CHs R4-8 C≡CH
A-1791 CI R4-15 C≡CH A- 1833 CHs R4-9 C≡CH
A-1792 CI R4-16 C≡CH A- 1834 CHs R4-10 C≡CH
A-1793 CI R4-17 C≡CH A- 1835 CHs R4-1 1 C≡CH
A-1794 CI R4-18 C≡CH A- 1836 CHs R4-12 C≡CH
A-1795 CI R4-19 C≡CH A- 1837 CHs R4-13 C≡CH
A-1796 CI R4-20 C≡CH A- 1838 CHs R4-14 C≡CH
A-1797 CI R4-21 C≡CH A- 1839 CHs R4-15 C≡CH
A-1798 CI R4-22 C≡CH A- 1840 CHs R4-16 C≡CH
A-1799 CI R4-23 C≡CH A-1841 CHs R4-17 C≡CH
A-1800 CI R4-24 C≡CH A- 1842 CHs R4-18 C≡CH
A-1801 Br R4-1 C≡CH A- 1843 CHs R4-19 C≡CH
A-1802 Br R4-2 C≡CH A- 1844 CHs R4-20 C≡CH
A-1803 Br R4-3 C≡CH A- 1845 CHs R4-21 C≡CH
A-1804 Br R4-4 C≡CH A- 1846 CHs R4-22 C≡CH
A-1805 Br R4-5 C≡CH A- 1847 CHs R4-23 C≡CH
A-1806 Br R4-6 C≡CH A- 1848 CHs R4-24 C≡CH
A-1807 Br R4-7 C≡CH A- 1849 CHF2 R4-1 C≡CH
A-1808 Br R4-8 C≡CH A- 1850 CHF2 R4-2 C≡CH
A-1809 Br R4-9 C≡CH A-1851 CHF2 R4-3 C≡CH
A-1810 Br R4-10 C≡CH A- 1852 CHF2 R4-4 C≡CH
A-181 1 Br R4-1 1 C≡CH A- 1853 CHF2 R4-5 C≡CH
A-1812 Br R4-12 C≡CH A- 1854 CHF2 R4-6 C≡CH
A-1813 Br R4-13 C≡CH A- 1855 CHF2 R4-7 C≡CH
A-1814 Br R4-14 C≡CH A- 1856 CHF2 R4-8 C≡CH
A-1815 Br R4-15 C≡CH A- 1857 CHF2 R4-9 C≡CH
A-1816 Br R4-16 C≡CH A- 1858 CHF2 R4-10 C≡CH
A-1817 Br R4-17 C≡CH A- 1859 CHF2 R4-1 1 C≡CH
A-1818 Br R4-18 C≡CH A- 1860 CHF2 R4-12 C≡CH
A-1819 Br R4-19 C≡CH A-1861 CHF2 R4-13 C≡CH
A-1820 Br R4-20 C≡CH A- 1862 CHF2 R4-14 C≡CH line Y R4 R10 line Y R4 R10
A-1863 CHF2 R4-15 C≡CH A- 1905 OCHF2 R4-9 C≡CH
A-1864 CHF2 R4-16 C≡CH A- 1906 OCHF2 R4-10 C≡CH
A-1865 CHF2 R4-17 C≡CH A- 1907 OCHF2 R4-1 1 C≡CH
A-1866 CHF2 R4-18 C≡CH A- 1908 OCHF2 R4-12 C≡CH
A-1867 CHF2 R4-19 C≡CH A- 1909 OCHF2 R4-13 C≡CH
A-1868 CHF2 R4-20 C≡CH A-1910 OCHF2 R4-14 C≡CH
A-1869 CHF2 R4-21 C≡CH A-191 1 OCHF2 R4-15 C≡CH
A-1870 CHF2 R4-22 C≡CH A-1912 OCHF2 R4-16 C≡CH
A-1871 CHF2 R4-23 C≡CH A-1913 OCHF2 R4-17 C≡CH
A-1872 CHF2 R4-24 C≡CH A-1914 OCHF2 R4-18 C≡CH
A-1873 OCHs R4-1 C≡CH A-1915 OCHF2 R4-19 C≡CH
A-1874 OCH3 R4-2 C≡CH A-1916 OCHF2 R4-20 C≡CH
A-1875 OCHs R4-3 C≡CH A-1917 OCHF2 R4-21 C≡CH
A-1876 OCHs R4-4 C≡CH A-1918 OCHF2 R4-22 C≡CH
A-1877 OCH3 R4-5 C≡CH A-1919 OCHF2 R4-23 C≡CH
A-1878 OCH3 R4-6 C≡CH A- 1920 OCHF2 R4-24 C≡CH
A-1879 OCH3 R4-7 C≡CH A-1921 OCF3 R4-1 C≡CH
A-1880 OCH3 R4-8 C≡CH A- 1922 OCF3 R4-2 C≡CH
A-1881 OCH3 R4-9 C≡CH A- 1923 OCF3 R4-3 C≡CH
A-1882 OCH3 R4-10 C≡CH A- 1924 OCF3 R4-4 C≡CH
A-1883 OCH3 R4-1 1 C≡CH A- 1925 OCF3 R4-5 C≡CH
A-1884 OCH3 R4-12 C≡CH A- 1926 OCF3 R4-6 C≡CH
A-1885 OCH3 R4-13 C≡CH A- 1927 OCF3 R4-7 C≡CH
A-1886 OCH3 R4-14 C≡CH A- 1928 OCF3 R4-8 C≡CH
A-1887 OCH3 R4-15 C≡CH A- 1929 OCF3 R4-9 C≡CH
A-1888 OCH3 R4-16 C≡CH A- 1930 OCF3 R4-10 C≡CH
A-1889 OCH3 R4-17 C≡CH A-1931 OCF3 R4-1 1 C≡CH
A-1890 OCH3 R4-18 C≡CH A- 1932 OCF3 R4-12 C≡CH
A-1891 OCH3 R4-19 C≡CH A- 1933 OCF3 R4-13 C≡CH
A-1892 OCH3 R4-20 C≡CH A- 1934 OCF3 R4-14 C≡CH
A-1893 OCH3 R4-21 C≡CH A- 1935 OCF3 R4-15 C≡CH
A-1894 OCH3 R4-22 C≡CH A- 1936 OCF3 R4-16 C≡CH
A-1895 OCH3 R4-23 C≡CH A- 1937 OCF3 R4-17 C≡CH
A-1896 OCH3 R4-24 C≡CH A- 1938 OCF3 R4-18 C≡CH
A-1897 OCHF2 R4-1 C≡CH A- 1939 OCF3 R4-19 C≡CH
A-1898 OCHF2 R4-2 C≡CH A- 1940 OCF3 R4-20 C≡CH
A-1899 OCHF2 R4-3 C≡CH A-1941 OCF3 R4-21 C≡CH
A-1900 OCHF2 R4-4 C≡CH A- 1942 OCF3 R4-22 C≡CH
A-1901 OCHF2 R4-5 C≡CH A- 1943 OCF3 R4-23 C≡CH
A-1902 OCHF2 R4-6 C≡CH A- 1944 OCF3 R4-24 C≡CH
A-1903 OCHF2 R4-7 C≡CH A- 1945 CF3 R4-1 C≡CH
A-1904 OCHF2 R4-8 C≡CH A- 1946 CF3 R4-2 C≡CH line Y R4 R10 line Y R4 R10
A-1947 CFs R4-3 C≡CH A- 1985 R4-17 C≡CH
A-1948 CFs R4-4 C≡CH A- 1986 R4-18 C≡CH
A-1949 CFs R4-5 C≡CH
A- 1987 R4-19 C≡CH
A-1950 CFs R4-6 C≡CH
A- 1988 R4-20 C≡CH
A-1951 CFs R4-7 C≡CH
A-1952 CFs R4-8 C≡CH A- 1989 R4-21 C≡CH
A-1953 CFs R4-9 C≡CH A- 1990 R4-22 C≡CH
A-1954 CFs R4-10 C≡CH A-1991 R4-23 C≡CH
A-1955 CFs R4-1 1 C≡CH
A- 1992 R4-24 C≡CH
A-1956 CFs R4-12 C≡CH
A- 1993 cPr R4-1 C≡CH
A-1957 CFs R4-13 C≡CH
A- 1994 cPr R4-2 C≡CH
A-1958 CFs R4-14 C≡CH
A- 1995 cPr R4-3 C≡CH
A-1959 CFs R4-15 C≡CH
A- 1996 cPr R4-4 C≡CH
A-1960 CFs R4-16 C≡CH
A- 1997 cPr R4-5 C≡CH
A-1961 CFs R4-17 C≡CH
A- 1998 cPr R4-6 C≡CH
A-1962 CFs R4-18 C≡CH
A- 1999 cPr R4-7 C≡CH
A-1963 CFs R4-19 C≡CH
A-2000 cPr R4-8 C≡CH
A-1964 CFs R4-20 C≡CH
A-2001 cPr R4-9 C≡CH
A-1965 CFs R4-21 C≡CH
A-2002 cPr R4-10 C≡CH
A-1966 CFs R4-22 C≡CH
A-2003 cPr R4-1 1 C≡CH
A-1967 CFs R4-23 C≡CH
A-2004 cPr R4-12 C≡CH
A-1968 CFs R4-24 C≡CH
A-2005 cPr R4-13 C≡CH
A-1969 R4-1 C≡CH
A-2006 cPr R4-14 C≡CH
A-1970 R4-2 C≡CH
A-2007 cPr R4-15 C≡CH
A-1971 R4-3 C≡CH A-2008 cPr R4-16 C≡CH
A-1972 R4-4 C≡CH A-2009 cPr R4-17 C≡CH
A-1973 R4-5 C≡CH A-2010 cPr R4-18 C≡CH
A-201 1 cPr R4-19 C≡CH
A-1974 R4-6 C≡CH
A-2012 cPr R4-20 C≡CH
A-1975 R4-7 C≡CH
A-2013 cPr R4-21 C≡CH
A-1976 R4-8 C≡CH A-2014 cPr R4-22 C≡CH
A-1977 R4-9 C≡CH A-2015 cPr R4-23 C≡CH
A-1978 R4-10 C≡CH A-2016 cPr R4-24 C≡CH
A-2017 H R4-1 cPr
A-1979 R4-1 1 C≡CH
A-2018 H R4-2 cPr
A-1980 R4-12 C≡CH
A-2019 H R4-3 cPr
A-1981 R4-13 C≡CH A-2020 H R4-4 cPr
A-1982 R4-14 C≡CH A-2021 H R4-5 cPr
A-1983 R4-15 C≡CH A-2022 H R4-6 cPr
A-2023 H R4-7 cPr
A-1984 R4-16 C≡CH
A-2024 H R4-8 cPr line Y R4 R10 line Y R4 R10
A-2025 H R4-9 cPr A-2067 CI R4-3 cPr
A-2026 H R4-10 cPr A-2068 CI R4-4 cPr
A-2027 H R4-1 1 cPr A-2069 CI R4-5 cPr
A-2028 H R4-12 cPr A-2070 CI R4-6 cPr
A-2029 H R4-13 cPr A-2071 CI R4-7 cPr
A-2030 H R4-14 cPr A-2072 CI R4-8 cPr
A-2031 H R4-15 cPr A-2073 CI R4-9 cPr
A-2032 H R4-16 cPr A-2074 CI R4-10 cPr
A-2033 H R4-17 cPr A-2075 CI R4-1 1 cPr
A-2034 H R4-18 cPr A-2076 CI R4-12 cPr
A-2035 H R4-19 cPr A-2077 CI R4-13 cPr
A-2036 H R4-20 cPr A-2078 CI R4-14 cPr
A-2037 H R4-21 cPr A-2079 CI R4-15 cPr
A-2038 H R4-22 cPr A-2080 CI R4-16 cPr
A-2039 H R4-23 cPr A-2081 CI R4-17 cPr
A-2040 H R4-24 cPr A-2082 CI R4-18 cPr
A-2041 F R4-1 cPr A-2083 CI R4-19 cPr
A-2042 F R4-2 cPr A-2084 CI R4-20 cPr
A-2043 F R4-3 cPr A-2085 CI R4-21 cPr
A-2044 F R4-4 cPr A-2086 CI R4-22 cPr
A-2045 F R4-5 cPr A-2087 CI R4-23 cPr
A-2046 F R4-6 cPr A-2088 CI R4-24 cPr
A-2047 F R4-7 cPr A-2089 Br R4-1 cPr
A-2048 F R4-8 cPr A-2090 Br R4-2 cPr
A-2049 F R4-9 cPr A-2091 Br R4-3 cPr
A-2050 F R4-10 cPr A-2092 Br R4-4 cPr
A-2051 F R4-1 1 cPr A-2093 Br R4-5 cPr
A-2052 F R4-12 cPr A-2094 Br R4-6 cPr
A-2053 F R4-13 cPr A-2095 Br R4-7 cPr
A-2054 F R4-14 cPr A-2096 Br R4-8 cPr
A-2055 F R4-15 cPr A-2097 Br R4-9 cPr
A-2056 F R4-16 cPr A-2098 Br R4-10 cPr
A-2057 F R4-17 cPr A-2099 Br R4-1 1 cPr
A-2058 F R4-18 cPr A-2100 Br R4-12 cPr
A-2059 F R4-19 cPr A-2101 Br R4-13 cPr
A-2060 F R4-20 cPr A-2102 Br R4-14 cPr
A-2061 F R4-21 cPr A-2103 Br R4-15 cPr
A-2062 F R4-22 cPr A-2104 Br R4-16 cPr
A-2063 F R4-23 cPr A-2105 Br R4-17 cPr
A-2064 F R4-24 cPr A-2106 Br R4-18 cPr
A-2065 CI R4-1 cPr A-2107 Br R4-19 cPr
A-2066 CI R4-2 cPr A-2108 Br R4-20 cPr line Y R4 R10 line Y R4 R10
A-2109 Br R4-21 cPr A-2151 CHF2 R4-15 cPr
A-21 10 Br R4-22 cPr A-2152 CHF2 R4-16 cPr
A-21 1 1 Br R4-23 cPr A-2153 CHF2 R4-17 cPr
A-21 12 Br R4-24 cPr A-2154 CHF2 R4-18 cPr
A-21 13 CHs R4-1 cPr A-2155 CHF2 R4-19 cPr
A-21 14 CHs R4-2 cPr A-2156 CHF2 R4-20 cPr
A-21 15 CHs R4-3 cPr A-2157 CHF2 R4-21 cPr
A-21 16 CHs R4-4 cPr A-2158 CHF2 R4-22 cPr
A-21 17 CHs R4-5 cPr A-2159 CHF2 R4-23 cPr
A-21 18 CHs R4-6 cPr A-2160 CHF2 R4-24 cPr
A-21 19 CHs R4-7 cPr A-2161 OCHs R4-1 cPr
A-2120 CHs R4-8 cPr A-2162 OCHs R4-2 cPr
A-2121 CHs R4-9 cPr A-2163 OCHs R4-3 cPr
A-2122 CHs R4-10 cPr A-2164 OCHs R4-4 cPr
A-2123 CHs R4-1 1 cPr A-2165 OCHs R4-5 cPr
A-2124 CHs R4-12 cPr A-2166 OCHs R4-6 cPr
A-2125 CHs R4-13 cPr A-2167 OCHs R4-7 cPr
A-2126 CHs R4-14 cPr A-2168 OCHs R4-8 cPr
A-2127 CHs R4-15 cPr A-2169 OCHs R4-9 cPr
A-2128 CHs R4-16 cPr A-2170 OCHs R4-10 cPr
A-2129 CHs R4-17 cPr A-2171 OCHs R4-1 1 cPr
A-2130 CHs R4-18 cPr A-2172 OCHs R4-12 cPr
A-2131 CHs R4-19 cPr A-2173 OCHs R4-13 cPr
A-2132 CHs R4-20 cPr A-2174 OCHs R4-14 cPr
A-2133 CHs R4-21 cPr A-2175 OCHs R4-15 cPr
A-2134 CHs R4-22 cPr A-2176 OCHs R4-16 cPr
A-2135 CHs R4-23 cPr A-2177 OCHs R4-17 cPr
A-2136 CHs R4-24 cPr A-2178 OCHs R4-18 cPr
A-2137 CHF2 R4-1 cPr A-2179 OCHs R4-19 cPr
A-2138 CHF2 R4-2 cPr A-2180 OCHs R4-20 cPr
A-2139 CHF2 R4-3 cPr A-2181 OCHs R4-21 cPr
A-2140 CHF2 R4-4 cPr A-2182 OCHs R4-22 cPr
A-2141 CHF2 R4-5 cPr A-2183 OCHs R4-23 cPr
A-2142 CHF2 R4-6 cPr A-2184 OCHs R4-24 cPr
A-2143 CHF2 R4-7 cPr A-2185 OCHF2 R4-1 cPr
A-2144 CHF2 R4-8 cPr A-2186 OCHF2 R4-2 cPr
A-2145 CHF2 R4-9 cPr A-2187 OCHF2 R4-3 cPr
A-2146 CHF2 R4-10 cPr A-2188 OCHF2 R4-4 cPr
A-2147 CHF2 R4-1 1 cPr A-2189 OCHF2 R4-5 cPr
A-2148 CHF2 R4-12 cPr A-2190 OCHF2 R4-6 cPr
A-2149 CHF2 R4-13 cPr A-2191 OCHF2 R4-7 cPr
A-2150 CHF2 R4-14 cPr A-2192 OCHF2 R4-8 cPr line Y R4 R10 line Y R4 R10
A-2193 OCHF2 R4-9 cPr A-2235 CF3 R4-3 cPr
A-2194 OCHF2 R4-10 cPr A-2236 CF3 R4-4 cPr
A-2195 OCHF2 R4-1 1 cPr A-2237 CF3 R4-5 cPr
A-2196 OCHF2 R4-12 cPr A-2238 CF3 R4-6 cPr
A-2197 OCHF2 R4-13 cPr A-2239 CF3 R4-7 cPr
A-2198 OCHF2 R4-14 cPr A-2240 CF3 R4-8 cPr
A-2199 OCHF2 R4-15 cPr A-2241 CF3 R4-9 cPr
A-2200 OCHF2 R4-16 cPr A-2242 CF3 R4-10 cPr
A-2201 OCHF2 R4-17 cPr A-2243 CF3 R4-1 1 cPr
A-2202 OCHF2 R4-18 cPr A-2244 CF3 R4-12 cPr
A-2203 OCHF2 R4-19 cPr A-2245 CF3 R4-13 cPr
A-2204 OCHF2 R4-20 cPr A-2246 CF3 R4-14 cPr
A-2205 OCHF2 R4-21 cPr A-2247 CF3 R4-15 cPr
A-2206 OCHF2 R4-22 cPr A-2248 CF3 R4-16 cPr
A-2207 OCHF2 R4-23 cPr A-2249 CF3 R4-17 cPr
A-2208 OCHF2 R4-24 cPr A-2250 CF3 R4-18 cPr
A-2209 OCF3 R4-1 cPr A-2251 CF3 R4-19 cPr
A-2210 OCF3 R4-2 cPr A-2252 CF3 R4-20 cPr
A-221 1 OCF3 R4-3 cPr A-2253 CF3 R4-21 cPr
A-2212 OCF3 R4-4 cPr A-2254 CF3 R4-22 cPr
A-2213 OCF3 R4-5 cPr A-2255 CF3 R4-23 cPr
A-2214 OCF3 R4-6 cPr A-2256 CF3 R4-24 cPr
A-2215 OCF3 R4-7 cPr A-2257 C≡CH R4-1 cPr
A-2216 OCF3 R4-8 cPr A-2258 C≡CH R4-2 cPr
A-2217 OCF3 R4-9 cPr A-2259 C≡CH R4-3 cPr
A-2218 OCF3 R4-10 cPr A-2260 C≡CH R4-4 cPr
A-2219 OCF3 R4-1 1 cPr A-2261 C≡CH R4-5 cPr
A-2220 OCF3 R4-12 cPr A-2262 C≡CH R4-6 cPr
A-2221 OCF3 R4-13 cPr A-2263 C≡CH R4-7 cPr
A-2222 OCF3 R4-14 cPr A-2264 C≡CH R4-8 cPr
A-2223 OCF3 R4-15 cPr A-2265 C≡CH R4-9 cPr
A-2224 OCF3 R4-16 cPr A-2266 C≡CH R4-10 cPr
A-2225 OCF3 R4-17 cPr A-2267 C≡CH R4-1 1 cPr
A-2226 OCF3 R4-18 cPr A-2268 C≡CH R4-12 cPr
A-2227 OCF3 R4-19 cPr A-2269 C≡CH R4-13 cPr
A-2228 OCF3 R4-20 cPr A-2270 C≡CH R4-14 cPr
A-2229 OCF3 R4-21 cPr A-2271 C≡CH R4-15 cPr
A-2230 OCF3 R4-22 cPr A-2272 C≡CH R4-16 cPr
A-2231 OCF3 R4-23 cPr A-2273 C≡CH R4-17 cPr
A-2232 OCF3 R4-24 cPr A-2274 C≡CH R4-18 cPr
A-2233 CF3 R4-1 cPr A-2275 C≡CH R4-19 cPr
A-2234 CF3 R4-2 cPr A-2276 C≡CH R4-20 cPr line Y R4 R10 line Y R4 R10
A-2277 C≡CH R4-21 cPr A-2291 cPr R4-1 1 cPr
A-2278 C≡CH R4-22 cPr A-2292 cPr R4-12 cPr
A-2279 C≡CH R4-23 cPr A-2293 cPr R4-13 cPr
A-2280 C≡CH R4-24 cPr A-2294 cPr R4-14 cPr
A-2281 cPr R4-1 cPr A-2295 cPr R4-15 cPr
A-2282 cPr R4-2 cPr A-2296 cPr R4-16 cPr
A-2283 cPr R4-3 cPr A-2297 cPr R4-17 cPr
A-2284 cPr R4-4 cPr A-2298 cPr R4-18 cPr
A-2285 cPr R4-5 cPr A-2299 cPr R4-19 cPr
A-2286 cPr R4-6 cPr A-2300 cPr R4-20 cPr
A-2287 cPr R4-7 cPr A-2301 cPr R4-21 cPr
A-2288 cPr R4-8 cPr A-2302 cPr R4-22 cPr
A-2289 cPr R4-9 cPr A-2303 cPr R4-23 cPr
A-2290 cPr R4-10 cPr A-2304 cPr R4-24 cPr
Particular embodiments of the compounds I are the following compounds: 1-1 .G, 1-1. H, 1-1 .1, 1-2.G, I-2.H, I-2.I; I-3.G, I-3.H, I-3.I, I-4.G, I-4.H, I-4.I; that are compiled in the Tables 1 -1 to 1-8, Tables 2-1 to 2-8, Tables 3-1 to 3-8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Figure imgf000124_0001
Figure imgf000124_0002
Figure imgf000124_0003
Figure imgf000124_0004
I-4.G I-4. H I-4. I
Table 1-1 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.G.1 -1.B-1 to 1-1 . G.1 -1. B-192, compounds I-2.G.1 -
1. B-1 to I-2.G.1 -1. B-192, compounds I-3.G.1 -1.B-1 to I-3.G.1-1 .B-192 compounds I-4.G.1 -1.B-1 to I-4.G.1 -1. B-192).
Table 1-2 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.G.1 -2.B-1 to 1-1 .G.1 -2. B-192, compounds I-2.G.1 -
2. B-1 to I-2.G.1 -2.B-192, compounds I-3.G.1 -2.B-1 to I-3.G.1-2. B-192 compounds I-4.G.1 -2.B-1 to I-4.G.1 -2.B-192).
Table 1-3 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.G.1 -3.B-1 to 1-1 .G.1 -3.B-192, compounds I-2.G.1 -
3. B-1 to I-2.G.1 -3.B-192, compounds I-3.G.1 -3.B-1 to I-3.G.1-3.B-192 compounds I-4.G.1 -3.B-1 to I-4.G.1 -3.B-192).
Table 1-4 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .G.1-4.B-1 to 1-1.G.1 -4.B-192, compounds I-2.G.1-4.B-1 to I- 2.G.1 -4.B-192, compounds I-3.G.1 -4.B-1 to I-3.G.1-4.B-192 compounds I-4.G.1 -4.B-1 to I-
4. G.1 -4.B-192).
Table 1-5 Compounds of the formula 1-1. G, I-2.G, I-3.G, I-4.G in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.G.1 -5.B-1 to 1-1 .G.1 -5.B-192, compounds I-2.G.1 -
5. B-1 to I-2.G.1 -5.B-192, compounds I-3.G.1 -5.B-1 to I-3.G.1-5.B-192 compounds I-4.G.1 -5.B-1 to I-4.G.1 -5.B-192).
Table 1-6 Compounds of the formula 1-1. G, I-2.G, I-3.G, I-4.G in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .G.1-6.B-1 to 1-1.G.1 -6.B-192, compounds I- 2.G.1 -6.B-1 to I-2.G.1-6.B-192, compounds I-3.G.1 -6.B-1 to I-3.G.1 -6.B-192 compounds I- 4.G.1 -6.B-1 to I-4.G.1-6.B-192).
Table 1-7 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .G.1-7.B-1 to 1-1.G.1 -7.B-192, compounds I-2.G.1-7.B-1 to I- 2.G.1 -7.B-192, compounds I-3.G.1 -7.B-1 to I-3.G.1-7.B-192 compounds I-4.G.1 -7.B-1 to I- 4.G.1 -7.B-192).
Table 1-8 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.G.1 -8.B-1 to 1-1 .G.1 -8.B-192, compounds I-2.G.1 - 8.B-1 to I-2.G.1 -8.B-192, compounds I-3.G.1 -8.B-1 to I-3.G.1-8.B-192 compounds I-4.G.1 -8.B-1 to I-4.G.1 -8.B-192).
Table 2-1 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.H.2-1 .B-1 to I-1.H.2-1.B-192, compounds I-2.H.2-
1. B-1 to I-2.H.2-1.B-192, compounds I-3.H.2-1.B-1 to I-3.H.2-1.B-192 compounds I-4.H.2-1.B-1 to I-4.H.2-1 .B-192).
Table 2-2 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.H.2-2.B-1 to I-1.H.2-2.B-192, compounds I-2.H.2-
2. B-1 to I-2.H.2-2.B-192, compounds I-3.H.2-2.B-1 to I-3.H.2-2.B-192 compounds I-4.H.2-2.B-1 to I-4.H.2-2.B-192).
Table 2-3 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .H.2-3.B-1 to I-1.H.2-3.B-192, compounds I-2.H.2-
3. B-1 to I-2.H.2-3.B-192, compounds I-3.H.2-3.B-1 to I-3.H.2-3.B-192 compounds I-4.H.2-3.B-1 to I-4.H.2-3.B-192).
Table 2-4 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is Br and the mean- ing for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .H.2-4.B-1 to I-1.H.2-4.B-192, compounds I-2.H.2-4.B-1 to I- 2.H.2-4.B-192, compounds I-3.H.2-4.B-1 to I-3.H.2-4.B-192 compounds I-4.H.2-4.B-1 to I-4.H.2-
4. B-192).
Table 2-5 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .H.2-5.B-1 to I-1.H.2-5.B-192, compounds I-2.H.2-
5. B-1 to I-2.H.2-5.B-192, compounds I-3.H.2-5.B-1 to I-3.H.2-5.B-192 compounds I-4.H.2-5.B-1 to I-4.H.2-5.B-192).
Table 2-6 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .H.2-6.B-1 to I-1.H.2-6.B-192, compounds I- 2.H.2-6.B-1 to I-2.H.2-6.B-192, compounds I-3.H.2-6.B-1 to I-3.H.2-6.B-192 compounds I-4.H.2-
6. B-1 to I-4.H.2-6.B-192).
Table 2-7 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is H and the mean- ing for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .H.2-7.B-1 to I-1.H.2-7.B-192, compounds I-2.H.2-7.B-1 to I- 2.H.2-7.B-192, compounds I-3.H.2-7.B-1 to I-3.H.2-7.B-192 compounds I-4.H.2-7.B-1 to I-4.H.2-
7. B-192).
Table 2-8 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .H.2-8.B-1 to I-1.H.2-8.B-192, compounds I-2.H.2-
8. B-1 to I-2.H.2-8.B-192, compounds I-3.H.2-8.B-1 to I-3.H.2-8.B-192 compounds I-4.H.2-8.B-1 to I-4.H.2-8.B-192).
Table 3-1 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1.1.3-1 .B-1 to 1-1.1.3-1 . B-192, compounds 1-2.1.3-1 . B-1 to I-2.I.3- 1.B-192, compounds 1-3.1.3-1. B-1 to 1-3.1.3-1 .B-192 compounds 1-4.1.3-1. B-1 to 1-4.1.3-1 .B-192).
Table 3-2 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .1.3-2. B-1 to 1-1.1.3-2. B-192, compounds I-2.I.3-2.B-1 to I- 2.I.3-2.B-192, compounds I-3.I.3-2.B-1 to I-3.I.3-2. B-192 compounds I-4.I.3-2.B-1 to I-4.I.3-2.B- 192).
Table 3-3 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .1.3-3. B-1 to 1-1.1.3-3. B-192, compounds I-2.I.3-3.B-1 to I- 2.I.3-3.B-192, compounds I-3.I.3-3.B-1 to I-3.I.3-3. B-192 compounds I-4.I.3-3.B-1 to I-4.I.3-3.B- 192).
Table 3-4 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds I-1.I.3-4.B-1 to I-1.I.3-4.B-192, compounds I-2.I.3-4.B-1 to I-2.I.3- 4.B-192, compounds I-3.I.3-4.B-1 to I-3.1.3-4.B-192 compounds I-4.I.3-4.B-1 to I-4.I.3-4.B-192).
Table 3-5 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1 .1.3-5. B-1 to I-1.I.3-5.B-192, compounds I-2.I.3-5.B-1 to I- 2.I.3-5.B-192, compounds I-3.I.3-5.B-1 to I-3.I.3-5.B-192 compounds I-4.I.3-5.B-1 to I-4.I.3-5.B- 192).
Table 3-6 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1.1.3-6. B-1 to 1-1 .1.3-6. B-192, compounds I-2.I.3-6.B-1 to I-2.I.3-6.B-192, compounds I-3.I.3-6.B-1 to I-3.I.3-6.B-192 compounds I-4.I.3-6.B-1 to I-4.I.3- 6.B-192).
Table 3-7 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is H and the meaning for the combination of R4 and R10for each individual compound corresponds in each case to one line of Table B (compounds 1-1.1.3-7. B-1 to 1-1.1.3-7. B-192, compounds I-2.I.3-7.B-1 to I-2.I.3-
7. B-192, compounds I-3.I.3-7.B-1 to I-3.1.3-7.B-192 compounds I-4.I.3-7.B-1 to I-4.I.3-7.B-192). Table 3-8 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds 1-1.1.3-8. B-1 to 1-1.1.3-8. B-192, compounds I-2.I.3-8.B-1 to I-2.I.3-
8. B-192, compounds I-3.I.3-8.B-1 to I-3.I.3-8.B-192 compounds I-4.I.3-8.B-1 to I-4.I.3-8.B-192). Particular embodiments of the compounds I are the following compounds: X-1.G, X-1.H, X- 1.1, X- 2.G, X-2.H, X-2.1; X-3.G, X-3.H, X-3.1, X-4.G, X-4.H, X-4.1; that are compiled in the Tables 1-1 to 1-8, Tables 2-1 to 2-8, Tables 3-1 to 3-8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Figure imgf000128_0001
X-1.G X-1.G X-1.1
Figure imgf000128_0002
-3.G -3.H -3.1
Figure imgf000128_0003
X4.G X4.H X-4.1
Table 1-1 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .G.1-1 .B-1 to X-1.G.1 -1 .B-192, compounds X- 2.G.1 -1.B-1 to X-2.G.1-1 .B-192, compounds X-3.G.1 -1 .B-1 to X-3.G.1 -1.B-192 compounds X- 4.G.1 -1.B-1 to X-4.G.1-1 .B-192).
Table 1-2 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .G.1-2. B-1 to X-1.G.1 -2.B-192, compounds X- 2.G.1 -2.B-1 to X-2.G.1-2.B-192, compounds X-3.G.1 -2.B-1 to X-3.G.1 -2.B-192 compounds X- 4.G.1 -2.B-1 to X-4.G.1-2.B-192).
Table 1-3 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1. G.1-3. B-1 to X-1 .G.1-3.B-192, compounds X- 2.G.1 -3.B-1 to X-2.G.1-3.B-192, compounds X-3.G.1 -3.B-1 to X-3.G.1 -3.B-192 compounds X- 4.G.1 -3.B-1 to X-4.G.1-3.B-192).
Table 1-4 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .G.1-4. B-1 to X-1.G.1 -4.B-192, compounds X- 2.G.1 -4.B-1 to X-2.G.1-4.B-192, compounds X-3.G.1 -4.B-1 to X-3.G.1 -4.B-192 compounds X- 4.G.1 -4.B-1 to X-4.G.1-4.B-192).
Table 1-5 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .G.1-5. B-1 to X-1.G.1 -5.B-192, compounds X- 2.G.1 -5.B-1 to X-2.G.1-5.B-192, compounds X-3.G.1 -5.B-1 to X-3.G.1 -5.B-192 compounds X- 4.G.1 -5.B-1 to X-4.G.1-5.B-192).
Table 1-6 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .G.1-6. B-1 to X-1 .G.1-6.B-192, compounds X- 2.G.1 -6.B-1 to X-2.G.1-6.B-192, compounds X-3.G.1 -6.B-1 to X-3.G.1 -6.B-192 compounds X- 4.G.1 -6.B-1 to X-4.G.1-6.B-192).
Table 1-7 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .G.1-7. B-1 to X-1.G.1 -7.B-192, compounds X- 2.G.1 -7.B-1 to X-2.G.1-7.B-192, compounds X-3.G.1 -7.B-1 to X-3.G.1 -7.B-192 compounds X- 4.G.1 -7.B-1 to X-4.G.1-7.B-192).
Table 1-8 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .G.1-8. B-1 to X-1.G.1 -8.B-192, compounds X- 2.G.1 -8.B-1 to X-2.G.1-8.B-192, compounds X-3.G.1 -8.B-1 to X-3.G.1 -8.B-192 compounds X- 4.G.1 -8.B-1 to X-4.G.1-8.B-192).
Table 2-1 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-1.B-1 to X-1.H.2-1 .B-192, compounds X-2.H.2- 1.B-1 to X-2. H.2-1 .B-192, compounds X-3. H.2-1 .B-1 to X-3. H.2-1.B-192 compounds X-4.H.2-
1. B-1 to X-4. H.2-1 . B-192).
Table 2-2 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-2.B-1 to X-1.H.2-2.B-192, compounds X-2.H.2-
2. B-1 to X-2.H.2-2.B-192, compounds X-3.H.2-2.B-1 to X-3.H.2-2.B-192 compounds X-4.H.2- 2.B-1 to X-4.H.2-2.B-192).
Table 2-3 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-3.B-1 to X-1.H.2-3.B-192, compounds X-2.H.2- 3.B-1 to X-2.H.2-3.B-192, compounds X-3.H.2-3.B-1 to X-3.H.2-3.B-192 compounds X-4.H.2-
3. B-1 to X-4.H.2-3.B-192).
Table 2-4 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-4.B-1 to X-1.H.2-4.B-192, compounds X-2.H.2-
4. B-1 to X-2.H.2-4.B-192, compounds X-3.H.2-4.B-1 to X-3.H.2-4.B-192 compounds X-4.H.2-
4. B-1 to X-4.H.2-4.B-192).
Table 2-5 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-5.B-1 to X-1.H.2-5.B-192, compounds X-2.H.2-
5. B-1 to X-2.H.2-5.B-192, compounds X-3.H.2-5.B-1 to X-3.H.2-5.B-192 compounds X-4.H.2- 5.B-1 to X-4.H.2-5.B-192).
Table 2-6 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-6. B-1 to X-1.H.2-6. B-192, compounds X- 2.H.2-6.B-1 to X-2.H.2-6.B-192, compounds X-3.H.2-6.B-1 to X-3.H.2-6.B-192 compounds X- 4.H.2-6.B-1 to X-4.H.2-6.B-192).
Table 2-7 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-7.B-1 to X-1.H.2-7.B-192, compounds X-2.H.2- 7.B-1 to X-2.H.2-7.B-192, compounds X-3.H.2-7.B-1 to X-3.H.2-7.B-192 compounds X-4.H.2-
7. B-1 to X-4.H.2-7.B-192).
Table 2-8 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .H.2-8.B-1 to X-1.H.2-8.B-192, compounds X-2.H.2-
8. B-1 to X-2.H.2-8.B-192, compounds X-3.H.2-8.B-1 to X-3.H.2-8.B-192 compounds X-4.H.2- 8.B-1 to X-4.H.2-8.B-192).
Table 3-1 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is CH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .1.3-1. B-1 to X-1.1.3-1. B-192, compounds X-2.1.3- 1.B-1 to X-2.1.3-1.B-192, compounds X-3.1.3-1.B-1 to X-3.1.3-1 .B-192 compounds X-4.1.3-1.B-1 to X-4.1.3-1. B-192).
Table 3-2 Compounds of the formula X-1.1, X-2.1, X-3.1, X-4.1 in which R9 is CHF2 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .1.3-2. B-1 to X-1.1.3-2. B-192, compounds X-2.1.3- 2.B-1 to X-2.l.3-2.B-192, compounds X-3.I.3-2.B-1 to X-3.I.3-2. B-192 compounds X-4.I.3-2.B-1 to X-4.I.3-2.B-192).
Table 3-3 Compounds of the formula X-1.1, X-2.1, X-3.1, X-4.1 in which R9 is C≡CH and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .1.3-3. B-1 to X-1.1.3-3. B-192, compounds X-2.1.3- 3. B-1 to X-2.l.3-3.B-192, compounds X-3.I.3-3.B-1 to X-3.I.3-3.B-192 compounds X-4.I.3-3.B-1 to X-4.I.3-3.B-192).
Table 3-4 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is Br and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1.1.3-4. B-1 to X-1 .1.3-4. B-192, compounds X-2.1.3-4. B-1 to X- 2.I.3-4.B-192, compounds X-3.I.3-4.B-1 to X-3.I.3-4.B-192 compounds X-4.I.3-4.B-1 to X-4.l.3-
4. B-192).
Table 3-5 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is OCH3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .1.3-5. B-1 to X-1 .1.3-5. B-192, compounds X-2.1.3-
5. B-1 to X-2.l.3-5.B-192, compounds X-3.I.3-5.B-1 to X-3.I.3-5. B-192 compounds X-4.I.3-5.B-1 to X-4.I.3-5.B-192).
Table 3-6 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R9 is cyclopropyl and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1.1.3-6. B-1 to X-1 .1.3-6. B-192, compounds X- 2.I.3-6.B-1 to X-2.I.3-6.B-192, compounds X-3.I.3-6.B-1 to X-3.I.3-6.B-192 compounds X-4.I.3-
6. B-1 to X-4.1.3-6. B-192).
Table 3-7 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.1 in which R9 is H and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1.1.3-7. B-1 to X-1 .1.3-7. B-192, compounds X-2.1.3-7. B-1 to X- 2.I.3-7.B-192, compounds X-3.I.3-7.B-1 to X-3.I.3-7.B-192 compounds X-4.I.3-7.B-1 to X-4.l.3-
7. B-192).
Table 3-8 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.1 in which R9 is CF3 and the meaning for the combination of R4 and R10 for each individual compound corresponds in each case to one line of Table B (compounds X-1 .1.3-8. B-1 to X-1 .1.3-8. B-192, compounds X-2.1.3-
8. B-1 to X-2.l.3-8.B-192, compounds X-3.I.3-8.B-1 to X-3.I.3-8. B-192 compounds X-4.I.3-8.B-1 to X-4.I.3-8.B-192).
Table B
Please note that following R4 structure are in the Table A named as follows
No. R4 R10 No. R4 R10
B-1 R4-1 H B-8 R4-8 H
B-2 R4-2 H B-9 R4-9 H
B-3 R4-3 H B-10 R4-10 H
B-4 R4-4 H B-1 1 R4-1 1 H
B-5 R4-5 H B-12 R4-12 H
B-6 R4-6 H B-13 R4-13 H
B-7 R4-7 H B-14 R4-14 H No. R4 R10 No. R4 R10
B-15 R4-15 H B-45 R4-21 Br
B-16 R4-16 H B-46 R4-22 Br
B-17 R4-17 H B-47 R4-23 Br
B-18 R4-18 H B-48 R4-24 Br
B-19 R4-19 H B-49 R4-1 CHs
B-20 R4-20 H B-50 R4-2 CHs
B-21 R4-21 H B-51 R4-3 CHs
B-22 R4-22 H B-52 R4-4 CHs
B-23 R4-23 H B-53 R4-5 CHs
B-24 R4-24 H B-54 R4-6 CHs
B-25 R4-1 Br B-55 R4-7 CHs
B-26 R4-2 Br B-56 R4-8 CHs
B-27 R4-3 Br B-57 R4-9 CHs
B-28 R4-4 Br B-58 R4-10 CHs
B-29 R4-5 Br B-59 R4-1 1 CHs
B-30 R4-6 Br B-60 R4-12 CHs
B-31 R4-7 Br B-61 R4-13 CHs
B-32 R4-8 Br B-62 R4-14 CHs
B-33 R4-9 Br B-63 R4-15 CHs
B-34 R4-10 Br B-64 R4-16 CHs
B-35 R4-1 1 Br B-65 R4-17 CHs
B-36 R4-12 Br B-66 R4-18 CHs
B-37 R4-13 Br B-67 R4-19 CHs
B-38 R4-14 Br B-68 R4-20 CHs
B-39 R4-15 Br B-69 R4-21 CHs
B-40 R4-16 Br B-70 R4-22 CHs
B-41 R4-17 Br B-71 R4-23 CHs
B-42 R4-18 Br B-72 R4-24 CHs
B-43 R4-19 Br B-73 R4-1 CH F2
B-44 R4-20 Br B-74 R4-2 CH F2 No. R4 R10 No. R4 R10
B-75 R4-3 CHF2 B-105 R4-9 CFs
B-76 R4-4 CHF2 B-106 R4-10 CFs
B-77 R4-5 CHF2 B-107 R4-1 1 CFs
B-78 R4-6 CHF2 B-108 R4-12 CFs
B-79 R4-7 CHF2 B-109 R4-13 CFs
B-80 R4-8 CHF2 B-1 10 R4-14 CFs
B-81 R4-9 CHF2 B-1 1 1 R4-15 CFs
B-82 R4-10 CHF2 B-1 12 R4-16 CFs
B-83 R4-1 1 CHF2 B-1 13 R4-17 CFs
B-84 R4-12 CHF2 B-1 14 R4-18 CFs
B-85 R4-13 CHF2 B-1 15 R4-19 CFs
B-86 R4-14 CHF2 B-1 16 R4-20 CFs
B-87 R4-15 CHF2 B-1 17 R4-21 CFs
B-88 R4-16 CHF2 B-1 18 R4-22 CFs
B-89 R4-17 CHF2 B-1 19 R4-23 CFs
B-90 R4-18 CHF2 B-120 R4-24 CFs
B-91 R4-19 CHF2 B-121 R4-1 OCHs
B-92 R4-20 CHF2 B-122 R4-2 OCHs
B-93 R4-21 CHF2 B-123 R4-3 OCHs
B-94 R4-22 CHF2 B-124 R4-4 OCHs
B-95 R4-23 CHF2 B-125 R4-5 OCHs
B-96 R4-24 CHF2 B-126 R4-6 OCHs
B-97 R4-1 CFs B-127 R4-7 OCHs
B-98 R4-2 CFs B-128 R4-8 OCHs
B-99 R4-3 CFs B-129 R4-9 OCHs
B-100 R4-4 CFs B-130 R4-10 OCHs
B-101 R4-5 CFs B-131 R4-1 1 OCHs
B-102 R4-6 CFs B-132 R4-12 OCHs
B-103 R4-7 CFs B-133 R4-13 OCHs
B-104 R4-8 CFs B-134 R4-14 OCHs No. R4 R10 No. R4 R10
B-135 R4-15 OCHs B-164 R4-20 C≡CH
B-136 R4-16 OCH3 B-165 R4-21 C≡CH
B-137 R4-17 OCHs B-166 R4-22 C≡CH
B-138 R4-18 OCHs B-167 R4-23 C≡CH
B-139 R4-19 OCH3 B-168 R4-24 C≡CH
B-140 R4-20 OCH3 B-169 R4-1 cPr
B-141 R4-21 OCH3 B-170 R4-2 cPr
B-142 R4-22 OCH3 B-171 R4-3 cPr
B-143 R4-23 OCH3 B-172 R4-4 cPr
B-144 R4-24 OCH3 B-173 R4-5 cPr
B-145 R4-1 C≡CH B-174 R4-6 cPr
B-146 R4-2 C≡CH B-175 R4-7 cPr
B-147 R4-3 C≡CH B-176 R4-8 cPr
B-148 R4-4 C≡CH B-177 R4-9 cPr
B-149 R4-5 C≡CH B-178 R4-10 cPr
B-150 R4-6 C≡CH B-179 R4-1 1 cPr
B-151 R4-7 C≡CH B-180 R4-12 cPr
B-152 R4-8 C≡CH B-181 R4-13 cPr
B-153 R4-9 C≡CH B-182 R4-14 cPr
B-154 R4-10 C≡CH B-183 R4-15 cPr
B-155 R4-1 1 C≡CH B-184 R4-16 cPr
B-156 R4-12 C≡CH B-185 R4-17 cPr
B-157 R4-13 C≡CH B-186 R4-18 cPr
B-158 R4-14 C≡CH B-187 R4-19 cPr
B-159 R4-15 C≡CH B-188 R4-20 cPr
B-160 R4-16 C≡CH B-189 R4-21 cPr
B-161 R4-17 C≡CH B-190 R4-22 cPr
B-162 R4-18 C≡CH B-191 R4-23 cPr
B-163 R4-19 C≡CH B-192 R4-24 cPr The compounds I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygo- mycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
The compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably, compounds I and compositions thereof, respectively are used for controlling a multi- tude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. pota- toes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to tar- geted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygen- ase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflow- ers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cul- tivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal pro- teins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdyster- oid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278,
WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coelop- tera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1 Ab toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothri- cin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Pro- tecta®, Bt1 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis- related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capa- ble to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants. Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Can- ada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassico/a or brassi- cae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. so/an/ or A. alternata), to- matoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. (anthracnose) on wheat and A. horde/ on barley; Bipolar/s and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydisj or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokin- iana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana. grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. bet/cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum. leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. soro- kin/ana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glo- merella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthrac- nose stalk rot), soft fruits, potatoes (e. g. C. coccodes. black dot), beans (e. g. C. lindemuthi- anum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cy- cloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. lirio- dendri, teleomorph: Neonectria liriodendri. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D.
phaseolorum (damping off) on soybeans; Drechslera (s n. Helminthosporium, teleomorph: Pyr- enophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis. tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formiti- poria (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; E/sinoe SOD. on pome fruits (E pyri), soft fruits (E veneta: anthracnose) and vines (E ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Ery- siphe spp. (powdery mildew) on sugar beets (E betae), vegetables (e. g. E pisl), such as cucurbits (e. g. E cichoracearum), cabbages, rape (e. g. E cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. gra- minearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. so/anl( sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G zeae) and rice (e. g. G fujikuroi. Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypiion cotton; Grainstaining complex on rice; G 'uignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp . (syn. Drechslera, teleomorph: Cochiioboius) on corn, cereals and rice; Hemileia spp., e. g. A/, vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseo/ή (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. /ara, fructicola and fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco {P. tabacina) and soybeans (e. g. P. manshurica);
Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Phy- soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P.
megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad- leaved trees (e. g. P. ramorum. sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. ha/stediion sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat {P. graminis) and sugar beets {P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapes/a yal- lundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. hum/lion hop; Pseudopezicu/a tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. horde/ (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagion asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. bet/cola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Saro- cladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. ro/fsiior S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum
(Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucker!) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Lepto- sphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici(syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis. corn smut) and sugar cane; Venturis spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae o strawberries, rape, potatoes and tomatoes.
The compounds I and compositions thereof, respectively, are also suitable for controlling harm- ful fungi in the protection of stored products or harvest and in the protection of materials.
The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma pp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Hum/cola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Con/- ophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Ser- pula spp. and 7/ro/77yc?es spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma pp., Alternaria pp., Paecilomyces spp. and Zygomycetes such as Mucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms. According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
The compounds I and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effec- tive amount of compounds I and compositions thereof, respectively.
The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.
The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
The compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.
The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
The compounds I, their N-oxides and salts can be converted into customary types of agrochem- ical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; gly- cols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective col- loid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sul- fates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkox- ylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based sur- factants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolygluco- sides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyeth- ylene amines.
Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e. g. alizarin-, azo- and phthalogencyanine colorants).
Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compound I and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a compound I and 1-10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I and 5-10 wt% emulsifiers (e. g. calcium dodecylbenzenesul- fonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I and 1 -10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1- 2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME)
5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and ar- ylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocya- nate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solu- tion of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g. hexameth- ylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 - 10 wt%. The wt% relate to the total CS composition.
xi) Dustable powders (DP, DS)
1 -10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
xii) Granules (GR, FG)
0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-low volume liquids (UL)
1 -50 wt% of a compound I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.
The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum). For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The com- positions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, com- pound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propa- gation material (preferably seeds) are generally required.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1 .
A pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term "pesticide" includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if ap- propriate.
Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and option- ally a further active component 3) as defined herein.
Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.
The following list of pesticides II (e. g. pesticidally-active substances and biopesticides), in conjunction with which the compounds I can be used, is intended to illustrate the possible combinations but does not limit them:
A) Respiration inhibitors
Inhibitors of complex III at Q0 site: azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1.2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), man- destrobin (A.1 .10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1 .17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-meth- oxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chlorodincarb
(A.1 .20), famoxadone (A.1 .21 ), fenamidone (A.1.21 ), methyl-/V-[2-[(1 ,4-dimethyl-5-phenyl- pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1-[2-[[1 -(4-chlorophenyl)py- razol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1 .25), ( 2 )-5-[1 -(2,4-di- chlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino- y3-dimethyl-pent-v3-enamide (A.1.34), (Z,2-r)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-rnethoxyimino- V,3-dimethyl-pent-3-enamide (A.1 .35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxy- methylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38);
- inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),
[(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-di- oxo-1 ,5-dioxonan-7-yl] 2-rnethylpropanoate (A.2.3), fenpicoxamid (A.2.4); - inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), ox- ycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyra- ziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 inpyrfluxam (A.3.22), /V-[(22)-2-[3-chloro-5-(2-cyclopropylethynyl)-2-pyridyl]-2-isopropoxyimino-ethyl]-3- (difluoromethyl)-1 -methyl-pyrazole-4-carboxamide (A.3.23), fluindapyr (A.3.28), methyl (E)-2- [2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflu- cypram (A.3.31 ), 2-(difluoromethyl)-N-(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide
(A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1 ,1 -dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1 ,1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carbox- amide (A.3.39);
- other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), di- nobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12);
B) Sterol biosynthesis inhibitors (SBI fungicides)
- C14 demethylase inhibitors: triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromucona- zole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1 .6), dinicona- zole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1 .9), fluquinconazole (B.1.10), flusi- lazole (B.1 .1 1 ), flutriafol (B.1 .12), hexaconazole (B.1 .13), imibenconazole (B.1.14), ipcona- zole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1 .19), paclobu- trazole (B.1 .20), penconazole (B.1.21 ), propiconazole (B.1 .22), prothioconazole (B.1 .23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1 .26), triadimefon (B.1 .27), triadimenol (B.1.28), triticonazole (B.1 .29), uniconazole (B.1 .30), 2-(2,4-difluorophenyl)-1 ,1 - difluoro-3-(tetrazol-1 -yl)-1 -[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31 ), 2-(2,4-difluorophenyl)-1 ,1-difluoro-3-(tetrazol-1-yl)-1 -[5-[4-(trifluoromethoxy)phenyl]-2- pyridyl]propan-2-ol (B.1.32), ipfentrifluconazole (B.1 .37), mefentrifluconazole (B.1.38), 2- (chloromethyl)-2-methyl-5-(p-tolylmethyl)-1 -(1 ,2,4-triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1 .44), pefurazoate (B.1.45), prochloraz (B.1 .46), triflumizol (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1 .49), pyrifenox (B.1.50), triforine (B.1.51 ), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)metha- nol (B.1.52);
- Delta 14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spi- roxamine (B.2.8);
- Inhibitors of 3-keto reductase: fenhexamid (B.3.1 ); - Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 );
C) Nucleic acid synthesis inhibitors
- phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiralaxyl (C.1 .3), metalaxyl (C.1 .4), metalaxyl-M (C.1 .5), ofurace (C.1 .6), oxadixyl (C.1 .7);
- other nucleic acid synthesis inhibitors: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
D) Inhibitors of cell division and cytoskeleton
- tubulin inhibitors: benomyl (D.1 .1 ), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1 .4), thiophanate-methyl (D.1 .5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyri- dazine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1 .7), N-eth- yl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- N-(2-fluoroethyl)butanamide (D.1 .10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroeth- yl)-2-methoxy-acetamide (D.1 .1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanam- ide (D.1 .12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1 .16);
- other cell division inhibitors: diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
E) Inhibitors of amino acid and protein synthesis
- methionine synthesis inhibitors: cyprodinil (E.1 .1 ), mepanipyrim (E.1.2), pyrimethanil (E.1.3);
- protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydro- chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
F) Signal transduction inhibitors
- MAP / histidine kinase inhibitors: fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1 .3), vinclozolin (F.1 .4), fludioxonil (F.1 .5);
- G protein inhibitors: quinoxyfen (F.2.1 );
G) Lipid and membrane synthesis inhibitors
- Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
- lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
- compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 );
- inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1 -{[3,5-bis(difluorome- thyl-1 H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperi- din-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl- pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.5), 4-[1 -[2-[3-(difluoromethyl)-5-(trifluoro- methyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.6), 4-[1- [2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N- tetralin-1 -yl-pyridine-2-carboxamide (G.5.8), 4-[1 -[2-[5-(difluoromethyl)-3-(trifluoromethyl)py- razol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1 -[2-[3,5- bis(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide
(G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin- 1 -yl-pyridine-2-carboxamide (G.5.1 1 );
H) Inhibitors with Multi Site Action
- inorganic active substances: Bordeaux mixture (H.1 .1 ), copper (H.1 .2), copper acetate
(H.1 .3), copper hydroxide (H.1 .4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1 .7);
- thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam
(H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
- organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene
(H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );
- guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3),
guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);
I) Cell wall synthesis inhibitors
- inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1.2);
- melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (I.2.3), dicy- clomet (I.2.4), fenoxanil (I.2.5);
J) Plant defence inducers
- acibenzolar-S-methyl (J.1 .1 ), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadi- one-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1 .7), phosphorous acid and its salts (J.1 .8), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-di- methoxyphenyl)thiadiazole-5-carboxamide (J.1 .10); K) Unknown mode of action
- bronopol (K.1.1 ), chinomethionat (K.1 .2), cyflufenamid (K.1 .3), cymoxanil (K.1 .4), dazomet (K.1.5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1 .8), difenzoquat (K.1 .9), difen- zoquat-methylsulfate (K.1 .10), diphenylamin (K.1.1 1 ), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14), flusulfamide (K.1 .15), flutianil (K.1.16), harpin (K.1 .17), metha- sulfocarb (K.1 .18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21 ), oxin- copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24), tecloftalam (K.1 .25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-eth- yl-N-methyl formamidine (K.1 .28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]- oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2- yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1 -(3,5-diflu- orophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .31 ), N'-[5-bromo- 6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol- 5-yl]-2-prop-2-ynyloxy-acetamide (K.1 .36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine (pyrisoxazole) (K.1 .37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]- pyridine (K.1.38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), picarbutrazox (K.1.41 ), pentyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carba- mate (K.1 .42), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxyme- thyl]-2-pyridyl]carbamate (K.1 .43), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phe- nyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1.45), quinofumelin (K.1.47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-me- thyl-2-pyridyl]quinazoline (K.1.51 ), 3-[(3,4-dichloroisothiazol-5-yl)methoxy]-1 ,2-benzothiazole 1 ,1 -dioxide (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), pyrifenamine (K.1 .54);
L) Biopesticides
M) Growth regulators
abscisic acid (M.1.1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dime- thipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gib- berellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadi- one-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
N) Herbicides from classes N.1 to N.15
N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepra- loxydim, tralkoxydim, 4-(4'-chloro-4-cyclo-,propyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy- 2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopro- pyl[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337- 45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-py- ran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tet- ramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cy- clopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihy- dro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1 ); 5-(acet- yloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-
3- one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihy- dro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51 -1 );
4- (2',4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-
5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS
1312340-83-2); 4-(2',4'-dichloro-4-ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-
5- 0X0-2 H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate; ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfu- ron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosul- furon-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfu- ron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imaza- mox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, di- closulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, py- rithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]- benzoic acid-1-methyhethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]-"methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromo- phenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8); flu- carbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thien- carbazone, thiencarbazone-methyl; triafamone; N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, sidu- ron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham- ethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, pro- panil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;
N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pen- tyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrim- idin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4-tri- fluoro-methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452098-92-9), N tetrahy- drofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyhphenoxy)-5-methyl-1 H- pyrazole-1-carboxamide (CAS 452099-05-7), N tetrahydro-"furfuryl-3-(2-chloro-6-fluoro-4- trifluoro-,methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7- fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihy- dro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0),
1 - methyl-6-trifluoro-,methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-ben- zo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (E)-4-[2-chloro- 5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-
2- enoate (CAS 948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]- 1 -methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4);
N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,
norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)_,pyrimi- dine (CAS 180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintri- one, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltri- one, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potas- sium, glyphosate-trimesium (sulfosate);
N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;
N.8 DHP synthase inhibitors: asulam;
N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendi- methalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethena- mid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napro- pamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000154_0001
Figure imgf000154_0002
N.1 1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS
175899-01-1 );
N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as amino- pyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quin- merac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino-
3- chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl
4- amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661 -72-9);
N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-so- dium;
N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydra- zide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, me- thyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane;
O) Insecticides from classes 0.1 to 0.29
0.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, bu- tocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; acephate, aza- methiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosa- lone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, pro- thiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;
0.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil,
flufiprole, pyrafluprole, pyriprole;
0.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, del- tamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and trans- fluthrin; DDT, methoxychlor;
0.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam;
4,5-dihydro-/V-nitro-1-(2-oxiranylmethyl)-1 A/-imidazol-2-amine, (2£)-1-[(6-chloropyridin-3-yl)me- thyl^/V^nitro^-pentylidenehydrazinecarboximidamide; 1-[(6-chloropyridin-3-yl)methyl]-7-me- thyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; nicotine; sulfoxaflor, f I u py rad if u ron e, trif I u mezopy ri m ;
0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram;
0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbe- mectin;
0.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;
0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
0.9 Chordotonal organ TRPV channel modulators: pymetrozine, flonicamid;
O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin; etoxazole;
0.1 1 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaeri- cus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Ba- cillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp.
kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;
0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;
0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium;
0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron, chlorfluazuron, diflubenzuron, flu- cycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;
0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin;
0.17 Moulting disruptors: cyromazine;
0.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;
0.19 Octopamin receptor agonists: amitraz;
O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl,
fluacrypyrim, bifenazate; 1 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrim- idifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;
2 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyano- phenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecar- boxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)- amino]phenyl]methylene]-hydrazinecarboxamide;
3 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen, spiromesifen, spirotetramat, spi- ropidion;
4 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
5 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen;
6 Ryanodine receptor-modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cycla- niliprole, tetraniliprole; (R)-3-chloro-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluoro-l-(trifluoromethyl)- ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N1-{2-methyl-4- [1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)- phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]- carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole- 3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl- lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluorometh- yl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carba- moyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-di- bromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluo- romethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-meth- ylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro- 2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole- 5-carboxamide; 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyri- dyl)-1 H-pyrazole-5-carboxamide; N-[4-chloro-2-[[(1 ,1 -dimethylethyl)amino]carbonyl]-6-meth- ylphenyl]-1 -(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; cyhalodi- amide;
7: Chordotonal organ Modulators - undefined target site: flonicamid;
8. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinome- thionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1 -en- 10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2- one, 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, Bacillus firmus, flupyrimin, fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(tri- fluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 5- [3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; 3-(benzoylmethyla- mino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)p nyl]-2-fluoro-benzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide; N-[3-[[[2-iodo-4-[1 ,2,2,2-tetra- fluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-m benzamide; N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluorome- thyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide; 4-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phe- nyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]-6(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-m thyl-benzamide; 2-chloro-N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(tri- fluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; 4-cyano-N-[2-cyano-5- [[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2- methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4- [1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; N-[5-[[2-chloro- 6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phe- nyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1 -(tri- fluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; N-[5- [[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2- cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-
[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-ben- zamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluorome- thyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-ben- zamide; 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridi- nyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimi- dine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-
6- [2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol- 5-yl]-3-methylthio-propanamide; N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; N,2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-[4- chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide; N-[4-chloro-2- (3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thia- zol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3- methylthio-propanamide; 1 -[(6-chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-
7- methyl-8-nitro-imidazo[1 ,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-
1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; 1 -(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole- 4-carboxamide; N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4- carboxamide; 1 -[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-car- boxamide; 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1- [1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N-me- thyl-1-(2-fluoro-1 -methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4- difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4-difluo- rocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, N-(1-methylethyl)-2-(3- pyridinyl)-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carbox- amide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-(2,2,2-tri- fluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H- indazole-5-carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecar- boxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; N- (2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; 2-(3-pyridinyl )-N-(2-pyrimidi- nylmethyl )-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H- indazole-5-carboxamide, tyclopyrazoflor; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-
3- (3,3,3-trifluoropropylsulfinyl)propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-di- fluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-
4- yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide; sarolaner, lotilaner, N- [4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2-pentafluoroethyl)- 4-(trifluoromethyl)-1 A -pyrazole-5-carboxamide; M. UN.22a 2-(3-ethylsulfonyl-2-pyridyl)-3-me- thyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]- 3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 4-[5-(3,5-dichlorophenyl)-5-(trifluorome- thyl)-4 isoxazol-3-yl]-N[(4 )-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide, 4-[5- (3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4A isoxazol-3-yl]-/V-[(4 )-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide; N[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-me- thyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, /V-[4-chloro-3- [(1 -cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoro- methyl)pyrazole-3-carboxamide; acynonapyr; benzpyrimoxan; chloro-/V-(1 -cyanocyclopro- pyl)-5-[1-[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4- yl]benzamide.
The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244,
JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272;
US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271 , WO 1 1/028657, WO 12/168188, WO 07/006670, WO 1 1/77514; WO 13/047749, WO 10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224, WO 1 1/135833, CN 1907024, CN 1456054, CN 103387541 , CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/1 16251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/16551 1 , WO 1 1/081 174, WO 13/47441 ). The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one fur- ther fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with indi- vidual compounds I or individual fungicides from groups A) to K).
By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).
This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
When applying compound I and a pesticide II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
In the binary mixtures and compositions according to the invention the weight ratio of the component 1 ) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50: 1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1 .
According to further embodiments of the binary mixtures and compositions, the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1 .
According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1 :1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
In the ternary mixtures, i.e. compositions according to the invention comprising the component 1 ) and component 2) and a compound III (component 3), the weight ratio of component 1 ) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1 ) and component 3) usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1.
Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1 ).
These ratios are also suitable for inventive mixtures applied by seed treatment.
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q0 site in group A), more preferably selected from compounds (A.1 .1 ), (A.1 .4), (A.1 .8), (A.1 .9), (A.1 .10), (A.1.12), (A.1 .13), (A.1.14), (A.1 .17), (A.1.21 ), (A.1 .25), (A.1.34) and (A.1.35); particularly selected from (A.1 .1 ), (A.1 .4), (A.1 .8), (A.1 .9), (A.1 .13), (A.1.14), (A.1.17), (A.1 .25), (A.1.26), (A.1 .27), (A.1.30), (A.1 .31 ), (A.1.32), (A.1 .34) and (A.1 .35).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q, site in group A), more preferably selected from com- pounds (A.2.1 ), (A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.1 1 ), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21 ), (A.3.22), (A.3.23), (A.3.28), (A.3.31 ), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39); particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.31 ), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration nhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.1 1 ); in particular (A.4.1 1 ).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1 .4), (B.1 .5), (B.1 .8), (B.1 .10), (B.1.1 1 ), (B.1 .12), (B.1.13), (B.1 .17), (B.1.18), (B.1 .21 ), (B.1.22), (B.1.23), (B.1 .25), (B.1.26), (B.1 .29), (B.1.34), (B.1 .37), (B.1.38), (B.1 .43) and (B.1 .46); particularly selected from (B.1.5), (B.1.8), (B.1 .10), (B.1.17), (B.1.22), (B.1.23), (B.1 .25), (B.1.33), (B.1 .34), (B.1.37), (B.138), (B.1.43) and (B.1.46).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from Delta 14-reductase inhibitors in group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1 .1 ), (C.1 .2), (C.1.4) and (C.1.5); particularly selected from (C.1 .1 ) and (C.1.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably selected from compounds (C.2.6),(C.2.7) and (C.2.8).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1 ), (D.1 .2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1 .2), (D.1.5) and (D.2.6).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1 ), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1.2), (F.1.4) and (F.1.5). Preference is also given to mixtures comprising as component 2) at least one active substance selected from group G), more preferably selected from compounds (G.3.1 ), (G.3.3), (G.3.6), (G.5.1 ), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.1 1 ); particularly selected from (G.3.1 ), (G.5.1 ), (G.5.2) and (G.5.3).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5),
(H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (1.2.2) and (I.2.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1 .2), (J.1.5) and (J.1 .8); in particular (J.1.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1.41 ), (K.1 .42), (K.1.44), (K.1 .45), (K.1.47) and (K.1.49); particularly selected from (K.1 .41 ), (K.1.44), (K.1 .45), (K.1.47) and (K.1 .49).
The mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I. Concerning usual ingredients of such compositions refer- ence is made to the explanations given for the compositions containing compounds I.
Synthesis example
With due modification of the starting compounds, the procedures shown in the synthesis examples below were used to obtain further compounds I. The resulting compounds, together with physical data, are listed in Table I below.

Claims

Claims
1. Compounds of formula I
Figure imgf000163_0001
wherein
is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted by groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4 halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or
substituted by groups R1 b which independently of one another are selected from:
R1 b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio; is in each case independently selected from H, halogen, OH, CN, N02, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; wherein the acyclic moieties of R2 are unsubstituted or substituted by groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or
substituted by groups R2b which independently of one another are selected from: R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl,
C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3;
R4 is Ci-C6-alkyl, which is substituted by a five-, six- or ten-membered heteroaryl, wherein the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S;
wherein the alkyl moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R4a halogen, OH, CN, N02, SH, NH2, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogenalkoxy; and
wherein one or two CH2 groups of alkyl moieties of R4 may be replaced by a group independently selected from C(=0), (=CH2) or form a three- four- five or six-membered carbocyle which han include optionally one O as ring member; and
wherein the heteroaryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from:
R b halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4- alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-CrC6-alkyl, Ci-C4-alkoxy-CrC4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx is as defined above;
n is 0, 1 , 2 or
R5 is H;
R6 is H;
A is selected from below group:
Figure imgf000165_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.; wherein Y is in each case independently selected from H, F, CI, Br, I, OH, CN, NO2, Ci-Ce-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- Ce-alkoxy, Ci-C6-halogenalkoxy, ORY, S(0)zRY, NHRY, N(RY)2, C(=0)RY, C(=0)ORY, NH(C(=0)RY, N(C(=0)RY)2, NH-S02-Rx, C(RY)=NO(RY),
RY is in each case independently selected from Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-
C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cy- cloalkyl, C3-C6-halogencycloalkyl and phenyl; wherein the phenyl group is unsub- stituted or substituted from the group consisting of halogen, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
z is 0, 1 or 2;
wherein the acyclic moieties of Y are unsubstituted or substituted by groups Ya which independently of one another are selected from:
Ya halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents RY1a selected from the group consisting of halogen, OH, CN, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;
wherein the carbocyclic and phenyl moieties of Y are unsubstituted or substituted by groups Yb which independently of one another are selected from:
Yb halogen, OH, CN, CrC4-alkyl, CrC4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
Rx is as defined above;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl),
N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein Rx is defined above; wherein R' and R" are in- dependently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is inde- pendently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-al- kyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl and phenyl; and
wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which inde- pendently of one another are selected from:
R78a halogen, OH, CN, C C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa se- lected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl,
Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubstituted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH, CN, C C4-alkyl, C C4-alkoxy, C C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4- alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-CrC6-alkyl, S(0)n- aryl, C C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci- Ce-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3- C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is as defined above;
RY is as defined above;
wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH, CN, d-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or
substituted by groups R9b which independently of one another are selected from:
R9b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from the substituents as defined for R9, wherein the possible substituents for R10 are R10a and R10b , respectively, which correspond to R9a and R9b, respectively;
together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN ; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m, wherein m is 0, 1 , 2, 3 or 4;
is in each case independently selected from halogen, OH, CN, NO2, SH , NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R11 are unsubstituted or substituted with identical or different groups R11a which independently of one another are selected from:
R11a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R11 unsubstituted or substituted with identical or different groups R11 b which independently of one another are selected from:
R11 b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; with the provisio that if A is phenyl,
R1 is H;
and the N-oxides and the agriculturally acceptable salts thereof.
2. The compounds of claim 1 , wherein
R1 is H;
R2 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R2 are unsubstituted or substituted by groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloal- kyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4- halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or substituted by groups R2b which independently of one another are selected from: R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3 is in each case independently selected from CH3, CH2F, CHF2 and CF3;
R4 is Ci-C6-alkyl, which is substituted by a five-, six- or ten-membered heteroaryl, wherein the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S;
wherein the alkyl moieties of R4 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R4a, which independently of one another are selected from:
R4a halogen, OH, CN, N02, SH, NH2, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-halo- genalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogen- alkoxy; and
wherein one or two CH2 groups of alkyl moieties of R4 may be replaced by a group independently selected from C(=0), (=CH2) or form a three- four- five or six-mem- bered carbocyle which han include optionally one O as ring member; and
wherein the heteroaryl moieties of R4 are independently unsubstituted or substituted with identical or different groups R4b, which independently of one another are selected from:
R b halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2,
NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, d-Ce-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx is as defined above;
n is 0, 1 , 2 or
R5 is H;
R6 is H;
A is selected from below group:
Figure imgf000169_0001
Figure imgf000170_0001
wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I . ; wherein
Y is in each case independently selected from H , F, CI , Br, I , OH , CN , NO2, Ci-C6-al- kyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-al- kynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkynyl C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, ORY, S(0)zRY„ N H RY, N (RY)2, C(=0)RY, C(=0)ORY, N H(C(=0) RY, N(C(=0) RY)2, N H-S02-Rx, C(RY)=NO(RY),
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; wherein the phenyl group is unsubstituted or substituted from the group consisting of halogen, CN , OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
z is 0, 1 or 2;
wherein the acyclic moieties of Y are unsubstituted or substituted by groups Ya which independently of one another are selected from:
Ya halogen, OH , CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents RY1a selected from the group consisting of halogen, OH , CN Ci- C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic and phenyl moieties of Y are unsubstituted or substituted by groups Yb which independently of one another are selected from:
Yb halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Ce-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio; is as defined above;
o is 0, 1 , 2 or 3; and
R78 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl,
C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein Rx is defined above; wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-al- kyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl and phenyl; and
wherein the acyclic moieties of R78 are unsubstituted or substituted by R78a which independently of one another are selected from:
R78a halogen, OH, CN, C C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R78aa selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R78 are unsubsti- tuted or substituted by R78b which independently of one another are selected from:
R78b halogen, OH, CN, C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;
R9 is in each case independently selected from H, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-al- kynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-
C4-alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-R*, S(0)n-CrC6-alkyl, S(0)n- aryl, C C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci-
Ce-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3- C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is as defined above;
RY is as defined above;
wherein the acyclic moieties of R9 are unsubstituted or substituted by groups R9a which independently of one another are selected from:
R9a halogen, OH, CN, CrC6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or substituted by groups R9b which independently of one another are selected from:
R9b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R10 is in each case independently selected from the substituents as defined for R9, wherein the possible substituents for R10 are R10a and R10b , respectively, which correspond to R9a and R9b, respectively;
R9, R10 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or heteroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci- C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R11)m, wherein m is 0, 1 , 2, 3 or 4;
R11 is in each case independently selected from halogen, OH, CN, NO2, SH, N H2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R11 are unsubstituted or substituted with identical or different groups R11a which independently of one another are selected from:
R11 a halogen, OH, CN, CrC6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, d-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cy- cloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R11 unsubstituted or substituted with identical or different groups R11b which independently of one another are selected from:
R11 b halogen, OH, CN, C C4-alkyl, C C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;
and the N-oxides and the agriculturally acceptable salts thereof.
3. The compounds of claims 1 to 2, wherein R2 is H, CI, F, Ci-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl wherein the acyclic moieties of R2 are unsubstituted or substituted by halogen.
4. The compounds of claims 1 to 3, R3 is CH3.
5. The compounds of claims 1 to 4, wherein R4 is Ci-alkyl substituted by five-, six- or ten- membered heteroaryl; wherein the heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S.
6. The compounds of claims 1 to 5, wherein Y is H, F, CI, Br, CN, Ci-C4-alkyl, Ci-C4-halo- genalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C6- alkoxy or Ci-C6-halogenalkoxy, wherein the acyclic moieties of Y are unsubstituted or substituted by halogen.
7. The compounds of claims 1 to 6, wherein A is
Figure imgf000173_0001
8. The compounds of any one of claims 1 to 7, wherein R9 and R10 independently are selected from CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6-cy- cloalkyl.
RY is d-Ce-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl or C2-C6-alkynyl.
9. A process for the synthesis of compounds I of claim 1 , comprising the step of:
a) reacting a compound X
Figure imgf000174_0001
10. The intermediate compounds X as defined in claim 9.
1 1 . A composition, comprising one compound of formula I, as defined in any of the claims 1 to 8, an N-oxide or an agriculturally acceptable salt thereof.
12. The composition according to claim 1 1 , comprising additionally a further active substance.
13. A use of a compound of formula I, as defined in any of the claims 1 to 8, and of an agriculturally acceptable salt thereof or of the compositions, as defined in any of the claims 1 1 or 12, for combating phytopathogenic fungi.
14. A method for combating phytopathogenic fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I, as defined in any of the claims 1 to 8 or with a composition, as defined in any of the claims 1 1 or 13.
15. Seed, coated with at least one compound of formula I, as defined in any of the claims 1 to 8, and/or an agriculturally acceptable salt thereof or with a composition, as defined in any of the claims 1 1 or 13, in an amount of from 0.1 to 10 kg per 100 kg of seed.
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