WO2019002158A1 - Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi - Google Patents

Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi Download PDF

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WO2019002158A1
WO2019002158A1 PCT/EP2018/066854 EP2018066854W WO2019002158A1 WO 2019002158 A1 WO2019002158 A1 WO 2019002158A1 EP 2018066854 W EP2018066854 W EP 2018066854W WO 2019002158 A1 WO2019002158 A1 WO 2019002158A1
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ch
ci
phenyl
alkyl
c6
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PCT/EP2018/066854
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French (fr)
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Wassilios Grammenos
Violeta TERTERYAN-SEISER
Jan Klaas Lohmann
Maria Angelica QUINTERO PALOMAR
Marcus Fehr
Tobias MENTZEL
Ian Robert CRAIG
Thomas Grote
Christian Winter
Ana Escribano Cuesta
Michael Seet
Georg Christoph RUDOLF
Bernd Mueller
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Basf Se
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

The present invention relates to trifluoromethyloxadiazoles of the formula I, or the N-oxides, or the agriculturally useful salts thereof, and the use thereof for controlling phytopathogenic fungi; to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi, the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof; and to agrochemical compositions comprising at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, and further comprising seeds.

Description

Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi

The present invention relates to trifluoromethyloxadiazoles of the formula I, or the N-oxides, or the agriculturally useful salts thereof, and the use thereof for controlling phytopathogenic fungi; to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi, the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof; and to agrochemical compositions comprising at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, and further comprising seeds.

Similar 5-trifluoromethyl-1 ,2,4-oxadiazoles are known as fungicides from WO 2017/085098, WO 2017/085100 and WO 2017/093348.

In many cases, in particular at low application rates, the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an objective of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic fungi. Another object of the present invention is to provide fungicides with improved toxicological properties. This objective is achieved by the oxadiazole compounds of the formula I, or the N-oxides, or their agriculturally useful salts for controlling phytopathogenic fungi.

Accordingly, the present invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof,

Figure imgf000002_0001

wherein:

A is phenyl or a 5- or 6-membered aromatic heterocycle; wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the phenyl ring or the aromatic heterocycle is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different groups RA wherein

RA is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or

Ci-C6-haloalkoxy;

W is -C(=0)- or -C(=S)-;

R1 is hydrogen, formyl, Ci-C6-alkyl, Ci-C6-alkoxy, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, C2-C6 alkenyl, C2-C6-alkynyl, Ci-C6-alkoxyimino-Ci-C4-alkyl, C2-C6-alkenyloxyimino-Ci-C4-alkyl, C2-C6-alkynyloxyimino-Ci-C4-alkyl, -C(=0)R2, -C(=0)OR2, -C(=0)NH2, -C(=0)NHR2, -C(=0)N(R2)2, phenyl-Ci-C4-alkyl, phenyl-Ci-C4-alkenyl, phenyl-Ci-C4-alkynyl, heteroaryl- Ci-C4-alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selec- ted from N, O and S as ring member atoms; and wherein the heteroaryl group in the group heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different groups R1a;

or R1 is a bicyclic carbocycle of the formula Ra

Figure imgf000003_0001

wherein

Ca and Cb are bridgehead carbon atoms;

X is a direct single bond or a divalent group selected from the group consisting of - CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-, -CH2-CH=CH-,

-CH=CH-CH2- and -CH=CH-CH=CH-;

Y and Z independently of each other are a divalent group selected from the group

consisting of -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-,

-CH2-CH=CH-, -CH=CH-CH2- and -CH=CH-CH=CH-;

or R1 is a tricyclic carbocycle of the formula Rb

H

Figure imgf000003_0002

wherein

Ca and Cb are bridgehead carbon atoms;

X is a direct single bond or a divalent group selected from the group consisting of - CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-, -CH2-CH=CH-,

-CH=CH-CH2- and -CH=CH-CH=CH-;

Y and Z independently of each other are a divalent group selected from the group

consisting of -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-,

-CH2-CH=CH-, -CH=CH-CH2- and -CH=CH-CH=CH-; and wherein groups Y and Z are attached to the bridgehead carbon atoms Ca and Cb;

T is a divalent group selected from the group consisting of -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-, -CH2-CH=CH-, -CH=CH-CH2- and

-CH=CH-CH=CH-; and wherein the group T is attached to one carbon atom in each of the groups Y and Z;

and with the proviso that, if R1 is a tricyclic carbocycle of the formula Rb, wherein X is a direct single bond or a divalent group -CH2-, the groups T and Z independently of each other are a divalent group selected from the group consisting of -CH2-CH2-, -(CH2)3-, - (CH2)4-, -CH=CH-, -CH2-CH=CH-, -CH=CH-CH2- and -CH=CH-CH=CH-; and wherein the groups Ra or Rb are connected to the the remainder of the compounds of the formula I through one of the ring carbon atoms; and wherein the groups Ra or Rb are unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of radicals selected from the group consisting of oxo, hydroxy, halogen, Ci-C3-alkyl, C1-C3- haloalkyl, C3-C6-cycloalkyl, vinylidene and dichlorovinylidene;

R1a is halogen, oxo, cyano, NO2, OH, SH, NH2, Ci-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy, d-Ce-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, -NHSO2-C1-C4- alkyl, (C=0)-Ci-C4-alkyl, C(=0)-Ci-C4-alkoxy, Ci-C6-alkylsulfonyl, hydroxyCi-C4-alkyl, C(=0)-NH2, C(=0)-NH(Ci-C4-alkyl), Ci-C4-alkylthio-Ci-C4-alkyl, aminoCi-C4-alkyl, C1-C4- alkylamino-Ci-C4-alkyl, diCi-C4-alkylamino-Ci-C4-alkyl, aminocarbonyl-Ci-C4-alkyl or

C1 -C4-a I koxy-C1 -C4-a I ky I ;

R2 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy or C3-C8-cycloalkyl; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, oxo, cyano,

Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, aminoCi-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, diCi-C4- alkylamino-Ci-C4-alkyl or Ci-C4-alkoxy-Ci-C4-alkyl;

m is 0, 1 or 2;

R3, R4 independently of each other are selected from the group consisting of hydrogen,

halogen, cyano, Ci-C4-alkyl, Ci-C4-alkenyl, Ci-C4-alkynyl, Ci-C4-haloalkyl and

Ci-C4-alkoxy; or

R3 and R4 together with the carbon atom to which they are bound form a saturated 3- to

7-membered carbocycle or a saturated 3- to 6-membered heterocycle; wherein the saturated heterocycle includes beside carbon atoms 1 , 2 or 3 heteroatoms independently selected from the group consisiting of N, O and S as ring member atoms; and wherein said N ring member atom is substituted with the group RN; wherein

RN is hydrogen, Ci-C6-alkyl or halogen;

and wherein said S ring member atom is unsubstituted or substituted with 1 or 2 oxo radicals; and wherein one or two CH2 groups of the saturated carbocycle or of the saturated heterocycle may be replaced by one or two groups independently selected from -C(=0)- and -C(=S)-; and wherein the carbon ring member atoms of the saturated carbocycle or of the saturated heterocycle are unsubstituted or substituted with a total number of 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy and Cs-Cs-cycloalkyl.

Agriculturally acceptable salts of the compounds of the formula I 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 the compounds I. 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 be substituted with one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, 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 acceptable 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 a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

Compounds of the formula I can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers arising from restricted rotation about a single bond of asymmetric groups and geometric isomers. They also form part of the subject matter of the present invention. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual

stereoisomers, or as an optically active form.

Compounds of the formula I can be present in different crystal modifications whose biological activity may differ. They also form part of the subject matter of the present invention.

In respect of the variables, the embodiments of the intermediates obtained during preparation of compounds I correspond to the embodiments of the compounds of formula I. The term

"compounds I" refers to compounds of the formula I.

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 "oxo" refers to an oxygen atom =0, which is bound to a carbon atom or sulfur atom, thus forming, for example, a ketonyl -C(=0)- or sulfinyl -S(=0)- group.

The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 - methylpropyl, 2-methylpropyl, and 1 ,1 -dimethylethyl.

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, 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, such as ethynyl, 1 -propynyl, 2-propynyl (propargyl), 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl.

The term "Ci-C6-haloalkyl" refers to a straight-chained or branched alkyl group having 1 to 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, for example chloromethyl,

bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 - fluoroethyl, 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 and pentafluoroethyl, 2- fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3- chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3- trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1 -(fluoromethyl)-2-fluoroethyl, l -(chloromethyl)- 2-chloroethyl, 1 -(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.

The term "Ci-C6-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as defined above) which is bonded via an oxygen, at any position in the alkyl group, for example methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2- methylpropoxy or 1 ,1 -dimethylethoxy.

The term "Ci-C6-haloalkoxy" refers to a Ci-C6-alkoxy group as defined above, wherein some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 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-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH2F)-2-fluoroethoxy, 1 -(CH2CI)-2-chloroethoxy, 1 -(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.

The terms "phenyl-Ci-C4-alkyl or heteroaryl-Ci-C4-alkyl" refer to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a phenyl or hetereoaryl radical respectively.

The term "Ci-C4-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above). Likewise, the term "Ci-C4-alkylthio-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkylthio group.

The term "Ci-C6-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-haloalkylthio" as used herein refers to straight-chain or branched haloalkyi group having 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the haloalkyi group.

The term "Ci-C6-alkylsulfinyl" refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded through a -S(=0)- moiety, at any position in the alkyl group, for example methylsulfinyl and ethylsulfinyl, and the like. Accordingly, the term "C1-C6- haloalkylsulfinyl" refers to straight-chain or branched haloalkyi group having 1 to 6 carbon atoms (as defined above), bonded through a -S(=0)- moiety, at any position in the haloalkyi group. The term "Ci-C6-alkylsulfonyl" refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above), bonded through a -S(=0)2- moiety, at any position in the alkyl group, for example methylsulfonyl. Accordingly, the term "Ci-C6-haloalkylsulfonyl" refers to straight-chain or branched haloalkyi group having 1 to 6 carbon atoms (as defined above), bonded through a -S(=0)2- moiety, at any position in the haloalkyl group.

The term "Ci-C4-alkoxyimino" refers to a divalent imino radical (Ci-C4-alkyl-0-N=) carrying one Ci-C4-alkoxy group as substituent, e.g. methylimino, ethylimino, propylimino,

1 -methylethylimino, butylimino, 1 -methylpropylimino, 2-methylpropylimino, 1 ,1 - dimethylethylimino and the like.

The term "Ci-C6-alkoxyimino-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein two hydrogen atoms of one carbon atom of the alkyl radical are replaced by a divalent C1-C6- alkoxyimino radical (Ci-C6-alkyl-0-N=) as defined above.

The term "C2-C6-alkenyloxyimino-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein two hydrogen atoms of one carbon atom of the alkyl radical are replaced

by a divalent C2-C6-alkenyloxyimino radical (C2-C6-alkenyl-0-N=).

The term "C2-C6-alkynyloxyimino-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein two hydrogen atoms of one carbon atom of the alkyl radical are replaced by a divalent

C2-C6-alkynyloxyimino radical (C2-C6-alkynyl-0-N=).

The term "C3-C8-cycloalkyl-Ci-C6-alkyl" refers to alkyl having 1 to 6 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a Cs-Cs-cycloalkyl group.

The term "hydroxyCi-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a OH group.

The term "aminoCi-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a NH2 group.

The term "Ci-C6-alkylamino" refers to an amino group, which is substituted with one residue independently selected from the group that is defined by the term Ci-C6-alkyl. Likewise the term "diCi-C6-alkylamino" refers to an amino group, which is substituted with two residues independently selected from the group that is defined by the term Ci-C6-alkyl.

The term "Ci-C4-alkylamino-Ci-C4-alkyl" refers to refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkyl-NH- group which is bound through the nitrogen. Likewise the term "diCi-C4-alkylamino-Ci-C4-alkyl" refers to refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a (Ci-C4-alkyl)2N- group which is bound through the nitrogen.

The term "aminocarbonyl-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a -(C=0)-NH2 group.

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, 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, such as ethynyl, 1 -propynyl,

2- propynyl (propargyl), 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl.

The term "Cs-Cs-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

The term "Cs-Cs-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

The terms "C(=0)-Ci-C4-alkyl" or "C(=0)-Ci-C4-alkoxy" refer to a radical which is attached through the carbon atom of the -C(=0)- group as indicated by the number valence of the carbon atom.

The term "formyl" refers to a group -C(=0)H.

The term "aliphatic" refers to compounds or radicals composed of carbon and hydrogen and which are non-aromatic compounds. An "alicyclic" compound or radical is an organic compound that is both aliphatic and cyclic. They contain one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character.

The terms "cyclic moiety" or "cyclic group" refer to a radical which is an alicyclic ring or an aromatic ring, such as, for example, phenyl or heteroaryl.

The term "and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with..." refers to aliphatic groups, cyclic groups and groups, which contain an aliphatic and a cyclic moiety in one group, such as in, for example, C3-C8-cycloalkyl-Ci-C4-alkyl; therefore a group which contains an aliphatic and a cyclic moiety both of these moieties may be substituted or unsubstituted independently of each other.

The term "vinylidene" refers to a group =CH2, the term "dichlorovinylidene" refers to a group =CCI2.

The term "wherein R1 is connected to the group W through one of the ring carbon atoms of the groups Ra or Rb" in the context of this invention means that R1 is attached to the group W through one carbon atom of the groups Ra or Rb, which includes any carbon atom of groups X, Y, Z, T and the bridgehead carbon atoms Ca and Cb, thereby substituting a hydrogen atom on said carbon atom.

The term "phenyl" refers to an aromatic ring systems incuding six carbon atoms (commonly referred to as benzene ring. In association with the group A the term "phenyl" is to be interpreted as a benzene ring or phenylene ring, which is attached to both, the oxadiazole moiety and the -CR3R4- or the tetrazolone ring.

The term "heteroaryl", unless defined otherwise, refers to aromatic monocyclic or polycyclic ring systems incuding besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms.

The term "saturated 3- to 7-membered carbocycle" is to be understood as meaning monocyclic saturated carbocycles having 3, 4 or 5 carbon ring members. Examples include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.

The term "3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms", is to be understood as meaning both, aromatic mono- and bicyclic

heteroaromatic ring systems, and also saturated and partially unsaturated heterocycles, for example:

a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of N, O and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, 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 N, O and S as ring members such as 2-tetrahydro- furanyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,

5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 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- isoxazolin-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- dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol- 4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4- tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl,

2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 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

hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6- tetrahydro[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- oxazepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals.

The term "5- or 6-membered heteroaryl" or the term "5- or 6-membered aromatic heterocycle" refer 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, 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. In respect of the variables, the embodiments of the intermediates correspond to the

embodiments of the compounds I. Preference is given to those compounds I and, where applicable, also to compounds of all subformulae provided herein, e. g. formulae 1.1 , 1.2, 1.1 a, I .A, I.B, I.C, I.D, I.E, I.F, I.G, I.H, I.J, I.K, I.L and I.M, wherein the variables A, RA, W, R , R a, R2, Ra, Rb, X, Y, Z, T, m, R3 and R4 have independently of each other or more preferably in combination (any possible combination of 2 or more substituents as defined herein) the following meanings:

In one aspect of the invention group A is phenyl which is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different groups RA as defined or preferably defined herein and wherein the group -CR3R4- or the tetrazolone ring is attached to the phenyl ring in para-pos\t\on with regard to the oxadiazole group.

In one aspect of the invention A is phenyl which is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different groups RA as defined or preferably defined herein and wherein the group -CR3R4- or the tetrazolone ring is attached to the phenyl ring in /^e s-position with regard to the oxadiazole group.

In a further aspect of the invention A is phenyl which is substituted with 1 or 2 identical or different groups RA as defined or preferably defined herein and wherein the group -CR3R4- or the tetrazolone ring is attached to the phenyl ring in para-pos\t\on with regard to the oxadiazole group.

oxadiazole In one embodiment A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted with 1 or 2 identical or different groups RA as defined or preferably defined herein; particularly RA is chlorine, fluorine or methyl.

In a further embodiment A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted with 1 or 2 identical or different groups RA as defined or preferably defined herein; particularly RA is chlorine, fluorine or methyl; and wherein the group -CR3R4- or the tetrazolone ring is attached to the 6-membered aromatic heterocycle in para-pos\t\on with regard to the oxadiazole group. In a further preferred embodiment A is a 5-membered aromatic heterocycle, in particular a thiophene ring, more particularly a 2,5-thiophenyl ring, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted with 1 or 2 identical or different groups RA as defined or preferably defined herein; particularly RA is chlorine, fluorine or methyl. In one embodiment the invention relates to compounds of the formula I, wherein the moiety A is defined as in subformulae (A.1 ) to (A.30),

Figure imgf000011_0001

(A.1 ) (A.2) (A3) (A4) (A5)

Figure imgf000011_0002

(A.6) (A.7) (A8) (A9) (A 10)

Figure imgf000011_0003

(A1 1 ) (A12) (A13) (A14) (A15)

Figure imgf000011_0004

(A 16) (A 17) (A 18) (A 19) (A20)

Figure imgf000011_0005

(A.21 ) (A.22) (A.23) (A.24) (A.25)

Figure imgf000011_0006

(A.26) (A.27) (A.28) (A.29) (A.30) wherein #1 denotes the position which is bound to the oxadiazole moiety and #2 denotes the position, which is connected to the group -CR3R4- or the tetrazolone ring of compounds of the formula I; and wherein A is unsubstituted or substituted with 1 or 2 identical or different groups RA and wherein RA is as defined or preferably defined herein. In another embodiment A as defined in any one of subformulae (A.1 ) to (A.30) is unsubstituted or substituted with 1 or 2 identical or different groups RA; and wherein RA is chlorine, fluorine or methyl. In a preferred embodiment A as defined in any one of subformulae (A.1 ) to (A.30) is unsubstituted.

In a preferred embodiment RA is independently selected from the group consisting of halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl. In another preferred embodiment RA is independently selected from the group consisting of halogen, methyl or ethyl. More preferably RA is independently selected from the group consisting of halogen, in particular RA is fluorine.

Further embodiments with regard to the meaning of radical R1 are as follows:

Embodiment 1 .1 : R1 is hydrogen, formyl, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl,

Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are

unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl,

Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl.

Embodiment 1 .2: R1 is hydrogen, methyl, ethyl, /7-propyl, /so-propyl, /7-butyl, /so-butyl, sec-butyl, fe/7-butyl or cyclopropyl

Embodiment 1.3: R1 is hydrogen.

Embodiment 1.4: R1 is formyl.

Embodiment 1.5: R1 is Ci-C6-alkoxy.

Embodiment 1 .6: R1 is -C(=0)R2 or-C(=0)OR2; wherein R2 is hydrogen, d-Ce-alkyl or Cs-Cs- cycloalkyl; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, oxo, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl; preferably from the group consisting of halogen, Ci-C6-alkyl and Cs-Cs-cycloalkyl.

Embodiment 1 .7: R1 is -C(=0)NH2, -C(=0)NHR2 or -C(=0)N(R2)2, wherein R2 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy or Cs-Cs-cycloalkyl; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, oxo, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl,

Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl, preferably from the group consisting of halogen, Ci-C6-alkyl and Cs-Cs-cycloalkyl.

Embodiment 1 .8: R1 is phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6- membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl .

Embodiment 1 .9: R1 is Cs-Cs-cycloalkyl or Cs-Cs-cycloalkenyl; and wherein the cyclic group is unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl,

Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl .

Embodiment 1 .10: R1 is Ci-C6-alkyl; and wherein the alkyl group is unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl .

Embodiment 1 .1 1 : R1 is difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 3,3,3- trifluoropropyl, CH2CF2CF3 or CF2CF2CF5, CH(CH3)CF3, CH2CF2CH3, CH2C(CH3)2F,

CH2CH(CH3)CF3 or CH2C(CH3)2CF3.

Embodiment 1 .12: R1 is Ci-C6-alkoxyimino-Ci-C4-alkyl, C2-C6-alkenyloxyimino-Ci-C4-alkyl or C2-C6-a I ky ny loxy i m i n 0-C1 -C4-a I ky I .

Embodiment 1 .13: R1 is a bicyclic carbocycle ula Ra

Figure imgf000013_0001

H'

wherein

Ca and Cb are bridgehead carbon atoms;

X is a direct single bond or a divalent group selected from the group consisting of -CH2- and -CH2-CH2-;

Y and Z independently of each other are a divalent group selected from the group consisting of - CH2- and -CH2-CH2-;

and wherein Ra is connected to the remainder of the compounds of formula I through one of the ring carbon atoms; and wherein Ra is unsubstituted or substituted with 1 or 2 radicals selected from the group consisting of oxo, hydroxy, halogen, Ci-C3-alkyl. bodiment 1 .14: R1 is a tricyclic carbocycle of the formula Rb

H

Figure imgf000013_0002

wherein

Ca and Cb are bridgehead carbon atoms;

X is a direct single bond or a divalent group selected from the group consisting of -CH2- and -CH2-CH2-;

Y and Z independently of each other are a divalent group selected from the group consisting of - CH2- and -CH2-CH2-; and wherein groups Y and Z are attached to the bridgehead carbon atoms Ca and Cb;

T is a divalent group selected from the group consisting of -CH2- and -CH2-CH2-; and

wherein the group T is attached to one carbon atom in each of the groups Y and Z;

and with the proviso that, if X is a direct single bond or a divalent group -CH2-, the groups T and Z independently of each other are a divalent group -CH2-CH2-;

and wherein Rb is connected to the remainder of the compounds of formula I through one of the ring carbon atoms; and wherein Rb is unsubstituted or substituted with 1 or 2 radicals selected from the group consisting of oxo, hydroxy, halogen, Ci-C3-alkyl.

Embodiment 1 .15: R1 is a bicyclic or tricyclic carbocycle selected from the group consisting of radicals R1.1 to R1.31 below; wherein each radical may be connected to the remainder of the compounds of formula I through one of the ring carbon atoms by substitution of one hydrogen atom; and wherein R1 is unsubstituted or substituted with 1 or 2 radicals selected from the group consisting of oxo, hydroxy, halogen and Ci-C3-alkyl.

Figure imgf000014_0001

R .7 R .8 R .9 R .10 R1.11 R .12

Figure imgf000014_0002

R1.25 R1.26 R1.27 R1.28 R1.29 R1.30 R1.31 bodiment 1 .16: R1 is selected from the group consisting of R1.32 to R1.57 below, particularly from R1.32 to R1.49, which are further unsubstituted, and wherein "#C" indicates the carbon ato

Figure imgf000015_0001

1.32 R1.33 R1.34 R1.35 R1.36 R1.37 R1.38

Figure imgf000015_0002

R1.52

Figure imgf000015_0003

R1.53 R1.54 R1.55 R1.56 R1.57

In one embodiment R1a is selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl.

In another aspect of the invention R1a is selected from the group consisting of fluorine, chlorine, cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy or cyclopropyl.

In a preferred aspect of the invention R1a is selected from the group consisting of halogen, Ci-C6-alkyl and Cs-Cs-cycloalkyl; particularly from methyl, ethyl, fluorine and chlorine; more particularly from fluorine and chlorine.

In one embodiment R2 is independently selected from the group consisting of hydrogen,

Ci-C6-alkyl, Ci-C6-alkoxy or Cs-Cs-cycloalkyl; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, oxo, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl.

In one embodiment R2 is independently selected from the group consisting of hydrogen,

Ci-C6-alkyl, Ci-C6-alkoxy or Cs-Cs-cycloalkyl; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen,

Ci-C6-alkyl and Cs-Cs-cycloalkyl.

In one aspect of the invention m is 0 or 1 , in particular m is 0. In another aspect of the invention m is 1 or 2. In a further aspect of the invention m is 1 . In yet another embodiment m is 2.

In one aspect of the invention m is 1 and radicals R3 and R4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl or trifluoromethyl; or R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring.

Further embodiments with regard to the meaning of radicals R3 and R4 are as follows:

Embodiment 3.1 : R3 and R4 independently of each other are hydrogen, halogen, Ci-C6-alkyl or Ci-C6-haloalkyl; or R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring, wherein the cyclopropyl ring is unsubstituted.

Embodiment 3.2: R3 and R4 independently of each other are hydrogen or Ci-C4-alkyl;

Embodiment 3.3: R3 and R4 independently of each other are hydrogen, methyl or ethyl.

Embodiment 3.4: R3 and R4 are independently of each other hydrogen, fluorine, chlorine, methyl or trifluoromethyl; or R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring, wherein the cyclopropyl ring is unsubstituted.

Embodiment 3.5: R3 and R4 are both hydrogen.

Embodiment 3.6: R3 is hydrogen and R4 is methyl.

Embodiment 3.7: R3 and R4 are both methyl.

Embodiment 3.8: R3 and R4 are both fluorine.

Embodiment 3.9: R3 and R4 are both trifluoromethyl.

Embodiment 3.10: R3 and R4 together with the carbon atom to which they are bound form a saturated monocyclic 3- to 5-membered saturated heterocycle or saturated carbocycle; and wherein the saturated heterocycle includes beside one or more carbon atoms no heteroatoms or 1 or 2 heteroatoms independently selected from N, O and S as ring member atoms; and wherein the heterocycle or the carbocycle is unsubstituted or substituted 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano and Ci-C2-alkyl.

Embodiment 3.1 1 : R3 and R4 together with the carbon atom to which they are bound form a 3- or 4-membered carbocylic ring; and wherein the carbocylic ring is unsubstituted.

Embodiment 3.12: R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring, wherein the cyclopropyl ring is unsubstituted.

Embodiment 3.13: R3 and R4 together with the carbon atom to which they are bound form a saturated 3-membered heterocycle; wherein the heterocycle includes beside two carbon atoms one heteroatom selected from N, O and S as ring member atoms; and wherein the heterocycle is unsubstituted or substituted 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano and Ci-C2-alkyl.

Embodiment 3.14: R3 is methyl and R4 is fluorine. Embodiment 3.15: the moiety -(CR3R4)m- in compounds I is selected from the group consisting of the divalent groups -CH2-, -CH2CH2-, #-CH(CH3)-CH2-, #-C(CH3)2-CH2-, #-CH2-CH(CH3)- and #-CH2-C(CH3)2-, wherein # denotes the position, which is bound to group A in compounds I. Embodiment 3.16: R3 is hydrogen and R4 is trifluoromethyl.

In one aspect of the present invention the group W is -C(=0)-. In another aspect W is -C(=S)-.

In further aspects of the present invention the embodiments E.1 to E.288 listed in Table E represent preferred combinations of the embodiments, which are defined above for each of the variables m, R3, R4, W and R1.

Table E:

Embodi Embodi Embodi Embodi Embodi Embodi ment ment ment ment ment ment

m R3, R4 W R1 m R3, R4 W R1

E.1 0 - -C(=0)- 1.1 E.32 1 3.1 -C(=0)- 1.16

E.2 0 - -C(=0)- 1.2 E.33 1 3.4 -C(=0)- 1.1

E.3 0 - -C(=0)- 1.3 E.34 1 3.4 -C(=0)- 1.2

E.4 0 - -C(=0)- 1.4 E.35 1 3.4 -C(=0)- 1.3

E.5 0 - -C(=0)- 1.5 E.36 1 3.4 -C(=0)- 1.4

E.6 0 - -C(=0)- 1.6 E.37 1 3.4 -C(=0)- 1.5

E.7 0 - -C(=0)- 1.7 E.38 1 3.4 -C(=0)- 1.6

E.8 0 - -C(=0)- 1.8 E.39 1 3.4 -C(=0)- 1.7

E.9 0 - -C(=0)- 1.9 E.40 1 3.4 -C(=0)- 1.8

E.10 0 - -C(=0)- 1.10 E.41 1 3.4 -C(=0)- 1.9

E.11 0 - -C(=0)- 1.11 E.42 1 3.4 -C(=0)- 1.10

E.12 0 - -C(=0)- 1.12 E.43 1 3.4 -C(=0)- 1.11

E.13 0 - -C(=0)- 1.13 E.44 1 3.4 -C(=0)- 1.12

E.14 0 - -C(=0)- 1.14 E.45 1 3.4 -C(=0)- 1.13

E.15 0 - -C(=0)- 1.15 E.46 1 3.4 -C(=0)- 1.14

E.16 0 - -C(=0)- 1.16 E.47 1 3.4 -C(=0)- 1.15

E.17 1 3.1 -C(=0)- 1.1 E.48 1 3.4 -C(=0)- 1.16

E.18 1 3.1 -C(=0)- 1.2 E.49 1 3.5 -C(=0)- 1.1

E.19 1 3.1 -C(=0)- 1.3 E.50 1 3.5 -C(=0)- 1.2

E.20 1 3.1 -C(=0)- 1.4 E.51 1 3.5 -C(=0)- 1.3

E.21 1 3.1 -C(=0)- 1.5 E.52 1 3.5 -C(=0)- 1.4

E.22 1 3.1 -C(=0)- 1.6 E.53 1 3.5 -C(=0)- 1.5

E.23 1 3.1 -C(=0)- 1.7 E.54 1 3.5 -C(=0)- 1.6

E.24 1 3.1 -C(=0)- 1.8 E.55 1 3.5 -C(=0)- 1.7

E.25 1 3.1 -C(=0)- 1.9 E.56 1 3.5 -C(=0)- 1.8

E.26 1 3.1 -C(=0)- 1.10 E.57 1 3.5 -C(=0)- 1.9

E.27 1 3.1 -C(=0)- 1.11 E.58 1 3.5 -C(=0)- 1.10

E.28 1 3.1 -C(=0)- 1.12 E.59 1 3.5 -C(=0)- 1.11

E.29 1 3.1 -C(=0)- 1.13 E.60 1 3.5 -C(=0)- 1.12

E.30 1 3.1 -C(=0)- 1.14 E.61 1 3.5 -C(=0)- 1.13

E.31 1 3.1 -C(=0)- 1.15 E.62 1 3.5 -C(=0)- 1.14 Embodi Embodi Embodi Embodi Embodi Embodi ment ment ment ment ment ment m R3, R4 W R1 m R3, R4 W R1

E.63 1 3.5 -C(=0)- 1.15 E.106 1 3.8 -C(=0)- 1.10

E.64 1 3.5 -C(=0)- 1.16 E.107 1 3.8 -C(=0)- 1.11

E.65 1 3.6 -C(=0)- 1.1 E.108 1 3.8 -C(=0)- 1.12

E.66 1 3.6 -C(=0)- 1.2 E.109 1 3.8 -C(=0)- 1.13

E.67 1 3.6 -C(=0)- 1.3 E.110 1 3.8 -C(=0)- 1.14

E.68 1 3.6 -C(=0)- 1.4 E.111 1 3.8 -C(=0)- 1.15

E.69 1 3.6 -C(=0)- 1.5 E.112 1 3.8 -C(=0)- 1.16

E.70 1 3.6 -C(=0)- 1.6 E.113 1 3.12 -C(=0)- 1.1

E.71 1 3.6 -C(=0)- 1.7 E.114 1 3.12 -C(=0)- 1.2

E.72 1 3.6 -C(=0)- 1.8 E.115 1 3.12 -C(=0)- 1.3

E.73 1 3.6 -C(=0)- 1.9 E.116 1 3.12 -C(=0)- 1.4

E.74 1 3.6 -C(=0)- 1.10 E.117 1 3.12 -C(=0)- 1.5

E.75 1 3.6 -C(=0)- 1.11 E.118 1 3.12 -C(=0)- 1.6

E.76 1 3.6 -C(=0)- 1.12 E.119 1 3.12 -C(=0)- 1.7

E.77 1 3.6 -C(=0)- 1.13 E.120 1 3.12 -C(=0)- 1.8

E.78 1 3.6 -C(=0)- 1.14 E.121 1 3.12 -C(=0)- 1.9

E.79 1 3.6 -C(=0)- 1.15 E.122 1 3.12 -C(=0)- 1.10

E.80 1 3.6 -C(=0)- 1.16 E.123 1 3.12 -C(=0)- 1.11

E.81 1 3.7 -C(=0)- 1.1 E.124 1 3.12 -C(=0)- 1.12

E.82 1 3.7 -C(=0)- 1.2 E.125 1 3.12 -C(=0)- 1.13

E.83 1 3.7 -C(=0)- 1.3 E.126 1 3.12 -C(=0)- 1.14

E.84 1 3.7 -C(=0)- 1.4 E.127 1 3.12 -C(=0)- 1.15

E.85 1 3.7 -C(=0)- 1.5 E.128 1 3.12 -C(=0)- 1.16

E.86 1 3.7 -C(=0)- 1.6 E.129 1 3.15 -C(=0)- 1.1

E.87 1 3.7 -C(=0)- 1.7 E.130 1 3.15 -C(=0)- 1.2

E.88 1 3.7 -C(=0)- 1.8 E.131 1 3.15 -C(=0)- 1.3

E.89 1 3.7 -C(=0)- 1.9 E.132 1 3.15 -C(=0)- 1.4

E.90 1 3.7 -C(=0)- 1.10 E.133 1 3.15 -C(=0)- 1.5

E.91 1 3.7 -C(=0)- 1.11 E.134 1 3.15 -C(=0)- 1.6

E.92 1 3.7 -C(=0)- 1.12 E.135 1 3.15 -C(=0)- 1.7

E.93 1 3.7 -C(=0)- 1.13 E.136 1 3.15 -C(=0)- 1.8

E.94 1 3.7 -C(=0)- 1.14 E.137 1 3.15 -C(=0)- 1.9

E.95 1 3.7 -C(=0)- 1.15 E.138 1 3.15 -C(=0)- 1.10

E.96 1 3.7 -C(=0)- 1.16 E.139 1 3.15 -C(=0)- 1.11

E.97 1 3.8 -C(=0)- 1.1 E.140 1 3.15 -C(=0)- 1.12

E.98 1 3.8 -C(=0)- 1.2 E.141 1 3.15 -C(=0)- 1.13

E.99 1 3.8 -C(=0)- 1.3 E.142 1 3.15 -C(=0)- 1.14

E.100 1 3.8 -C(=0)- 1.4 E.143 1 3.15 -C(=0)- 1.15

E.101 1 3.8 -C(=0)- 1.5 E.144 1 3.15 -C(=0)- 1.16

E.102 1 3.8 -C(=0)- 1.6 E.145 0 - -C(=S)- 1.1

E.103 1 3.8 -C(=0)- 1.7 E.146 0 - -C(=S)- 1.2

E.104 1 3.8 -C(=0)- 1.8 E.147 0 - -C(=S)- 1.3

E.105 1 3.8 -C(=0)- 1.9 E.148 0 - -C(=S)- 1.4 Embodi Embodi Embodi Embodi Embodi Embodi ment ment ment ment ment ment m R3, R4 W R1 m R3, R4 W R1

E.149 0 - -C(=S)- 1.5 E.192 1 3.4 -C(=S)- 1.16

E.150 0 - -C(=S)- 1.6 E.193 1 3.5 -C(=S)- 1.1

E.151 0 - -C(=S)- 1.7 E.194 1 3.5 -C(=S)- 1.2

E.152 0 - -C(=S)- 1.8 E.195 1 3.5 -C(=S)- 1.3

E.153 0 - -C(=S)- 1.9 E.196 1 3.5 -C(=S)- 1.4

E.154 0 - -C(=S)- 1.10 E.197 1 3.5 -C(=S)- 1.5

E.155 0 - -C(=S)- 1.11 E.198 1 3.5 -C(=S)- 1.6

E.156 0 - -C(=S)- 1.12 E.199 1 3.5 -C(=S)- 1.7

E.157 0 - -C(=S)- 1.13 E.200 1 3.5 -C(=S)- 1.8

E.158 0 - -C(=S)- 1.14 E.201 1 3.5 -C(=S)- 1.9

E.159 0 - -C(=S)- 1.15 E.202 1 3.5 -C(=S)- 1.10

E.160 0 - -C(=S)- 1.16 E.203 1 3.5 -C(=S)- 1.11

E.161 1 3.1 -C(=S)- 1.1 E.204 1 3.5 -C(=S)- 1.12

E.162 1 3.1 -C(=S)- 1.2 E.205 1 3.5 -C(=S)- 1.13

E.163 1 3.1 -C(=S)- 1.3 E.206 1 3.5 -C(=S)- 1.14

E.164 1 3.1 -C(=S)- 1.4 E.207 1 3.5 -C(=S)- 1.15

E.165 1 3.1 -C(=S)- 1.5 E.208 1 3.5 -C(=S)- 1.16

E.166 1 3.1 -C(=S)- 1.6 E.209 1 3.6 -C(=S)- 1.1

E.167 1 3.1 -C(=S)- 1.7 E.210 1 3.6 -C(=S)- 1.2

E.168 1 3.1 -C(=S)- 1.8 E.211 1 3.6 -C(=S)- 1.3

E.169 1 3.1 -C(=S)- 1.9 E.212 1 3.6 -C(=S)- 1.4

E.170 1 3.1 -C(=S)- 1.10 E.213 1 3.6 -C(=S)- 1.5

E.171 1 3.1 -C(=S)- 1.11 E.214 1 3.6 -C(=S)- 1.6

E.172 1 3.1 -C(=S)- 1.12 E.215 1 3.6 -C(=S)- 1.7

E.173 1 3.1 -C(=S)- 1.13 E.216 1 3.6 -C(=S)- 1.8

E.174 1 3.1 -C(=S)- 1.14 E.217 1 3.6 -C(=S)- 1.9

E.175 1 3.1 -C(=S)- 1.15 E.218 1 3.6 -C(=S)- 1.10

E.176 1 3.1 -C(=S)- 1.16 E.219 1 3.6 -C(=S)- 1.11

E.177 1 3.4 -C(=S)- 1.1 E.220 1 3.6 -C(=S)- 1.12

E.178 1 3.4 -C(=S)- 1.2 E.221 1 3.6 -C(=S)- 1.13

E.179 1 3.4 -C(=S)- 1.3 E.222 1 3.6 -C(=S)- 1.14

E.180 1 3.4 -C(=S)- 1.4 E.223 1 3.6 -C(=S)- 1.15

E.181 1 3.4 -C(=S)- 1.5 E.224 1 3.6 -C(=S)- 1.16

E.182 1 3.4 -C(=S)- 1.6 E.225 1 3.7 -C(=S)- 1.1

E.183 1 3.4 -C(=S)- 1.7 E.226 1 3.7 -C(=S)- 1.2

E.184 1 3.4 -C(=S)- 1.8 E.227 1 3.7 -C(=S)- 1.3

E.185 1 3.4 -C(=S)- 1.9 E.228 1 3.7 -C(=S)- 1.4

E.186 1 3.4 -C(=S)- 1.10 E.229 1 3.7 -C(=S)- 1.5

E.187 1 3.4 -C(=S)- 1.11 E.230 1 3.7 -C(=S)- 1.6

E.188 1 3.4 -C(=S)- 1.12 E.231 1 3.7 -C(=S)- 1.7

E.189 1 3.4 -C(=S)- 1.13 E.232 1 3.7 -C(=S)- 1.8

E.190 1 3.4 -C(=S)- 1.14 E.233 1 3.7 -C(=S)- 1.9

E.191 1 3.4 -C(=S)- 1.15 E.234 1 3.7 -C(=S)- 1.10 Embodi Embodi Embodi Embodi Embodi Embodi ment ment ment ment ment ment m R3, R4 W R1 m R3, R4 W R1

E.235 1 3.7 -C(=S)- 1.11 E.262 1 3.12 -C(=S)- 1.6

E.236 1 3.7 -C(=S)- 1.12 E.263 1 3.12 -C(=S)- 1.7

E.237 1 3.7 -C(=S)- 1.13 E.264 1 3.12 -C(=S)- 1.8

E.238 1 3.7 -C(=S)- 1.14 E.265 1 3.12 -C(=S)- 1.9

E.239 1 3.7 -C(=S)- 1.15 E.266 1 3.12 -C(=S)- 1.10

E.240 1 3.7 -C(=S)- 1.16 E.267 1 3.12 -C(=S)- 1.11

E.241 1 3.8 -C(=S)- 1.1 E.268 1 3.12 -C(=S)- 1.12

E.242 1 3.8 -C(=S)- 1.2 E.269 1 3.12 -C(=S)- 1.13

E.243 1 3.8 -C(=S)- 1.3 E.270 1 3.12 -C(=S)- 1.14

E.244 1 3.8 -C(=S)- 1.4 E.271 1 3.12 -C(=S)- 1.15

E.245 1 3.8 -C(=S)- 1.5 E.272 1 3.12 -C(=S)- 1.16

E.246 1 3.8 -C(=S)- 1.6 E.273 1 3.15 -C(=S)- 1.1

E.247 1 3.8 -C(=S)- 1.7 E.274 1 3.15 -C(=S)- 1.2

E.248 1 3.8 -C(=S)- 1.8 E.275 1 3.15 -C(=S)- 1.3

E.249 1 3.8 -C(=S)- 1.9 E.276 1 3.15 -C(=S)- 1.4

E.250 1 3.8 -C(=S)- 1.10 E.277 1 3.15 -C(=S)- 1.5

E.251 1 3.8 -C(=S)- 1.11 E.278 1 3.15 -C(=S)- 1.6

E.252 1 3.8 -C(=S)- 1.12 E.279 1 3.15 -C(=S)- 1.7

E.253 1 3.8 -C(=S)- 1.13 E.280 1 3.15 -C(=S)- 1.8

E.254 1 3.8 -C(=S)- 1.14 E.281 1 3.15 -C(=S)- 1.9

E.255 1 3.8 -C(=S)- 1.15 E.282 1 3.15 -C(=S)- 1.10

E.256 1 3.8 -C(=S)- 1.16 E.283 1 3.15 -C(=S)- 1.11

E.257 1 3.12 -C(=S)- 1.1 E.284 1 3.15 -C(=S)- 1.12

E.258 1 3.12 -C(=S)- 1.2 E.285 1 3.15 -C(=S)- 1.13

E.259 1 3.12 -C(=S)- 1.3 E.286 1 3.15 -C(=S)- 1.14

E.260 1 3.12 -C(=S)- 1.4 E.287 1 3.15 -C(=S)- 1.15

E.261 1 3.12 -C(=S)- 1.5 E.288 1 3.15 -C(=S)- 1.16

In one embodiment the invention relates to compounds of the formula 1.1 or to compounds of the formula 1.2, or the N-oxides, or the agriculturally acceptable salts thereof,

Figure imgf000020_0001
wherein n is 0, 1 or 2; and wherein the meaning of the variables W, R3, R4, m and R1 are as defined herein for compounds of the formula I or as preferably defined in embodiments E.1 to E.288 in Table E; and wherein RA is as defined or preferably defined herein for compounds of the formula I.

A preferred embodiment relates to compounds of the formula 1.1 or to compounds of the formula 1.2 as defined above, wherein the meaning of the variables W, R3, R4, m and R1 are as defined herein for compounds of the formula I or as preferably defined in embodiments E.1 to E.288 in Table E; and wherein n is 0 or 1 and RA is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl; in particular fluorine.

In a further embodiment the invention relates to compounds 1.1 , wherein n is 0; m is 1 ; and wherein R3 and R4 are fluorine; or R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring; and wherein the meaning of the variables W, and R1 are as defined or preferably defined herein for compounds of the formula I.

In a further embodiment the invention relates to compounds 1.1 , wherein n is 0; m is 1 ; and wherein R3 and R4 are hydrogen; or R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring; and wherein the meaning of the variables W, and R1 are as defined or preferably defined herein for compounds of the formula I.

In a further embodiment the invention relates to compounds 1.1 , wherein n is 0; m is 1 ; and wherein R3 and R4 are independently selected from the group consisting of hydrogen or methyl; or R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring; and wherein the meaning of the variables W, and R1 are as defined or preferably defined herein for compounds of the formula I.

In a further embodiment the invention relates to the group of compounds 1.1 a of the formula 1.1 , or the N-oxides, or the agriculturally acceptable salts thereof, wherein:

RA is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl;

n is O or l ;

W is -C(=0)-;

R1 is as defined herein for compounds of the formula I, or as preferably defined in any one of Embodiments 1.1 to 1 .16;

m is 0, 1 or 2;

R3 and R4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl or trifluoromethyl; or

R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring.

In a further embodiment the invention relates to the group of compounds 1.1 b of the formula 1.1 , or the N-oxides, or the agriculturally acceptable salts thereof, wherein:

n is 0;

W is -C(=0)-;

R1 is as defined herein for compounds of the formula I, or as preferably defined in any one of Embodiments 1 .1 to 1 .16;

m is 1 ; R3 and R4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl or trifluoromethyl; in particular both R3 and R4 are hydrogen.

In a further embodiment the invention relates to the group of compounds 1.1 b, or the N-oxides, or the agriculturally acceptable salts thereof, wherein R1 is hydrogen or Ci-C6-alkyl; and wherein the alkyl group is unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl; in particular R1 is hydrogen, methyl, ethyl, /7-propyl, /so-propyl, /7-butyl, /so-butyl, sec-butyl or fe/7-butyl.

In one embodiment, the present invention relates to compounds of the formulae I.A, I.B, I.C, I.D, I.E, I.F, I.G, I.H, I.J, I.K, I.L and I.M and to their use for controlling phytopathogenic fungi, wherein the radical R1 is as defined or preferably defined herein.

Figure imgf000022_0001

I.J I.K

Figure imgf000023_0001

Preference is given to compounds of the formula I, which are compiled in Tables 1 to 12 below, and which may be used according to the invention.

Table 1 : Compounds of the formula I. A, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.A.A-1 to I.A.A-452). This means, for example, that a compound of formula I. A, wherein R1 is /so-propyl (corresponding to the definition A-4 in Table A) is named I.A.A-4.

Table 2: Compounds of the formula I.B, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.B.A-1 to I.B.A-452).

Table 3: Compounds of the formula I.C, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.C.A-1 to I.C.A-452)

Table 4: Compounds of the formula I.D, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.D.A-1 to I.D.A-452).

Table 5: Compounds of the formula I.E, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.E.A-1 to I.E.A-452).

Table 6: Compounds of the formula I.F, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.F.A-1 to I.F.A-452).

Table 7: Compounds of the formula I.G, in which R1 for each individual compound corresponds in each case toone line A-1 to A-452 of Table A (compounds I.G.A-1 to I.G.A-452).

Table 8: Compounds of the formula I.H, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.H. A-1 to I.H.A-452)

Table 9: Compounds of the formula I.J, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.J .A-1 to I.J.A-452).

Table 10: Compounds of the formula I.K, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.K.A-1 to I.K.A-452).

Table 1 1 : Compounds of the formula I.L, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.L.A-1 to I.L.A-452).

Table 12: Compounds of the formula I.M, in which R1 for each individual compound corresponds in each case to one line A-1 to A-452 of Table A (compounds I.M.A-1 to I.M.A-452).

Table A:

No. R1 No. R1

A-1 CHs A-9 C(CH3)3

A-2 CH2CH3 A-10 difluoromethyl

A-3 CH2CH2CH3 A-1 1 trifluoromethyl

A-4 CH(CH3)2 A-12 2,2-difluoroethyl

A-5 CH2CH2CH2CH3 A-13 2,2,2-trifluoroethyl

A-6 CH(CH3)CH2CH3 A-14 2-chloro-2-fluoroethyl

A-7 CH2CH(CH3)CH3 A-15 2-chloro-2,2-difluoroethyl

A-8 CH(CH2CH3)2 A-16 2,2,2-trichloroethyl No. R1 No. R1

A-17 pentafluoroethyl A-57 -C( =0)OCH2CH2CH2CH3

A-18 3,3,3-trifluoropropyl A-58 -C( =0)OCH(CH3)CH2CH3

A-19 CH2CF2CF3 A-59 -C( =0)OCH2CH(CH3)CH3

A-20 CF2CF2CF3 A-60 -C( =0)OCH(CH2CH3)2

A-21 CH(CH3)CF3 A-61 -C( =0)OC(CH3)3

A-22 CH2CF2CH3 A-62 -C( =0)OCHF2

A-23 CH2C(CH3)2F A-63 -C( =0)OCF3

A-24 CH2CH(CH3)CF3 A-64 -C( =0)0-cyclopropyl

A-25 CH2C(CH3)2CF3 A-65 -C( =0)0(1 -methyl-cyclopropyl)

A-26 formyl A-66 -C( =0)0-cyclobutyl

A-27 -C(=0)CH3 A-67 -C( =0)0-cylopentyl

A-28 -C(=0)CH2CH3 A-68 -C( =0)0-cyclohexyl

A-29 -C(=0)CH2CH2CH3 A-69 -C( =0)0-phenyl

A-30 -C(=0)CH(CH3)2 A-70 -C( =0)0(2-F-phenyl)

A-31 -C(=0)CH2CH2CH2CH3 A-71 -C( =0)0(3-F-phenyl)

A-32 -C(=0)CH(CH3)CH2CH3 A-72 -C( =0)0(4-F-phenyl)

A-33 -C(=0)CH2CH(CH3)CH3 A-73 -C( =0)0(2-CI-phenyl)

A-34 -C(=0)CH(CH2CH3)2 A-74 -C( =0)0(3-CI-phenyl)

A-35 -C(=0)C(CH3)3 A-75 -C( =0)0(4-CI-phenyl)

A-36 -C(=0)CHF2 A-76 -C( =0)0(2-methyl-phenyl)

A-37 -C(=0)CF3 A-77 -C( =0)0(3-methyl-phenyl)

A-38 -C(=0)-cyclopropyl A-78 -C( =0)0(4-methyl-phenyl)

A-39 -C(=0)(1 -methyl-cyclopropyl) A-79 -C( =0)NHCH3

A-40 -C(=0)-cyclobutyl A-80 -C( =0)NHCH2CH3

A-41 -C(=0)-cylopentyl A-81 -C( =0)NHCH2CH2CH3

A-42 -C(=0)-cyclohexyl A-82 -C( =0)NHCH(CH3)2

A-43 -C(=0)-phenyl A-83 -C( =0)NHCH2CH2CH2CH3

A-44 -C(=0)(2-F-phenyl) A-84 -C( =0)NHCH(CH3)CH2CH3

A-45 -C(=0)(3-F-phenyl) A-85 -C( =0)NHCH2CH(CH3)CH3

A-46 -C(=0)(4-F-phenyl) A-86 -C( =0)NHCH(CH2CH3)2

A-47 -C(=0)(2-CI-phenyl) A-87 -C( =0)NHC(CH3)3

A-48 -C(=0)(3-CI-phenyl) A-88 -C( =0)NHCHF2

A-49 -C(=0)(4-CI-phenyl) A-89 -C( =0)NHCF3

A-50 -C(=0)(2-methyl-phenyl) A-90 -C( =0)NH-cyclopropyl

A-51 -C(=0)(3-methyl-phenyl) A-91 -C( =0)NH(1 -methyl-cyclopropyl)

A-52 -C(=0)(4-methyl-phenyl) A-92 -C( =0)NH-cyclobutyl

A-53 -C(=0)OCH3 A-93 -C( =0)NH-cylopentyl

A-54 -C(=0)OCH2CH3 A-94 -C( =0)NH-cyclohexyl

A-55 -C(=0)OCH2CH2CH3 A-95 -C( =0)NH-phenyl

A-56 -C(=0)OCH(CH3)2 A-96 -C( =0)NH(2-F-phenyl) No. R1 No. R1

A-97 -C( =0)NH(3-F-phenyl) A-136 -CH2C(=NOCH2CH3)H

A-98 -C( =0)NH(4-F-phenyl) A-137 -CH2C(=NOCH3)CH3

A-99 -C( =0)NH(2-CI-phenyl) A-138 -CH2C(=NOCH2CH3)CH3

A-100 -C( =0)NH(3-CI-phenyl) A-139 1 -methyl-cyclopropyl

A-101 -C( =0)NH(4-CI-phenyl) A-140 1 -trifluormethy-lcyclopropyl

A-102 -C( =0)NH(2-methyl-phenyl) A-141 1 -fluorocyclopropyl

A-103 -C( =0)NH(3-methyl-phenyl) A-142 1 -ethylcyclopropyl

A-104 -C( =0)NH(4-methyl-phenyl) A-143 1 -chlorocyclopropyl

A-105 -C( =0)N(CH3)2 A-144 1 -isopropyl-cyclopropyl

A-106 -C( =0)N(CH3)(CH2CH3) A-145 1 -propylcyclopropyl

A-107 -C( =0)N(CH3)(CH2CH2CH3) A-146 1 -methoxy-cyclopropyl

A-108 -C( =0)N(CH3)(CH(CH3)2) A-147 1 -ethoxy-cyclopropyl

A-109 -C( =0)N(CH3)(CH2CH2CH2CH3) A-148 1 -trifluormethoxy-cyclopropyl

A-1 10 -C( =0)N(CH3)(CH(CH3)CH2CH3) A-149 1 -(difluoromethyl)-cyclopropyl

A-1 1 1 -C( =0)N(CH3)(CH2CH(CH3)CH3) A-150 1 -(methyl-carbamoyl)-cyclopropyl

A-1 12 -C( =0)N(CH3)(CH(CH2CH3)2) A-151 1 -(ethylcarbamoyl)-cyclopropyl

A-1 13 -C( =0)N(CH3)(C(CH3)3) A-152 1 -(isopropylcarb-amoyl)-

A-1 14 -C( =0)N(CH3)(CHF2) cyclopropyl

A-1 15 -C( =0)N(CH3)(CF3) A-153 1 -(propylcarb-amoyl)cyclopropyl

A-1 16 -C( =0)N(CH3)(cyclopropyl) A-154 2-methyl-cyclopropyl

A-1 17 -C( =0)N(CH3)(1 -methyl- A-155 2-trifluormethyl-cyclopropyl

cyclopropyl) A-156 2-fluorocyclopropyl

A-1 18 -C( =0)N(CH3)(cyclobutyl) A-157 2-ethylcyclopropyl

A-1 19 -C( =0)N(CH3)(cylopentyl) A-158 2-chlorocyclopropyl

A-120 -C( =0)N(CH3)(cyclohexyl) A-159 2-isopropylcyclo-propyl

A-121 -C( =0)N(CH3)(phenyl) A-160 2-propylcyclopropyl

A-122 -C( =0)N(CH3)(2-F-phenyl) A-161 2-methoxycyclo-propyl

A-123 -C( =0)N(CH3)(3-F-phenyl) A-162 2-ethoxycyclo-propyl

A-124 -C( =0)N(CH3)(4-F-phenyl) A-163 2-trifluormethoxy-cyclopropyl

A-125 -C( =0)N(CH3)(2-CI-phenyl) A-164 2-(difluoromethyl)-cyclopropyl

A-126 -C( =0)N(CH3)(3-CI-phenyl) A-165 2-(methylcarb-amoyl)-cyclopropyl

A-127 -C( =0)N(CH3)(4-CI-phenyl) A-166 2-(ethylcarb-amoyl)cyclopropyl

A-128 -C( =0)N(CH3)(2-methyl-phenyl) A-167 2-(isopropylcarb-amoyl)-

A-129 -C( =0)N(CH3)(3-methyl-phenyl) cyclopropyl

A-130 -C( =0)N(CH3)(4-methyl-phenyl) A-168 2-(propylcarb-amoyl)-cyclopropyl

A-131 -C( =NOCH3)H A-169 1 ,2-dimethylcyclo-propyl

A-132 -C( =NOCH2CH3)H A-170 1 ,2-difluorocyclo-propyl

A-133 -C( =NOCH3)CH3 A-171 1 ,2-dichlorocyclo-propyl

A-134 -C( =NOCH2CH3)CH3 A-172 2,2-dimethylcyclo-propyl

A-135 -CH2C(=NOCH3)H A-173 2,2-difluorocyclo-propyl No. R1 No. R1

A-174 2,2-dichlorocyclo-propyl A-213 2-(methylcarb-amoyl)-cyclopropyl

A-175 1 -fluoro-2-methyl-cyclopropyl) A-214 2-(ethylcarb-amoyl)cyclopropyl

A-176 1 -chloro-2-methyl-cyclopropyl) A-215 2-(isopropylcarb-amoyl)-

A-177 2-fluoro-1 -methyl-cyclopropyl cyclopropyl

A-178 2-chloro-1 -methyl-cyclopropyl A-216 2-(propylcarb-amoyl)cyclopropyl

A-179 1 -chloro-2-fluoro-cyclopropyl A-217 1 ,2-dimethyl-cyclopropyl

A-180 2-chloro-1 -fluoro-cyclopropyl A-218 1 ,2-difluoro-cyclopropyl

A-181 2, 2-difluoro-1 -methyl-cyclopropyl A-219 1 ,2-dichloro-cyclopropyl

A-182 2, 2-dichoro-1 -methyl-cyclopropyl A-220 2,2-dimethyl-cyclopropyl

A-183 1 -fluoro-2,2-di-methyl-cyclopropyl A-221 2,2-difluoro-cyclopropyl

A-184 1 -chloro-2,2-di-methyl-cyclopropyl A-222 2,2-dichloro-cyclopropyl

A-185 1 -chloro-2,2-difluoro-cyclopropyl A-223 1 -fluoro-2-methyl-cyclopropyl

A-186 2, 2-dichloro-1 -fluoro-cyclopropyl A-224 1 -chloro-2-methyl-cyclopropyl

A-187 1 -methyl-cyclopropyl A-225 2-fluoro-1 -methyl-cyclopropyl

A-188 1 -trifluormethyl-cyclopropyl A-226 2-chloro-1 -methyl-cyclopropyl

A-189 1 -fluorocyclopropyl A-227 1 -chloro-2 -fluoro-cyclopropyl

A-190 1 -ethylcyclopropyl A-228 2-chloro-1 -fluoro-cyclopropyl

A-191 1 -chlorocyclopropyl A-229 2, 2-difluoro-1 -methyl-cyclopropyl

A-192 1 -isopropylcyclo-propyl A-230 2, 2-dichoro-1 -methyl-cyclopropyl

A-193 1 -propylcyclopropyl A-231 1 -fluoro-2,2-di-methyl-cyclopropyl

A-194 1 -methoxy-cyclopropyl A-232 1 -chloro-2, 2-di-methyl-cyclopropyl

A-195 1 -ethoxy-cyclopropyl A-233 1 -chloro-2, 2-di-fluoro-cyclopropyl

A-196 1 -trifluormethoxy-cyclopropyl A-234 2, 2-dichloro-1 -fluoro-cyclopropyl

A-197 1 -(difluoro-methyl)cyclopropyl A-235 cyclobutyl

A-198 1 -(methylcarb-amoyl)-cyclopropyl A-236 cylopentyl

A-199 1 -(ethylcarb-amoyl)cyclopropyl A-237 cyclohexyl

A-200 1 -(isopropylcarb-amoyl)- A-238 1 -methyl-cyclopentyl

cyclopropyl A-239 2-methyl-cyclopentyl

A-201 1 -(propylcarb-amoyl)-cyclopropyl A-240 2,2-dimethyl-cyclopentyl

A-202 2-methyl-cyclopropyl A-241 3-methyl-cyclopentyl

A-203 2-trifluormethyl-cyclopropyl A-242 3,3-dimethyl-cyclopentyl

A-204 2-fluorocyclopropyl A-243 1 -methylpyrrolidin-2-yl

A-205 2-ethylcyclopropyl A-244 1 -methylpyrrolidin-3-yl

A-206 2-chlorocyclopropyl A-245 2-pyridinyl

A-207 2-isopropyl-cyclopropyl A-246 3-pyridinyl

A-208 2-propylcyclopropyl A-247 4-pyridinyl

A-209 2-methoxy-cyclopropyl A-248 1 -pyrazolyl

A-210 2-ethoxy-cyclopropyl A-249 1 H-pyrazol-4-yl

A-21 1 2-trifluormethoxy-cyclopropyl A-250 1 H-pyrazol-5-yl

A-212 2-(difluoromethyl)-cyclopropyl A-251 phenyl No. R1 No. R1

A-252 2-F-phenyl A-292 2,3-dichloro-phenyl

A-253 3-F-phenyl A-293 2,4-dichloro-phenyl

A-254 4-F-phenyl A-294 2,5-dichloro-phenyl

A-255 2-CI-phenyl A-295 2,6-dichloro-phenyl

A-256 3-CI-phenyl A-296 2-F-3-CI-phenyl

A-257 4-CI-phenyl A-297 2-F-4-CI-phenyl

A-258 2-methyl-phenyl A-298 2-F-5-CI-phenyl

A-259 3-methyl-phenyl A-299 2-F-6-CI-phenyl

A-260 4-methyl-phenyl A-300 3-F-4-CI-phenyl

A-261 2-ethyl-phenyl A-301 3-F-5-CI-phenyl

A-262 3-ethyl-phenyl A-302 2-CI-3-F-phenyl

A-263 4-ethyl-phenyl A-303 2-CI-4-F-phenyl

A-264 2-isopropyl-phenyl A-304 2-CI-5-F-phenyl

A-265 3-isopropyl-phenyl A-305 3-CI-4-F-phenyl

A-266 4-isopropyl-phenyl A-306 2-F-3-methyl-phenyl

A-267 2-(2,2,2-trifluoro-ethyl)-phenyl A-307 2-F-4-methyl-phenyl

A-268 3-(2,2,2-trifluoro-ethyl)-phenyl A-308 2-F-5-methyl-phenyl

A-269 4-(2,2,2-trifluoro-ethyl)-phenyl A-309 2-F-6-methyl-phenyl

A-270 2-trifluoromethyl-phenyl A-310 3-F-4-methyl-phenyl

A-271 3-trifluoromethyl-phenyl A-31 1 3-F-5-methyl-phenyl

A-272 4-trifluoromethyl-phenyl A-312 2-methyl-3-F-phenyl

A-273 2-methoxy-phenyl A-313 2-methyl-4-F-phenyl

A-274 3-methoxy-phenyl A-314 2-methyl-5-F-phenyl

A-275 4-methoxy-phenyl A-315 3-methyl-4-F-phenyl

A-276 2-trifluoromethoxy-phenyl A-316 2-F-3-CF3-phenyl

A-277 3-trifluoromethoxy-phenyl A-317 2-F-4-CF3-phenyl

A-278 4-trifluoromethoxy-phenyl A-318 2-F-5-CF3-phenyl

A-279 2-difluoromethoxy-phenyl A-319 2-F-6-CF3-phenyl

A-280 3-difluoromethoxy-phenyl A-320 3-F-4-CF3-phenyl

A-281 4-difluoromethoxy-phenyl A-321 3-F-5-CF3-phenyl

A-282 2-(2,2,2-trifluoro-ethoxy)-phenyl A-322 2-CF3-3-F-phenyl

A-283 3-(2,2,2-trifluoro-ethoxy)-phenyl A-323 2-CF3-4-F-phenyl

A-284 4-(2,2,2-trifluoro-ethoxy)-phenyl A-324 2-CF3-5-F-phenyl

A-285 2-cyano-phenyl A-325 3-CF3-4-F-phenyl

A-286 3-cyano-phenyl A-326 2-F-3-OMe-phenyl

A-287 4-cyano-phenyl A-327 2-F-4-OMe-phenyl

A-288 2,3-difluoro-phenyl A-328 2-F-5-OMe-phenyl

A-289 2,4-difluoro-phenyl A-329 2-F-6-OMe-phenyl

A-290 2,5-difluoro-phenyl A-330 3-F-4-OMe-phenyl

A-291 2,6-difluoro-phenyl A-331 3-F-5-OMe-phenyl No. R1 No. R1

A-332 2-OMe-3-F-phenyl A-372 2-CF3-3-CI-phenyl

A-333 2-OMe-4-F-phenyl A-373 2-CF3-4-CI-phenyl

A-334 2-OMe-5-F-phenyl A-374 2-CF3-5-CI-phenyl

A-335 3-OMe-4-F-phenyl A-375 3-CF3-4-CI-phenyl

A-336 2-F-3-OCHF2-phenyl A-376 2-CI-3-OMe-phenyl

A-337 2-F-4-OCHF2-phenyl A-377 2-CI-4-OMe-phenyl

A-338 2-F-5-OCHF2-phenyl A-378 2-CI-5-OMe-phenyl

A-339 2-F-6-OCHF2-phenyl A-379 2-CI-6-OMe-phenyl

A-340 3-F-4-OCHF2-phenyl A-380 3-CI-4-OMe-phenyl

A-341 3-F-5-OCHF2-phenyl A-381 3-CI-5-OMe-phenyl

A-342 2-OCHF2-3-F-phenyl A-382 2-OMe-3-CI-phenyl

A-343 2-OCHF2-4-F-phenyl A-383 2-OMe-4-CI-phenyl

A-344 2-OCHF2-5-F-phenyl A-384 2-OMe-5-CI-phenyl

A-345 3-OCHF2-4-F-phenyl A-385 3-OMe-4-CI-phenyl

A-346 2-F-3-CN-phenyl A-386 2-CI-3-OCHF2-phenyl

A-347 2-F-4-CN-phenyl A-387 2-CI-4-OCHF2-phenyl

A-348 2-F-5-CN-phenyl A-388 2-CI-5-OCHF2-phenyl

A-349 2-F-6-CN-phenyl A-389 2-CI-6-OCHF2-phenyl

A-350 3-F-4-CN-phenyl A-390 3-CI-4-OCHF2-phenyl

A-351 3-F-5-CN-phenyl A-391 3-CI-5-OCHF2-phenyl

A-352 2-CN-3-F-phenyl A-392 2-OCHF2-3-CI-phenyl

A-353 2-CN-4-F-phenyl A-393 2-OCHF2-4-CI-phenyl

A-354 2-CN-5-F-phenyl A-394 2-OCHF2-5-CI-phenyl

A-355 3-CN-4-F-phenyl A-395 3-OCHF2-4-CI-phenyl

A-356 2-CI-3-methyl-phenyl A-396 2-CI-3-CN-phenyl

A-357 2-CI-4-methyl-phenyl A-397 2-CI-4-CN-phenyl

A-358 2-CI-5-methyl-phenyl A-398 2-CI-5-CN-phenyl

A-359 2-CI-6-methyl-phenyl A-399 2-CI-6-CN-phenyl

A-360 3-CI-4-methyl-phenyl A-400 3-CI-4-CN-phenyl

A-361 3-CI-5-methyl-phenyl A-401 3-CI-5-CN-phenyl

A-362 2-methyl-3-CI-phenyl A-402 2-CN-3-CI-phenyl

A-363 2-methyl-4-CI-phenyl A-403 2-CN-4-CI-phenyl

A-364 2-methyl-5-CI-phenyl A-404 2-CN-5-CI-phenyl

A-365 3-methyl-4-CI-phenyl A-405 3-CN-4-CI-phenyl

A-366 2-CI-3-CF3-phenyl A-406 CH2-cyclopropyl

A-367 2-CI-4-CF3-phenyl A-407 CH2-cyclopentyl

A-368 2-CI-5-CF3-phenyl A-408 CH2-cyclohexyl

A-369 2-CI-6-CF3-phenyl A-409 CH2-(4-quinolinyl)

A-370 3-CI-4-CF3-phenyl A-410 CH2-(2-pyridyl)

A-371 3-CI-5-CF3-phenyl A-41 1 CH2-(3-pyridyl) No. R1 No. R1

A-412 CH2-(4-pyridyl) A-433 (2-CI-phenyl)-methyl

A-413 CH2-(2-thienyl) A-434 (3-CI-phenyl)-methyl

A-414 CH2-(3-thienyl) A-435 (4-CI-phenyl)-methyl

A-415 CH2-(N-methyl-3-pyrazolyl) A-436 (2-methyl-phenyl)-methyl

A-416 CH2-(N-methyl-4-pyrazolyl) A-437 (3-methyl-phenyl)-methyl

A-417 CH2-(1 -pyrazolyl) A-438 (4-methyl-phenyl)-methyl

A-418 CH2-(2-oxazolyl) A-439 (2-methoxy-phenyl)methyl

A-419 CH2-(4-oxazolyl) A-440 (3-methoxy-phenyl)methyl

A-420 CH2-(5-oxazolyl) A-441 (4-methoxy-phenyl)methyl

A-421 CH2-(2-(1 ,3,4-oxadiazolyl)) A-442 (2-cyano-phenyl)methyl

A-422 CH2-(2-furyl) A-443 (3-cyano-phenyl)methyl

A-423 CH2-(3-furyl) A-444 (4-cyano-phenyl)methyl

A-424 3-hydroxypropyl A-445 (2,3-difluoro-phenyl)methyl

A-425 CH2-(N-methyl-3-pyrrolidinyl) A-446 (2, 4-difluoro-phenyl) methyl

A-426 3-dimethyl-aminopropyl A-447 (2,5-difluoro-phenyl)methyl

A-427 2-dimethyl-aminoethyl A-448 (2,6-difluoro-phenyl)methyl

A-428 3-pyrrolidinyl A-449 (2,3-dichloro-phenyl)methyl

A-429 benzyl A-450 (2,4-dichloro-phenyl)methyl

A-430 (2-F-phenyl)methyl A-451 (2,5-dichloro-phenyl)methyl

A-431 (3-F-phenyl)methyl A-452 (2,6-dichloro-phenyl)methyl

A-432 (4-F-phenyl)methyl

A skilled person will recognize that oxadiazole compounds of type I can be accessed by treating nitriles of type II with hydroxylamine or its hydrochloric acid salt in an organic solvent and in the presence of a base. For precedents see, for example, WO 2009/074950, WO 2006/013104, EP 1932843. Subsequently, the intermediate hydroxyacetamidine is reacted with trifluoroacetic anhydride in an organic solvent, preferably an ethereal solvent, at temperatures between 0 °C and 100 °C, preferably at room temperature, as previously described in WO 2013/008162.

Figure imgf000029_0001

II I

Compounds of formula II can be prepared from compounds of formula III, by reaction with compounds of the formula LG-R1 wherein LG is a leaving group, for example chlorine or bromine, and in the presence of a base in a suitable solvent, such as, for example,

tetrahydrofuran, and at a temperature between 0°C and 85°C. For related examples see WO 2015041360.

Figure imgf000030_0001

Compounds of formula II wherein R1 is aryl or hetaryl can be prepared from compounds of formula III, by a copper mediated N-arylation with boronic acids (HO)2B-R1 in the presence of a base, for example pyridine, and a copper salt, for example, copper acetate, in a suitable solvent, such as, for example, dichloromethane and at a temperature between 0°C and 85°C.

For related examples see Bioorganic & Medicinal Chemistry Letters 2010, 20(13), 3920-3924.

Compounds of formula III can be prepared from isocyanates of formula IV, by treatment with sodium azide or with trimethylsilyl azide in the presence of aluminum chloride in a suitable polar solvent, such as, for example, Λ/,/V-dimethyl acetamide or /V/V-dimethyl formamide, typically at a temperature between 25°C and 150°C. The reaction is followed by the addition of water and an excess of a mineral acid. For related examples see EP 638561 .

Figure imgf000030_0002

IV III

Isocyanates of formula IV are either commercially available or can be prepared from amines of formula V, by treatment with phosgene or triphosgene in the presence of a base, for example trimethylamine, in a suitable solvent, such as, for example, dichloromethane, and at a temperature between 0°C and 85°C. For related examples see Bioorganic & Medicinal

Chemistry Letters 2010, 20(24), 7397-7400.

Figure imgf000030_0003

IV

V

Compounds of formula II wherein R1 is Ci-C6-alkoxy can be prepared from compounds of formula Ilia, by treatment with Hal-R1 wherein Hal is chlorine or bromine in the presence of a base, for example sodium hydride, in a suitable solvent, such as, for example, tetrahydrofurane at a temperature between 25°C and 125°C. For related examples see JP 1 1 180965.

Figure imgf000030_0004

Ilia II

Compounds of formula Ilia can be prepared by catalytic hydrogenolysis of compounds of formula 1Mb. For related examples see WO 98/01431.

Figure imgf000031_0001

Illb IHa

Compounds of formula Illb can be accessed by reaction of a compound of formula I lie with 4- benzyloxy-1 H-tetrazol-5-on in the presence of a base, for example sodium hydride, in a suitable solvent, such as A ,AAdimethylformamide and at a temperature between 25°C and 135°C. For related examples see: Bulletin of the Korean Chemical Society 1990, 1 1 (6), 543-546. 4- benzyloxy-1 H-tetrazol-5-on is commercially available. Compounds of type 111 o are either commercially available or can be prepared from readily accessible starting materials following standard procedures.

Figure imgf000031_0002
lllc

Illb

Compounds of formula I wherein R1 is formyl can be prepared by reaction of the compound I, wherein R1 is hydrogen, with 1 A benzotriazole-l -carboxaldehyde in the presence of a base, for example n-butyllithium, in a suitable solvent, such as tetrahydrofuran, and at a temperature between -25°C and 75°C. For related examples see Journal of Organic Chemistry 2012, 77(5), 2149-2158.

Figure imgf000031_0003

l (R = H) l (R = CHO)

Carboxamide derivatives of the formula I can be transferred into the corresponding thiocarbonyl derivatives by reaction with Lawsson's reagent or other suphurizing agents under conditions that are known to a skilled person and which are described in literature. For related examples see WO 2014065413, WO 201 1054871 .

The compounds of the formula I or compositions comprising said compounds according to the invention and the mixtures comprising said compounds and compositions, 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 following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example, but not limited to the genus Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella; Basdiomycota (Basidiomycetes), for example, but not limited to the genus Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example, but not limited to the genus Chytridiales, and Synchytrium; Deuteromycetes (syn. Fungi imperfect!), for example, but not limited to the genus Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (syn. Oomycetes), for example but not limited to the genus Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes, for example but not limited to the genus Plasmodiophora; Zygomycetes, for example, but not limited to the genus Rhizopus.

Some of the compounds of the formula I and the compositions according to the invention 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 multitude 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.

potatoes), 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 mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait. The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:

A/bugo 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 brassicola or brassicae), sugar beets (A tenuis), fruits, rice, soybeans, potatoes (e. g. A so/an/or A.

alternata), tomatoes (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 r/ftc/ (anthracnose) on wheat and A horde/ on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (/9. maydis) or Northern leaf blight (.?. zeicoia) on corn, e. g. spot blotch (.?. sorokiniana) on cereals and e. g. z?. cvyzae 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. iy//77/'(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. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvurrr. 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. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H.

oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C.

gossypii), corn (e. g. C. graminico/a: Anthracnose stalk rot), soft fruits, potatoes (e. g. C.

coccodes. black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicoia (leaf spots) on soybeans and ornamentals; Cycloconium 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 liriodendri, 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 (syn. Helminthosporium, teleomorph: Pyrenophora) 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 Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum),

Phaeoacremonium aleophilum and/or Botryosphaeria obtusa, Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampe/ina: anthracnose); Enty/oma oryzae (leaf smut) on rice; Ep/coccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi), 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. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani 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 fujikurot. Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G gossypii on cotton; Grainstaining complex on rice; Guignardia 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. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoll) (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. M. laxa, M. 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. vitico/a: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum);

Physoderma 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. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Po/ymyxa 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 yallundae) 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. co/lo-cygni (Ramu\ar\a leaf spots, Physiological leaf spots) on barley and R. bet/cola on sugar beets; Rh/zocton/a spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. so/ani (root and stem rot) on soybeans, R. so/ani (sheath blight) on rice or R. cerea/is (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;

Sarocladium oryzae and S. a ttenua turn (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:

Leptosphaeria [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); T/i/et/a 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; Venturia 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 on strawberries, rape, potatoes and tomatoes.

In a preferred embodiment the compounds I, their mixtures with other active compounds as defined herein and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to 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, and Puccinia sorghi (common rust) on maize, Puccinia polysora (southern rust) on maize; and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.

The compounds I and compositions thereof, respectively, are also suitable for controlling harmful 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 spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Hum/cola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., 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 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 agrochemical 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

Grubemann, 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; glycols; 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 colloid, 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 sulfates 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 alkoxylates 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 surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. 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 polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene 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

hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine 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 dodecylbenzenesulfonate 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 arylphenol 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 isocyanate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g.

hexamethylenediamine) 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 compositions 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, compound 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 propagation 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 appropriate.

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 optionally 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), mandestrobin (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), trifloxy- strobin (A.1 .17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)- 2-methoxyimino-Nmethyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chloro- dincarb (A.1.20), famoxadone (A.1 .21 ), fenamidone (A.1 .21 a), methyl-N[2-[(1 ,4-dimethyl- 5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-Nmethoxy-carbamate (A.1.22), metyltetrapole (A.1.25), (Z;2 )-5-[1 -(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-/V,3-dimethyl- pent-3-enamide (A.1 .34), (Z,2 )-5-[1 -(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-/V,3- dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1 .36), bifujunzhi (A.1.37), 2-(ortho- ((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38);

- inhibitors of complex III at Q, site: cyazofamid (A.2.1), amisulbrom (A.2.2),

[(65,7^,8 ¾-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-di- oxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A, 2.4), florylpicoxamid (A.2.5);

- 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.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluindapyr (A.3.28), methyl ( )-2-[2-[(5-cyano- 2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflucypram (A.3.31), 2-(difluoromethyl)-N(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2- (difluoromethyl)-/V-[(3 )-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-[(3 )-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2- (difluoromethyl)-N(l ,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2- (difluoromethyl)-N[(3 )-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[(3 )-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39);

- other respiration inhibitors: diflumetorim (A.4.1); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (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.4.11); silthiofam (A.4.12);

B) Sterol biosynthesis inhibitors (SBI fungicides)

- C14 demethylase inhibitors: triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromu- conazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothio- conazole (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, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro- phenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);

- Delta14-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), spiroxamine (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), pyridachlometyl (D.1 .6), /V-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]butanamide (D.1 .8), AAethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2- methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/V-(2- fluoroethyl)butanamide (D.1 .10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-AA(2-fluoroethyl)-2- methoxy-acetamide (D.1 .1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-AApropyl-butanamide (D.1 .12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-Npropyl-acetamide (D.1.13), 2- [(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-AApropyl-acetamide (D.1.14),

2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-AA(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1 .15), 4-(2-bromo-4-fluoro-phenyl)-AA(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(difluoro- methyl-1 A pyrazol-l -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 pyrazol-1 -yl]- acetyl}piperidin-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methane- sulfonate (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-Nte- tralin-1 -yl-pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]- 4-piperidyl]-Ntetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(tri- fluoromethyl)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]-/V-tetralin-1 -yl-pyri- dine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-pipen- dyl]-Ntetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoro- methyl)pyrazol-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]-Ntetralin-1-yl-pyridine-2-car- boxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-

Ntetralin-1-yl-pyridine-2-carboxamide (G.5.11);

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.3.11);

- 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 ,5 ^[1,4]di- thiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2A,6A)-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 (I.2.2), carpropamid (1.2.3),

dicyclomet (I.2.4), fenoxanil (1.2.5);

J) Plant defence inducers

- acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexa- dione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N(2,4-dimethoxyphenyl)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), di- fenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11), 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), /V-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-Nethyl-N-methyl formamidine (K.1.27), /Vi(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-eth- yl-N-methyl formamidine (K.1.28), /V-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]- oxy]-2,5-dimethyl-phenyl]-Nethyl-Nmethyl-formamidine (K.1 .29), ^(S-bromo-e-indan^-yl- oxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1 .30), /V-[5-bromo-6-[1 -(3,5-diflu- orophenyl)ethoxy]-2-methyl-3-pyndyl]-Nethyl-Nmethyl-formamidine (K.1 .31 ), ^[S-bromo- 6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-Nethyl-Nmethyl-formamidine (K.1 .32), A -[5-bromo-2-methyl-6-(1 -phenylethoxy)-3-pyridyl]-Nethyl-Nmethyl-formami (K.1 .33), A i(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-Nethyl-N forma- midine (K.1 .34), A i(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl- /V-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-pynmidin-2-yl)-2-methyl-1 A benzoimidazole (K.1 .39), ethyl (2)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), picarbutrazox (K.1 .41 ), pentyl N[6-[[(2)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carba- mate (K.1 .42), but-3-ynyl N[6-[[(2)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxy- methyl]-2-pyridyl]carbamate (K.1 .43), ipflufenoquin (K.1 .44), quinofumelin (K.1 .47), 2-(6- benzyl-2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2- pyridyl]quinazoline (K.1 .51 ), dichlobentiazox (K.1 .52), /Vi(2,5-dimethyl-4-phenoxy-phenyl)-N- ethyl-N-methyl-formamidine (K.1 .53), pyrifenamine (K.1 .54);

M) Growth regulators

abscisic acid (M.1 .1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, /V-6-benzyl adenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid , trinexapac-ethyl, 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, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclo-,propyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hy- droxy-2,2,6,6-tetramethyl-2 pyran-3(6 75-one (1312337-72-6); 4-(2',4'-dichloro-4-cyclo- propyltU '-bipheny -S-y -S-hydroxy^^^^-tetramethyl^Aji-pyran-SieA j-one (1312337-45- 3); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2 7i-pyran- 3{6H)-one (1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1 , 1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl- 2A -pyran-3,5(4A ,6A )-dione (1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'- fluoro[1 ,r-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2A -pyran-3-one (1312337-48-6);

5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 , 1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetra- methyl-2A pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)- 3,6-dihydro-2,2,6,6-tetramethyl-2 pyran-3-one (1312340-82-1 ); 5-(acetyloxy)-4-(2',4'-di- chloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2 7i-pyran-3-one (1033760- 55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl- 5-0X0-2 A£pyran-3-yl carbonic acid methyl ester (1312337-51 -1 ); 4-(2',4'-dichloro -4-cyclo- propyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2A7Lpyran-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-tetra- methyl-5-oxo-2 pyran-3-yl carbonic acid methyl ester (1312340-83-2); 4-(2',4'-dichloro- 4-ethyh[1 ,1 '-bipheny -S-y -S^-dihydro^^^^-tetramethyl-S-oxo^A pyran-S-yl carbonic acid methyl ester (1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate, vernolate;

N.2 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, meta- zosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazo- sulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusul- furon, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imaza- mox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, diclo- sulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan, pyroxsulam; bispyri- bac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithio- bac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]- benzoic acid-1 -methyhethyl ester (420138-41 -6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]- phenyl]-"methyl]amino]-benzoic acid propyl ester (420138-40-5), AA(4-bromophenyl)-

2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (420138-01 -8); flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, 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, propanil; 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-tetrahydropyrimi- din-3-yl)phenoxy]-2-pyridyloxy]acetate (353292-31-6), Nethyl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1 A pyrazole-l -carboxamide (452098-92-9), /V-tetrahydrofurfuryl- 3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l -carboxamide (915396-43- 9), Nethyl-3-(2-chloro-6-fluoro-4-trifluoromethyhphenoxy)-5-methyl-1 A pyrazole-l -carbox- amide (452099-05-7), Ntetrahydro^furfuryl-3-(2-chloro-6-fluoro-4-trifluoro-,methylphenoxy)- 5-methyl-1 pyrazole-1 -carboxamide (452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-

Figure imgf000047_0001
,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2 7i-benzo[1 ,4]oxazin-6-yl)- 4,5,6,7-tetrahydro-isoindole-1 ,3-dione (13001 18-96-0), 1 -methyl-6-trifluoro-"methyl- 3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2 7i-benzo[1 ,4]oxazin-6-yl)-1 A pyrimidine- 2,4-dione (13041 13-05-0), methyl ( )-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 methyl- pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (948893-00-3), 3-[7-chloro-5-fluoro- 2-(trifluoromethyl)-1 A benzimidazol^-y -l -methyl-6-(trifluoromethyl)-1 / pyrimidine-2,4-di- one (212754-02-4);

N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,

norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;

N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate- potassium, 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, pen- dimethalin, 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, dimethen- amid-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 imgf000047_0002

11.1

II.2

Figure imgf000048_0001

Figure imgf000048_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 (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 aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopy- ralid 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 (943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, meco- prop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, 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 (1390661 -72-

9);

N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam, naptalam- sodium;

N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, di- fenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flu- renol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydra- zide, mefluidide, metam, methiozolin (403640-27-7), methyl azide, methyl bromide, methyl- dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane; Insecticides from classes 0.1 to 0.29

Acetylcholine esterase (AChE) inhibitors: aldicarb (0.1.1), alanycarb (0.1.2), bendiocarb (0.1.3), benfuracarb (0.1.4), butocarboxim (0.1.5), butoxycarboxim (0.1.6), carbaryl

(0.1.7), carbofuran (0.1.8), carbosulfan (0.1.9), ethiofencarb (0.1.10), fenobucarb (0.1.11), formetanate (0.1.12), furathiocarb (0.1.13), isoprocarb (0.1.14), methiocarb (0.1.15), methomyl (0.1.16), metolcarb (0.1.17), oxamyl (0.1.18), pirimicarb (0.1.19), propoxur

(0.1.20), thiodicarb (0.1.21), thiofanox (0.1.22), trimethacarb (0.1.23), XMC (0.1.24), xylylcarb (0.1.25), triazamate (0.1.26), acephate (0.1.27), azamethiphos (0.1.28), azinphos-ethyl (0.1.29), azinphosmethyl (0.1.30), cadusafos (0.1.31), chlorethoxyfos

(0.1.32), chlorfenvinphos (0.1.33), chlormephos (0.1.34), chlorpyrifos (0.1.35), chlorpyrifos- methyl (0.1.36), coumaphos (0.1.37), cyanophos (0.1.38), demeton-S-methyl (0.1.39), diazinon (0.1.40), dichlorvos/ DDVP (0.1.41), dicrotophos (0.1.42), dimethoate (0.1.43), dimethylvinphos (0.1.44), disulfoton (0.1.45), EPN (0.1.46), ethion (0.1.47), ethoprophos (0.1.48), famphur (0.1.49), fenamiphos (0.1.50), fenitrothion (0.1.51), fenthion (0.1.52), fosthiazate (0.1.53), heptenophos (0.1.54), imicyafos (0.1.55), isofenphos (0.1.56), isopropyl O-(methoxyaminothio-phosphoryl) salicylate (0.1.57), isoxathion (0.1.58), malathion (0.1.59), mecarbam (0.1.60), methamidophos (0.1.61), methidathion (0.1.62), mevinphos (0.1.63), monocrotophos (0.1.64), naled (0.1.65), omethoate (0.1.66), oxydemeton-methyl (0.1.67), parathion (0.1.68), parathion-methyl (0.1.69), phenthoate (0.1.70), phorate (0.1.71), phosalone (0.1.72), phosmet (0.1.73), phosphamidon (0.1.74), phoxim (0.1.75), pirimiphos- methyl (0.1.76), profenofos (0.1.77), propetamphos (0.1.78), prothiofos (0.1.79), pyraclofos (0.1.80), pyridaphenthion (0.1.81), quinalphos (0.1.82), sulfotep (0.1.83), tebupirimfos (0.1.84), temephos (0.1.85), terbufos (0.1.86),

tetrachlorvinphos (0.1.87), thiometon (0.1.88), triazophos (0.1.89), trichlorfon (0.1.90), vamidothion (0.1.91);

GABA-gated chloride channel antagonists: endosulfan (0.2.1), chlordane (0.2.2), ethiprole

(0.2.3), fipronil (0.2.4), flufiprole (0.2.5), pyrafluprole (0.2.6), pyriprole (0.2.7);

Sodium channel modulators: acrinathrin (0.3.1), allethrin (0.3.2), d-cis-trans allethrin

(0.3.3), d-trans allethrin (0.3.4), bifenthrin (0.3.5), kappa-bifenthrin (0.3.6), bioallethrin

(0.3.7), bioallethrin S-cylclopentenyl (0.3.8), bioresmethrin (0.3.9), cycloprothrin (0.3.10), cyfluthrin (0.3.11), beta-cyfluthrin (0.3.12), cyhalothrin (0.3.13), lambda-cyhalothrin

(0.3.14), gamma-cyhalothrin (0.3.15), cypermethrin (0.3.16), alpha-cypermethrin (0.3.17), beta-cypermethrin (0.3.18), theta-cypermethrin (0.3.19), zeta-cypermethrin (0.3.20), cyphenothrin (0.3.21), deltamethrin (0.3.22), empenthrin (0.3.23), esfenvalerate (0.3.24), etofenprox (0.3.25), fenpropathrin (0.3.26), fenvalerate (0.3.27), flucythrinate (0.3.28), flumethrin (0.3.29), tau-fluvalinate (0.3.30), halfenprox (0.3.31), heptafluthrin (0.3.32), imiprothrin (0.3.33), meperfluthrin (0.3.34), metofluthrin (0.3.35), momfluorothrin (0.3.36), epsilon-momfluorothrin (0.3.37), permethrin (0.3.38), phenothrin (0.3.39), prallethrin (O.3.40), profluthrin (0.3.41), pyrethrin (pyrethrum) (0.3.42), resmethrin (0.3.43), silafluofen (0.3.44), tefluthrin (0.3.45), kappa-tefluthrin (0.3.46), tetramethylfluthrin (0.3.47), tetramethrin (0.3.48), tralomethrin (0.3.49), transfluthrin (0.3.50), DDT (0.3.51),

methoxychlor (0.3.52);

Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid (0.4.1), clothianidin (0.4.2), cycloxaprid (0.4.3), dinotefuran (0.4.4), imidacloprid (0.4.5), nitenpyram (0.4.6), thiacloprid (0.4.7), thiamethoxam (0.4.8), 4,5-dihydro-Nnitro-1 -(2-oxiranylmethyl)-1 imidazol-2-amine (0.4.9), (2 )-1 -[(6-chloropyridin-3-yl)methyl]-/V-nitro-2-pentylidene- hydrazinecarboximidamide (0.4.10), 1 -[(6-chloropyndin-3-yl)methyl]-7-methyl-8-nitro-5- propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine (0.4.1 1 ), nicotine (0.4.12), sulfoxaflor (0.4.13), flupyradifurone (0.4.14), triflumezopyrim (0.4.15);

0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad (0.5.1 ), spinetoram (0.5.2);

0.6 Chloride channel activators: abamectin (0.6.1 ), emamectin benzoate (0.6.2), ivermectin (0.6.3), lepimectin (0.6.4), milbemectin (0.6.5);

0.7 Juvenile hormone mimics: hydroprene (0.7.1 ), kinoprene (0.7.2), methoprene (0.7.3), fenoxycarb (0.7.4), pyriproxyfen (0.7.5);

0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide (0.8.1 ) and other alkyl halides, chloropicrin (0.8.2), sulfuryl fluoride (0.8.3), borax (0.8.4), tartar emetic (0.8.5);

0.9 Chordotonal organ TRPV channel modulators: pymetrozine (0.9.1 ), pyrifluquinazon (0.9.2), flonicamid (0.9.3);

O.10 Mite growth inhibitors: clofentezine (O.10.1 ), hexythiazox (O.10.2), diflovidazin (O.10.3), etoxazole (0.10.4);

0.1 1 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus

sphaericus and the insecticdal proteins they produce: Bacillus thuringiensis subsp.

Israelensis (0.1 1 .1 ), Bacillus sphaericus (0.1 1 .2), Bacillus thuringiensis subsp. aizawai (0.1 1 .3), Bacillus thuringiensis subsp. kurstakHQA ^ A), Bacillus thuringiensis subsp.

tenebrionis (0.1 1 .5), the Bt crop proteins: Cry1 Ab (0.1 1 .6), Cry1 Ac (0.1 1 .7), Cry1 Fa

(0.1 1 .8), Cry2Ab (0.1 1 .9), mCry3A (0.1 1 .10), Cry3Ab (0.1 1 .1 1 ), Cry3Bb (0.1 1 .12),

Cry34/35Ab1 (0.1 1 .13);

0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron (0.12.1 ), azocyclotin (0.12.2), cyhexatin (0.12.3), fenbutatin oxide (0.12.4), propargite (0.12.5), tetradifon (0.12.6);

0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr

(0.13.1 ), DNOC (0.13.2), sulfluramid (0.13.3);

0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap (0.14.1 ), cartap hydrochloride (0.14.2), thiocyclam (0.14.3), thiosultap sodium (0.14.4);

0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron (0.15.1 ), chlorfluazuron (0.15.2), diflubenzuron (0.15.3), flucycloxuron (0.15.4), flufenoxuron (0.15.5), hexaflumuron

(0.15.6), lufenuron (0.15.7), novaluron (0.15.8), noviflumuron (0.15.9), teflubenzuron

(O.15.10), triflumuron (0.15.1 1 );

0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin (0.16.1 );

0.17 Moulting disruptors: cyromazine (0.17.1 );

0.18 Ecdyson receptor agonists: methoxyfenozide (0.18.1 ), tebufenozide (0.18.2),

halofenozide (0.18.3), fufenozide (0.18.4), chromafenozide (0.18.5);

0.19 Octopamin receptor agonists: amitraz (0.19.1 );

O.20 Mitochondrial complex I II electron transport inhibitors: hydramethylnon (O.20.1 ),

acequinocyl (O.20.2), fluacrypyrim (O.20.3), bifenazate (O.20.4);

0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin (0.21 .1 ), fenpyroximate

(0.21 .2), pyrimidifen (0.21 .3), pyridaben (0.21 .4), tebufenpyrad (0.21 .5), tolfenpyrad

(0.21 .6), rotenone (0.21 .7);

0.22 Voltage-dependent sodium channel blockers: indoxacarb (0.22.1 ), metaflumizonev (0.22.2), 2-[2-(4-cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide (0.22.3), N(3-chloro-2-methylphenyl)-2-[(4- chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-h

(0.22.4);

3 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen (0.23.1 ), spiromesifen (0.23.2), spirotetramat (0.23.3), spiropidion (0.23.4);

4 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide (0.24.1 ), calcium phosphide (0.24.2), phosphine (0.24.3), zinc phosphide (0.24.4), cyanide (0.24.5); 5 Mitochondrial complex II electron transport inhibitors: cyenopyrafen (0.25.1 ), cyflumetofen (0.25.2);

6 Ryanodine receptor-modulators: flubendiamide (0.26.1 ), chlorantraniliprole (0.26.2), cyantraniliprole (0.26.3), cyclaniliprole (0.26.4), tetraniliprole (0.26.5), ( ¾-3-chloro- V-{2- methyl-4-[1 ,2,2,2 -tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-/^-(1 -methyl-2- methylsulfonylethyl)phthalamide (0.26.6), (S)-3-chloro-N-{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethy ethylJphenylJ-A^I -methyl-2-methylsulfonylethyl)phthalamide (0.26.7), methyl-2-[3,5-dibromo-2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 pyrazol-S-ylJcarbonyl}- amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate (0.26.8), N[4,6-dichloro-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole- 3-carboxamide (0.26.9), N[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6- methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide (0.26.10), N[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro- 2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide (0.26.1 1 ), N[4,6-dichloro-2-[(di-2- propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide (0.26.12), N[4,6-dibromo-2-[(diethyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide (0.26.13), N[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3- bromo-1 -(3-chloro-2-pyridinyl)-1 A pyrazole-S-carboxamide (0.26.14), 3-chloro-1 -(3-chloro-2- pyridinyl)-/V-[2,4-dichloro-6-[[(1 -cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 A pyrazole- 5-carboxamide (0.26.15), 3-bromo-N[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5- dichloro-2-pyridyl)-1 pyrazole-5-carboxamide (0.26.16), N[4-chloro-2-[[(1 ,1 - dimethylethyl)amino]carbonyl]-6-methylphenyl]-1 -(3-chloro-2-pyridinyl)-3-(fluoromethoxy)- 1 pyrazole-S-carboxamide (0.26.17), cyhalodiamide (0.26.18);

7: Chordotonal organ Modulators - undefined target site: flonicamid (0.27.1 );

8. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen (0.28.1 ), afoxolaner (0.28.2), azadirachtin (0.28.3), amidoflumet (0.28.4), benzoximate (0.28.5), broflanilide (0.28.6), bromopropylate (0.28.7), chinomethionat (0.28.8), cryolite (0.28.9), dicloromezotiaz (O.28.10), dicofol (0.28.1 1 ), flufenerim (0.28.12), flometoquin (0.28.13), fluensulfone (0.28.14), fluhexafon (0.28.15), fluopyram (0.28.16), fluralaner (0.28.17), metoxadiazone (0.28.18), piperonyl butoxide (0.28.19), pyflubumide (O.28.20), pyridalyl (0.28.21 ), tioxazafen (0.28.22), 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 Η-λ ,2,4-triazole-5-amine (0.28.23), Bacillus f/rmus \^ 582 (0.28.24), flupyrimin (0.28.25), fluazaindolizine (0.28.26), 4-[5-(3,5-di- chlorophenyl)-5-(trifluoromethyl)-4 isoxazol-3-yl]-2-methyl-N(1 -oxothietan-3-yl)benzami (0.28.27), fluxametamide (0.28.28), 5-[3-[2,6-dichloro-4-(3,3- dichloroallyloxy)phenoxy]propoxy]-1 A pyrazole (0.28.1 ), 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 (0.28.29), 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 (O.28.30), N[5-[[2-chloro-6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]- 2-cyano-phenyl]-4-cyano-2-methyl-benzamide (0.28.31 ), N-[5-[[2-bromo-6-chloro-4-[2,2,2-tri- fluoro-1 -hydroxy-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano- 2-methyl-benzamide (0.28.32), N[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoro- methyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide (0.28.33), 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-benzamide (0.28.34), 4-cyano-N[2-cyano-5-[[2,6-dichloro-4- [1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzami (0.28.35), N[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]- carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide (0.28.36); 2-(1 ,3-dioxan-2-yl)-6- [2-(3-pyridinyl)-5-thiazolyl]-pyridine (0.28.37), 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2- pyridinyl]-pyrimidine (0.28.38), 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pynmidine (0.28.39), N-methylsulfonyl-6-[2-(3-pyndyl)thiazol-5-yl]pyridine-2-carboxamide (O.28.40), ΛΑ methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide (0.28.41 ), 1 -[(6-chloro-3- pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1 ,2-a]pyridin (0.28.42), 1 -[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2- a]pyridin-5-ol (0.28.43), 1 -isopropyl-A ,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.28.44), 1 -(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.28.45), A/,5-dimethyl-/V-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-car- boxamide (0.28.46), 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide (0.28.47), /V-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-meth-yl-/\A pyridazin-4-yl-pyrazole-4-carboxamide (0.28.48), 1 -(1 ,2-dimethylpropyl)-/V,5-dimethyl- Npyridazin-4-yl-pyrazole-4-carboxamide (0.28.49), 1 -[1 -(1 -cyanocyclopropyl)ethyl]-/V,5-di- methyl-Npyridazin-4-yl-pyrazole-4-carboxamide (0.28.50), N-methyl-1 -(2-fluoro-1 -methyl- propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.28.51 ), 1 -(4,4-di- fluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.28.52), 1 - (4,4-difluorocyclohexyl)-A',5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.28.53), ΛΑ (1 -methylethyl)-2-(3-pyridinyl)-2 A£indazole-4-carboxamide (0.28.54), N-cyclopropyl- 2-(3-pyridinyl)-2 indazole-4-carboxamide (0.28.55), Ncyclohexyl-2-(3-pyridinyl)-2 indazole-4-carboxamide (0.28.56), 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2 7i-indazole-4- carboxamide (0.28.57), 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2A7Lindazole-

5- carboxamide (0.28.58), methyl 2-[[2-(3-pyridinyl)-2 indazol-5- yl]carbonyl]hydrazinecarboxylate (0.28.59), N[(2,2-difluorocyclopropyl)methyl]-2-(3- pyridinyl)-2 indazole-5-carboxamide (O.28.60), N(2,2-difluoropropyl)-2-(3-pyridinyl)-2 indazole-5-carboxamide (0.28.61 ), 2-(3-pyridinyl )-N(2-pyrimidinylmethyl )-2 7Lindazole-5- carboxamide (0.28.62), N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2A7Lindazole-5-car- boxamide (0.28.63), tyclopyrazoflor (0.28.64), sarolaner (0.28.65), lotilaner (0.28.66),

N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1 -methyl-3-(1 ,1 ,2,2,2-penta- fluoroethyl)-4-(trifluoromethyl)-1 7i-pyrazole-5-carboxamide (0.28.67), M.UN.22a 2-(3- ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (0.28.68), 2-[3- ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imi

(0.28.69), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4 isoxazol-3-yl]-N[(4 )-2-ethyl- 3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide (0.28.70), 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4 isoxazol-3-yl]-N[(4 ^-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl^ benzamide (0.28.71 ), /V-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide (0.28.72), /V-[4-chloro-3-[(1 -cy- anocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)- pyrazole-3-carboxamide (0.28.73), acynonapyr (0.28.74), benzpyrimoxan (0.28.75), chloro- ΛΑ(1 -cyanocyclopropyl)-5-[1 -[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)- 4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide (0.28.76), oxazosulfyl (0.28.77),

[(25,3 ?,4 ?,55,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N[4-[1 -[4-(tri- fluoromethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate (0.28.78),

[(25,3 ?,4 ?,55,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1 -[4-(trifluoro- methoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate (0.28.79), [(25,3 ?,4 ?,55,6S)-3,5- dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-/V-[4-[1 -[4-(1 , 1 ,2,2,2- pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate (O.28.80), [(25,3 ?,4 ?,55,6S)- 3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]-/V-[4-[1 -[4-(1 ,1 ,2,2,2-penta- fluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate (0.28.81 ), (22)-3-(2- isopropylphenyl)-2-[( )-[4-[1 -[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3- yl]phenyl]methylenehydrazono]thiazolidin-4-one (0.28.82).

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 lU PAC 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 further 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 individual 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.

Accordingly, the present invention furthermore relates to mixtures comprising one compound of the formula I (component 1 , a group represented by the expression "(I)") and one pesticide II (component 2), wherein pesticide II is an active ingredients selected from the groups A) to O) defined above.

Further embodiments B-1 to B-683 listed in Table B below relate to mixtures comprising as active components one of the in the present specification individualized compounds of the formula I, which is selected from the group of compounds I.A.A-1 to I.A.A-452, I.B.A-1 to I.B.A- 452, I.C.A-1 to I.C.A-452, I.D.A-1 to I.D.A-452, I.E.A-1 to I.E.A-452, I.F.A-1 to I.F.A-452, I.G.A-1 to I.G.A-452, I.H.A-1 to I.H.A-452, I.J.A-1 to I.J.A-452, I.K.A-1 to I.K.A-452, I.L.A-1 to I.L.A-452, I.M.A-1 to I.M.A-452, as defined in tables 1 to 12 (component 1 , a group represented by the expression "(I)") and one pesticide II selected from the groups A) to O) as defined herein (component 2, for example, (A.1.1 ) or azoxystrobin, in embodiment B-1 ).

Further embodiments B-1 to B-683 listed in Table B below relate to the mixtures comprising as active components one of the in the present specification individualized compounds of the formula I, which is selected from the group of compounds Ex-1 and Ex-2 as defined in Table I below.

Preferably, the compositions described in Table B comprise the active components in synergistically effective amounts.

Table B:

B-1 : (I) + (A.1 .1 ), B-2: (I) + (A.1.2), B-3: (I) + (A.1 .3), B-4: (I) + (A.1.4), B-5: (I) + (A.1.5), B-6: (I) + (A.1.6), B-7: (I) + (A.1.7), B-8: (I) + (A.1 .8), B-9: (I) + (A.1 .9), B-10: (I) + (A.1 .10), B-1 1 : (I) + (A.1.1 1 ), B-12: (I) + (A.1 .12), B-13: (I) + (A.1 .13), B-14: (I) + (A.1.14), B-15: (I) + (A.1 .15), B-16: (I) + (A.1.16), B-17: (I) + (A.1.17), B-18: (I) + (A.1 .18), B-19: (I) + (A.1 .19), B-20: (I) + (A.1.20), B-21 : (I) + (A.1.21 ), B-22: (I) + (A.1.21 a), B-23: (I) + (A.1.22), B-24: (I) + (A.1.25), B-25: (I) +

(A.1.34), B-26: (I) + (A.1 .35), B-27: (I) + (A.1 .36), B-28: (I) + (A.1.37), B-29: (I) + (A.1 .38), B-30: (I) + (A.2.1 ), B-31 : (I) + (A.2.2), B-32: (I) + (A.2.3), B-33: (I) + (A.2.4), B-34: (I) + (A.2.5), B-35: (I) + (A.3.1 ), B-36: (I) + (A.3.2), B-37: (I) + (A.3.3), B-38: (I) + (A.3.4), B-39: (I) + (A.3.5), B-40: (I) + (A.3.6), B-41 : (I) + (A.3.7), B-42: (I) + (A.3.8), B-43: (I) + (A.3.9), B-44: (I) + (A.3.10), B-45: (I) + (A.3.1 1 ), B-46: (I) + (A.3.12), B-47: (I) + (A.3.13), B-48: (I) + (A.3.14), B-49: (I) + (A.3.15), B-50: (I) + (A.3.16), B-51 : (I) + (A.3.17), B-52: (I) + (A.3.18), B-53: (I) + (A.3.19), B-54: (I) + (A.3.20), B-55: (I) + (A.3.21 ), B-56: (I) + (A.3.22), B-57: (I) + (A.3.23), B-58: (I) + (A.3.24), B-59: (I) + (A.3.25), B-60: (I) + (A.3.26), B-61 : (I) + (A.3.27), B-62: (I) + (A.3.28), B-63: (I) + (A.3.30), B-64: (I) + (A.3.31 ), B-65: (I) + (A.3.32), B-66: (I) + (A.3.33), B-67: (I) + (A.3.34), B-68: (I) + (A.3.35), B-69: (I) + (A.3.36), B-70: (I) + (A.3.37), B-71 : (I) + (A.3.38), B-72: (I) + (A.3.39), B-73: (I) +

(A.4.1 ), B-74: (I) + (A.4.2), B-75: (I) + (A.4.3), B-76: (I) + (A.4.4), B-77: (I) + (A.4.5), B-78: (I) + (A.4.6), B-79: (I) + (A.4.7), B-80: (I) + (A.4.8), B-81 : (I) + (A.4.9), B-82: (I) + (A.4.10), B-83: (I) + (A.4.1 1 ), B-84: (I) + (A.4.12), B-85: (I) + (B.1.1 ), B-86: (I) + (B.1.2), B-87: (I) + (B.1.3), B-88: (I) + (B.1 .4), B-89: (I) + (B.1 .5), B-90: (I) + (B.1.6), B-91 : (I) + (B.1.7), B-92: (I) + (B.1.8), B-93: (I) + (B.1.9), B-94: (I) + (B.1.10), B-95: (I) + (B.1.11), B-96: (I) + (B.1.12), B-97: (I) + (B.1.13), B-98: (I) + (B.1.14), B-99: (I) + (B.1.15), B-100: (I) + (B.1.16), B-101: (I) + (B.1.17), B-102: (I) +

(B.1.18), B-103: (I) + (B.1.19), B-104: (I) + (B.1.20), B-105: (I) + (B.1.21), B-106: (I) + (B.1.22), B-107: (I) + (B.1.23), B-108: (I) + (B.1.24), B-109: (I) + (B.1.25), B-110: (I) + (B.1.26), B-111: (I) + (B.1.27), B-112: (I) + (B.1.28), B-113: (I) + (B.1.29), B-114: (I) + (B.1.30), B-115: (I) + (B.1.31), B-116: (I) + (B.1.32), B-117: (I) + (B.1.37), B-118: (I) + (B.1.38), B-119: (I) + (B.1.39), B-120: (I) + (B.1.40), B-121: (I) + (B.1.41), B-122: (I) + (B.1.42), B-123: (I) + (B.1.43), B-124: (I) + (B.1.44), B-125: (I) + (B.1.45), B-126: (I) + (B.1.46), B-127: (I) + (B.1.47), B-128: (I) + (B.1.48), B-129: (I) + (B.1.49), B-130: (I) + (B.1.50), B-131: (I) + (B.1.51), B-132: (I) + (B.1.52), B-133: (I) + (B.2.1), B-134: (I) + (B.2.2), B-135: (I) + (B.2.3), B-136: (I) + (B.2.4), B-137: (I) + (B.2.5), B-138: (I) +

(B.2.6), B-139: (I) + (B.2.7), B-140: (I) + (B.2.8), B-141: (I) + (B.3.1), B-142: (I) + (B.4.1), B-143: (I) + (C.1.1), B-144: (I) + (C.1.2), B-145: (I) + (C.1.3), B-146: (I) + (C.1.4), B-147: (I) + (C.1.5), B- 148: (I) + (C.1.6), B-149: (I) + (C.1.7), B-150: (I) + (C.2.1), B-151: (I) + (C.2.2), B-152: (I) + (C.2.3), B-153: (I) + (C.2.4), B-154: (I) + (C.2.5), B-155: (I) + (C.2.6), B-156: (I) + (C.2.7), B-157: (I) + (C.2.8), B-158: (I) + (D.1.1), B-159: (I) + (D.1.2), B-160: (I) + (D.1.3), B-161: (I) + (D.1.4), B- 162: (I) + (D.1.5), B-163: (I) + (D.1.6), B-164: (I) + (D.1.7), B-165: (I) + (D.1.8), B-166: (I) + (D.1.9), B-167: (I) + (D.1.10), B-168: (I) + (D.1.11), B-169: (I) + (D.1.12), B-170: (I) + (D.1.13), B- 171: (I) + (D.1.14), B-172: (I) + (D.1.15), B-173: (I) + (D.1.16), B-174: (I) + (D.2.1), B-175: (I) + (D.2.2), B-176: (I) + (D.2.3), B-177: (I) + (D.2.4), B-178: (I) + (D.2.5), B-179: (I) + (D.2.6), B-180: (I) + (D.2.7), B-181: (I) + (E.1.1), B-182: (I) + (E.1.2), B-183: (I) + (E.1.3), B-184: (I) + (E.2.1), B- 185: (I) + (E.2.2), B-186: (I) + (E.2.3), B-187: (I) + (E.2.4), B-188: (I) + (E.2.5), B-189: (I) + (E.2.6), B-190: (I) + (F.1.1), B-191: (I) + (F.1.2), B-192: (I) + (F.1.3), B-193: (I) + (F.1.4), B-194: (I) + (F.1.5), B-195: (I) + (F.2.1), B-196: (I) + (G.1.1), B-197: (I) + (G.1.2), B-198: (I) + (G.1.3), B- 199: (I) + (G.1.4), B-200: (I) + (G.2.1), B-201: (I) + (G.2.2), B-202: (I) + (G.2.3), B-203: (I) + (G.2.4), B-204: (I) + (G.2.5), B-205: (I) + (G.2.6), B-206: (I) + (G.2.7), B-207: (I) + (G.3.1), B-208: (I) + (G.3.2), B-209: (I) + (G.3.3), B-210: (I) + (G.3.4), B-211: (I) + (G.3.5), B-212: (I) + (G.3.6), B-213: (I) + (G.3.7), B-214: (I) + (G.4.1), B-215: (I) + (G.5.1), B-216: (I) + (G.5.2), B-217: (I) + (G.5.3), B-218: (I) + (G.5.4), B-219: (I) + (G.5.5), B-220: (I) + (G.5.6), B-221: (I) + (G.5.7), B-222: (I) + (G.5.8), B-223: (I) + (G.5.9), B-224: (I) + (G.5.10), B-225: (I) + (G.5.11), B-226: (I) + (H.1.1), B-227: (I) + (H.1.2), B-228: (I) + (H.1.3), B-229: (I) + (H.1.4), B-230: (I) + (H.1.5), B-231: (I) +

(H.1.6), B-232: (I) + (H.1.7), B-233: (I) + (H.2.1), B-234: (I) + (H.2.2), B-235: (I) + (H.2.3), B-236: (I) + (H.2.4), B-237: (I) + (H.2.5), B-238: (I) + (H.2.6), B-239: (I) + (H.2.7), B-240: (I) + (H.2.8), B- 241: (I) + (H.2.9), B-242: (I) + (H.3.1), B-243: (I) + (H.3.2), B-244: (I) + (H.3.3), B-245: (I) + (H.3.4), B-246: (I) + (H.3.5), B-247: (I) + (H.3.6), B-248: (I) + (H.3.7), B-249: (I) + (H.3.8), B-250: (I) + (H.3.9), B-251: (I) + (H.3.10), B-252: (I) + (H.3.11), B-253: (I) + (H.4.1), B-254: (I) + (H.4.2), B-255: (I) + (H.4.3), B-256: (I) + (H.4.4), B-257: (I) + (H.4.5), B-258: (I) + (H.4.6), B-259: (I) + (H.4.7), B-260: (I) + (H.4.8), B-261: (I) + (H.4.9), B-262: (I) + (H.4.10), B-263: (I) + (1.1.1), B-264: (I) + (1.1.2), B-265: (I) + (1.2.1), B-266: (I) + (I.2.2), B-267: (I) + (I.2.3), B-268: (I) + (I.2.4), B-269: (I) + (I.2.5), B-270: (I) + (J.1.1), B-271: (I) + (J.1.2), B-272: (I) + (J.1.3), B-273: (I) + (J.1.4), B- 274: (I) + (J.1.5), B-275: (I) + (J.1.6), B-276: (I) + (J.1.7), B-277: (I) + (J.1.8), B-278: (I) + (J.1.9), B-279: (I) + (J.1.10), B-280: (I) + (K.1.1), B-281: (I) + (K.1.2), B-282: (I) + (K.1.3), B-283: (I) + (K.1.4), B-284: (I) + (K.1.5), B-285: (I) + (K.1.6), B-286: (I) + (K.1.7), B-287: (I) + (K.1.8), B-288: (I) + (K.1.9), B-289: (I) + (K.1.10), B-290: (I) + (K.1.11), B-291: (I) + (K.1.12), B-292: (I) +

(K.1.13), B-293: (I) + (K.1.14), B-294: (I) + (K.1.15), B-295: (I) + (K.1.16), B-296: (I) + (K.1.17), B-297: (I) + (K.1.18), B-298: (I) + (K.1.19), B-299: (I) + (K.1.20), B-300: (I) + (K.1.21), B-301: (I) + (K.1.22), B-302: (I) + (K.1.23), B-303: (I) + (K.1.24), B-304: (I) + (K.1.25), B-305: (I) + (K.1.26), B-306: (I) + (K.1.27), B-307: (I) + (K.1.28), B-308: (I) + (K.1.29), B-309: (I) + (K.1.30), B-310: (I) + (K.1.31), B-311: (I) + (K.1.32), B-312: (I) + (K.1.33), B-313: (I) + (K.1.34), B-314: (I) + (K.1.35), B-315: (I) + (K.1.36), B-316: (I) + (K.1.37), B-317: (I) + (K.1.38), B-318: (I) + (K.1.39), B-319: (I) + (K.1.40), B-320: (I) + (K.1.41), B-321: (I) + (K.1.42), B-322: (I) + (K.1.43), B-323: (I) + (K.1.44), B-324: (I) + (K.1.45), B-325: (I) + (K.1.46), B-326: (I) + (K.1.47), B-327: (I) + (K.1.48), B-328: (I) + (K.1.49), B-329: (I) + (K.1.50), B-330: (I) + (K.1.51), B-331: (I) + (K.1.52), B-332: (I) + (K.1.53), B-333: (I) + (K.1.54), B-334: (I) + (0.1.1), B-335: (I) + (0.1.2), B-336: (I) + (0.1.3), B-337: (I) + (0.1.4), B-338: (I) + (0.1.5), B-339: (I) + (0.1.6), B-340: (I) + (0.1.7), B-341: (I) + (0.1.8), B-342: (I) + (0.1.9), B-343: (I) + (0.1.10), B-344: (I) + (0.1.11), B-345: (I) + (0.1.12), B-346: (I) +

(0.1.13), B-347: (I) + (0.1.14), B-348: (I) + (0.1.15), B-349: (I) + (0.1.16), B-350: (I) + (0.1.17), B-351: (I) + (0.1.18), B-352: (I) + (0.1.19), B-353: (I) + (0.1.20), B-354: (I) + (0.1.21), B-355: (I) + (0.1.22), B-356: (I) + (0.1.23), B-357: (I) + (0.1.24), B-358: (I) + (0.1.25), B-359: (I) +

(0.1.26), B-360: (I) + (0.1.27), B-361: (I) + (0.1.28), B-362: (I) + (0.1.29), B-363: (I) + (0.1.30), B-364: (I) + (0.1.31), B-365: (I) + (0.1.32), B-366: (I) + (0.1.33), B-367: (I) + (0.1.34), B-368: (I) + (0.1.35), B-369: (I) + (0.1.36), B-370: (I) + (0.1.37), B-371: (I) + (0.1.38), B-372: (I) +

(0.1.39), B-373: (I) + (0.1.40), B-374: (I) + (0.1.41), B-375: (I) + (0.1.42), B-376: (I) + (0.1.43), B-377: (I) + (0.1.44), B-378: (I) + (0.1.45), B-379: (I) + (0.1.46), B-380: (I) + (0.1.47), B-381: (I) + (0.1.48), B-382: (I) + (0.1.49), B-383: (I) + (0.1.50), B-384: (I) + (0.1.51), B-385: (I) +

(0.1.52), B-386: (I) + (0.1.53), B-387: (I) + (0.1.54), B-388: (I) + (0.1.55), B-389: (I) + (0.1.56), B-390: (I) + (0.1.57), B-391: (I) + (0.1.58), B-392: (I) + (0.1.59), B-393: (I) + (0.1.60), B-394: (I) + (0.1.61), B-395: (I) + (0.1.62), B-396: (I) + (0.1.63), B-397: (I) + (0.1.64), B-398: (I) +

(0.1.65), B-399: (I) + (0.1.66), B-400: (I) + (0.1.67), B-401: (I) + (0.1.68), B-402: (I) + (0.1.69), B-403: (I) + (0.1.70), B-404: (I) + (0.1.71), B-405: (I) + (0.1.72), B-406: (I) + (0.1.73), B-407: (I) + (0.1.74), B-408: (I) + (0.1.75), B-409: (I) + (0.1.76), B-410: (I) + (0.1.77), B-411: (I) +

(0.1.78), B-412: (I) + (0.1.79), B-413: (I) + (0.1.80), B-414: (I) + (0.1.81), B-415: (I) + (0.1.82), B-416: (I) + (0.1.83), B-417: (I) + (0.1.84), B-418: (I) + (0.1.85), B-419: (I) + (0.1.86), B-420: (I) + (0.1.87), B-421: (I) + (0.1.88), B-422: (I) + (0.1.89), B-423: (I) + (0.1.90), B-424: (I) +

(0.1.91), B-425: (I) + (0.2.1), B-426: (I) + (0.2.2), B-427: (I) + (0.2.3), B-428: (I) + (0.2.4), B- 429: (I) + (0.2.5), B-430: (I) + (0.2.6), B-431: (I) + (0.2.7), B-432: (I) + (0.3.1), B-433: (I) +

(0.3.2), B-434: (I) + (0.3.3), B-435: (I) + (0.3.4), B-436: (I) + (0.3.5), B-437: (I) + (0.3.6), B-438: (I) + (0.3.7), B-439: (I) + (0.3.8), B-440: (I) + (0.3.9), B-441: (I) + (0.3.10), B-442: (I) + (0.3.11), B-443: (I) + (0.3.12), B-444: (I) + (0.3.13), B-445: (I) + (0.3.14), B-446: (I) + (0.3.15), B-447: (I) + (0.3.16), B-448: (I) + (0.3.17), B-449: (I) + (0.3.18), B-450: (I) + (0.3.19), B-451: (I) +

(O.3.20), B-452: (I) + (0.3.21), B-453: (I) + (0.3.22), B-454: (I) + (0.3.23), B-455: (I) + (0.3.24), B-456: (I) + (0.3.25), B-457: (I) + (0.3.26), B-458: (I) + (0.3.27), B-459: (I) + (0.3.28), B-460: (I) + (0.3.29), B-461: (I) + (O.3.30), B-462: (I) + (0.3.31), B-463: (I) + (0.3.32), B-464: (I) +

(0.3.33), B-465: (I) + (0.3.34), B-466: (I) + (0.3.35), B-467: (I) + (0.3.36), B-468: (I) + (0.3.37), B-469: (I) + (0.3.38), B-470: (I) + (0.3.39), B-471 : (I) + (O.3.40), B-472: (I) + (0.3.41), B-473: (I) + (0.3.42), B-474: (I) + (0.3.43), B-475: (I) + (0.3.44), B-476: (I) + (0.3.45), B-477: (I) +

(0.3.46), B-478: (I) + (0.3.47), B-479: (I) + (0.3.48), B-480: (I) + (0.3.49), B-481: (I) + (O.3.50), B-482: (I) + (0.3.51), B-483: (I) + (0.3.52), B-484: (I) + (0.4.1), B-485: (I) + (0.4.2), B-486: (I) + (0.4.3), B-487: (I) + (0.4.4), B-488: (I) + (0.4.5), B-489: (I) + (0.4.6), B-490: (I) + (0.4.7), B-491: (I) + (0.4.8), B-492: (I) + (0.4.9), B-493: (I) + (0.4.10), B-494: (I) + (0.4.1 1 ), B-495: (I) +

(0.4.12), B-496: (I) + (0.4.13), B-497: (I) + (0.4.14), B-498: (I) + (0.4.15), B-499: (I) + (0.5.1 ), B-500: (I) + (0.5.2), B-501 : (I) + (0.6.1 ), B-502: (I) + (0.6.2), B-503: (I) + (0.6.3), B-504: (I) + (0.6.4), B-505: (I) + (0.6.5), B-506: (I) + (0.7.1 ), B-507: (I) + (0.7.2), B-508: (I) + (0.7.3), B-509: (I) + (0.7.4), B-510: (I) + (0.7.5), B-51 1 : (I) + (0.8.1 ), B-512: (I) + (0.8.2), B-513: (I) + (0.8.3), B-514: (I) + (0.8.4), B-515: (I) + (0.8.5), B-516: (I) + (0.9.1 ), B-517: (I) + (0.9.2), B-518: (I) + (0.9.3), B-519: (I) + (O.10.1 ), B-520: (I) + (O.10.2), B-521 : (I) + (O.10.3), B-522: (I) + (O.10.4), B-523: (I) + (0.1 1 .1 ), B-524: (I) + (0.1 1 .2), B-525: (I) + (0.1 1 .3), B-526: (I) + (0.1 1 .4), B-527: (I) + (0.1 1 .5), B-528: (I) + (0.1 1 .6), B-529: (I) + (0.1 1 .7), B-530: (I) + (0.1 1 .8), B-531 : (I) +

(0.1 1 .9), B-532: (I) + (0.1 1 .10), B-533: (I) + (0.1 1 .1 1 ), B-534: (I) + (0.1 1 .12), B-535: (I) +

(0.1 1 .13), B-536: (I) + (0.12.1 ), B-537: (I) + (0.12.2), B-538: (I) + (0.12.3), B-539: (I) +

(0.12.4), B-540: (I) + (0.12.5), B-541 : (I) + (0.12.6), B-542: (I) + (0.13.1 ), B-543: (I) + (0.13.2), B-544: (I) + (0.13.3), B-545: (I) + (0.14.1 ), B-546: (I) + (0.14.2), B-547: (I) + (0.14.3), B-548: (I) + (0.14.4), B-549: (I) + (0.15.1 ), B-550: (I) + (0.15.2), B-551 : (I) + (0.15.3), B-552: (I) +

(0.15.4), B-553: (I) + (0.15.5), B-554: (I) + (0.15.6), B-555: (I) + (0.15.7), B-556: (I) + (0.15.8), B-557: (I) + (0.15.9), B-558: (I) + (O.15.10), B-559: (I) + (0.15.1 1 ), B-560: (I) + (0.16.1 ), B-561 : (I) + (0.17.1 ), B-562: (I) + (0.18.1 ), B-563: (I) + (0.18.2), B-564: (I) + (0.18.3), B-565: (I) +

(0.18.4), B-566: (I) + (0.18.5), B-567: (I) + (0.19.1 ), B-568: (I) + (O.20.1 ), B-569: (I) + (O.20.2), B-570: (I) + (O.20.3), B-571 : (I) + (O.20.4), B-572: (I) + (0.21 .1 ), B-573: (I) + (0.21 .2), B-574: (I) + (0.21 .3), B-575: (I) + (0.21 .4), B-576: (I) + (0.21 .5), B-577: (I) + (0.21 .6), B-578: (I) +

(0.21 .7), B-579: (I) + (0.22.1 ), B-580: (I) + (0.22.2), B-581 : (I) + (0.22.3), B-582: (I) + (0.22.4), B-583: (I) + (0.23.1 ), B-584: (I) + (0.23.2), B-585: (I) + (0.23.3), B-586: (I) + (0.23.4), B-587: (I) + (0.24.1 ), B-588: (I) + (0.24.2), B-589: (I) + (0.24.3), B-590: (I) + (0.24.4), B-591 : (I) +

(0.24.5), B-592: (I) + (0.25.1 ), B-593: (I) + (0.25.2), B-594: (I) + (0.26.1 ), B-595: (I) + (0.26.2), B-596: (I) + (0.26.3), B-597: (I) + (0.26.4), B-598: (I) + (0.26.5), B-599: (I) + (0.26.6), B-600: (I) + (0.26.7), B-601 : (I) + (0.26.8), B-602: (I) + (0.26.9), B-603: (I) + (0.26.10), B-604: (I) +

(0.26.1 1 ), B-605: (I) + (0.26.12), B-606: (I) + (0.26.13), B-607: (I) + (0.26.14), B-608: (I) +

(0.26.15), B-609: (I) + (0.26.16), B-610: (I) + (0.26.17), B-61 1 : (I) + (0.26.18), B-612: (I) +

(0.27.1 ), B-613: (I) + (0.28.1 ), B-614: (I) + (0.28.2), B-615: (I) + (0.28.3), B-616: (I) + (0.28.4), B-617: (I) + (0.28.5), B-618: (I) + (0.28.7), B-619: (I) + (0.28.8), B-620: (I) + (0.28.9), B-621 : (I) + (O.28.10), B-622: (I) + (0.28.1 1 ), B-623: (I) + (0.28.12), B-624: (I) + (0.28.13), B-625: (I) +

(0.28.14), B-626 (I) + (0.28.15), B- 627 (I) + (0.28.16), B-628 (I) + (0.28.17), B-629 (I) +

(0.28.18), B-630 (I) + (0.28.19), B- 631 (I) + (O.28.20), B-632 (I) + (0.28.21 ), B-633 (I) +

(0.28.22), B-634 (I) + (0.28.23), B- 635 (I) + (0.28.24), B-636 (I) + (0.28.25), B-637 (I) +

(0.28.26), B-638 (I) + (0.28.27), B- 639 (I) + (0.28.28), B-640 (I) + (0.28.29), B-641 (I) +

(O.28.30), B-642 (I) + (0.28.31 ), B- 643 (I) + (0.28.42), B-644 (I) + (0.28.43), B-645 (I) +

(0.28.44), B-646 (I) + (0.28.45), B- 647 (I) + (0.28.46), B-648 (I) + (0.28.47), B-649 (I) +

(0.28.48), B-650 (I) + (0.28.49), B- 651 (I) + (O.28.50), B-652 (I) + (0.28.51 ), B-653 (I) +

(0.28.52), B-654 (I) + (0.28.53), B- 655 (I) + (0.28.54), B-656 (I) + (0.28.55), B-657 (I) +

(0.28.56), B-658 (I) + (0.28.57), B- 659 (I) + (0.28.58), B-660 (I) + (0.28.59), B-661 (I) +

(O.28.60), B-662 (I) + (0.28.61 ), B- 663 (I) + (0.28.62), B-664 (I) + (0.28.63), B-665 (I) +

(0.28.64), B-666 (I) + (0.28.65), B- 667 (I) + (0.28.66), B-668 (I) + (0.28.67), B-669 (I) +

(0.28.68), B-670 (I) + (0.28.69), B- 671 (I) + (O.28.70), B-672 (I) + (0.28.71 ), B-673 (I) +

(0.28.72), B-674 (I) + (0.28.73), B- 675 (I) + (0.28.74), B-676 (I) + (0.28.75), B-677 (I) + (0.28.76), B-678: (I) + (0.28.77), B-679: (I) + (0.28.78), B-680: (I) + (0.28.79), B-681 : (I) + (O.28.80), B-682: (I) + (0.28.81 ), B-683: (I) + (0.28.82).

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 reference is made to the explanations given for the compositions containing compounds I.

The mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the

Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). In addition, it is refered to the explanations regarding the fungicidal activity of the compounds and the compositions containing compounds I, respectively.

I. Synthesis

This example illustrates the preparation of 4-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]-1 H-tetrazol-5-one (Ex-2)

1.1 ) Preparation of 1 -iodo-4-(isocyanatomethyl)benzene

To a solution of triphosgene (51.0 g, 171.64 mmol) in dichloromethane (500 ml.) was added a suspension of (4-iodophenyl)methanamine (40.0 g, 171.64 mmol) dropwise at 0°C. Then to the mixture was added triethylamine (34.7 g, 343.28 mmol) in dichloromethane (500 ml.) dropwise at 0°C. Then the reaction was stirred at 20°C for 8 hours. The mixture was poured into water and extracted with dichloromethane. The organic layers were washed with brine dried over sodium sulfate, filtered and concentrated. The title compound was used directly without further purification. 1.2) Preparation of 4-[(4-iodophenyl)methyl]-1 H-tetrazol-5-one

The suspension of 1 -iodo-4-(isocyanatomethyl)benzene (5.0 g, 19.3 mmol) in trimethylsilyl azide (4.5 g, 38.6 mmol) was stirred at 100°C for 8 hours. The mixture was purified by flash chromatography to afford the title compound (2.0 g, 34%) as a yellow solid. 1.3) Preparation of 1 -[(4-iodophenyl)methyl]-4-(2-trimethylsilylethoxymethyl)tetrazol-5-one

To a suspension of 4-[(4-iodophenyl)methyl]-1 H-tetrazol-5-one (2.0 g, 6.62 mmol) in acetonitrile (30 ml.) was added potassium carbonate (1 .8 g, 13.24 mmol) in portions and 2- (trimethylsilyl)ethoxymethyl chloride (1 .3 g, 7.95 mmol) dropwise. Then the reaction

was stirred at 70°C for 8 hours. The mixture was filtered and the filtrate was concentrated. The crude product was purified by flash chromatography to afford the title compound (1 .6 g, 56%) as a yellow oil. 1H NMR (400 MHz, CDCI3): δ = 7.71 (d, 2H), 7.15 (d, 2H), 5.31 - 5.29 (m, 2H), 5.05 (s, 2H), 3.70 - 3.59 (m, 2H), 0.97 - 0.92 (m, 2H), 0.01 - 0.04 (m, 9H).

1.4) Preparation of 4-[[5-oxo-4-(2-trimethylsilylethoxymethyl)tetrazol-1 -yl]methyl]benzonitrile To a solution of 1 -[(4-iodophenyl)methyl]-4-(2-trimethylsilylethoxymethyl)tetrazol-5-one (1.6 g, 3.70 mmol) in A ,AAdimethylformamide (20 ml.) was added zinc cyanide (869 mg, 7.40 mmol) and tetrakis(triphenylphosphine)palladium(0) (855 mg, 0.74 mmol) under nitrogen atmosphere. Then the reaction was stirred at 100°C for 3 hours. The mixture was filtered and water was added to the filtrate. Then the mixture was extracted with ethyl acetate. The organic layers were combined, washed with brine dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to afford the title compound (650 mg, 53% ) as yellow oil. 1H NMR (400 MHz, CDCI3): δ = 7.67 (d, 2H), 7.50 (d, 2H), 5.31 (s, 2H), 5.17 (s, 2H), 3.72 - 3.63 (m, 2H), 1.01 - 0.89 (m, 2H), 0.04 - 0.09 (m, 9H). 1.5) Preparation of N-hydroxy-4-[[5-oxo-4-(2-trimethylsilylethoxymethyl)tetrazol-1 - yl]methyl]benzamidine

To a solution of 4-[[5-oxo-4-(2-trimethylsilylethoxymethyl)tetrazol-1 -yl]methyl]benzonitrile (650 mg, 1 .96 mmol) in ethanol (10 ml.) was added hydroxylamine hydrochloride (164 mg, 2.35 mmol) and triethylamine (397 mg, 3.92 mmol), then the reaction was stirred at 50°C for 5 hours. The mixture was concentrated to afford the title compound (1 .3 g, crude) and used directly without further purification. H NMR (400 MHz, CDCI3): δ = 7.62 (d, 2H), 7.46 - 7.37 (m, 2H), 5.34 - 5.28 (m, 2H), 5.16 - 5.05 (m, 2H), 4.86 (br s, 2H), 3.76 - 3.62 (m, 3H), 1.00 - 0.88 (m, 2H), -0.02 (s, 9H) 1.6) Preparation of 1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-4-(2- trimethylsilylethoxymethyl)tetrazol-5-one

To a solution of N-hydroxy-4-[[5-oxo-4-(2-trimethylsilylethoxymethyl)tetrazol-1 - yl]methyl]benzamidine (1 .3 g, 3.57 mmol) in dimethylacetamide (30 ml.) was added

trifluoroacetic anhydride (1 .5 g, 7.13 mmol) at 0°C. Then the reaction was stirred at 15°C for 8 hours. The mixture was quenched with a saturated aqueous solution of sodium hydrogen carbonate (30 ml_). Then the suspended solid was filtered, the cake was dissolved in methyl fe/7-butylether and washed with brine, dried over sodium sulfate, filtered and concentrated to the title compound (650 mg, 75% over two steps) as yellow oil. 1H NMR (400 MHz, CDCI3): δ = 8.13 (d, 2H), 7.55 (d, 2H), 5.37 - 5.30 (m, 2H), 5.20 (s, 2H), 3.79 - 3.65 (m, 2H), 1.00 - 0.86 (m, 2H), 0.04 -0.06 (m, 9H).

1.7) Preparation of 4-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-1 H-tetrazol-5- one To a solution of 1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-4-(2- trimethylsilylethoxymethyl)tetrazol-5-one (600 mg, 1.36 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (1 mL) at 0°C, then the reaction was stirred at 30°C for 3 hours. After addition of water (10 mL) the reaction mixture was washed three times with a saturated aquous solution of sodium hydrogen carbonate (10 mL). The combined organic phase was dried over sodium sulfate, filtered and concentrated to obtain the crude product. The crude product was washed with n- exane, filtered, and the solid was concentrated to afford the title compound (130 mg, 31 %) as a yellow solid. 1H NMR (400 MHz, CDCI3): δ = 8.14 (d, 2H), 7.55 (d, 2H), 5.48 (s, 1 H), 5.19 (s, 2H).

The compounds listed in Table I were prepared in an analogous manner.

Table I: Compounds Ex-1 and Ex-2 of the formula I.Ex, wherein the meaning of the variables are as defined in each line.

Figure imgf000061_0001

Figure imgf000061_0002

* HPLC: High Performance Liquid Chromatography; HPLC-column Kinetex XB C18 1 ,7μ (50 2,1 mm); eluent: acetonitrile / water + 0.1 % trifluoroacetic acid (gradient from 5:95 to 100 : 0 1 .5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1 .5 min). MS:

Quadrupol Electrospray lonisation, 80 V (positive mode). Rt: retention time in minutes.

II. Biological examples for fungicidal activity The fungicidal action of the compounds of formula I was demonstrated by the following experiments: The spray solutions were prepared in several steps: The stock solution were prepared by mixting acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) solvent-emulsifier of 99 to 1 . This mixture was added to 25 mg of the compound to give a total of 5 mL. Water was then added to total volume of 100 mL. This stock solution was diluted with the described solvent- emulsifier-water mixture to the given concentration. 11.1 ) Curative control of soy bean rust on soy beans caused by Phakopsora pachyrhizi

Leaves of pot-grown soy bean seedlings were inoculated with spores of Phakopsora pachyrhizi. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and 20 to 24°C for 24 hours. The next day the plants were cultivated for 3 days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. Then the plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. Then the trial plants were cultivated for 14 days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 63 ppm of the active compound Ex-1 showed a diseased leaf area of at most 1 %, whereas the untreated plants showed 100% diseased leaf area.

11.2) Protective control of soy bean rust on soy beans caused by Phakopsora pachyrhizi Leaves of pot-grown soy bean seedlings were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. The trial plants were cultivated for 2 day in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. Then the plants were inoculated with spores of Phakopsora pachyrhizi. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and 20 to 24°C for 24 hours. The trial plants were cultivated for fourteen days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 63 ppm of the active compounds Ex-1 and Ex-2 showed a diseased leaf area of at most 7%, whereas the untreated plants showed 90% diseased leaf area. 11.3) Curative control of brown rust on wheat caused by Puccinia recondita

The first two developed leaves of pot-grown wheat seedling were dusted with spores of

Puccinia recondita. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber without light and a relative humidity of 95 to 99% and 20 to 24°C for 24 hours. The next day the plants were cultivated for 3 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%. Then the plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. Then the trial plants were cultivated for 8 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 63 ppm of the active compound Ex-1 showed a diseased leaf area of 4%, whereas the untreated plants showed 90% diseased leaf area. 11.4) Preventative control of brown rust on wheat caused by Puccinia recondita

The first two developed leaves of pot-grown wheat seedling were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The next day the plants were inoculated with spores of Puccinia recondita. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber without light and a relative humidity of 95 to 99% and 20 to 24°C for 24 hours. Then the trial plants were cultivated for 6 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 63 ppm of the active compounds Ex-1 and Ex-2 showed a diseased leaf area of at most 25%, whereas the untreated plants showed 90% diseased leaf area.

Claims

Claims
1 . Compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof,
Figure imgf000064_0001
is phenyl or a 5- or 6-membered aromatic heterocycle; wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N , O and S as ring member atoms; and wherein the phenyl ring or the aromatic heterocycle is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or
Ci-C6-haloalkoxy;
is -C(=0)- or -C(=S)-;
is hydrogen, formyl, Ci-C6-alkyl, Ci-C6-alkoxy, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxyimino-Ci-C4-alkyl, C2-C6-alkenyloxyimino- Ci-C4-alkyl, C2-C6-alkynyloxyimino-Ci-C4-alkyl, -C(=0)R2, -C(=0)OR2, -C(=0)N H2, -C(=0)N H R2,
Figure imgf000064_0002
phenyl-Ci-C4-alkyl, phenyl-Ci-C4-alkenyl, phenyl- Ci-C4-alkynyl, heteroaryl-Ci-C4-alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N , O and S as ring member atoms; and wherein the heteroaryl group in the group heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N , O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different groups R1 a;
R1 is a bicyclic carbocycle of the formula Ra
H
X CA
Ra
c-
H'
wherein
Ca and Cb are bridgehead carbon atoms;
X is a direct single bond or a divalent group selected from the group consisting of -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-, -CH2-CH=CH-,
-CH=CH-CH2- and -CH=CH-CH=CH-;
Y and Z independently of each other are a divalent group selected from the group consisting of -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-,
-CH2-CH=CH-, -CH=CH-CH2- and -CH=CH-CH=CH-;
is a tricyclic carbocycle of the formula Rb
H
Figure imgf000065_0001
wherein
Ca and Cb are bridgehead carbon atoms;
X is a direct single bond or a divalent group selected from the group consisting of -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-, -CH2-CH=CH-,
-CH=CH-CH2- and -CH=CH-CH=CH-;
Y and Z independently of each other are a divalent group selected from the group consisting of -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-,
-CH2-CH=CH-, -CH=CH-CH2- and -CH=CH-CH=CH-; and wherein groups Y and Z are attached to the bridgehead carbon atoms Ca and Cb;
T is a divalent group selected from the group consisting of -CH2-, -CH2-CH2- , -(CH2)3-, -(CH2)4-, -CH=CH-, -CH2-CH=CH-, -CH=CH-CH2- and
-CH=CH-CH=CH-; and wherein the group T is attached to one carbon atom in each of the groups Y and Z;
and with the proviso that, if R1 is a tricyclic carbocycle of the formula Rb, wherein X is a direct single bond or a divalent group -CH2-, the groups T and Z independently of each other are a divalent group selected from the group consisting of -CH2-CH2- , -(CH2)3-, -(CH2)4-, -CH=CH-, -CH2-CH=CH-, -CH=CH-CH2- and -CH=CH-CH=CH-; and wherein the groups Ra or Rb are connected to the the remainder of the compounds of the formula I through one of the ring carbon atoms; and wherein the groups Ra or Rb are unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of radicals selected from the group consisting of oxo, hydroxy, halogen, Ci-C3-alkyl, Ci-C3-haloalkyl, C3-C6-cycloalkyl, vinylidene and
dichlorovinylidene;
is halogen, oxo, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C3- cycloalkyl, -NHS02-Ci-C4-alkyl, (C=0)-Ci-C4-alkyl, C(=0)-Ci-C4-alkoxy, Ci-C6- alkylsulfonyl, hydroxyCi-C4-alkyl, C(=0)-NH2, C(=0)-NH(Ci-C4-alkyl), Ci-C4- alkylthio-Ci-C4-alkyl, aminoCi-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, diCi-C4- alkylamino-Ci-C4-alkyl, aminocarbonyl-Ci-C4-alkyl or Ci-C4-alkoxy-Ci-C4-alkyl;
is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy or C3-C8-cycloalkyl; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, oxo, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, aminoCi-C4-alkyl, C1-C4- alkylamino-Ci-C4-alkyl, diCi-C4-alkylamino-Ci-C4-alkyl or Ci-C4-alkoxy-Ci-C4-alkyl; m is 0, 1 or 2;
R3, R4 independently of each other are selected from the group consisting of hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-alkenyl, Ci-C4-alkynyl, Ci-C4-haloalkyl and
Ci-C4-alkoxy; or
R3 and R4 together with the carbon atom to which they are bound form a saturated 3- to 7-membered carbocycle or a saturated 3- to 6-membered heterocycle; wherein the saturated heterocycle includes beside carbon atoms 1 , 2 or 3 heteroatoms independently selected from the group consisiting of N, O and S as ring member atoms; and wherein said N ring member atom is substituted with the group RN; wherein
RN is hydrogen, Ci-C6-alkyl or halogen;
and wherein said S ring member atom is unsubstituted or substituted with 1 or 2 oxo radicals; and wherein one or two CH2 groups of the saturated carbocycle or of the saturated heterocycle may be replaced by one or two groups independently selected from -C(=0)- and -C(=S)-; and wherein the carbon ring member atoms of the saturated carbocycle or of the saturated heterocycle are unsubstituted or substituted with a total number of 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C1-C6- alkyl, Ci-C6-alkoxy and Cs-Cs-cycloalkyl.
Compounds according to claim 1 , wherein A in compounds of the formula I is phenyl.
Compounds according to claim 1 , of the formula 1.1 , or the N-oxides, or the agriculturally acceptable salts t
Figure imgf000066_0001
wherein n is 0 or 1 , and wherein the meaning of the variables RA, W, m, R3, R4 and R1 are as defined in claim 1 for compounds of the formula I.
Compounds according to any one of claims 1 to 3, wherein n is 0.
Compounds according to any one of claims 1 to 4, wherein m is 1 and radicals R3 and R4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl or trifluoromethyl; or R3 and R4 together with the carbon atom to which they are bound form a cyclopropyl ring.
Compounds according to any one of claims 1 to 5, wherein W is -C(=0)-. Compounds according to any one of claims 1 to 6, wherein m is 0. Compounds according to any one of claims 1 to 7, wherein R1 is hydrogen, methyl, ethyl, /7-propyl, /so-propyl, /7-butyl, /so-butyl, sec-butyl, fe/f-butyl or cyclopropyl.
An agrochemical composition, which comprises an auxiliary and at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, as defined in any one of claims 1 to 8.
An agrochemical composition according to claim 9, further comprising seed, wherein the amount of the compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, is from 0.1 g to 10 kg per 100 kg of seed.
1 1 . The use of compounds as defined in any one of claims 1 to 8 for combating
phytopathogenic harmful fungi.
12. A method for combating phytopathogenic harmful fungi, which process comprises treating the fungi, the plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I , or an N-oxide, or an agriculturally acceptable salt thereof, as defined in any one of claims 1 to 8.
PCT/EP2018/066854 2017-06-30 2018-06-25 Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi WO2019002158A1 (en)

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Citations (97)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 SHIONOGI &amp; CO., LTD. Azolyl cycloalkanol derivatives and agricultural fungicides
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
WO1994001546A1 (en) 1992-07-01 1994-01-20 Cornell Research Foundation, Inc. Elicitor of the hypersensitive response in plants
EP0638561A1 (en) 1993-08-05 1995-02-15 Nihon Bayer Agrochem K.K. Process for the production of 1-substituted-5(4H)-tetrazolinones
WO1998001431A1 (en) 1996-07-03 1998-01-15 Nissan Chemical Industries, Ltd. Carbamoyltetrazolinones and herbicides
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
JPH11180965A (en) 1997-12-24 1999-07-06 Nissan Chem Ind Ltd New carbamoyltetrazolinone and herbicide
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
CN1309897A (en) 2000-02-24 2001-08-29 沈阳化工研究院 Unsaturated oximino ether bactericide
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
EP1201648A1 (en) 1999-08-05 2002-05-02 IHARA CHEMICAL INDUSTRY Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003016303A1 (en) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
CN1456054A (en) 2003-03-25 2003-11-19 浙江省化工研究院 Methoxy methyl acrylate compounds as bactericidal agent
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2006013104A1 (en) 2004-08-05 2006-02-09 Santhera Pharmaceuticals (Schweiz) Ag Heterocyclic compounds useful as dpp- iv inhibitors
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
WO2007006670A1 (en) 2005-07-07 2007-01-18 Basf Aktiengesellschaft N-thio-anthranilamid compounds and their use as pesticides
CN1907024A (en) 2005-08-03 2007-02-07 浙江化工科技集团有限公司 Methoxyl group displacement methyl acrylate compound bactericidal agent
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
WO2007129454A1 (en) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. 1,2-benzisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
WO2008013622A2 (en) 2006-07-27 2008-01-31 E. I. Du Pont De Nemours And Company Fungicidal azocyclic amides
EP1932843A1 (en) 2006-12-14 2008-06-18 sanofi-aventis Sulfonyl-phenyl-2H-(1,2,4) oxadiazole-5-one derivatives, processes for their preparation and their use as pharmaceuticals
WO2009074950A2 (en) 2007-12-10 2009-06-18 Actelion Pharmaceuticals Ltd Thiophene derivatives as agonists of s1p1/edg1
WO2009090181A2 (en) 2008-01-15 2009-07-23 Bayer Cropscience Sa Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
WO2009094442A2 (en) 2008-01-22 2009-07-30 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives as fungicides
WO2010069882A1 (en) 2008-12-17 2010-06-24 Syngenta Participations Ag Isoxazole derivatives for use as fungicides
WO2010139271A1 (en) 2009-06-05 2010-12-09 中国中化股份有限公司 E-type phenyl acrylic ester compounds containing substituted anilino pyrimidine group and uses thereof
WO2011028657A1 (en) 2009-09-01 2011-03-10 Dow Agrosciences Llc Synergistic fungicidal compositions containing a 5-fluoropyrimidine derivative for fungal control in cereals
WO2011054871A1 (en) 2009-11-06 2011-05-12 Bayer Cropscience Ag Insecticidal arylpyrroline compounds
WO2011077514A1 (en) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Plant disease control composition and method for controlling plant diseases by applying the composition
WO2011081174A1 (en) 2010-01-04 2011-07-07 日本曹達株式会社 Nitrogen-containing heterocyclic compound and agricultural/horticultural germicide
WO2011135833A1 (en) 2010-04-28 2011-11-03 Sumitomo Chemical Company, Limited Plant disease control composition and its use
WO2012084812A1 (en) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
WO2012165511A1 (en) 2011-05-31 2012-12-06 クミアイ化学工業株式会社 Method for controlling diseases in rice plant
WO2012168188A1 (en) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Active compound combinations
WO2013008162A1 (en) 2011-07-08 2013-01-17 Novartis Ag Novel trifluoromethyl-oxadiazole derivatives and their use in the treatment of disease
WO2013007767A1 (en) 2011-07-13 2013-01-17 Basf Se Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013010862A1 (en) 2011-07-15 2013-01-24 Basf Se Fungicidal alkyl-substituted 2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013024009A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013024010A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013047749A1 (en) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Production method for 4, 4-difluoro-3,4-dihydroisoquinoline derivative
WO2013047441A1 (en) 2011-09-26 2013-04-04 日本曹達株式会社 Agricultural and horticultural bactericide composition
WO2013092224A1 (en) 2011-12-21 2013-06-27 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi resistant to qo inhibitors
WO2013116251A2 (en) 2012-02-01 2013-08-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazole mixtures
WO2013127704A1 (en) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Active compound combinations containing a thiazoylisoxazoline and a fungicide
WO2013162072A1 (en) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Tetrazolinone compounds and its use as pesticides
CN103387541A (en) 2012-05-10 2013-11-13 中国中化股份有限公司 Preparation method of substituted pyrazolylether compound
WO2014060177A1 (en) 2012-10-16 2014-04-24 Syngenta Participations Ag Fungicidal compositions
WO2014065413A1 (en) 2012-10-26 2014-05-01 日本たばこ産業株式会社 Triazole-isoxazole compound and medical use thereof
WO2015041360A1 (en) 2013-09-20 2015-03-26 住友化学株式会社 Tetrazolinone compound and use thereof
EP2865265A1 (en) 2014-02-13 2015-04-29 Bayer CropScience AG Active compound combinations comprising phenylamidine compounds and biological control agents
WO2015065922A1 (en) 2013-10-28 2015-05-07 Dexcom, Inc. Devices used in connection with continuous analyte monitoring that provide the user with one or more notifications, and related methods
WO2015185485A1 (en) * 2014-06-06 2015-12-10 Basf Se Use of substituted oxadiazoles for combating phytopathogenic fungi
WO2017085098A1 (en) 2015-11-19 2017-05-26 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2017085100A1 (en) 2015-11-19 2017-05-26 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2017093348A1 (en) 2015-12-02 2017-06-08 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017118689A1 (en) * 2016-01-08 2017-07-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives

Patent Citations (97)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 SHIONOGI &amp; CO., LTD. Azolyl cycloalkanol derivatives and agricultural fungicides
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
WO1994001546A1 (en) 1992-07-01 1994-01-20 Cornell Research Foundation, Inc. Elicitor of the hypersensitive response in plants
EP0638561A1 (en) 1993-08-05 1995-02-15 Nihon Bayer Agrochem K.K. Process for the production of 1-substituted-5(4H)-tetrazolinones
WO1998001431A1 (en) 1996-07-03 1998-01-15 Nissan Chemical Industries, Ltd. Carbamoyltetrazolinones and herbicides
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
JPH11180965A (en) 1997-12-24 1999-07-06 Nissan Chem Ind Ltd New carbamoyltetrazolinone and herbicide
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
EP1201648A1 (en) 1999-08-05 2002-05-02 IHARA CHEMICAL INDUSTRY Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
CN1309897A (en) 2000-02-24 2001-08-29 沈阳化工研究院 Unsaturated oximino ether bactericide
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003016303A1 (en) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
CN1456054A (en) 2003-03-25 2003-11-19 浙江省化工研究院 Methoxy methyl acrylate compounds as bactericidal agent
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2006013104A1 (en) 2004-08-05 2006-02-09 Santhera Pharmaceuticals (Schweiz) Ag Heterocyclic compounds useful as dpp- iv inhibitors
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
WO2007006670A1 (en) 2005-07-07 2007-01-18 Basf Aktiengesellschaft N-thio-anthranilamid compounds and their use as pesticides
CN1907024A (en) 2005-08-03 2007-02-07 浙江化工科技集团有限公司 Methoxyl group displacement methyl acrylate compound bactericidal agent
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
WO2007129454A1 (en) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. 1,2-benzisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
WO2008013622A2 (en) 2006-07-27 2008-01-31 E. I. Du Pont De Nemours And Company Fungicidal azocyclic amides
EP1932843A1 (en) 2006-12-14 2008-06-18 sanofi-aventis Sulfonyl-phenyl-2H-(1,2,4) oxadiazole-5-one derivatives, processes for their preparation and their use as pharmaceuticals
WO2009074950A2 (en) 2007-12-10 2009-06-18 Actelion Pharmaceuticals Ltd Thiophene derivatives as agonists of s1p1/edg1
WO2009090181A2 (en) 2008-01-15 2009-07-23 Bayer Cropscience Sa Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance
WO2009094442A2 (en) 2008-01-22 2009-07-30 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives as fungicides
WO2010069882A1 (en) 2008-12-17 2010-06-24 Syngenta Participations Ag Isoxazole derivatives for use as fungicides
WO2010139271A1 (en) 2009-06-05 2010-12-09 中国中化股份有限公司 E-type phenyl acrylic ester compounds containing substituted anilino pyrimidine group and uses thereof
WO2011028657A1 (en) 2009-09-01 2011-03-10 Dow Agrosciences Llc Synergistic fungicidal compositions containing a 5-fluoropyrimidine derivative for fungal control in cereals
WO2011054871A1 (en) 2009-11-06 2011-05-12 Bayer Cropscience Ag Insecticidal arylpyrroline compounds
WO2011077514A1 (en) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Plant disease control composition and method for controlling plant diseases by applying the composition
WO2011081174A1 (en) 2010-01-04 2011-07-07 日本曹達株式会社 Nitrogen-containing heterocyclic compound and agricultural/horticultural germicide
WO2011135833A1 (en) 2010-04-28 2011-11-03 Sumitomo Chemical Company, Limited Plant disease control composition and its use
WO2012084812A1 (en) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
WO2012165511A1 (en) 2011-05-31 2012-12-06 クミアイ化学工業株式会社 Method for controlling diseases in rice plant
WO2012168188A1 (en) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Active compound combinations
WO2013008162A1 (en) 2011-07-08 2013-01-17 Novartis Ag Novel trifluoromethyl-oxadiazole derivatives and their use in the treatment of disease
WO2013007767A1 (en) 2011-07-13 2013-01-17 Basf Se Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013010862A1 (en) 2011-07-15 2013-01-24 Basf Se Fungicidal alkyl-substituted 2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013024009A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013024010A1 (en) 2011-08-12 2013-02-21 Basf Se N-thio-anthranilamide compounds and their use as pesticides
WO2013047441A1 (en) 2011-09-26 2013-04-04 日本曹達株式会社 Agricultural and horticultural bactericide composition
WO2013047749A1 (en) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Production method for 4, 4-difluoro-3,4-dihydroisoquinoline derivative
WO2013092224A1 (en) 2011-12-21 2013-06-27 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi resistant to qo inhibitors
WO2013116251A2 (en) 2012-02-01 2013-08-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazole mixtures
WO2013127704A1 (en) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Active compound combinations containing a thiazoylisoxazoline and a fungicide
WO2013162072A1 (en) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Tetrazolinone compounds and its use as pesticides
CN103387541A (en) 2012-05-10 2013-11-13 中国中化股份有限公司 Preparation method of substituted pyrazolylether compound
WO2014060177A1 (en) 2012-10-16 2014-04-24 Syngenta Participations Ag Fungicidal compositions
WO2014065413A1 (en) 2012-10-26 2014-05-01 日本たばこ産業株式会社 Triazole-isoxazole compound and medical use thereof
WO2015041360A1 (en) 2013-09-20 2015-03-26 住友化学株式会社 Tetrazolinone compound and use thereof
WO2015065922A1 (en) 2013-10-28 2015-05-07 Dexcom, Inc. Devices used in connection with continuous analyte monitoring that provide the user with one or more notifications, and related methods
EP2865265A1 (en) 2014-02-13 2015-04-29 Bayer CropScience AG Active compound combinations comprising phenylamidine compounds and biological control agents
WO2015185485A1 (en) * 2014-06-06 2015-12-10 Basf Se Use of substituted oxadiazoles for combating phytopathogenic fungi
WO2017085098A1 (en) 2015-11-19 2017-05-26 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2017085100A1 (en) 2015-11-19 2017-05-26 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2017093348A1 (en) 2015-12-02 2017-06-08 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017118689A1 (en) * 2016-01-08 2017-07-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
"Technical Monograph", May 2008, CROPLIFE INTERNATIONAL, article "Catalogue of pesticide formulation types and international coding system"
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 20, no. 13, 2010, pages 3920 - 3924
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 20, no. 24, 2010, pages 7397 - 7400
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 11, no. 6, 1990, pages 543 - 546
CAN. J. PLANT SCI., vol. 48, no. 6, 1968, pages 587 - 94
JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 5, 2012, pages 2149 - 2158
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
KNOWLES: "Agrow Reports DS256", 2006, T&F INFORMA, article "Adjuvants and additives"
MCCUTCHEON'S: "McCutcheon's Directories", vol. 1, 2008, article "Emulsifiers & Detergents"
MOLLET; GRUBEMANN: "Formulation technology", 2001, WILEY VCH

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