WO2017067839A1 - Microbiocidal phenylamidine derivatives - Google Patents

Microbiocidal phenylamidine derivatives Download PDF

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Publication number
WO2017067839A1
WO2017067839A1 PCT/EP2016/074545 EP2016074545W WO2017067839A1 WO 2017067839 A1 WO2017067839 A1 WO 2017067839A1 EP 2016074545 W EP2016074545 W EP 2016074545W WO 2017067839 A1 WO2017067839 A1 WO 2017067839A1
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formula
alkyl
compounds
groups
substituted
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PCT/EP2016/074545
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French (fr)
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Matthias Weiss
Sarah Sulzer-Mosse
Julien Daniel Henri GAGNEPAIN
Thomas James HOFFMAN
Werner Zambach
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Syngenta Participations Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/20—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Definitions

  • the present invention relates to novel phenylamidine derivatives, which have microbiocidal activity, e.g. as active ingredients, in particular fungicidal activity.
  • the invention also relates to preparation of these phenylamidine derivatives, to intermediates useful in the preparation of these phenylamidine derivatives, to the preparation of these intermediates, to agrochemical compositions which comprise at least one of the phenylamidine derivatives, to preparation of these compositions and to the use of the phenylamidine derivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.
  • R 1 and R 2 each independently represent hydrogen, Ci-C4 alkyl, Ci-C4fluoroalkyl, C2- C 4 alkenyl, C2-C4 alkynyl or C3-C6 cycloalkyl; or
  • R 1 and R 2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom;
  • R 3 represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C3 fluoroalkoxy or C3-C6 cycloalkyl;
  • Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -0-, wherein the -Q1 -
  • Q2-Q3- linkage does not contain contiguous oxygen atoms
  • R 4 and R 5 each independently represents hydrogen, cyano, aryl (which may be substituted with one to three R 8 groups), heteroaryl (which may be substituted with one or two R 8 groups), heterocyclyl (which may be substituted with one or two R 8 groups), hydroxy, Ci-Cs alkyl, C2-C8 alkenyl, C2-Cs alkynyl, Ci-Cs haloalkyl, Ci-Cs alkoxy, C3-C8 cycloalkyl (which may be substituted with one to three R 8 groups); or R 4 and R 5 together with the carbon atom to which they are attached form a three to eight- membered saturated or partially-unsaturated carbocyclic group (which may be substituted with one to three R 8 groups, and which may contain one or two oxygen atoms, one or two sulphur atoms or NR 9 , wherein R 9 is hydrogen, C1-C4 alkoxy, C2-C4 alkynyl or Ci- C 4 alky
  • R 6 and R 7 each independently represent hydrogen, fluoro, C1-C3 alkyl, Ci-Csfluoroalkyl or C3-C5 cycloalkyl; or R 6 and R 7 together with carbon atom to which they are attached to form a three to six membered saturated cyclic group which may optionally contain an oxygen or sulfur atom; and
  • the present invention provides an agrochemical composition comprising a compound of formula (I).
  • Compounds of formula (I) may be used to control phytopathogenic microorganisms.
  • a compound of formula (I), or a composition comprising a compound of formula (I), according to the invention may be applied directly to the phytopathogen, or to the locus of a phytopathogen, in particular to a plant susceptible to attack by phytopathogens.
  • the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to control a phytopathogen.
  • the present invention provides a method of controlling
  • phytopathogens comprising applying a compound of formula (I), or a composition
  • Compounds of formula (I) are particularly effective in the control of phytopathogenic fungi.
  • the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to control phytopathogenic fungi.
  • the present invention provides a method of controlling
  • phytopathogenic fungi comprising applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to said phytopathogenic fungi, or to the locus of said phytopathogenic fungi, in particular to a plant susceptible to attack by phytopathogenic fungi.
  • substituents are indicated as being optionally substituted, this means that they may or may not carry one or more identical or different substituents, e.g. one to three substituents. Normally not more than three such optional substituents are present at the same time.
  • substituents are indicated as being substituted, e.g. alkyl, this includes those groups that are part of other groups, e.g. the alkyl in alkylthio.
  • halogen refers to fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
  • Alkyl substituents may be straight-chained or branched. Alkyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl and the isomers thereof, for example, iso- propyl, iso-butyl, sec-butyl, ie f-butyl or iso-amyl.
  • Alkenyl substituents can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably C2-C6, more preferably C2-C 4 and most preferably C2-C3 alkenyl groups.
  • Alkynyl substituents can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C2-C6, more preferably C2-C 4 and most preferably C2-C3 alkynyl groups.
  • Haloalkyl groups may contain one or more identical or different halogen atoms and, for example, may stand for CH2CI, CHC , CCIs, CH2F, CHF 2 , CF 3 , CF3CH2, CH3CF2, CF3CF2 or CCI3CCI2.
  • Haloalkenyl groups are alkenyl groups, respectively, which are substituted with one or more of the same or different halogen atoms and are, for example, 2,2-difluorovinyl or 1 ,2-dichloro-2-fluoro-vinyl.
  • Alkoxy means a radical -OR, where R is alkyl, e.g. as defined above.
  • Alkoxy groups include, but are not limited to, methoxy, ethoxy, 1 -methylethoxy, propoxy, butoxy, 1 - methylpropoxy and 2-methylpropoxy.
  • Cyano means a -CN group.
  • Amino means an -IMH2 group.
  • Hydroxyl or hydroxy stands for a -OH group.
  • Carbocyclic rings include cycloalkyl and cycloalkenyl groups.
  • Cycloalkyl may be saturated or partially unsaturated, preferably fully saturated, and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Aryl groups (either alone or as part of a larger group, such as e.g. aryloxy, aryl-alkyl) are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl.
  • Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heteroaryl groups either alone or as part of a larger group, such as e.g.
  • heteroaryloxy, heteroaryl-alkyl are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
  • single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
  • [1 ,2,4] triazolyl furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl.
  • bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
  • heteroaryl groups are preferred, pyridyl being most preferred.
  • the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heterocyclyl groups or heterocyclic rings are non-aromatic ring structures containing up to 10 atoms including one or more (preferably one, two or three) heteroatoms selected from O, S and N.
  • monocyclic groups include, oxetanyl, 4,5-dihydro-isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, thianyl,
  • bicyclic groups examples include 2,3-dihydro- benzofuranyl, benzo[1 ,4]dioxolanyl, benzo[1 ,3]dioxolanyl, chromenyl, and 2,3-dihydro-benzo- [1 ,4]dioxinyl.
  • a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three
  • Formula (I) is intended to include all those possible isomeric forms and mixtures thereof.
  • the present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I).
  • formula (I) is intended to include all possible tautomers.
  • the present invention includes all possible tautomeric forms for a compound of formula (I).
  • the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book
  • R 1 , R 2 , R 3 , Q1 , Q2, Q3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are, in any combination thereof, as set out below:
  • R 1 and R 2 each independently represent hydrogen, Ci-C4 alkyl, C1-C4 fluoroalkyi, or C3-C6 cycloalkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group.
  • R 1 and R 2 each independently represent hydrogen, C1-C4 alkyl or C3- C6 cycloalkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a five to six- membered saturated cyclic group.
  • R 1 and R 2 each independently represent hydrogen, Ci-C 4 alkyl or cyclopropyl.
  • R 1 and R 2 each independently represent Ci-C3 alkyl or cyclopropyl.
  • R 1 represents methyl and R 2 represents ethyl or isopropyl.
  • R 3 represents fluoro, chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyi, C1-C2 alkoxy, or C1-C3 fluoroalkoxy.
  • R 3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyi, or C1-C2 alkoxy.
  • R 3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyi, or C1-C2 alkoxy.
  • R 3 represents chloro, C1-C2 alkyl or C1-C2 fluoroalkyi.
  • R 3 represents chloro or methyl.
  • Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -0-, wherein only one of Q1 , Q2 and Q3 can be -O- or alternatively both of Q1 and Q3 are -0-, and wherein R 6 and R 7 each independently represent hydrogen, fluoro, C1-C2 alkyl or C1-C2 fluoroalkyi; or R 6 and R 7 together with carbon atom to which they are attached to form a cyclopropyl group.
  • Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -0-, wherein only one of Q1 , Q2 and Q3 can be -O- or alternatively both of Q1 and Q3 are -0-, and wherein R 6 and R 7 each independently represent hydrogen, fluoro or Ci-C2 alkyl; or R 6 and R 7 together with carbon atom to which they are attached to form a cyclopropyl group.
  • Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or - 0-, wherein only one of Q1 , Q2 and Q3 can be -0-, and wherein R 6 and R 7 each
  • R 6 and R 7 independently represent hydrogen, fluoro or methyl; or R 6 and R 7 together with carbon atom to which they are attached to form a cyclopropyl group.
  • Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -O-, wherein only one of Q1 , Q2 and Q3 can be -0-, and wherein R 6 and R 7 each independently represent hydrogen, fluoro or methyl.
  • Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -0-, wherein Q2 is -C(R 6 )(R 7 )- and only one of Q1 and Q3 can be -0-, and wherein R 6 and R 7 each independently represent hydrogen;
  • R 4 and R 5 each independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R 8 groups), heteroaryl (wherein the heteroaryl is pyridyl, pyrimidinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, thiazolyl, or quinolinyl, and wherein the heteroaryl may be substituted with one or two R 8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R 8 groups), Ci-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R 8 groups
  • R 4 and R 5 each independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R 8 groups), heteroaryl (wherein the heteroaryl is pyridyl, thiophenyl, oxazolyl or thiazolyl, and wherein the heteroaryl may be substituted with one or two R 8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R 8 groups), C1-C6 alkyl, C2- C6 alkenyl, C1-C3 fluoroalkyi, C1-C4 alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R 8 groups); or R 4 and R 5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one to three R 8 groups, and which may contain
  • R 4 represents hydrogen or C1-C6 alkyl
  • R 5 represents phenyl (which may be substituted with one to three R 8 groups), heteroaryl (wherein the heteroaryl is pyridyl or thiophenyl, and wherein the heteroaryl may be substituted with one or two R 8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two methyl groups), C1-C6 alkyl, Ci- C3 fluoroalkyl, C1-C4 alkoxy or C3-C6 cycloalkyl (which may be substituted with one to three R 8 groups); or R 4 and R 5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one or two groups independently selected from C1-C4 alkyl and C1-C3 alkoxy, and which may contain
  • R 4 represents hydrogen or C1-C3 alkyl
  • R 5 represents phenyl
  • C1-C6 alkyl or C3-C6 cycloalkyl (which may be substituted with one or two groups independently selected from C1-C3 alkyl or C1-C3 alkoxy); or R 4 and R 5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy, and which may contain NR 9 , wherein R 9 is C1-C4 alkoxy); wherein each R 8 independently represents fluoro, chloro, cyano, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy or C1-C2 fluoroalkoxy.
  • R 4 represents hydrogen, methyl or ethyl
  • R 5 represents phenyl (which may be substituted with one to three R 8 groups) or C1-C6 alkyl; or R 4 and R 5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy); wherein each R 8 independently represents fluoro, chloro, cyano, methyl, trifluoromethyl, C1-C3 alkoxy, trifluoromethoxy or difluoromethoxy.
  • R 6 and R 7 are each independently represent hydrogen, fluoro, C1-C2 alkyl or C1-C2 fluoroalkyl; or R 6 and R 7 together with carbon atom to which they are attached to form a cyclopropyl group; More preferably R 6 and R 7 are each independently represent hydrogen, fluoro or C1-C2 alkyl; or R 6 and R 7 together with carbon atom to which they are attached to form a
  • R 6 and R 7 are each independently represent hydrogen, fluoro or methyl; or R 6 and R 7 together with carbon atom to which they are attached to form a cyclopropyl group;
  • R 6 and R 7 are each independently represent hydrogen, fluoro or methyl
  • R 6 and R 7 each independently represent hydrogen.
  • each R 8 independently represents fluoro, chloro, cyano, C1-C2 alkyl, C1-C2 fluoroalkyi, C1-C3 alkoxy or C1-C2 fluoroalkoxy;
  • each R 8 independently represents fluoro, chloro, cyano, methyl, trifluoromethyl, C1-C3 alkoxy, trifluoromethoxy or difluoromethoxy.
  • a preferred group of compounds according to the invention are those of formula (1-1 ):
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I), or a salt or N- oxide thereof.
  • Preferred definitions of R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds formula (I).
  • One group of compounds according to this embodiment are compounds of formula (I- 1A) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "preferably" above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (1-1 B) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (1-1 C) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "even more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (1-1 D) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably still” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (1-1 E) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "most preferably” above for the compounds of formula (I).
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I), or a salt or N- oxide thereof.
  • Preferred definitions of R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I).
  • One group of compounds according to this embodiment are compounds of formula (I- 2A) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-2B) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-2C) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "even more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-2D) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably still” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-2E) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "most preferably” above for the compounds of formula (I).
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I), or a salt or N- oxide thereof.
  • Preferred definitions of R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I).
  • One group of compounds according to this embodiment are compounds of formula (I- 3A) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-3B) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-3C) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "even more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-3D) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably still” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-3E) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "most preferably” above for the compounds of formula (I).
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I), or a salt or N- oxide thereof.
  • Preferred definitions of R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I).
  • One group of compounds according to this embodiment are compounds of formula (I- 4A) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-4B) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-4C) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "even more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-4D) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably still” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-4E) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "most preferably” above for the compounds of formula (I).
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I), or a salt or N- oxide thereof.
  • Preferred definitions of R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I).
  • each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-5B) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-5C) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "even more preferably” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-5D) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "more preferably still” above for the compounds of formula (I).
  • Another group of compounds according to this embodiment are compounds of formula (I-5E) wherein each of the definitions R 1 , R 2 , R 3 , R 4 and R 5 is as defined according to the corresponding definition denoted under "most preferably” above for the compounds of formula (I).
  • a further preferred group of compounds according to the invention are those of formula (I-6) which are compounds of formula (I) wherein R 1 and R 2 each independently represent hydrogen, Ci-C4 alkyl, Ci-C4 fluoroalkyl, or C3-C6 cycloalkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group; R 3 represents fluoro, chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, or C1-C3 fluoroalkoxy; Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or - 0-, wherein only one of Q1 , Q2, Q3 can be -O- or alternatively both of Q1 and Q3 are -0-; R 4 and R 5 each independently represents hydrogen, cyano, phenyl (which may be substituted
  • One group of compounds according to this embodiment are compounds of formula (I- 6a) which are compounds of formula (I-6) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (l-6b) which are compounds of formula (I-6) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is
  • Another group of compounds according to this embodiment are compounds of formula (l-6c) which are compounds of formula (I-6) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (l-6d) which are compounds of formula (I-6) wherein Q1 is -CH2 -, Q2 is -O . and Q3
  • Another group of compounds according to this embodiment are compounds of formula (l-6e) which are compounds of formula (I-6) wherein Q1 is -CH2 -, Q2 is -CH2 - and A further preferred group of compounds according to the invention are those of formula (I-7) which are compounds of formula (I) wherein R 1 and R 2 each independently represent hydrogen, C1-C4 alkyl or C3-C6 cycloalkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a five to six- membered saturated cyclic group; R 3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, or C1-C2 alkoxy; Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -0-, wherein only one of Q1 , Q2, Q3 can be -O- or alternatively both of Q1 and Q3 are -0-; R 4 and R
  • Another group of compounds according to this embodiment are compounds of formula (l-7b) which are compounds of formula (I-7) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is Another group of compounds according to this embodiment are compounds of formula (l-7c) which are compounds of formula (I-7) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (l-7d) which are compounds of formula (I-7) wherein Q1 is -CH2 -, Q2 is -O . and Q3
  • Another group of compounds according to this embodiment are compounds of formula (l-7e) which are compounds of formula (I-7) wherein Q1 is -CH2 -, Q2 is -CH2 - and
  • a further preferred group of compounds according to the invention are those of formula (I-8) which are compounds of formula (I) wherein R 1 and R 2 each independently represent hydrogen, C1-C4 alkyl or cyclopropyl; R 3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, or C1-C2 alkoxy; Q1 , Q2 and Q3 each independently represent - C(R 6 )(R 7 )- or -0-, wherein only one of Q1 , Q2, Q3 can be -0-; R 4 represents hydrogen or Ci- C6 alkyl; R 5 represents phenyl (which may be substituted with one to three R 8 groups), heteroaryl (wherein the heteroaryl is pyridyl or thiophenyl, and wherein the heteroaryl may be substituted with one or two R 8 groups), heterocyclyl (wherein the heterocyclyl is
  • R 4 and R 5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one or two groups independently selected from C1-C4 alkyl and Ci- C3 alkoxy, and which may contain an oxygen atom or NR 9 , wherein R 9 is C1-C4 alkoxy);
  • R 6 and R 7 each independently represent hydrogen, fluoro or methyl; or R 6 and R 7 together with carbon atom to which they are attached to form a cyclopropyl group; and each R 8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl
  • One group of compounds according to this embodiment are compounds of formula (I- 8a) which are compounds of formula (I-8) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (l-8b) which are compounds of formula (I-8) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is
  • Another group of compounds according to this embodiment are compounds of formula (l-8c) which are compounds of formula (I-8) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (l-8d) which are compounds of formula (I-8) wherein Q1 is -CH2 -, Q2 is -O . and Q3
  • Another group of compounds according to this embodiment are compounds of formula (l-8e) which are compounds of formula (I-8) wherein Q1 is -CH2 -, Q2 is -CH2 - and
  • a further preferred group of compounds according to the invention are those of formula (I-9) which are compounds of formula (I) wherein R 1 and R 2 each independently represent C1-C3 alkyl or cyclopropyl; R 3 represents chloro, C1-C2 alkyl or C1-C2 fluoroalkyl; Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -0-, wherein only one of Q1 , Q2, Q3 can be -0-; R 4 represents hydrogen or C1-C3 alkyl; R 5 represents phenyl (which may be substituted with one to three R 8 groups), C1-C6 alkyl or C3-C6 cycloalkyl (which may be substituted with one or two groups independently selected from C1-C3 alkyl or C1-C3 alkoxy); or R 4 and R 5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substitute
  • each R 8 independently represents fluoro, chloro, cyano, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy or C1-C2 fluoroalkoxy; or a salt or N-oxide thereof.
  • One group of compounds according to this embodiment are compounds of formula (I- 9a) which are compounds of formula (I-9) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (l-9b) which are compounds of formula (I-9) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is
  • Another group of compounds according to this embodiment are compounds of formula (l-9c) which are compounds of formula (I-9) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (l-9d) which are compounds of formula (I-9) wherein Q1 is -CH2 -, Q2 is -O . and Q3
  • Another group of compounds according to this embodiment are compounds of formula (l-9e) which are compounds of formula (I-9) wherein Q1 is -CH2 -, Q2 is -CH2 - and
  • a further preferred group of compounds according to the invention are those of formula (1-10) which are compounds of formula (I) wherein R 1 represents methyl; R 2 represents ethyl or isopropyl; R 3 represents chloro or methyl; Q1 , Q2 and Q3 each independently represent -C(R 6 )(R 7 )- or -0-, wherein Q2 is -C(R 6 )(R 7 )- and wherein only one of Q1 and Q3 can be -0-; R 4 represents hydrogen, methyl or ethyl; R 5 represents phenyl (which may be substituted with one to three R 8 groups) or C1-C6 alkyl; or R 4 and R 5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy); R 6 and R 7 each independently represent hydrogen; and each R 8 independently represents fluoro, chloro, cyano,
  • One group of compounds according to this embodiment are compounds of formula (I- 10a) which are compounds of formula (1-10) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (1-1 Ob) which are compounds of formula (1-10) wherein Q1 is -0-, Q2 is -CH2 - and
  • Another group of compounds according to this embodiment are compounds of formula (1-1 Oc) which are compounds of formula (1-10) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
  • Another group of compounds according to this embodiment are compounds of formula (1-1 Od) which are compounds of formula (1-10) wherein Q1 is -Chb -, Q2 is -O .
  • Another group of compounds according to this embodiment are compounds of formula (1-1 Oe) which are compounds of formula (1-10) wherein Q1 is -CH2 -, Q2 is -CH2 - and
  • Compounds according to the invention may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased
  • Table A.1 discloses 195 compounds A.1.1 to A.1 .195 of formula (IA) wherein Q1 is - 0-, Q2 is -CH2-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table A.2 discloses 195 compounds A.2.1 to A.2.195 of formula (IA) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table A.3 discloses 195 compounds A.3.1 to A.3.195 of formula (IA) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table A.4 discloses 195 compounds A.4.1 to A.4.195 of formula (IA) wherein Q1 is - C(CH 3 ) 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table A.5 discloses 195 compounds A.5.1 to A.5.195 of formula (IA) wherein Q1 is - CF 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table A.6 discloses 195 compounds A.6.1 to A.6.195 of formula (IA) wherein Q1 is -
  • Table A.7 discloses 195 compounds A.7.1 to A.7.195 of formula (IA) wherein Q1 is - 0-, Q2 is - C(CH 3 ) 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table A.8 discloses 195 compounds A.8.1 to A.8.195 of formula (IA) wherein Q1 is - CH 2 -, Q2 is - CH 2-! Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table B.1 discloses 195 compounds B.1 .1 to B.1 .195 of formula (IB) wherein Q1 is - 0-, Q2 is -CH 2- , Q3 is -CH 2- and R4 and R5 are defined in table Z.
  • Table B.2 discloses 195 compounds B.2.1 to B.2.195 of formula (IB) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table B.3 discloses 195 compounds B.3.1 to B.3.195 of formula (IB) wherein Q1 is -
  • Table B.4 discloses 195 compounds B.4.1 to B.4.195 of formula (IB) wherein Q1 is - C(CH 3 ) 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table B.5 discloses 195 compounds B.5.1 to B.5.195 of formula (IB) wherein Q1 is - CF 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table B.6 discloses 195 compounds B.6.1 to B.6.195 of formula (IB) wherein Q1 is - 0-, Q2 is - CH 2-! Q3 is -O- and R4 and R5 are defined in table Z.
  • Table B.7 discloses 195 compounds B.7.1 to B.7.195 of formula (IB) wherein Q1 is - 0-, Q2 is - C(CH 3 ) 2-! Q3 is -O- and R4 and R5 are defined in table Z.
  • Table B.8 discloses 195 compounds B.8.1 to B.8.195 of formula (IB) wherein Q1 is -
  • Table d discloses 195 compounds C.1 .1 to C.1 .195 of formula (IC) wherein Q1 is 0-, Q2 is -CH 2- , Q3 is -CH 2- and R4 and R5 are defined in table Z.
  • Table C.2 discloses 195 compounds C.2.1 to C.2.195 of formula (IC) wherein Q1 is
  • Table C.3 discloses 195 compounds C.3.1 to C.3.195 of formula (IC) wherein Q1 is CH 2 -, Q2 is - CH 2-! Q3 is -O- and R4 and R5 are defined in table Z.
  • Table C.4 discloses 195 compounds C.4.1 to C.4.195 of formula (IC) wherein Q1 is C(CH 3 ) 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table C.5 discloses 195 compounds C.5.1 to C.5.195 of formula (IC) wherein Q1 is CF 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table C.6 discloses 195 compounds C.6.1 to C.6.195 of formula (IC) wherein Q1 is 0-, Q2 is - CH 2-! Q3 is -O- and R4 and R5 are defined in table Z.
  • Table C.7 discloses 195 compounds C.7.1 to C.7.195 of formula (IC) wherein Q1 is
  • Table C.8 discloses 195 compounds C.8.1 to C.8.195 of formula (IC) wherein Q1 is CH 2 -, Q2 is - CH 2-! Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table D.1 discloses 195 compounds D.1 .1 to D.1 .195 of formula (ID) wherein Q1 is - 0-, Q2 is -CH2-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table D.2 discloses 195 compounds D.2.1 to D.2.195 of formula (ID) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table D.3 discloses 195 compounds D.3.1 to D.3.195 of formula (ID) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table D.4 discloses 195 compounds D.4.1 to D.4.195 of formula (ID) wherein Q1 is - C(CH 3 ) 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table D.5 discloses 195 compounds D.5.1 to D.5.195 of formula (ID) wherein Q1 is -
  • Table D.6 discloses 195 compounds D.6.1 to D.6.195 of formula (ID) wherein Q1 is - 0-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table D.7 discloses 195 compounds D.7.1 to D.7.195 of formula (ID) wherein Q1 is - 0-, Q2 is - C(CH 3 ) 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table D.8 discloses 195 compounds D.8.1 to D.8.195 of formula (ID) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table E.1 discloses 195 compounds E.1.1 to E.1 .195 of formula (IE) wherein Q1 is - 0-, Q2 is -CH 2 -, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table E.2 discloses 195 compounds E.2.1 to E.2.195 of formula (IE) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table E.3 discloses 195 compounds E.3.1 to E.3.195 of formula (IE) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table E.4 discloses 195 compounds E.4.1 to E.4.195 of formula (IE) wherein Q1 is -
  • Table E.5 discloses 195 compounds E.5.1 to E.5.195 of formula (IE) wherein Q1 is - CF 2 -, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table E.6 discloses 195 compounds E.6.1 to E.6.195 of formula (IE) wherein Q1 is - 0-, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table E.7 discloses 195 compounds E.7.1 to E.7.195 of formula (IE) wherein Q1 is 0-, Q2 is - C(CH 3 ) 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table E.8 discloses 195 compounds E.8.1 to E.8.195 of formula (IE) wherein Q1 is CH2-, Q2 is - CH2-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table F.1 discloses 195 compounds F.1.1 to F.1.195 of formula (IF) wherein Q1 is 0-, Q2 is -CH2-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table F.2 discloses 195 compounds F.2.1 to F.2.195 of formula (IF) wherein Q1 is CH2-, Q2 is -0-, Q3 is -CH 2 - and R4 and R5 are defined in table Z.
  • Table F.3 discloses 195 compounds F.3.1 to F.3.195 of formula (IF) wherein Q1 is
  • Table F.4 discloses 195 compounds F.4.1 to F.4.195 of formula (IF) wherein Q1 is C(CH 3 ) 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • Table F.5 discloses 195 compounds F.5.1 to F.5.195 of formula (IF) wherein Q1 is CF 2 -, Q2 is - CH 2 -, Q3 is -O- and R4 and R5 are defined in table Z.
  • TableF.6 discloses 195 compounds F.6.1 to F.6.195 of formula (IF) wherein Q1 is - , Q2 is - CH 2-! Q3 is -O- and R4 and R5 are defined in table Z.
  • Table F.7 discloses 195 compounds F.7.1 to F.7.195 of formula (IF) wherein Q1 is 0-, Q2 is - C(CH 3 ) 2- , Q3 is -O- and R4 and R5 are defined in table Z.
  • Table F.8 discloses 195 compounds F.8.1 to F.8.195 of formula (IF) wherein Q1 is
  • aniline (II) Treatment of aniline (II) with a formamide of formula R 1 R 2 NCHO in the presence of POC or SOC in an inert organic solvent as described in Tetrahedron 1990, 6058-61 12.
  • compounds of formula (lla) can be prepared by the reaction of compounds of formula (III), wherein X is selected from -CI, -Br, -I, -OTf (Tf is
  • R a1 is -H or a protection group as described in Protective Groups in Organic Synthesis, Greene and Wuts, 4 th Edition, Wiley 2006, in the presence of a catalyst.
  • a suitable protection group R a1 is preferably selected from a group of amides, carbamates,
  • compounds of formula (Ilia), wherein Q1 and Q2 each independently represent -C(R 6 )(R 7 )- can be prepared by the reaction of compounds of formula (IV), wherein Y is selected from -CI, -Br, -I or -NHR a1 with R a1 being a protection group as described above, with an aldehyde or ketone of formula (V) or an appropriate acetal of formula (Va) thereof, with R b1 being an alkyl, in the presence of a promoter.
  • the reaction is preferably run in an inert organic solvent like toluene, chlorobenzene or xylenes at a temperature between 0 °C and 140 °C.
  • the promoter can be a catalytic, stoichiometric or superstoichiometric amount of a lewis or bronsted acid as described in Eur. J. Org. Chem. 2011 , 5195-5231.
  • the promoter is a bronsted acid selected from the class of sulfonic acids or a mineral acid.
  • the synthesis of ketals of formula (Va) is well known and representative examples are described in Protective Groups in Organic Synthesis, Greene and Wuts 4 th Edition, Wiley 2006.
  • compounds of formula (IV) can be derived from compounds of formula (VI), wherein R b2 is -H or alkyl and Z is selected from -CI, -Br, -I, -NHR a1 and -N0 2 , by reaction with organometallic reagents, preferably organomagnesium- and/or
  • compounds of formula (1Mb), wherein Q3 represents - C(R 6 )(R 7 )- can be prepared by the reaction of compounds of formula (VII) with an aldehyde or ketone of formula (Vb) or an appropriate acetal of formula (Vc) thereof, with R10 being an alkyl, in the presence of a promoter.
  • the reaction is preferably run in an inert organic solvent like toluene, chlorobenzene or xylenes at a temperature between 0 °C and 140 °C.
  • the promoter can be a catalytic, stoichiometric or superstoichiometric amount of a lewis or bronsted acid as described in Eur. J. Org.
  • the promoter is a bronsted acid selected from the class of sulfonic acids or a mineral acid.
  • the synthesis of ketals of formula (VI) is well known and examples are described in Protective Groups in Organic S nthesis, Greene and Wuts, 4 th Edition, Wiley 2006.
  • compounds of formula (VII), wherein Q3 represents - C(R 6 )(R 7 )- can be derived from compounds of formula (VIII), wherein Rb1 is -H or alkyl and Z is selected from -CI, -Br, -I, -NHR a1 or -NC>2, by reaction with organometallic reagents, preferably organomagnesium- and/or organolithium-reagents in an inert solvent, and/or a reducing agent as described in Comprehensive Organic Functional Group Transformation, Katritzky, Meth-Cohn and Rees, Elsevier, 1995.
  • organometallic reagents preferably organomagnesium- and/or organolithium-reagents in an inert solvent, and/or a reducing agent as described in Comprehensive Organic Functional Group Transformation, Katritzky, Meth-Cohn and Rees, Elsevier, 1995.
  • compounds of formula (Xa) and (Xb) can be prepared by alkylation of hydroxyl compounds of formula (XI) or (XIa) with a suitably activated electrophile (Xlla) or (XI lb), wherein Xa is selected from -Br, -I, -OTs (Ts is para-toluenesulfonyl), -OTf or -Oms (Ms is methylsulfonyl), in the presence of a base in polar, aprotic solvents.
  • Ts is para-toluenesulfonyl
  • -OTf or -Oms Ms is methylsulfonyl
  • compounds of formula (XIII), wherein Q2 represents - C(R 6 )(R 7 ), can be also prepared from compounds of formula (XIV) by treatment with a catalyst in an inert solvent between 0°C and 100 °C to induce cyclization and subsequent hydrogenation of the olefinic bond with a Pd-, Pt-, Ru-, -Ir or Rh-based catalyst.
  • a catalyst in an inert solvent between 0°C and 100 °C to induce cyclization and subsequent hydrogenation of the olefinic bond with a Pd-, Pt-, Ru-, -Ir or Rh-based catalyst.
  • compounds of formula (XI I la) can be also prepared from compounds of formula (XVI) by several reported methods, of which some are outlined below: a) by treatment with an allylic electrophile of formula (VXa) and a catalyst as described in Chemistry letters 1976, p:523-524.
  • compounds of formula (I lie), wherein either R 4 or R 5 is hydrogen, can be also prepared from compounds of formula (XVII) by treatment with an organomagnesium or organolithium reagent, followed by reduction of intermediate compounds of formula (XVIIa) as described in Angew. Chem. Int. Ed. 2014, 53, 14428- 14432.
  • compounds of formula (XlXa) can be prepared from compounds of formula (XX) by several methods methods, of which the most frequently used are described below:
  • the compounds of formula (I) can be used in the agricultural sector and related fields of use e.g. as active ingredients for controlling plant pests or on non-living materials for control of spoilage microorganisms or organisms potentially harmful to man.
  • the novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and may be used for protecting numerous cultivated plants.
  • the compounds of formula (I) can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
  • fungicide as used herein means a compound that controls, modifies, or prevents the growth of fungi.
  • fungicidally effective amount means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.
  • compounds of formula (I) as dressing agents for the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings (for example rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
  • the propagation material can be treated with a composition comprising a compound of formula (I) before planting: seed, for example, can be dressed before being sown.
  • the compounds of formula (I) can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation.
  • the composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing.
  • the invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.
  • the compounds according to present invention can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene
  • the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.
  • Compounds of formula (I) and fungicidal compositions containing them may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens. They are effective in controlling a broad spectrum of plant diseases, such as foliar pathogens of ornamental, turf, vegetable, field, cereal, and fruit crops.
  • fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses, which may be controlled are for example:
  • Absidia corymbifera Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. comprising B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C.
  • Coccidioides immitis Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae,
  • Cryptococcus neoformans Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp,
  • Epidermophyton spp Erwinia amylovora, Erysiphe spp. including E. cichoracearum,
  • Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp. Including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp,
  • Sclerotinia spp Sclerotium spp, Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp,. Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T.
  • Trichophyton spp Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.
  • compounds of formula (I) and fungicidal compositions containing them may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and/or Mucoromycete classes.
  • pathogens may include:
  • Oomycetes including Phytophthora diseases such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora and Phytophthora erythroseptica; Pythium diseases such as those caused by Pythium
  • Ascomycetes including blotch, spot, blast or blight diseases and/or rots for example those caused by Pleosporales such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii,
  • Pleosporales such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii,
  • Ophiosphaerella graminicola Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophora tritici-repentis, Alternaria alternata, Alternaria brassicicola, Alternaria solani and Alternaria tomatophila, Capnodiales such as Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae and
  • Microdochium nivale Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita,
  • Botryosphaeriales such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta
  • cucurbitacearum cucurbitacearum
  • anthracnoses for example those caused by Glommerelales such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii,
  • Gerlachia nivale Gibberella fujikuroi
  • Gibberella zeae Gibberella zeae
  • Gliocladium spp. Myrothecium verrucaria
  • Nectria ramulariae Trichoderma viride
  • Trichothecium roseum Trichothecium roseum
  • Verticillium theobromae Myrothecium verrucaria
  • Basidiomycetes including smuts for example those caused by Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia stri if orm i s sp.
  • Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae
  • rusts for example those caused by Pucciniales such as Cerotelium fic
  • Puccinia striiformis f.sp. Secalis Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Tha
  • Blastocladiomycetes such as Physoderma maydis.
  • Mucoromycetes such as Choanephora cucurbitarum.; Mucor spp.; Rhizopus arrhizus,
  • the compounds and compositions comprising them may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species as well as certain protozoa.
  • target crops and/or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St.
  • perennial and annual crops such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries
  • cereals for example barley, maize (corn), millet, oats
  • Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
  • herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme
  • legumes for example beans, lentils, peas and soya beans
  • the useful plants and / or target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g. Bt. and VIP varieties) as well as disease resistant, herbicide tolerant (e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties.
  • suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.
  • useful plants and/or “target crops” is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® , Herculex I® and
  • useful plants and/or target crops is to be understood as including those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include ⁇ -endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.
  • Vip vegetative insecticidal proteins
  • insecticidal proteins of bacteria colonising nematodes and toxins produced by scorpions, arachnids, wasps and fungi.
  • An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds).
  • An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds).
  • Crops or seed material thereof can also be resistant to multiple types of pests (so- called stacked transgenic events when created by genetic modification).
  • a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
  • useful plants and/or target crops is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called “pathogenesis-related proteins” (PRPs, see e.g. EP-A-0 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191 .
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as ⁇ -endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp.
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as ⁇ -endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect- specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors;
  • ribosome-inactivating proteins such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP- glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.
  • RIP ribosome-inactivating proteins
  • ⁇ - endotoxins for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701 ).
  • Truncated toxins for example a truncated CrylAb, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • amino acid replacements preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a
  • CrylAc toxin a CrylAc toxin
  • Bollgard I® cotton variety that expresses a CrylAc toxin
  • Bollgard II® cotton variety that expresses a CrylAc and a Cry2Ab toxin
  • VipCot® cotton variety that expresses a Vip3A and a CrylAb toxin
  • NewLeaf® potato variety that expresses a Cry3A toxin
  • transgenic crops are: 1 . Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St.
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B- 1 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810.
  • NK603 ⁇ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material” is understood to denote seeds.
  • Pesticidal agents referred to herein using their common name are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.
  • the compounds of formula (I) may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • Such carriers are for example described in WO 97/33890.
  • Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers.
  • the particles contain the active ingredient retained in a solid matrix.
  • Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required.
  • Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
  • Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates.
  • Encapsulated droplets are typically 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring.
  • Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene- butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired
  • Pressurised sprayers wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.
  • Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.
  • Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1 ,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, ⁇ , ⁇ -dimethyl formamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glyco
  • Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
  • a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1 % to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes.
  • Typical surface active agents include salts of alkyl sulfates, such as
  • alkylarylsulfonate salts such as calcium
  • dodecylbenzenesulfonate alkylphenol-alkylene oxide addition products, such as
  • nonylphenol-C.sub. 18 ethoxylate alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate;
  • quaternary amines such as lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • block copolymers of ethylene oxide and propylene oxide such as polyethylene glycol stearate
  • salts of mono and dialkyl phosphate esters such as lauryl trimethylammonium chloride
  • adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
  • the invention also provides for the use of provides a composition comprising a compound of formula (I) according to the present invention together with one or more pesticides, plant nutrients or plant fertilizers.
  • the combination may also encompass specific plant traits incorporated into the plant using any means, for example conventional breeding or genetic modification.
  • Suitable examples of plant nutrients or plant fertilizers are calcium sulfate (CaS0 4 ), calcium nitrate (Ca(NC>3)2.4H20), calcium carbonate (CaCC ), potassium nitrate (KNO3), magnesium sulfate (MgS0 4 ), potassium hydrogen phosphate (KH2PO4), manganese sulfate (MnSCU), copper sulfate (CuS0 4 ), zinc sulfate (ZnS0 4 ), nickel chloride (NiC ), cobalt sulfate (C0SO4), potassium hydroxide (KOH), sodium chloride (NaCI), boric acid (H3BO3) and metal salts thereof (Na2Mo0 4 ).
  • CaS0 4 calcium sulfate
  • Ca(NC>3)2.4H20 calcium carbonate
  • CaCC calcium carbonate
  • KNO3 potassium nitrate
  • KNO3 magnesium sulfate
  • MgS0 4 magnesium sulf
  • the nutrients may be present in an amount of 5% to 50% by weight, preferably of 10% to 25% by weight or of 15% to 20% by weight each.
  • Preferred additional nutrients are urea ((Nhb ⁇ CO), melamine (C3H6N6), potassium oxide (K2O), and inorganic nitrates.
  • the most preferred additional plant nutrient is potassium oxide. Where the preferred additional nutrient is urea, it is present in an amount of generally 1 % to 20% by weight, preferably 2% to 10% by weight or of 3% to 7% by weight.
  • Suitable examples of pesticides are acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, , dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine
  • organophosphorous fungicides organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, zinc fung
  • benzoylcyclohexanedione herbicides carbamate herbicides, carbanilate herbicides, chloroacetanilide herbicides, chlorotriazine herbicides, cyclohexene oxmie herbicides, cyclopropylisoxazole herbicides, dicarboximide herbicides, dinitroaniline herbicides, dinitrophenol herbicides, diphenyl ether herbicides, dithiocarbamate herbicides,
  • fluoroalkyltriazine herbicides halogenated aliphatic herbicides, imidazolinone herbicides, inorganic herbicides, methoxytriazine herbicides, methylthiotriazine herbicides, nitrile herbicides, nitrophenyl ether herbicides, organophosphorous herbicides, oxadiazolone herbicides, oxazole herbicides, phenoxy herbicides, phenoxyacetic herbicides,
  • phenoxybutyric herbicides phenoxypropionic herbicides, phenylenediamine herbicides, phenylurea herbicides, phthalic acid herbicides, picolinic acid herbicides, pyrazole
  • herbicides pyridazine herbicides, pyridazinone herbicides, pyridine herbicides,
  • pyrimidinediamine herbicides pyrimidinyloxybenzylamine herbicides, pyrimidinylsulfonylurea herbicides, quaternary ammonium herbicides, quinolinecarboxylic acid herbicides, sulfonamide herbicides, sulfonanilide herbicides, sulfonylurea herbicides, thiadiazolylurea herbicides, thioamide herbicides, thiocarbamate herbicides, thiocarbonate herbicides, thiourea herbicides, triazine herbicides, triazinone herbicides, triazinylsulfonylurea herbicides, triazole herbicides, triazolone herbicides, triazolopyrimidine herbicides, uracil herbicides, urea herbicides, microbials, plant extracts, pheromones, macrobials and other biologicals.
  • TX refers to a compound selected from Tables A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) and Table E (below):
  • an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
  • an acaricide selected from the group of substances consisting of 1 ,1 -bis(4-chloro- phenyl)-2-ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-/V-methyl-/V-1 -naphthylacetamide (lUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (lUPAC name) (981 ) + TX, abamectin (1 ) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithion (870) + T
  • oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phenkapton (1330) + TX, phenthoate (631 ) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos-methyl (652) + TX,
  • polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + 5 TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671 ) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridaphenthion (701 ) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (71 1 ) + TX, quintiofos (1381 ) + TX
  • trifenofos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX,
  • an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne
  • an anthelmintic selected from the group of substances consisting of abamectin (1 ) +
  • avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1 -hydroxy-1 /-/- pyridine-2-thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1 12
  • a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Hopkins (scientific name) (
  • Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX,
  • a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name) (542) and methyl bromide (537) + TX,
  • a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine
  • an insect pheromone selected from the group of substances consisting of (£)-dec-5- en-1 -yl acetate with (£)-dec-5-en-1 -ol (lUPAC name) (222) + TX, (£)-tridec-4-en-1 -yl acetate (lUPAC name) (829) + TX, (£)-6-methylhept-2-en-4-ol (lUPAC name) (541 ) + TX, (£,Z)- tetradeca-4,10-dien-1 -yl acetate (lUPAC name) (779) + TX, (Z)-dodec-7-en-1 -yl acetate (lUPAC name) (285) + TX, (Z)-hexadec-l 1 -enal (lUPAC name) (436) + TX, (Z)-hexadec-l 1 - en-1 -yl acetate (lUPAC name) (437)
  • an insect repellent selected from the group of substances consisting of 2-(octylthio)- ethanol (lUPAC name) (591 ) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1 137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX,
  • an insecticide selected from the group of substances consisting of 1 -dichloro-1 - nitroethane (lUPAC/Chemical Abstracts name) (1058) + TX, 1 ,1 -dichloro-2,2-bis(4- ethylphenyl)ethane (lUPAC name) (1056), + TX, 1 ,2-dichloropropane (lUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 -bromo-2-chloroethane (lUPAC/Chemical Abstracts name) (916) + TX, 2,2,2- trichloro-1 -(3,4-dichlorophenyl)ethyl acetate (lUPAC name) (1451 ) + TX, 2,2-dichlorovinyl 2- ethylsulfinyle
  • cyanofenphos (1019) + TX, cyanophos (184) + TX, cyanthoate (1020) + TX, cyclethrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201 ) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (alternative name) [CCN] + TX, d-limonene (alternative name) [CCN] + TX, cZ-tetramethrin (alternative name) (788) + TX, DAEP (1031 ) + TX, dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, deme
  • pentachlorophenoxide (623) + TX, sodium selenate (lUPAC name) (1401 ) + TX, sodium thiocyanate [CCN] + TX, sophamide (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, te
  • a nematicide selected from the group of substances consisting of AKD-3088
  • a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX
  • a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,
  • a rodenticide selected from the group of substances consisting of 2-isovalerylindan- 1 ,3-dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891 ) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX,
  • a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)- ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2- enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB- 599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX, an animal repellent selected from the group of substances consisting of
  • a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
  • a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX, and biologically active compounds selected from the group consisting of azaconazole (60207-31 -0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [1 16255-48-2] + TX, cyproconazole [94361 -06-5] + TX, difenoconazole [1 19446-68-3] + TX, diniconazole [83657- 24-3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [1 14369-43-6] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674
  • a biologically active compound selected from the group consisting of N-[(5-chloro- 35 2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-pyrazole-4- carboxamide + TX, 2,6-Dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)- tetrone + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol- 3-amine + TX, 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1 -methyl-pyrazole-4- carboxamide + TX, CAS 850881 -30-0 +
  • A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) and Table E (below) with active ingredients described above comprises a compound selected from Tables
  • the mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the
  • B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) and Table E (below) and one 35 or more active ingredients as described above can be applied, for example, in a single
  • compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
  • auxiliaries such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides
  • compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • Another aspect of invention is related to the use of a compound of formula (I) or of a preferred individual compound as above-defined, of a composition comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, or of a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • a further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.
  • plants e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms
  • a compound of formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants,
  • Controlling or preventing means reducing infestation by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.
  • a preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect.
  • the compounds of formula (I) can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation e.g. a composition containing the compound of formula (I), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I), may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • compositions that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention.
  • Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient.
  • the rate of application per hectare is preferably 1 g to 2000 g of active ingredient per hectare, more preferably 10 to 1000 g/ha, most preferably 10 to 600 g/ha.
  • convenient dosages are from 10mg to 1 g of active substance per kg of seeds.
  • compositions When the compositions are used for treating seed, rates of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably from 0.01 to 10g per kg of seed are generally sufficient.
  • composition comprising a compound of formula (I) according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development.
  • compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK
  • compositions may be produced in conventional manner, e.g. by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects).
  • appropriate formulation inerts diiluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects.
  • conventional slow release formulations may be employed where long lasting efficacy is intended.
  • Particularly formulations to be applied in spraying forms such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g.
  • a seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing formulation form e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • seed dressing formulations are known in the art.
  • Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g. as slow release capsules or microcapsules.
  • the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of formula (I) together with component (B) and (C), and optionally other active agents, particularly microbiocides or conservatives or the like.
  • Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent.
  • Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
  • LC/MS Liquid Chromatography Mass Spectroscopy and the description of the apparatus and the methods are:
  • Extractor 2.00 V
  • Source Temperature 150°C
  • Desolvation Temperature 350°C
  • Cone Gas Flow 0 L/Hr
  • Desolvation Gas Flow 650 L/Hr
  • Mass range 100 to 900 Da
  • an Acquity UPLC from Waters Binary pump, heated column compartment and diode-array detector.
  • Solvent degasser Binary pump, heated column compartment and diode-array detector.
  • Extractor 2.00 V
  • Source Temperature 150°C
  • Desolvation Temperature 350°C
  • Desolvation Gas Flow 650 L/Hr
  • Mass range 100 to 900 Da
  • Acquity UPLC from Waters Binary pump, heated column compartment and diode-array detector.
  • Solvent degasser binary pump, heated column compartment and diode-array detector.
  • Wettable powders a) b) c) active ingredient [compound of formula (I)] 25 % 50 % 75 % sodium lignosulfonate 5 % 5 %
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • Powders for drv seed treatment a) b) c) active ingredient [compound of formula (I)] 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % -
  • Talcum - 20 The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c)
  • Active ingredient [compound of formula (I)] 5 % 6 % 4 % talcum 95 %
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • Kaolin 82 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
  • polyethylene glycol (mol. wt. 200)
  • the finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
  • silicone oil (in the form of a 75 % emulsion in water) 1 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • active ingredient 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 %
  • Silicone oil (in the form of a 75 % emulsion in water) 0.2 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • 28 parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate- mixture (8:1 ).
  • This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved.
  • a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • Wheat leaf segments cv. Kanzler were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water.
  • the leaf disks were inoculated by shaking powdery mildew infected plants above the test plates 1 day after application.
  • the inoculated leaf disks were incubated at 20 °C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate chamber and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application).
  • Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water.
  • the leaf disks were inoculated with a spore suspension of the fungus 1 day after application.
  • the inoculated leaf segments were incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7-9 days after application).
  • Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. Plates were stored in darkness at 19°C and 75% rh. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6-8 days after application).
  • Phakopsora pachyrhizi / soybean / leaf disk preventative (soybean rust)
  • Four-week old soybean plants are sprayed in a spray chamber with the formulated test compound diluted in water.
  • Leaf disks are cut from treated plants and placed on agar into 24-well plates one day after application.
  • Leaf disks are inoculated by spraying them with a spore suspension on their lower leaf surface.
  • the percentage leaf disk area covered by disease is assessed when an appropriate level of disease appears on untreated check plants (12 - 14 days after application).

Abstract

Compounds of the formula (I), wherein R1, R2, R3, Q1, Q2, Q3, R4, R5, R6, R7, R8 and R9 are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

Description

Microbiocidal Phenylamidine Derivatives
The present invention relates to novel phenylamidine derivatives, which have microbiocidal activity, e.g. as active ingredients, in particular fungicidal activity. The invention also relates to preparation of these phenylamidine derivatives, to intermediates useful in the preparation of these phenylamidine derivatives, to the preparation of these intermediates, to agrochemical compositions which comprise at least one of the phenylamidine derivatives, to preparation of these compositions and to the use of the phenylamidine derivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.
Certain fungicidal phenylamidine compounds are described in WO 00/46184.
It has now surprisingly been found that certain novel bicyclic phenylamidine derivatives have favourable fungicidal properties.
The present invention therefore provides compounds of formula (I)
Figure imgf000002_0001
R1 and R2 each independently represent hydrogen, Ci-C4 alkyl, Ci-C4fluoroalkyl, C2- C4 alkenyl, C2-C4 alkynyl or C3-C6 cycloalkyl; or
R1 and R2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom;
R3 represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C3 fluoroalkoxy or C3-C6 cycloalkyl;
Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein the -Q1 -
Q2-Q3- linkage does not contain contiguous oxygen atoms;
R4 and R5 each independently represents hydrogen, cyano, aryl (which may be substituted with one to three R8 groups), heteroaryl (which may be substituted with one or two R8 groups), heterocyclyl (which may be substituted with one or two R8 groups), hydroxy, Ci-Cs alkyl, C2-C8 alkenyl, C2-Cs alkynyl, Ci-Cs haloalkyl, Ci-Cs alkoxy, C3-C8 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a three to eight- membered saturated or partially-unsaturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain one or two oxygen atoms, one or two sulphur atoms or NR9, wherein R9 is hydrogen, C1-C4 alkoxy, C2-C4 alkynyl or Ci- C4 alkyl);
R6 and R7 each independently represent hydrogen, fluoro, C1-C3 alkyl, Ci-Csfluoroalkyl or C3-C5 cycloalkyl; or R6 and R7 together with carbon atom to which they are attached to form a three to six membered saturated cyclic group which may optionally contain an oxygen or sulfur atom; and
Each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C3 fluoroalkoxy, C2-C4 alkynyl or C3-C6 cycloalkyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl; or a salt or N-oxide thereof.
In a second aspect the present invention provides an agrochemical composition comprising a compound of formula (I).
Compounds of formula (I) may be used to control phytopathogenic microorganisms.
Thus, in order to control a phytopathogen a compound of formula (I), or a composition comprising a compound of formula (I), according to the invention may be applied directly to the phytopathogen, or to the locus of a phytopathogen, in particular to a plant susceptible to attack by phytopathogens.
Thus, in a third aspect the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to control a phytopathogen.
In a further aspect the present invention provides a method of controlling
phytopathogens, comprising applying a compound of formula (I), or a composition
comprising a compound of formula (I), as described herein to said phytopathogen, or to the locus of said phytopathogen, in particular to a plant susceptible to attack by a
phytopathogen.
Compounds of formula (I) are particularly effective in the control of phytopathogenic fungi.
Thus, in a yet further aspect the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to control phytopathogenic fungi.
In a further aspect the present invention provides a method of controlling
phytopathogenic fungi, comprising applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to said phytopathogenic fungi, or to the locus of said phytopathogenic fungi, in particular to a plant susceptible to attack by phytopathogenic fungi.
Where substituents are indicated as being optionally substituted, this means that they may or may not carry one or more identical or different substituents, e.g. one to three substituents. Normally not more than three such optional substituents are present at the same time. Where a group is indicated as being substituted, e.g. alkyl, this includes those groups that are part of other groups, e.g. the alkyl in alkylthio.
The term "halogen" refers to fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
Alkyl substituents may be straight-chained or branched. Alkyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl and the isomers thereof, for example, iso- propyl, iso-butyl, sec-butyl, ie f-butyl or iso-amyl.
Alkenyl substituents (either alone or as part of a larger group, eg. alkenyloxy) can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl and allyl. The alkenyl groups are preferably C2-C6, more preferably C2-C4 and most preferably C2-C3 alkenyl groups.
Alkynyl substituents (either alone or as part of a larger group, eg. alkynyloxy) can be in the form of straight or branched chains. Examples are ethynyl and propargyl. The alkynyl groups are preferably C2-C6, more preferably C2-C4 and most preferably C2-C3 alkynyl groups.
Haloalkyl groups (either alone or as part of a larger group, eg. haloalkyloxy) may contain one or more identical or different halogen atoms and, for example, may stand for CH2CI, CHC , CCIs, CH2F, CHF2, CF3, CF3CH2, CH3CF2, CF3CF2 or CCI3CCI2.
Haloalkenyl groups (either alone or as part of a larger group, eg. haloalkenyloxy) are alkenyl groups, respectively, which are substituted with one or more of the same or different halogen atoms and are, for example, 2,2-difluorovinyl or 1 ,2-dichloro-2-fluoro-vinyl.
Alkoxy means a radical -OR, where R is alkyl, e.g. as defined above. Alkoxy groups include, but are not limited to, methoxy, ethoxy, 1 -methylethoxy, propoxy, butoxy, 1 - methylpropoxy and 2-methylpropoxy.
Cyano means a -CN group.
Amino means an -IMH2 group.
Hydroxyl or hydroxy stands for a -OH group.
Carbocyclic rings include cycloalkyl and cycloalkenyl groups.
Cycloalkyl may be saturated or partially unsaturated, preferably fully saturated, and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Aryl groups (either alone or as part of a larger group, such as e.g. aryloxy, aryl-alkyl) are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Heteroaryl groups (either alone or as part of a larger group, such as e.g.
heteroaryloxy, heteroaryl-alkyl) are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings. Preferably, single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur. Examples of monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
[1 ,2,4] triazolyl), furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl. Examples of bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Heterocyclyl groups or heterocyclic rings (either alone or as part of a larger group, such as heterocyclyl-alkyl) are non-aromatic ring structures containing up to 10 atoms including one or more (preferably one, two or three) heteroatoms selected from O, S and N. Examples of monocyclic groups include, oxetanyl, 4,5-dihydro-isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, thianyl,
[1 ,3]dioxolanyl, piperidinyl, piperazinyl, [1 ,4]dioxanyl, imidazolidinyl, [1 ,3,5]oxadiazinanyl, hexahydro-pyrimidinyl, [1 ,3,5]triazinanyl and morpholinyl or their oxidised versions such as 1 - oxo-thietanyl and 1 ,1 -dioxo-thietanyl. Examples of bicyclic groups include 2,3-dihydro- benzofuranyl, benzo[1 ,4]dioxolanyl, benzo[1 ,3]dioxolanyl, chromenyl, and 2,3-dihydro-benzo- [1 ,4]dioxinyl. Where a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three
substituents.
The presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in optically isomeric forms, i.e.
enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond. Formula (I) is intended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I). Likewise, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms for a compound of formula (I).
In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form.
N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book
"Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991 .
Preferred values of R1, R2, R3, Q1 , Q2, Q3 , R4, R5, R6, R7, R8 and R9 are, in any combination thereof, as set out below:
Preferably R1 and R2 each independently represent hydrogen, Ci-C4 alkyl, C1-C4 fluoroalkyi, or C3-C6 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group.
More preferably R1 and R2 each independently represent hydrogen, C1-C4 alkyl or C3- C6 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a five to six- membered saturated cyclic group.
Even more preferably R1 and R2 each independently represent hydrogen, Ci-C4 alkyl or cyclopropyl.
More preferably still R1 and R2 each independently represent Ci-C3 alkyl or cyclopropyl.
Most preferably R1 represents methyl and R2 represents ethyl or isopropyl.
Preferably R3 represents fluoro, chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyi, C1-C2 alkoxy, or C1-C3 fluoroalkoxy.
More preferably R3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyi, or C1-C2 alkoxy.
Even more preferably R3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyi, or C1-C2 alkoxy.
More preferably still R3 represents chloro, C1-C2 alkyl or C1-C2 fluoroalkyi.
Most preferably R3 represents chloro or methyl.
Preferably Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein only one of Q1 , Q2 and Q3 can be -O- or alternatively both of Q1 and Q3 are -0-, and wherein R6 and R7 each independently represent hydrogen, fluoro, C1-C2 alkyl or C1-C2 fluoroalkyi; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group.
More preferably Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein only one of Q1 , Q2 and Q3 can be -O- or alternatively both of Q1 and Q3 are -0-, and wherein R6 and R7 each independently represent hydrogen, fluoro or Ci-C2 alkyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group.
Even more preferably Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or - 0-, wherein only one of Q1 , Q2 and Q3 can be -0-, and wherein R6 and R7 each
independently represent hydrogen, fluoro or methyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group.
More preferably still Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -O-, wherein only one of Q1 , Q2 and Q3 can be -0-, and wherein R6 and R7 each independently represent hydrogen, fluoro or methyl.
Most preferably Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein Q2 is -C(R6)(R7)- and only one of Q1 and Q3 can be -0-, and wherein R6 and R7 each independently represent hydrogen;
Preferably R4 and R5 each independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl, pyrimidinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, thiazolyl, or quinolinyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R8 groups), Ci-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a three to eight- membered saturated or partially-unsaturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain one or two oxygen atoms, one or two sulphur atoms or NR9, wherein R9 is hydrogen, C1-C4 alkoxy or C2-C4 alkynyl); wherein each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C2 fluoroalkyi, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-O-C1- C4alkyl.
More preferably R4 and R5 each independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl, thiophenyl, oxazolyl or thiazolyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R8 groups), C1-C6 alkyl, C2- C6 alkenyl, C1-C3 fluoroalkyi, C1-C4 alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain an oxygen atom, a sulphur atom or NR9, wherein R9 is C1-C4 alkoxy or C2-C4 alkynyl); wherein each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl.
Even more preferably R4 represents hydrogen or C1-C6 alkyl; and R5 represents phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl or thiophenyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two methyl groups), C1-C6 alkyl, Ci- C3 fluoroalkyl, C1-C4 alkoxy or C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one or two groups independently selected from C1-C4 alkyl and C1-C3 alkoxy, and which may contain an oxygen atom or NR9, wherein R9 is C1-C4 alkoxy); wherein each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-O-C1- C4alkyl.
More preferably still R4 represents hydrogen or C1-C3 alkyl; and R5 represents phenyl
(which may be substituted with one to three R8 groups), C1-C6 alkyl or C3-C6 cycloalkyl (which may be substituted with one or two groups independently selected from C1-C3 alkyl or C1-C3 alkoxy); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy, and which may contain NR9, wherein R9 is C1-C4 alkoxy); wherein each R8 independently represents fluoro, chloro, cyano, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy or C1-C2 fluoroalkoxy.
Most preferably R4 represents hydrogen, methyl or ethyl; and R5 represents phenyl (which may be substituted with one to three R8 groups) or C1-C6 alkyl; or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy); wherein each R8 independently represents fluoro, chloro, cyano, methyl, trifluoromethyl, C1-C3 alkoxy, trifluoromethoxy or difluoromethoxy.
Preferably R6 and R7 are each independently represent hydrogen, fluoro, C1-C2 alkyl or C1-C2 fluoroalkyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group; More preferably R6 and R7 are each independently represent hydrogen, fluoro or C1-C2 alkyl; or R6 and R7 together with carbon atom to which they are attached to form a
cyclopropyl group;
Even more preferably R6 and R7 are each independently represent hydrogen, fluoro or methyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group;
More preferably still R6 and R7 are each independently represent hydrogen, fluoro or methyl;
Most preferably R6 and R7 each independently represent hydrogen.
Preferably each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C2 fluoroalkyi, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl;
More preferably each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyi, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl.
Even more preferably each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyi, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl;
More preferably still each R8 independently represents fluoro, chloro, cyano, C1-C2 alkyl, C1-C2 fluoroalkyi, C1-C3 alkoxy or C1-C2 fluoroalkoxy;
Most preferably each R8 independently represents fluoro, chloro, cyano, methyl, trifluoromethyl, C1-C3 alkoxy, trifluoromethoxy or difluoromethoxy.
A preferred group of compounds according to the invention are those of formula (1-1 ):
Figure imgf000009_0001
wherein R1, R2, R3, R4 and R5 are as defined for compounds of formula (I), or a salt or N- oxide thereof. Preferred definitions of R1, R2, R3, R4 and R5 are as defined for compounds formula (I). One group of compounds according to this embodiment are compounds of formula (I- 1A) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (1-1 B) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (1-1 C) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "even more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (1-1 D) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably still" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (1-1 E) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "most preferably" above for the compounds of formula (I).
Another preferred group of compounds according to the invention are those of formula (I-2):
Figure imgf000010_0001
wherein R1, R2, R3, R4 and R5 are as defined for compounds of formula (I), or a salt or N- oxide thereof. Preferred definitions of R1, R2, R3, R4 and R5 are as defined for compounds of formula (I).
One group of compounds according to this embodiment are compounds of formula (I- 2A) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-2B) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably" above for the compounds of formula (I). Another group of compounds according to this embodiment are compounds of formula (I-2C) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "even more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-2D) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably still" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-2E) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "most preferably" above for the compounds of formula (I).
Another preferred group of compounds according to the invention are those of formula (I-3):
Figure imgf000011_0001
(I-3)
wherein R1, R2, R3, R4 and R5 are as defined for compounds of formula (I), or a salt or N- oxide thereof. Preferred definitions of R1, R2, R3, R4 and R5 are as defined for compounds of formula (I).
One group of compounds according to this embodiment are compounds of formula (I- 3A) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-3B) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-3C) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "even more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-3D) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably still" above for the compounds of formula (I). Another group of compounds according to this embodiment are compounds of formula (I-3E) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "most preferably" above for the compounds of formula (I).
Another preferred group of compounds according to the invention are those of formula (I-4):
Figure imgf000012_0001
wherein R1, R2, R3, R4 and R5 are as defined for compounds of formula (I), or a salt or N- oxide thereof. Preferred definitions of R1, R2, R3, R4 and R5 are as defined for compounds of formula (I).
One group of compounds according to this embodiment are compounds of formula (I- 4A) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-4B) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-4C) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "even more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-4D) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably still" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-4E) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "most preferably" above for the compounds of formula (I).
Another preferred group of compounds according to the invention are those of formula (I-5):
Figure imgf000013_0001
R (I-5)
wherein R1, R2, R3, R4 and R5 are as defined for compounds of formula (I), or a salt or N- oxide thereof. Preferred definitions of R1, R2, R3, R4 and R5 are as defined for compounds of formula (I).
One group of compounds according to this embodiment are compounds of formula (I-
5A) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-5B) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-5C) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "even more preferably" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-5D) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "more preferably still" above for the compounds of formula (I).
Another group of compounds according to this embodiment are compounds of formula (I-5E) wherein each of the definitions R1, R2, R3, R4 and R5 is as defined according to the corresponding definition denoted under "most preferably" above for the compounds of formula (I).
A further preferred group of compounds according to the invention are those of formula (I-6) which are compounds of formula (I) wherein R1 and R2 each independently represent hydrogen, Ci-C4 alkyl, Ci-C4 fluoroalkyl, or C3-C6 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group; R3 represents fluoro, chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, or C1-C3 fluoroalkoxy; Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or - 0-, wherein only one of Q1 , Q2, Q3 can be -O- or alternatively both of Q1 and Q3 are -0-; R4 and R5 each independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl, pyrimidinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, thiazolyl, or quinolinyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R8 groups), Ci-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a three to eight- membered saturated or partially-unsaturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain one or two oxygen atoms, one or two sulphur atoms or NR9, wherein R9 is hydrogen, C1-C4 alkoxy or C2-C4 alkynyl); R6 and R7 each independently represent hydrogen, fluoro, Ci-C2 alkyl or C1-C2 fluoroalkyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group; and each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl; or a salt or N-oxide thereof.
One group of compounds according to this embodiment are compounds of formula (I- 6a) which are compounds of formula (I-6) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-6b) which are compounds of formula (I-6) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is
Another group of compounds according to this embodiment are compounds of formula (l-6c) which are compounds of formula (I-6) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-6d) which are compounds of formula (I-6) wherein Q1 is -CH2 -, Q2 is -O . and Q3
Another group of compounds according to this embodiment are compounds of formula (l-6e) which are compounds of formula (I-6) wherein Q1 is -CH2 -, Q2 is -CH2 - and A further preferred group of compounds according to the invention are those of formula (I-7) which are compounds of formula (I) wherein R1 and R2 each independently represent hydrogen, C1-C4 alkyl or C3-C6 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a five to six- membered saturated cyclic group; R3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, or C1-C2 alkoxy; Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein only one of Q1 , Q2, Q3 can be -O- or alternatively both of Q1 and Q3 are -0-; R4 and R5 each independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl, thiophenyl, oxazolyl or thiazolyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R8 groups), Ci-C6 alkyl, C2-C6 alkenyl, C1-C3 fluoroalkyl, Ci-C4 alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain an oxygen atom, a sulphur atom or NR9, wherein R9 is C1-C4 alkoxy or C2-C4 alkynyl); R6 and R7 each independently represent hydrogen, fluoro or Ci-C2 alkyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group; and each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl; or a salt or N-oxide thereof.
One group of compounds according to this embodiment are compounds of formula (I-
7a) which are compounds of formula (I-7) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-7b) which are compounds of formula (I-7) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is Another group of compounds according to this embodiment are compounds of formula (l-7c) which are compounds of formula (I-7) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-7d) which are compounds of formula (I-7) wherein Q1 is -CH2 -, Q2 is -O . and Q3
Another group of compounds according to this embodiment are compounds of formula (l-7e) which are compounds of formula (I-7) wherein Q1 is -CH2 -, Q2 is -CH2 - and
A further preferred group of compounds according to the invention are those of formula (I-8) which are compounds of formula (I) wherein R1 and R2 each independently represent hydrogen, C1-C4 alkyl or cyclopropyl; R3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, or C1-C2 alkoxy; Q1 , Q2 and Q3 each independently represent - C(R6)(R7)- or -0-, wherein only one of Q1 , Q2, Q3 can be -0-; R4 represents hydrogen or Ci- C6 alkyl; R5 represents phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl or thiophenyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is
tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two methyl groups), Ci-C6 alkyl, C1-C3 fluoroalkyl, C1-C4 alkoxy or C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one or two groups independently selected from C1-C4 alkyl and Ci- C3 alkoxy, and which may contain an oxygen atom or NR9, wherein R9 is C1-C4 alkoxy); R6 and R7 each independently represent hydrogen, fluoro or methyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group; and each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl; or a salt or N-oxide thereof.
One group of compounds according to this embodiment are compounds of formula (I- 8a) which are compounds of formula (I-8) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-8b) which are compounds of formula (I-8) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is
Another group of compounds according to this embodiment are compounds of formula (l-8c) which are compounds of formula (I-8) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-8d) which are compounds of formula (I-8) wherein Q1 is -CH2 -, Q2 is -O . and Q3
Another group of compounds according to this embodiment are compounds of formula (l-8e) which are compounds of formula (I-8) wherein Q1 is -CH2 -, Q2 is -CH2 - and
A further preferred group of compounds according to the invention are those of formula (I-9) which are compounds of formula (I) wherein R1 and R2 each independently represent C1-C3 alkyl or cyclopropyl; R3 represents chloro, C1-C2 alkyl or C1-C2 fluoroalkyl; Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein only one of Q1 , Q2, Q3 can be -0-; R4 represents hydrogen or C1-C3 alkyl; R5 represents phenyl (which may be substituted with one to three R8 groups), C1-C6 alkyl or C3-C6 cycloalkyl (which may be substituted with one or two groups independently selected from C1-C3 alkyl or C1-C3 alkoxy); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy, and which may contain NR9, wherein R9 is C1-C4 alkoxy); R6 and R7 each
independently represent hydrogen, fluoro or methyl; and each R8 independently represents fluoro, chloro, cyano, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy or C1-C2 fluoroalkoxy; or a salt or N-oxide thereof.
One group of compounds according to this embodiment are compounds of formula (I- 9a) which are compounds of formula (I-9) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-9b) which are compounds of formula (I-9) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is
Another group of compounds according to this embodiment are compounds of formula (l-9c) which are compounds of formula (I-9) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (l-9d) which are compounds of formula (I-9) wherein Q1 is -CH2 -, Q2 is -O . and Q3
Another group of compounds according to this embodiment are compounds of formula (l-9e) which are compounds of formula (I-9) wherein Q1 is -CH2 -, Q2 is -CH2 - and
A further preferred group of compounds according to the invention are those of formula (1-10) which are compounds of formula (I) wherein R1 represents methyl; R2 represents ethyl or isopropyl; R3 represents chloro or methyl; Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein Q2 is -C(R6)(R7)- and wherein only one of Q1 and Q3 can be -0-; R4 represents hydrogen, methyl or ethyl; R5 represents phenyl (which may be substituted with one to three R8 groups) or C1-C6 alkyl; or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy); R6 and R7 each independently represent hydrogen; and each R8 independently represents fluoro, chloro, cyano, methyl, trifluoromethyl, C1-C3 alkoxy, trifluoromethoxy or difluoromethoxy; or a salt or N-oxide thereof.
One group of compounds according to this embodiment are compounds of formula (I- 10a) which are compounds of formula (1-10) wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
Another group of compounds according to this embodiment are compounds of formula (1-1 Ob) which are compounds of formula (1-10) wherein Q1 is -0-, Q2 is -CH2 - and
Another group of compounds according to this embodiment are compounds of formula (1-1 Oc) which are compounds of formula (1-10) wherein Q1 is -0-, Q2 is -CH2 - and Q3 is -0-. Another group of compounds according to this embodiment are compounds of formula (1-1 Od) which are compounds of formula (1-10) wherein Q1 is -Chb -, Q2 is -O . and
Another group of compounds according to this embodiment are compounds of formula (1-1 Oe) which are compounds of formula (1-10) wherein Q1 is -CH2 -, Q2 is -CH2 - and
Compounds according to the invention may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased
biodegradability).
Specific examples of compounds of formula (I) are illustrated in the Tables A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8 and F.1 to F.8 that follow below:
The compounds disclosed in Tables A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8 and F.1 to F.8 can be prepared by the procedures described herein, and/or by synthetic methods generally known in the art.
Table A.1 discloses 195 compounds A.1.1 to A.1 .195 of formula (IA) wherein Q1 is - 0-, Q2 is -CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Figure imgf000018_0001
Table Z.
Entry R4 R5 Entry R4 R5
1 -H -CH2CH3 108 -CH2-(CH2)2-CH2-
2 -H -(CH2)2-CH3 109 -CH2-(CH2)3-CH2-
3 -H -(CH2)3-CH3 110 -CH2-(CH2)4-CH2-
4 -H -(CH2)4-CH3 111 -CH2-(CH2)5 -CH2-
5 -H -(CH2)5-CH3 112 -CH2CH2-0-CH2CH2-
6 -H vx 113 -CH2CH(CH3)-0-CH(CH3)CH2-
7 -H οΛ 114 -CH2C(CH3)2-0-C(CH3)2CH2-
8 -H cr- 115 -CH2CH2-S-CH2CH2-
9 -H CJA 116 -CH2CH(CH3)-S-CH(CH3)CH2-
Figure imgf000019_0001
Entry R4 R5 Entry R4 R5
35 -(CH2)2-CH3 v A 142 -CH(CH3)2 3,5-di-F-Ph
36 -(CH2)2-CH3 oA 143 -H 2,3-di-F-Ph
37 -(CH2)2-CH3 144 -CH3 2,3-di-F-Ph
38 -(CH2)2-CH3 CJA 145 -CH2CH3 2,3-di-F-Ph
39 -(CH2)2-CH3 -CH(CH3)2 146 -CH(CH3)2 2,3-di-F-Ph
40 -CH(CH3)2 -(CH2)3-CH3 147 -H 2,4-di-F-Ph
41 -CH(CH3)2 -(CH2)4-CH3 148 -CH3 2,4-di-F-Ph
42 -CH(CH3)2 -(CH2)5-CH3 149 -CH2CH3 2,4-di-F-Ph
43 -CH(CH3)2 150 -CH(CH3)2 2,4-di-F-Ph
44 -CH(CH3)2 oA 151 -H 3,4-di-F-Ph
45 -CH(CH3)2 152 -CH3 3,4-di-F-Ph
46 -CH(CH3)2 oA 153 -CH2CH3 3,4-di-F-Ph
47 -CH(CH3)2 -CH(CH3)2 154 -CH(CH3)2 3,4-di-F-Ph
48 -(CH2)3-CH3 155 -H 2-CI-Ph
49 νΛ -(CH2)4-CH3 156 -CH3 2-CI-Ph
50 νΛ -(CH2)5-CH3 157 -CH2CH3 2-CI-Ph
51 νΛ CJA 158 -CH(CH3)2 3-CI-Ph
52 -H 3,4,5-tri-F-Ph 159 -H 3-CI-Ph
53 -CH3 3,4,5-tri-F-Ph 160 -CH3 3-CI-Ph
54 -CH2CH3 3,4,5-tri-F-Ph 161 -CH2CH3 3-CI-Ph
55 -CH(CH3)2 3,4,5-tri-F-Ph 162 -CH(CH3)2 3-CI-Ph
56 -H 2-F-Ph 163 -H 4-CI-Ph
57 -CH3 2-F-Ph 164 -CH3 4-CI-Ph
58 -CH2CH3 2-F-Ph 165 -CH2CH3 4-CI-Ph
59 -CH(CH3)2 2-F-Ph 166 -CH(CH3)2 4-CI-Ph
60 -H 3-F-Ph 167 -H 4-Br-Ph
61 -CH3 3-F-Ph 168 -CH3 4-Br-Ph
62 -CH2CH3 3-F-Ph 169 -CH2CH3 4-Br-Ph
63 -CH(CH3)2 3-F-Ph 170 -H 2-CH3-Ph
Figure imgf000021_0001
Figure imgf000022_0001
Table A.2 discloses 195 compounds A.2.1 to A.2.195 of formula (IA) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table A.3 discloses 195 compounds A.3.1 to A.3.195 of formula (IA) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table A.4 discloses 195 compounds A.4.1 to A.4.195 of formula (IA) wherein Q1 is - C(CH3)2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table A.5 discloses 195 compounds A.5.1 to A.5.195 of formula (IA) wherein Q1 is - CF2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table A.6 discloses 195 compounds A.6.1 to A.6.195 of formula (IA) wherein Q1 is -
0-, Q2 is - CH2-! Q3 is -O- and R4 and R5 are defined in table Z.
Table A.7 discloses 195 compounds A.7.1 to A.7.195 of formula (IA) wherein Q1 is - 0-, Q2 is - C(CH3)2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table A.8 discloses 195 compounds A.8.1 to A.8.195 of formula (IA) wherein Q1 is - CH2-, Q2 is - CH2-! Q3 is -CH2- and R4 and R5 are defined in table Z.
Figure imgf000022_0002
Table B.1 discloses 195 compounds B.1 .1 to B.1 .195 of formula (IB) wherein Q1 is - 0-, Q2 is -CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table B.2 discloses 195 compounds B.2.1 to B.2.195 of formula (IB) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table B.3 discloses 195 compounds B.3.1 to B.3.195 of formula (IB) wherein Q1 is -
CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table B.4 discloses 195 compounds B.4.1 to B.4.195 of formula (IB) wherein Q1 is - C(CH3)2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table B.5 discloses 195 compounds B.5.1 to B.5.195 of formula (IB) wherein Q1 is - CF2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table B.6 discloses 195 compounds B.6.1 to B.6.195 of formula (IB) wherein Q1 is - 0-, Q2 is - CH2-! Q3 is -O- and R4 and R5 are defined in table Z.
Table B.7 discloses 195 compounds B.7.1 to B.7.195 of formula (IB) wherein Q1 is - 0-, Q2 is - C(CH3)2-! Q3 is -O- and R4 and R5 are defined in table Z.
Table B.8 discloses 195 compounds B.8.1 to B.8.195 of formula (IB) wherein Q1 is -
CH2-, Q2 is - CH2-! Q3 is -CH2- and R4 and R5 are defined in table Z.
Figure imgf000023_0001
Table d discloses 195 compounds C.1 .1 to C.1 .195 of formula (IC) wherein Q1 is 0-, Q2 is -CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table C.2 discloses 195 compounds C.2.1 to C.2.195 of formula (IC) wherein Q1 is
CH2-, Q2 is -0-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table C.3 discloses 195 compounds C.3.1 to C.3.195 of formula (IC) wherein Q1 is CH2-, Q2 is - CH2-! Q3 is -O- and R4 and R5 are defined in table Z.
Table C.4 discloses 195 compounds C.4.1 to C.4.195 of formula (IC) wherein Q1 is C(CH3)2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table C.5 discloses 195 compounds C.5.1 to C.5.195 of formula (IC) wherein Q1 is CF2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table C.6 discloses 195 compounds C.6.1 to C.6.195 of formula (IC) wherein Q1 is 0-, Q2 is - CH2-! Q3 is -O- and R4 and R5 are defined in table Z.
Table C.7 discloses 195 compounds C.7.1 to C.7.195 of formula (IC) wherein Q1 is
0-, Q2 is - C(CH3)2-! Q3 is -O- and R4 and R5 are defined in table Z.
Table C.8 discloses 195 compounds C.8.1 to C.8.195 of formula (IC) wherein Q1 is CH2-, Q2 is - CH2-! Q3 is -CH2- and R4 and R5 are defined in table Z.
Figure imgf000024_0001
Table D.1 discloses 195 compounds D.1 .1 to D.1 .195 of formula (ID) wherein Q1 is - 0-, Q2 is -CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table D.2 discloses 195 compounds D.2.1 to D.2.195 of formula (ID) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table D.3 discloses 195 compounds D.3.1 to D.3.195 of formula (ID) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table D.4 discloses 195 compounds D.4.1 to D.4.195 of formula (ID) wherein Q1 is - C(CH3)2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table D.5 discloses 195 compounds D.5.1 to D.5.195 of formula (ID) wherein Q1 is -
CF2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table D.6 discloses 195 compounds D.6.1 to D.6.195 of formula (ID) wherein Q1 is - 0-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table D.7 discloses 195 compounds D.7.1 to D.7.195 of formula (ID) wherein Q1 is - 0-, Q2 is - C(CH3)2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table D.8 discloses 195 compounds D.8.1 to D.8.195 of formula (ID) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Figure imgf000024_0002
Table E.1 discloses 195 compounds E.1.1 to E.1 .195 of formula (IE) wherein Q1 is - 0-, Q2 is -CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table E.2 discloses 195 compounds E.2.1 to E.2.195 of formula (IE) wherein Q1 is - CH2-, Q2 is -0-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table E.3 discloses 195 compounds E.3.1 to E.3.195 of formula (IE) wherein Q1 is - CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table E.4 discloses 195 compounds E.4.1 to E.4.195 of formula (IE) wherein Q1 is -
C(CH3)2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table E.5 discloses 195 compounds E.5.1 to E.5.195 of formula (IE) wherein Q1 is - CF2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table E.6 discloses 195 compounds E.6.1 to E.6.195 of formula (IE) wherein Q1 is - 0-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z. Table E.7 discloses 195 compounds E.7.1 to E.7.195 of formula (IE) wherein Q1 is 0-, Q2 is - C(CH3)2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table E.8 discloses 195 compounds E.8.1 to E.8.195 of formula (IE) wherein Q1 is CH2-, Q2 is - CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Figure imgf000025_0001
Table F.1 discloses 195 compounds F.1.1 to F.1.195 of formula (IF) wherein Q1 is 0-, Q2 is -CH2-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table F.2 discloses 195 compounds F.2.1 to F.2.195 of formula (IF) wherein Q1 is CH2-, Q2 is -0-, Q3 is -CH2- and R4 and R5 are defined in table Z.
Table F.3 discloses 195 compounds F.3.1 to F.3.195 of formula (IF) wherein Q1 is
CH2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table F.4 discloses 195 compounds F.4.1 to F.4.195 of formula (IF) wherein Q1 is C(CH3)2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table F.5 discloses 195 compounds F.5.1 to F.5.195 of formula (IF) wherein Q1 is CF2-, Q2 is - CH2-, Q3 is -O- and R4 and R5 are defined in table Z.
TableF.6 discloses 195 compounds F.6.1 to F.6.195 of formula (IF) wherein Q1 is - , Q2 is - CH2-! Q3 is -O- and R4 and R5 are defined in table Z.
Table F.7 discloses 195 compounds F.7.1 to F.7.195 of formula (IF) wherein Q1 is 0-, Q2 is - C(CH3)2-, Q3 is -O- and R4 and R5 are defined in table Z.
Table F.8 discloses 195 compounds F.8.1 to F.8.195 of formula (IF) wherein Q1 is
CH2-, Q2 is - CH2-! Q3 is -CH2- and R4 and R5 are defined in table Z.
Compounds of the present invention can be made as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).
The compounds of general formula (I) can be prepared by different routes, advantageously from the corresponding anilines having formula (II) as shown in scheme 1
Figure imgf000025_0002
(II) (I)
Scheme 1 . Among the various reported methods for this transformation, the most widely applied are the following:
1 ) Treatment of aniline (II) with an orthoamide having the formula R1R2NCH(OR10a)2 in an organic solvent at a temperature between 0 °C and 100 °C as described in J. Comb. 0/76/77. 2009,1 1 , 126-130.
2) Treatment of aniline (II) with a formamide of formula R1R2NCHO in the presence of POC or SOC in an inert organic solvent as described in Tetrahedron 1990, 6058-61 12.
3) Treatment of aniline (II) with an orthoester of the formula HC(OR10a)3, wherein R7 represents an alkyl, to form an iminoether which is subsequently treated with an amine of the formula R1R2NH as described in WO 2009088103.
As shown in scheme 2, compounds of formula (lla) can be prepared by the reaction of compounds of formula (III), wherein X is selected from -CI, -Br, -I, -OTf (Tf is
trifluoromethyesulfonyl) or -ONf (Nf is nonafluorobutylsulfonyl), with an amine of the formula hbNR31, wherein Ra1 is -H or a protection group as described in Protective Groups in Organic Synthesis, Greene and Wuts, 4th Edition, Wiley 2006, in the presence of a catalyst. A suitable protection group Ra1 is preferably selected from a group of amides, carbamates,
sulfonamides or benzyl, for which a person skilled in the art knows various ways of subsequent removal to generate the corresponding free anilines of general formula (II). The most commonly employed catalysts and reaction conditions for these aminations are described in Angew. Chem. Int. Ed. 2008, 47, 6338 - 6361 , Acc. Chem. Res. 2008, 1534- 1544 or Coord. Chem .Rev. 2004, 2337-2364 and are well known to a person skilled in the art.
Figure imgf000026_0001
Scheme 2.
A shown in scheme 3, some compounds of formula (lla) can be also prepared from compounds of formula (lib), wherein X is the same selection of groups as shown in scheme 2, by means of well established transition metal catalyzed cross coupling as described in Chem. Soc. Rev. 2011 , 40, 5049-5067, Chem. Soc. Rev. 2014, 43, 412-443 and Coord. Chem .Rev. 2004, 2337-2364.
Figure imgf000026_0002
Scheme 3.
As shown in scheme 4, compounds of formula (Ilia), wherein Q1 and Q2 each independently represent -C(R6)(R7)-, can be prepared by the reaction of compounds of formula (IV), wherein Y is selected from -CI, -Br, -I or -NHRa1 with Ra1 being a protection group as described above, with an aldehyde or ketone of formula (V) or an appropriate acetal of formula (Va) thereof, with Rb1 being an alkyl, in the presence of a promoter. The reaction is preferably run in an inert organic solvent like toluene, chlorobenzene or xylenes at a temperature between 0 °C and 140 °C. The promoter can be a catalytic, stoichiometric or superstoichiometric amount of a lewis or bronsted acid as described in Eur. J. Org. Chem. 2011 , 5195-5231. Preferably, the promoter is a bronsted acid selected from the class of sulfonic acids or a mineral acid. The synthesis of ketals of formula (Va) is well known and representative examples are described in Protective Groups in Organic Synthesis, Greene and Wuts 4th Edition, Wiley 2006.
Figure imgf000027_0001
(IV) (ma)
Scheme 4.
As shown in scheme 5, compounds of formula (IV) can be derived from compounds of formula (VI), wherein Rb2 is -H or alkyl and Z is selected from -CI, -Br, -I, -NHRa1 and -N02, by reaction with organometallic reagents, preferably organomagnesium- and/or
organolithium-reagents in an inert solvent, and/or a reducing agent as described in
Comprehensive Organic Functional Group Transformation, Katritzky, Meth-Cohn and Rees, Elsevier, 1995. In cases where Z is -NO2, an additional reduction step of the nitro group may be required to facilitate the transformation shown in scheme 4. Conversion of a -NO2 group into -NHa1 by means of a reducing agent followed by an optional protection, is a well-known transformation and obvious to a person skilled in the art.
Figure imgf000027_0002
(VI) (Via) (IV)
Scheme 5.
A shown in scheme 6, compounds of formula (1Mb), wherein Q3 represents - C(R6)(R7)-, can be prepared by the reaction of compounds of formula (VII) with an aldehyde or ketone of formula (Vb) or an appropriate acetal of formula (Vc) thereof, with R10 being an alkyl, in the presence of a promoter. The reaction is preferably run in an inert organic solvent like toluene, chlorobenzene or xylenes at a temperature between 0 °C and 140 °C. The promoter can be a catalytic, stoichiometric or superstoichiometric amount of a lewis or bronsted acid as described in Eur. J. Org. Chem. 2011 , 5195-5231. Preferably, the promoter is a bronsted acid selected from the class of sulfonic acids or a mineral acid. The synthesis of ketals of formula (VI) is well known and examples are described in Protective Groups in Organic S nthesis, Greene and Wuts, 4th Edition, Wiley 2006.
Figure imgf000028_0001
(lib)
Scheme 6
As shown in scheme 7, compounds of formula (VII), wherein Q3 represents - C(R6)(R7)-, can be derived from compounds of formula (VIII), wherein Rb1 is -H or alkyl and Z is selected from -CI, -Br, -I, -NHRa1 or -NC>2, by reaction with organometallic reagents, preferably organomagnesium- and/or organolithium-reagents in an inert solvent, and/or a reducing agent as described in Comprehensive Organic Functional Group Transformation, Katritzky, Meth-Cohn and Rees, Elsevier, 1995. In cases where Z is -NO2, an additional reduction step of the nitro group may be required to facilitate the transformation shown in scheme 6 Conversion of a -NO2 group into -NHa1 by means of a reducing agent followed by an optional protection, is a well known transformation and obvious to a person skilled in the art.
Figure imgf000028_0002
Scheme 7
A large selection of phenylacetic acid of formula (VI) and (VIII) are available from commercial vendors and the synthesis of substituted phenyl acetic acids is well described in the literature {Adv. Synth. Catal. 2011 , 353, 1565 - 1574 and references therein). Also, it is obvious to a person skilled in the art that the alpha-position of carbonyl compounds can be functionalized by deprotonation with a strong base and subsequent alkylation with an electrophile as described in March's Advanced Organic Chemistry, Smith and March, 6th edition, Wiley, 2007 to obtain certain compounds of formula (VI) and (VIII).
As shown in scheme 8, compounds of formula (IX), wherein Q3 represents -C(R6)(R7) and -R5 is able to form a carbon-carbon double bond to the adjacent carbon linking it with R4, 5 can be also prepared from compounds of formula (X) by one of the general methods
described below:
a) Through a palladium mediated intramolecular Heck-reactions as described in Organic Reactions Vol. 60, p. 157, Overman et al., Wiley, 2002.
b) Through reductive radical cyclization as described in Bull. Korean Chem. Soc. 10 2007, p. 2501.
c) Through a palladium mediated reductive cyclization as described in Tetrahedron Lett. 2007 2307-2310 and J. Am. Chem. Soc. 2015, 137.
Figure imgf000029_0001
Scheme 8
15 As shown in scheme 9, compounds of formula (Xa) and (Xb) can be prepared by alkylation of hydroxyl compounds of formula (XI) or (XIa) with a suitably activated electrophile (Xlla) or (XI lb), wherein Xa is selected from -Br, -I, -OTs (Ts is para-toluenesulfonyl), -OTf or -Oms (Ms is methylsulfonyl), in the presence of a base in polar, aprotic solvents. The formation of alkyl ethers is a well known reaction for which a person skilled in the art knows
20 numerous established reaction conditions.
Figure imgf000029_0002
Scheme 9.
The commonly used methods for the synthesis of electrophiles R-Xa as shown in scheme 9 can be found in in March's Advanced Organic Chemistry, Smith and March, 6th 25 edition, Wiley, 2007 and are obvious to a person skilled in the art.
A shown in scheme 10, compounds of formula (XIII), wherein Q2 represents - C(R6)(R7), can be also prepared from compounds of formula (XIV) by treatment with a catalyst in an inert solvent between 0°C and 100 °C to induce cyclization and subsequent hydrogenation of the olefinic bond with a Pd-, Pt-, Ru-, -Ir or Rh-based catalyst. Some preferred catalysts for the cyclization are described in Eur. J. Org. Chem. 2011 , 2334-2338 and references therein and consist of commercially available Pt- and Au-complexes.
Conditions and suitable catalysts for the hydrogenation of trisubstituted olefins are obvious to a person skilled in the art and can be found in March's Advanced Organic Chemistry, Smith and March, 6th edition, Wile , 2007.
Figure imgf000030_0001
(XIV) (XIII)
Scheme 10
As shown in scheme 1 1 , compounds of formula (XI I la) can be also prepared from compounds of formula (XVI) by several reported methods, of which some are outlined below: a) by treatment with an allylic electrophile of formula (VXa) and a catalyst as described in Chemistry letters 1976, p:523-524.
b) by treatment with an unsaturated carbonyl compound of formula (VXb), or a precursor thereof, as described in EP406758, followed by reduction of the intermediate acetal/hemiacetal as described in March's Advanced Organic Chemistry, Smith and March, 6th edition, Wiley, 2007.
c) by treatment with an unsaturated carbonyl compound of formula (VXc) followed by reduction of the intermediate chromanone as described in US 20060100460.
Figure imgf000030_0002
Scheme 1 1 .
As shown in scheme 12, compounds of formula (I lie), wherein either R4 or R5 is hydrogen, can be also prepared from compounds of formula (XVII) by treatment with an organomagnesium or organolithium reagent, followed by reduction of intermediate compounds of formula (XVIIa) as described in Angew. Chem. Int. Ed. 2014, 53, 14428- 14432.
Figure imgf000030_0003
(XVII)
(XVIIa) (lib)
Scheme 12. A selection of compounds of formula (XVII) is available from commercial vendors or can be prepared from readily available precursors as described in Tetrahedron Lett. 2003, 4007-4010; J. Med. Chem. 2010, 8760-8764 or WO 2005087714.
Compounds of formula (llld) as shown in scheme 13 can be prepared by many reported methods, of which the most commonly used are outlined below:
a) By treatment of compounds of formula (XVIIIa) with an organometallic reagent transferring R5 in an inert organic solvent at cryogenic temperature, followed by reaction with a ketal, acetal or geminal dihalide to induce cyclization as described in W01 1 107494.
b) By treatment of compounds of formula (XVI 11 b) with alkyl lithium, followed by reaction with a carbonyl compounds of formula R5C(0)R4 to produce an intermediate alcohol which can be cyclized with an appropriate ketal, acetal or geminal dihalide as described in J. Org. Chem. 1976 2628-33.
Figure imgf000031_0001
Scheme 13.
The synthesis of compounds of formula (XVIIIa) and (XVIIIb) from commercially available building blocks is described in Bioorg. Med. Chem. Lett. 2011 , 240-244 and is obvious to a person skilled in the art.
As shown in scheme 14, compounds of formula (Xlllb), wherein Q1 represents -O- or
-C(R6)(R7) and Q2 represents -C(R6)(R7), can be prepared from compounds of formula (XIV) by treatment with a bronsted acid in an inert solvent as described in J. Am. Chem. Soc,
2014, 136, pp 8851-8854.
Figure imgf000031_0002
(XIX) (Xlllb)
Scheme 14.
As shown in scheme 15, compounds of formula (XlXa) can be prepared from compounds of formula (XX) by several methods methods, of which the most frequently used are described below:
a) By treatment of compounds of formula (XX) with a diene of formula (XXa) in the presence of a palladium catalyst and a reducing agent as described in J. Am. Chem. Soc. 2015, 137. b) Treatment of compounds of formula (XX) with an organoboron reagent generated from a diene of formula (XXa) and 9-borabicyclononane in the presence of a palladium catalyst as described in Angew. Chem. Int. Ed. 2001 , 40, 4544-4568.
Figure imgf000032_0001
(XX) (XlXa)
Scheme 15.
Compounds of formula (XX) are available from commercial vendors and/or can be easily prepared from commercially available precursors using using standard synthesis techniques known to the person skilled in the art.
Certain intermediates described in the above schemes are novel and as such form a further aspect of the invention.
The compounds of formula (I) can be used in the agricultural sector and related fields of use e.g. as active ingredients for controlling plant pests or on non-living materials for control of spoilage microorganisms or organisms potentially harmful to man. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and may be used for protecting numerous cultivated plants. The compounds of formula (I) can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
It is also possible to use compounds of formula (I) as fungicide. The term "fungicide" as used herein means a compound that controls, modifies, or prevents the growth of fungi. The term "fungicidally effective amount" means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.
It is also possible to use compounds of formula (I) as dressing agents for the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings (for example rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: seed, for example, can be dressed before being sown. The compounds of formula (I) can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing. The invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.
Furthermore the compounds according to present invention can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene
management.
In addition, the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.
Compounds of formula (I) and fungicidal compositions containing them may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens. They are effective in controlling a broad spectrum of plant diseases, such as foliar pathogens of ornamental, turf, vegetable, field, cereal, and fruit crops.
These fungi and fungal vectors of disease, as well as phytopathogenic bacteria and viruses, which may be controlled are for example:
Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. inclusing B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C.
arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea,
Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae,
Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp,
Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum,
Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp. including H. capsulatum, Laetisaria fuciformis,
Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp,
Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp. Including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp,
Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi,
Sclerotinia spp, Sclerotium spp, Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp,. Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T.
pseudokoningii, T. viride,
Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.
In particular, compounds of formula (I) and fungicidal compositions containing them may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and/or Mucoromycete classes.
These pathogens may include:
Oomycetes, including Phytophthora diseases such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora and Phytophthora erythroseptica; Pythium diseases such as those caused by Pythium
aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare and Pythium ultimum; diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo Candida, Sclerophthora macrospora and Bremia lactucae; and others such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi and
Sclerospora graminicola.
Ascomycetes, including blotch, spot, blast or blight diseases and/or rots for example those caused by Pleosporales such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii,
Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophora tritici-repentis, Alternaria alternata, Alternaria brassicicola, Alternaria solani and Alternaria tomatophila, Capnodiales such as Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae and Cercosporella herpotrichoides, Cladosporium carpophilum, Cladosporium effusum,
Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii,
Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoides, Ramularia beticola, Ramularia collo-cygni, Magnaporthales such as Gaeumannomyces graminis, Magnaporthe grisea, Pyricularia oryzae, Diaporthales such as Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsa ceratosperma, and others such as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp., Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gi belli na cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola,
Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita,
Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis,
Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor, Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; powdery mildew diseases for example those caused by Erysiphales such as Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, Podosphaera leucotricha, Podospaera macularis
Golovinomyces cichoracearum, Leveillula taurica, Microsphaera diffusa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis; molds for example those caused by
Botryosphaeriales such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta
cucurbitacearum; anthracnoses for example those caused by Glommerelales such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii,
Glomerella cingulata, and Colletotrichum graminicola; and wilts or blights for example those caused by Hypocreales such as Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp. cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum, and Verticillium theobromae.
Basidiomycetes, including smuts for example those caused by Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia stri if orm i s sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae and Tilletia caries.
Blastocladiomycetes, such as Physoderma maydis.
Mucoromycetes, such as Choanephora cucurbitarum.; Mucor spp.; Rhizopus arrhizus,
As well as diseases caused by other species and genera closely related to those listed above.
In addition to their fungicidal activity, the compounds and compositions comprising them may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species as well as certain protozoa. Within the scope of present invention, target crops and/or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
The useful plants and / or target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g. Bt. and VIP varieties) as well as disease resistant, herbicide tolerant (e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties. By way of example, suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.
The term "useful plants" and/or "target crops" is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® , Herculex I® and
LibertyLink®.
The term "useful plants" and/or "target crops" is to be understood as including those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include δ-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi. An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so- called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
The term "useful plants" and/or "target crops" is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191 . The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect- specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors;
ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP- glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases. Further, in the context of the present invention there are to be understood by δ- endotoxins, for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701 ). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see
WO03/018810).
More examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO93/07278, W095/34656, EP-A-0
427 529, EP-A-451 878 and WO03/052073.
The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from
WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651 .
The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies
(Lepidoptera).
Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a
CrylAc toxin); Bollgard I® (cotton variety that expresses a CrylAc toxin); Bollgard II® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);
NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt1 1 corn borer (CB) trait) and Protecta®.
Further examples of such transgenic crops are: 1 . Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St.
Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1 Ab toxin. Bt1 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St.
Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B- 1 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/ES/96/02.
6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1 160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.
7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 χ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
The term "locus" as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation. The term "plants" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
The term "plant propagation material" is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material" is understood to denote seeds.
Pesticidal agents referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.
The compounds of formula (I) may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
Suitable carriers and adjuvants, e.g. for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound. Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.
Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores. Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene- butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates. Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired
concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurised sprayers, wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.
Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.
Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1 ,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, Ν,Ν-dimethyl formamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1 ,1 ,1 -trichloroethane, 2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octyl amine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerine and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for the dilution of concentrates.
Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
A broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1 % to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surface active agents include salts of alkyl sulfates, such as
diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium
dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as
nonylphenol-C.sub. 18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate;
quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.
Other adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
The invention also provides for the use of provides a composition comprising a compound of formula (I) according to the present invention together with one or more pesticides, plant nutrients or plant fertilizers. The combination may also encompass specific plant traits incorporated into the plant using any means, for example conventional breeding or genetic modification.
Suitable examples of plant nutrients or plant fertilizers are calcium sulfate (CaS04), calcium nitrate (Ca(NC>3)2.4H20), calcium carbonate (CaCC ), potassium nitrate (KNO3), magnesium sulfate (MgS04), potassium hydrogen phosphate (KH2PO4), manganese sulfate (MnSCU), copper sulfate (CuS04), zinc sulfate (ZnS04), nickel chloride (NiC ), cobalt sulfate (C0SO4), potassium hydroxide (KOH), sodium chloride (NaCI), boric acid (H3BO3) and metal salts thereof (Na2Mo04). The nutrients may be present in an amount of 5% to 50% by weight, preferably of 10% to 25% by weight or of 15% to 20% by weight each. Preferred additional nutrients are urea ((Nhb^CO), melamine (C3H6N6), potassium oxide (K2O), and inorganic nitrates. The most preferred additional plant nutrient is potassium oxide. Where the preferred additional nutrient is urea, it is present in an amount of generally 1 % to 20% by weight, preferably 2% to 10% by weight or of 3% to 7% by weight.
Suitable examples of pesticides are acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, , dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides,
organophosphorous fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, zinc fungicides, Benzoylureas, carbamates, chloronicotinyls, diacylhydrazines, diamides, fiproles, macrolides, nitroimines, nitromethylenes, organochlorines, organophosphates, organosilicons, organotins, phenylpyrazoles, phosphoric esters, pyrethroids, spinosyns, tetramic acid derivatives, tetronic acid derivatives, Antibiotic nematicides, avermectin nematicides, botanical nematicides, carbamate nematicides, oxime carbamate nematicides, organophosphorus nematicides, nematophagous fungi or bacteria, amide herbicides, anilide herbicides, arsenical herbicides, arylalanine herbicides, aryloxyphenoxypropionic herbicides,
benzofuranyl herbicides, benzoic acid herbicides, benzothiazole herbicides,
benzoylcyclohexanedione herbicides, carbamate herbicides, carbanilate herbicides, chloroacetanilide herbicides, chlorotriazine herbicides, cyclohexene oxmie herbicides, cyclopropylisoxazole herbicides, dicarboximide herbicides, dinitroaniline herbicides, dinitrophenol herbicides, diphenyl ether herbicides, dithiocarbamate herbicides,
fluoroalkyltriazine herbicides, halogenated aliphatic herbicides, imidazolinone herbicides, inorganic herbicides, methoxytriazine herbicides, methylthiotriazine herbicides, nitrile herbicides, nitrophenyl ether herbicides, organophosphorous herbicides, oxadiazolone herbicides, oxazole herbicides, phenoxy herbicides, phenoxyacetic herbicides,
phenoxybutyric herbicides, phenoxypropionic herbicides, phenylenediamine herbicides, phenylurea herbicides, phthalic acid herbicides, picolinic acid herbicides, pyrazole
herbicides, pyridazine herbicides, pyridazinone herbicides, pyridine herbicides,
pyrimidinediamine herbicides, pyrimidinyloxybenzylamine herbicides, pyrimidinylsulfonylurea herbicides, quaternary ammonium herbicides, quinolinecarboxylic acid herbicides, sulfonamide herbicides, sulfonanilide herbicides, sulfonylurea herbicides, thiadiazolylurea herbicides, thioamide herbicides, thiocarbamate herbicides, thiocarbonate herbicides, thiourea herbicides, triazine herbicides, triazinone herbicides, triazinylsulfonylurea herbicides, triazole herbicides, triazolone herbicides, triazolopyrimidine herbicides, uracil herbicides, urea herbicides, microbials, plant extracts, pheromones, macrobials and other biologicals.
The following mixtures of compounds of formula (I) with further active ingredients are preferred (wherein the term "TX" refers to a compound selected from Tables A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) and Table E (below):
an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
an acaricide selected from the group of substances consisting of 1 ,1 -bis(4-chloro- phenyl)-2-ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-/V-methyl-/V-1 -naphthylacetamide (lUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (lUPAC name) (981 ) + TX, abamectin (1 ) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithion (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881 ) + TX, arsenous oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (lUPAC name) (888) + TX, azocyclotin (46) + TX, azothoate (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX, benzoximate (71 ) + TX, benzyl benzoate (lUPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromo- cyclen (918) + TX, bromophos (920) + TX, bromophos-ethyl (921 ) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (lUPAC name) (1 1 1 ) + TX, camphechlor (941 ) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + TX, carbophenothion (947) + TX, CGA 50'439 (development code) (125) + TX, chino- methionat (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorfenethol (968) + TX, chlorfenson (970) + TX, chlorfensulfide (971 ) + TX, chlorfenvinphos (131 ) + TX, chlorobenzilate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, cufraneb (1013) + TX, cyanthoate (1020) + TX, cyflumetofen (CAS Reg. No.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201 ) + TX, DCPM (1032) + TX, DDT (219) + TX, demephion (1037) + TX, demephion-0 (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton- methyl (224) + TX, demeton-0 (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfon (1039) + TX, diafen- thiuron (226) + TX, dialifos (1042) + TX, diazinon (227) + TX, dichlofluanid (230) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071 ) + TX, dimefox (1081 ) + TX, dimethoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinocton (1090) + TX, dinopenton (1092) + TX, dinosulfon (1097) + TX, dinoterbon (1098) + TX, dioxathion (1 102) + TX, diphenyl sulfone (lUPAC name) (1 103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapyn (1 1 13) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1 121 ) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, ethoate- methyl (1 134) + TX, etoxazole (320) + TX, etrimfos (1 142) + TX, fenazaflor (1 147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1 157) + TX, fentrifanil (1 161 ) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1 166) + TX, flubenzimine (1 167) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX,
fluorbenside (1 174) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1 192) + TX, formparanate (1 193) + TX, gamma-HCH (430) + TX, glyodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (lUPAC/Chemical
Abstracts name) (1216) + TX, hexythiazox (441 ) + TX, iodomethane (lUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, isopropyl O-
(methoxyaminothiophosphoryl)salicylate (lUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephosfolan (1261 ) + TX, mesulfen (alternative name) [CCN] + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methidathion (529) + TX, methiocarb (530) + TX, methomyl (531 ) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (561 ) + TX,
morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC- 184 (compound code) + TX, NC-512 (compound code) + TX, nifluridide (1309) + TX, nikkomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb 1 :1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydeprofos (1324) + TX,
oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phenkapton (1330) + TX, phenthoate (631 ) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos-methyl (652) + TX,
polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + 5 TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671 ) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridaphenthion (701 ) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (71 1 ) + TX, quintiofos (1381 ) + TX, R-1492 (development code) (1382) + TX, RA-
10 17 (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI- 121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX,
15 tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name) + TX, thiocarboxime (1431 ) + TX, thiofanox (800) + TX, thiometon (801 ) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441 ) + TX, triarathene (1443) +
20 TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX,
trifenofos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX,
an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne
25 [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX,
an anthelmintic selected from the group of substances consisting of abamectin (1 ) +
30 TX, crufomate (101 1 ) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
35 an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1 -hydroxy-1 /-/- pyridine-2-thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1 12) + TX, fenaminosulf (1 144) + TX, formaldehyde (404) + TX, hydrargaphen (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (lUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (61 1 ) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX,
a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51 ) + TX, Bacillus thuringiensis subsp.
israelensis (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51 ) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151 ) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191 ) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431 ) + TX, Heterorhabditis bacteriophora and H. megidis
(alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491 ) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741 ) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX,
Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX,
a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name) (542) and methyl bromide (537) + TX,
a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine
(alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,
an insect pheromone selected from the group of substances consisting of (£)-dec-5- en-1 -yl acetate with (£)-dec-5-en-1 -ol (lUPAC name) (222) + TX, (£)-tridec-4-en-1 -yl acetate (lUPAC name) (829) + TX, (£)-6-methylhept-2-en-4-ol (lUPAC name) (541 ) + TX, (£,Z)- tetradeca-4,10-dien-1 -yl acetate (lUPAC name) (779) + TX, (Z)-dodec-7-en-1 -yl acetate (lUPAC name) (285) + TX, (Z)-hexadec-l 1 -enal (lUPAC name) (436) + TX, (Z)-hexadec-l 1 - en-1 -yl acetate (lUPAC name) (437) + TX, (Z)-hexadec-13-en-1 1 -yn-1 -yl acetate (lUPAC name) (438) + TX, (Z)-icos-13-en-10-one (lUPAC name) (448) + TX, (Z)-tetradec-7-en-1 -al (lUPAC name) (782) + TX, (Z)-tetradec-9-en-1 -ol (lUPAC name) (783) + TX, (Z)-tetradec-9- en-1 -yl acetate (lUPAC name) (784) + TX, (7£,9Z)-dodeca-7,9-dien-1 -yl acetate (lUPAC name) (283) + TX, (9Z,1 1 £)-tetradeca-9,1 1 -dien-1-yl acetate (lUPAC name) (780) + TX, (9Z, 12£)-tetradeca-9,12-dien-1 -yl acetate (lUPAC name) (781 ) + TX, 14-methyloctadec-1 - ene (lUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (lUPAC name) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemone (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1 -yl acetate (lUPAC name) (286) + TX, dodec-9-en-1 -yl acetate (lUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1 -yl acetate (lUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (lUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossyplure (alternative name) (420) + TX, grandlure (421 ) + TX, grandlure I (alternative name) (421 ) + TX, grandlure II (alternative name) (421 ) + TX, grandlure III (alternative name) (421 ) + TX, grandlure IV (alternative name) (421 ) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481 ) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2,13-dien-1 - yl acetate (lUPAC name) (588) + TX, octadeca-3,13-dien-1 -yl acetate (lUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, oryctalure (alternative name) (317) + TX, ostramone (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-1 1 -en-1 -yl acetate (lUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure Bi (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX,
an insect repellent selected from the group of substances consisting of 2-(octylthio)- ethanol (lUPAC name) (591 ) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1 137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX,
an insecticide selected from the group of substances consisting of 1 -dichloro-1 - nitroethane (lUPAC/Chemical Abstracts name) (1058) + TX, 1 ,1 -dichloro-2,2-bis(4- ethylphenyl)ethane (lUPAC name) (1056), + TX, 1 ,2-dichloropropane (lUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 -bromo-2-chloroethane (lUPAC/Chemical Abstracts name) (916) + TX, 2,2,2- trichloro-1 -(3,4-dichlorophenyl)ethyl acetate (lUPAC name) (1451 ) + TX, 2,2-dichlorovinyl 2- ethylsulfinylethyl methyl phosphate (lUPAC name) (1066) + TX, 2-(1 ,3-dithiolan-2-yl)phenyl dimethylcarbamate (lUPAC/ Chemical Abstracts name) (1 109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (lUPAC/Chemical Abstracts name) (935) + TX, 2-(4,5-dimethyl-1 ,3-dioxolan-2- yl)phenyl methylcarbamate (lUPAC/ Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5- xylyloxy)ethanol (lUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (lUPAC name) (984) + TX, 2-imidazolidone (lUPAC name) (1225) + TX, 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (lUPAC name)
(1284) + TX, 2-thiocyanatoethyl laurate (lUPAC name) (1433) + TX, 3-bromo-1 -chloroprop-1 - ene (lUPAC name) (917) + TX, 3-methyl-1 -phenylpyrazol-5-yl dimethylcarbamate (lUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (lUPAC name)
(1285) + TX, 5,5-dimethyl-3-oxocyclohex-1 -enyl dimethylcarbamate (lUPAC name) (1085) + TX, abamectin (1 ) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethion (alternative name) [CCN] + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (lUPAC name) (861 ) + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, allosamidin (alternative name) [CCN] + TX, allyxycarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminium phosphide (640) + TX, amidithion (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, athidathion (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41 ) + TX, azamethiphos (42) + TX, azinphos- ethyl (44) + TX, azinphos-methyl (45) + TX, azothoate (889) + TX, Bacillus thuringiensis delta endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (lUPAC/Chemical Abstracts name) (892) + TX, barthrin [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultap (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioallethrin (78) + TX, bioallethrin S- cyclopentenyl isomer (alternative name) (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX, bioresmethrin (80) + TX, bis(2-chloroethyl) ether (lUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromfenvinfos (914) + TX, bromocyclen (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921 ) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butathiofos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (lUPAC name) (1 1 1 ) + TX, camphechlor (941 ) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + TX, carbon disulfide (lUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (lUPAC name) (946) + TX, carbophenothion (947) + TX, carbosulfan (1 19) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclen (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyfos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131 ) + TX, chlorfluazuron (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141 ) + TX, chlorphoxim (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cismethrin (80) + TX, clocythrin (alternative name) + TX, cloethocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumithoate (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, crufomate (101 1 ) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX,
cyanofenphos (1019) + TX, cyanophos (184) + TX, cyanthoate (1020) + TX, cyclethrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201 ) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (alternative name) [CCN] + TX, d-limonene (alternative name) [CCN] + TX, cZ-tetramethrin (alternative name) (788) + TX, DAEP (1031 ) + TX, dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demephion (1037) + TX, demephion-0 (1037) + TX,
demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulphon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapthon (1050) + TX, dichlofenthion (1051 ) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (lUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081 ) + TX, dimetan (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimetilan (1086) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271 ) + TX, diofenolan (1099) + TX, dioxabenzofos (1 100) + TX, dioxacarb (1 101 ) + TX, dioxathion (1 102) + TX, disulfoton (278) + TX, dithicrofos (1 108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1 1 15) + TX, ecdysterone (alternative name) [CCN] + TX, El 1642 (development code) (1 1 18) + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, EMPC (1 120) + TX, empenthrin (292) + TX, endosulfan (294) + TX, endothion (1 121 ) + TX, endrin (1 122) + TX, EPBP (1 123) + TX, EPN (297) + TX, epofenonane (1 124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etaphos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, ethiprole (310) + TX, ethoate-methyl (1 134) + TX, ethoprophos (312) + TX, ethyl formate (lUPAC name) [CCN] + TX, ethyl-DDD
(alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1 136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimfos (1 142) + TX, EXD (1 143) + TX, famphur (323) + TX, fenamiphos (326) + TX, fenazaflor (1 147) + TX, fenchlorphos (1 148) + TX, fenethacarb (1 149) + TX, fenfluthrin (1 150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1 153) + TX, fenoxycarb (340) + TX, fenpirithrin (1 155) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fensulfothion (1 158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (CAS. Reg. No.: 272451 -65- 7) + TX, flucofuron (1 168) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1 171 ) + TX, flumethrin (372) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, fonofos (1 191 ) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1 192) + TX, formparanate (1 193) + TX, fosmethilan (1 194) + TX, fospirate (1 195) + TX, fosthiazate (408) + TX, fosthietan (1 196) + TX, furathiocarb (412) + TX, furethrin
(1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (121 1 ) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hyquincarb (1223) + TX, imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX, iodomethane (lUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (1231 ) + TX, isobenzan (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrin (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl 0-(methoxy- aminothiophosphoryl)salicylate (lUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, kelevan (1249) + TX, kinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirimfos (1251 ) + TX, lufenuron (490) + TX, lythidathion (1253) + TX, m-cumenyl methylcarbamate (lUPAC name) (1014) + TX, magnesium phosphide (lUPAC name) (640) + TX, malathion (492) + TX, malonoben (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarphon (1258) + TX, menazon (1260) + TX, mephosfolan (1261 ) + TX, mercurous chloride (513) + TX, mesulfenfos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (lUPAC/Chemical Abstracts name) (1268) + TX, methidathion (529) + TX, methiocarb (530) + TX, methocrotophos (1273) + TX, methomyl (531 ) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methothrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX,
metoxadiazone (1288) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561 ) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naftalofos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (lUPAC/Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nithiazine (131 1 ) + TX, nitrilacarb (1313) + TX, nitrilacarb 1 :1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI- 0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, 0-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (lUPAC name) (1057) + TX, 0,0-diethyl 0-4-methyl-2-oxo-2H-chromen-7-yl
phosphorothioate (lUPAC name) (1074) + TX, Ο,Ο-diethyl 0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (lUPAC name) (1075) + TX, O, Ο,Ο', O'-tetrapropyl dithiopyrophosphate (lUPAC name) (1424) + TX, oleic acid (lUPAC name) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616) + TX, penfluron (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (lUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX, phenkapton (1330) + TX, phenothrin (630) + TX, phenthoate (631 ) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (lUPAC name) (640) + TX, phoxim (642) + TX, phoxim-methyl (1340) + TX, pirimetaphos (1344) + TX, pirimicarb (651 ) + TX, pirimiphos- ethyl (1345) + TX, pirimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (lUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidophos (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacyl (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothiofos (686) + TX, prothoate (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, pyraclofos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridaphenthion (701 ) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708) + TX, quassia (alternative name) [CCN] + TX, quinalphos (71 1 ) + TX, quinalphos- methyl (1376) + TX, quinothion (1380) + TX, quintiofos (1381 ) + TX, R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (lUPAC/Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium
pentachlorophenoxide (623) + TX, sodium selenate (lUPAC name) (1401 ) + TX, sodium thiocyanate [CCN] + TX, sophamide (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, terallethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta- cypermethrin (204) + TX, thiacloprid (791 ) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, thicrofos (1428) + TX, thiocarboxime (1431 ) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometon (801 ) + TX, thionazin (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441 ) + TX, triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, trifenofos (1455) + TX, triflumuron (835) + TX, trimethacarb (840) + TX, triprene (1459) + TX, vamidothion (847) + TX, vaniliprole [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, cyenopyrafen [560121 -52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1 ] + TX, sulfoxaflor [946578-00-3] + TX, flufiprole [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2] + TX, triflumezopyrim (disclosed in WO 2012/0921 15) + TX, a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (lUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX,
pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, trifenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX, pyriprole [394730-71 -3] + TX,
a nematicide selected from the group of substances consisting of AKD-3088
(compound code) + TX, 1 ,2-dibromo-3-chloropropane (lUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2-dichloropropane (lUPAC/ Chemical Abstracts name) (1062) + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 ,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1 ,1 -dioxide (lUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (lUPAC name) (980) + TX, 5-methyl-6- thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid (lUPAC name) (1286) + TX, 6- isopentenylaminopurine (alternative name) (210) + TX, abamectin (1 ) + TX, acetoprole
[CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben
(alternative name) + TX, cadusafos (109) + TX, carbofuran (1 18) + TX, carbon disulfide (945) + TX, carbosulfan (1 19) + TX, chloropicrin (141 ) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dichlofenthion (1051 ) + TX, dicliphos
(alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ethoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothion (1 158) + TX, fosthiazate (408) + TX, fosthietan (1 196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (lUPAC name) (542) + TX, isamidofos (1230) + TX, isazofos (1231 ) + TX, ivermectin (alternative name) [CCN] + TX, kinetin
(alternative name) (210) + TX, mecarphon (1258) + TX, metam (519) + TX, metam- potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, Myrothecium verrucaria composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (lUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX,
a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX, a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,
a rodenticide selected from the group of substances consisting of 2-isovalerylindan- 1 ,3-dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891 ) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301 ) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1 183) + TX, flupropadine hydrochloride (1 183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (lUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (lUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, phosacetim (1336) + TX, phosphine (lUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341 ) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371 ) + TX, scilliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851 ) and zinc phosphide (640) + TX,
a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)- ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2- enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB- 599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX, an animal repellent selected from the group of substances consisting of
anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171 ) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridine- amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX, and biologically active compounds selected from the group consisting of azaconazole (60207-31 -0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [1 16255-48-2] + TX, cyproconazole [94361 -06-5] + TX, difenoconazole [1 19446-68-3] + TX, diniconazole [83657- 24-3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [1 14369-43-6] + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21 -0] + TX, hexaconazole [79983-71 -4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598- 92-7] + TX, ipconazole [125225-28-7] + TX, metconazole [1251 16-23-6] + TX, myclobutanil [88671 -89-0] + TX, pefurazoate [101903-30-4] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pyrifenox [88283-41 -4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1 ] + TX, simeconazole [149508-90-7] + TX, tebuconazole
[107534-96-3] + TX, tetraconazole [1 12281 -77-3] + TX, triadimefon [43121 -43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ancymidol [12771 -68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71 -9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221 -53-4] + TX, ethirimol [23947-60-6] + TX, dodemorph [1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564-91 -4] + TX, spiroxamine [1 18134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61 -2] + TX, mepanipyrim [1 10235-47-7] + TX, pyrimethanil [531 12-28-0] + TX, fenpiclonil [74738- 17-3] + TX, fludioxonil [131341 -86-1] + TX, benalaxyl [71626-1 1 -4] + TX, furalaxyl [57646-30- 7] + TX, metalaxyl [57837-19-1 ] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21 -7] + TX, debacarb [62732-91 -6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX, chlozolinate [84332-86-5] + TX, dichlozoline [24201 -58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61 -8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471 -44- 8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691 -80-3] + TX, flutolanil [66332-96-5] + TX, mepronil [55814-41 -0] + TX, oxycarboxin [5259-88-1 ] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [1 12-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961 -52-4] + TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1 , 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxim- methyl [143390-89-0] + TX, metominostrobin [133408-50-1 ] + TX, trifloxystrobin [141517-21 - 7] + TX, orysastrobin [248593-16-0] + TX, picoxystrobin [1 17428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, ferbam [14484-64-1 ] + TX, mancozeb [8018-01 -7] + TX, maneb [12427- 38-2] + TX, metiram [9006-42-2] + TX, propineb [12071 -83-9] + TX, thiram [137-26-8] + TX, zineb [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1] + TX, captan [133-06- 2] + TX, dichlofluanid [1085-98-9] + TX, fluoroimide [41205-21 -4] + TX, folpet [133-07-3 ] + TX, tolylfluanid [731 -27-1] + TX, bordeaux mixture [801 1 -63-0] + TX, copperhydroxid [20427- 59-2] + TX, copperoxychlorid [1332-40-7] + TX, coppersulfat [7758-98-7] + TX, copperoxid [1317-39-1] + TX, mancopper [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [131 -72-6] + TX, nitrothal-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos [26087-47-8] + TX, isoprothiolane [50512-35-1 ] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-S- 5 methyl [135158-54-2] + TX, anilazine [101 -05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01 -2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamid [180409-60-3] + TX, cymoxanil [57966-95- 7] + TX, dichlone [117-80-6] + TX, diclocymet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dicloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-
10 5] + TX, SYP-LI90 (Flumorph) [211867-47-9] + TX, dithianon [3347-22-6] + TX, ethaboxam
[162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, fenamidone [161326-34-7] + TX, fenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [2391 10-15-7] + TX, flusulfamide [106917-52-6] + TX, fenhexamid [126833-17-8] + TX, fosetyl-aluminium [39148-
15 24-8] + TX, hymexazol [10004-44-1 ] + TX, iprovalicarb [140923-17-7] + TX, IKF-916
(Cyazofamid) [120116-88-3] + TX, kasugamycin [6980-18-3] + TX, methasulfocarb [66952- 49-6] + TX, metrafenone [220899-03-6] + TX, pencycuron [66063-05-6] + TX, phthalide
[27355-22-2] + TX, polyoxins [1 1 1 13-80-7] + TX, probenazole [27605-76-1 ] + TX, propamocarb [25606-41 -1] + TX, proquinazid [189278-12-4] + TX, pyroquilon [57369-32-1 ] +
20 TX, quinoxyfen [124495-18-7] + TX, quintozene [82-68-8] + TX, sulfur [7704-34-9] + TX, tiadinil [223580-51 -6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [41814-78-2] + TX, triforine [26644-46-2] + TX, validamycin [37248-47-8] + TX, zoxamide (RH7281 ) [156052-68- 5] + TX, mandipropamid [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, sedaxane [874967-67-6] + TX, 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid (9-
25 dichloromethylene-1 ,2,3,4-tetrahydro-1 ,4-methano-naphthalen-5-yl)-amide (dislosed in WO 2007/048556) + TX, 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid (3',4',5'- trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343) + TX,
[(3S,4R,4aR,6S,6aS, 12R, 12aS, 12bS)-3-[(cyclopropylcarbonyl)oxy]- 1 ,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-1 1 -oxo-9-(3-
30 pyridinyl)-2/-/,1 1 /-/naphtho[2,1 -b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate
[915972-17-7] + TX and 1 ,3,5-trimethyl-N-(2-methyl-1 -oxopropyl)-N-[3-(2-methylpropyl)-4- [2,2,2-trifluoro-1 -methoxy-1 -(trifluoromethyl)ethyl]phenyl]-1 H-pyrazole-4-carboxamide
[926914-55-8] + TX,
or a biologically active compound selected from the group consisting of N-[(5-chloro- 35 2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-pyrazole-4- carboxamide + TX, 2,6-Dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)- tetrone + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol- 3-amine + TX, 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1 -methyl-pyrazole-4- carboxamide + TX, CAS 850881 -30-0 + TX, 3-(3,4-dichloro-1 ,2-thiazol-5-ylmethoxy)-1 ,2- benzothiazole 1 ,1 -dioxide + TX, 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N- methyl-acetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1 -yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, Oxathiapiprolin + TX, tert-butyl N-[6-[[[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2- pyridyl]carbamate + TX, N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2- carboxamide + TX, 3-(difluoromethyl)-1 -methyl-N-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyrazole-4- carboxamide + TX, 2,2,2-trifluoroethyl N-[2-methyl-1 -[[(4- methylbenzoyl)amino]methyl]propyl]carbamate + TX, (2RS)-2-[4-(4-chlorophenoxy)-a,a,o trifluoro-o-tolyl]-1 -(1 H-1 ,2,4-triazol-1 -yl)propan-2-ol + TX, (2RS)-2-[4-(4-chlorophenoxy)- a,a,a-trifluoro-o-tolyl]-3-methyl-1 -(1 H-1 ,2,4-triazol-1 -yl)butan-2-ol + TX, 2-(difluoromethyl)-N- [(3R)-3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4- phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5- dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1 -[2-[3,5- bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3- chloro-phenyl] methanesulfonate + TX, but-3-ynyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4- dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5- phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5- phenyl-pyridazine + TX, 3-(difluoromethyl)-1 -methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4- carboxamide + TX, 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4- methyl-tetrazol-5-one + TX, 1 -methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1 - yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, pydiflumetofen + TX, benzovindiflupyr
[1072957-71 -1 ] + TX, bacillus subtilis var. amyloliquefaciens Strain FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, U.S.A. and known under the trade name Tae ro®) + TX, and
Figure imgf000061_0001
The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop
Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1 ). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common 5 Names, Copyright © 1995-2004]; for example, the compound "acetoprole" is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.
Most of the active ingredients described above are referred to hereinabove by a so- called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the
10 designation used instead is given in round brackets for the particular compound; in that case, the lUPAC name, the lUPAC/Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "develoment code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed. "CAS Reg. No" means the Chemical Abstracts Registry Number.
15 The active ingredient mixture of the compounds of formula (I) selected from Tables
A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) and Table E (below) with active ingredients described above comprises a compound selected from Tables
A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) or Table E (below) and an active ingredient as described above preferably in a mixing ratio of from
20 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or
25 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. Those mixing ratios are by weight.
The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the
30 pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
The mixtures comprising a compound of formula (I) selected from Tables A.1 to A.8,
B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) and Table E (below) and one 35 or more active ingredients as described above can be applied, for example, in a single
"ready-mix" form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula (I) selected from Tables A.1 to A.8, B.1 to B.8, C.1 to C.8, D.1 to D.8, E.1 to E.8, F.1 to F.8 (above) and Table E (below) and the active ingredients as described above is not essential for working the present invention.
The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds I for the preparation of these compositions are also a subject of the invention.
Another aspect of invention is related to the use of a compound of formula (I) or of a preferred individual compound as above-defined, of a composition comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, or of a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
A further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.
Controlling or preventing means reducing infestation by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated. A preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
A formulation, e.g. a composition containing the compound of formula (I), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I), may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
The application methods for the compositions, that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per hectare is preferably 1 g to 2000 g of active ingredient per hectare, more preferably 10 to 1000 g/ha, most preferably 10 to 600 g/ha. When used as seed drenching agent, convenient dosages are from 10mg to 1 g of active substance per kg of seeds.
When the compositions are used for treating seed, rates of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably from 0.01 to 10g per kg of seed are generally sufficient.
Suitably, a composition comprising a compound of formula (I) according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development.
The compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.
Such compositions may be produced in conventional manner, e.g. by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects). Also conventional slow release formulations may be employed where long lasting efficacy is intended. Particularly formulations to be applied in spraying forms, such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g. the ondensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.
A seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds. Such seed dressing formulations are known in the art. Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g. as slow release capsules or microcapsules.
In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of formula (I) together with component (B) and (C), and optionally other active agents, particularly microbiocides or conservatives or the like. Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
EXAMPLES The Examples which follow serve to illustrate the invention. Certain compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1 .5 ppm, 0.8 ppm or 0.2 ppm.
Throughout this description, temperatures are given in degrees Celsius and "m.p." means melting point. LC/MS means Liquid Chromatography Mass Spectroscopy and the description of the apparatus and the methods are:
Method A:
Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters
10 (SQD, SQDII or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V,
Extractor: 2.00 V, Source Temperature: 150°C, Desolvation Temperature: 350°C, Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. 15 Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3 , 1 .8 mm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH, gradient: 10-100% B in 1.2 min; Flow (ml/min) 0.85
Method B:
Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters
(SQD, SQDII or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V,
Extractor: 2.00 V, Source Temperature: 150°C, Desolvation Temperature: 350°C, Cone Gas 25 Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector.
Solvent degasser, binary pump, heated column compartment and diode-array detector.
Column: Waters UPLC HSS T3, 1 .8 mm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile 30 + 0.05 % HCOOH, gradient: 10-100% B in 2.7 min; Flow (ml/min) 0.85
Formulation Examples Wettable powders a) b) c) active ingredient [compound of formula (I)] 25 % 50 % 75 % sodium lignosulfonate 5 % 5 %
sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % phenol polyethylene glycol ether - 2 %
(7-8 mol of ethylene oxide)
highly dispersed silicic acid 5 % 10 % 10 %
Kaolin 62 % 27 %
The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
Powders for drv seed treatment a) b) c) active ingredient [compound of formula (I)] 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % -
Kaolin 65 % 40 % -
Talcum - 20 The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
Emulsifiable concentrate
active ingredient [compound of formula (I)] 10 %
octylphenol polyethylene glycol ether 3 %
(4-5 mol of ethylene oxide)
calcium dodecylbenzenesulfonate 3 %
castor oil polyglycol ether (35 mol of ethylene oxide) 4 %
Cyclohexanone 30 %
xylene mixture 50 %
Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c)
Active ingredient [compound of formula (I)] 5 % 6 % 4 % talcum 95 %
Kaolin - 94 %
mineral filler - - 96 %
Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
Extruder granules
Active ingredient [compound of formula (I)] 15 %
sodium lignosulfonate 2 %
carboxymethylcellulose 1 %
Kaolin 82 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
Coated granules
Active ingredient [compound of formula (I)]
polyethylene glycol (mol. wt. 200)
Kaolin
The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
Suspension concentrate
active ingredient [compound of formula (I)] 40 %
propylene glycol 10 %
nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
Sodium lignosulfonate 10 %
carboxymethylcellulose 1 %
silicone oil (in the form of a 75 % emulsion in water) 1 %
Water 32 %
The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Flowable concentrate for seed treatment
active ingredient [compound of formula (I)] 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 %
1 ,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 %
Silicone oil (in the form of a 75 % emulsion in water) 0.2 %
Water 45.3 %
The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Slow Release Capsule Suspension
28 parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate- mixture (8:1 ). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.
The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns.
The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose. Preparation examples
Preparation of N-ethyl-N-methyl-N'-(7-methyl-1 -phenyl-isochroman-6-yl)formamidine
Figure imgf000070_0001
Preparation of 2-(4-methyl-3-nitro-phenyl)ethanol
Borane-dimethylsulfide (13 mL, 128 mmol) was added dropwise to a solution of 2-(4- methyl-3-nitro-phenyl)acetic acid (25.0 g, 128 mmol) in dry THF (260 mL) at RT. The resulting solution was gradually warmed to 50 °C and stirred for 60 min at this temperature. After cooling to RT, excess borane was quenched by slow addition of MeOH. The mixture was diluted with sat. NaHC03 and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (22.8 g, 1 19.5 mmol) as light yellow oil.
1H NMR (400 MHz, CDCI3): δ 7.86 (d, 1 H), 7.39 (dd, 8.1 , 1 H), 7.29 (d, 1 H), 3.91 (t, 2H), 2.92 (t, 2H), 2.58 (s, 3H). Preparation of 2-(3-amino-4-methyl-phenyl)ethanol
A suspension of 2-(4-methyl-3-nitro-phenyl)ethanol (22.0 g, 121 mmol) and Pd/C (1 .1 g, 10%-wt Pd) in methanol (360 mL) was hydrogenated at RT under 1 bar of hb until analysis by HPLC indicated full conversion of the starting material. The reaction mixture was filtrated through Celite and the filtrate was concentrated in vacuo to afford the title compound as tan solid (18 g, 1 19 mmol).
1H NMR (400 MHz, CDCI3): δ 7.00 (d, 1 H), 6.54-6.61 (m, 2H), 3.83 (t, 2H), 3.51 -3.71 (bs, 2H), 2.77 (t, 2H), 2.15 (s, 3H), 1 .33-1.48 (bs, 1 H).
Preparation of 7-methyl-1 -phenyl-isochroman-6-amine
A suspension of 2-(3-amino-4-methyl-phenyl)ethanol (0.10 g, 0.66 mmol), p- toluenesulfonic acid (0.14 g, 0.79 mmol) and benzaldehyde (0.07 g, 0.66 mmol) in toluene (2 mL) was warmed to 105 °C and stirred for 16 h at this temperature. The resulting slurry was cooled to RT and neutralized with sat. NaHC03-solution. The mixture was extracted with ethyl acetate; the organic layer was washed with brine, dried over MgS04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (0.09 g, 0.38 mmol) as off-white solid.
1H NMR (400 MHz, CDC ): δ 7.28-7.38 (m, 5H), 6.49 (s, 1 H), 6.43 (s, 1 H), 5.64 (s, 1 H), 4.15 (ddd, 1 H), 3.89 (ddd, 1 H), 3.55 (bs, 2H), 3.04 (ddd, 1 H), 2.69 (td, 1 H), 2.03 (s, 3H). Preparation of N-ethyl-N-methyl-N'-(7-methyl-1 -phenyl-isochroman-6-yl)formamidine
A solution of 7-methyl-1 -phenyl-isochroman-6-amine (0.29 g, 1 .22 mmol), p- toluenesulfonic acid (0.02 g, 0.12 mmol) and N-(dimethoxymethyl)-N-methyl-ethanamine (0.33 g, 2.45 mmol) in dry toluene (6 mL) was stirred for 16 h at 50 °C. The reaction was cooled to RT and diluted with sat. NaHC03-solution. The mixture was extracted with ethyl acetate; the organic layer was washed with brine, dried over MgS04, filtrated and
concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (0.35 g, 1.14 mmol) as light yellow oil.
1H NMR (400 MHz, CDCI3): δ 7.45 (bs, 1 H), 7.30-7.37 (m, 5H), 6.54 (s, 1 H), 6.51 (s, 1 H), 5.69 (s, 1 H), 4.1 1 -4.18 (m, 1 H), 3.90 (ddd, 1 H), 3.38 (bs, 2H), 3.01 -3.1 1 (m, 1 H), 3.00 (s, 3H), 2.74 (td, 1 H), 2.12 (s, 3H), 1.21 (t, 3H).
Preparation of N'-(7'-chlorospiro[cyclohexane-1 ,1 '-isochromanel-6'-yl)-N-ethyl-N-methyl- formamidine
Figure imgf000071_0001
Preparation of 2-(4-chloro-3-nitro-phenyl)ethanol
Borane-dimethylsulfide (0.6 mL, 5.57 mmol) was added dropwise to a solution of 2-(4- chloro-3-nitro-phenyl)acetic acid (1.0 g, 4.64 mmol) in dry THF (10 mL) at RT. The resulting solution was gradually warmed to 45 °C and stirred for 60 min at this temperature. After cooling to RT, excess borane was quenched by slow addition of MeOH. The mixture was diluted with sat. NaHC03 and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (0.75 g, 3.72 mmol) as light yellow solid.
1H NMR (400 MHz, CDC ): δ 7.78 (d, 1 H), 7.47-7.51 (m, 1 H), 7.39-7.44 (m, 1 H), 3.86-4.00 (m, 2H), 2.93 (t, 2H).
Preparation of 2-(3-amino-4-chloro-phenyl)ethanol
A suspension of 2-(4-chloro-3-nitro-phenyl)ethanol (0.62 g, 3.08 mmol) and iron powder (1 .03 g, 18.45 mmol) in acetic acid (10 mL) was gradually warmed to 80 °C and stirred for 60 min at this temperature. Acetic acid was removed in vacuo at 45 °C and the residue was taken up in ethyl acetate and sat. NaHC03. The layers were separated; the organic layer was washed with brine, dried over MgS04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (0.41 g, 2.36 mmol) as light yellow solid.
1H NMR (400 MHz, CDCI3): δ 7.18 (d, 1 H), 6.65 (d, 1 H), 6.57 (dd, 1 H), 3.83 (t, 2H), 2.76 (t, 2H).
Preparation of 7'-chlorospiro[cyclohexane-1 ,1 '-isochromanel-6'-amine
A suspension of 2-(3-amino-4-chloro-phenyl)ethanol (0.10 g, 0.58 mmol), p- toluenesulfonic acid (0.12g, 0.69 mmol) and 1 ,1 -dimethoxycyclohexane (0.09 g, 0.64 mmol) in toluene (1.8 mL) was warmed to 105 °C and stirred for 16 h at this temperature. The resulting suspension was cooled to RT and neutralized with sat. NaHC03-solution. The mixture was extracted with ethyl acetate; the organic layer was washed with brine, dried over MgS04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (0.14 g, 0.54 mmol) as colorless oil.
1H NMR (400 MHz, CDC ): δ 7.01 (s, 1 H), 6.49 (s, 1 H), 3.91 (bs, 1 H), 3.85 (t, 2H), 2.69 (t, 2H), 1 .85-1.96 (m, 2H), 1 .49-1.79 (m, 8H).
Preparation of N'-(7'-chlorospiro[cvclohexane-1 ,1 '-isochromanel-6'-yl)-N-ethyl-N-methyl- formamidine
A solution of 7'-chlorospiro[cyclohexane-1 ,1 '-isochromane]-6'-amine (0.04 g, 0.16 mmol), p-toluenesulfonic acid (0.003 g, 0.016 mmol) and N-(dimethoxymethyl)-N-methyl- ethanamine (0.06 g, 0.48 mmol) in dry toluene (0.6 mL) was stirred for 16 h at 50 °C in a sealed vial. The reaction was cooled to RT and diluted with sat. NaHC03-solution. The mixture was extracted with ethyl acetate; the organic layer was washed with brine, dried over MgS04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (0.045 g, 0.14 mmol) as light yellow oil.
1H NMR (400 MHz, CDCb): δ 7.34-7.58 (bs, 1 H), 7.10 (s, 1 H), 6.57 (s, 1 H), 3.87 (t, 2H), 3.21 -3.63 (bs, 2H), 3.02 (bs, 3H), 2.73 (t, 2H), 1 .87-1 .95 (m, 2H), 1 .51 -1 .82 (m, 8H), 1 .23 (t, 3H).
Preparation of N-ethyl-N-methyl-N'-(6-methyl-4-phenyl-chroman-7-yl)formamidine
Figure imgf000072_0001
Preparation of 1 -methyl-2-nitro-4-(3-phenylprop-2-vnoxy)benzene Diisopropyl azodicarboxylate (4.38 g, 20.57 mmol) was added to a solution of triphenyl-phosphine (5.40 g, 20.57 mmol) in dry THF (75 mL) at 0 °C and the resulting mixture was stirred for 5 min at 0 °C. A solution of 4-methyl-3-nitrophenol (3.0 g, 19.59 mmol) and 3-phenylprop-2-yn-1 -ol (2.72 g, 20.57 mmol) in THF (25 mL) was then added over 5 min and the resulting clear solution was allowed to warm to RT over 60 min. The solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to afford the title compound (5.19 g, 19.4 mmol) as yellow oil.
1H NMR (400 MHz, CDCI3): δ 7.71 (d, 1 H), 7.42-7.48 (m, 2H), 7.25-7.38 (m, 4H), 7.16-7.23 (m, 1 H), 4.97 (s, 2H), 2.56 (s, 3H)
Preparation of 2-methyl-5-(3-phenylprop-2-vnoxy)aniline
To a solution of 1 -methyl-2-nitro-4-(3-phenylprop-2-ynoxy)benzene (2.0 g, 7.48 mmol) in EtOH (65 mL) was added zinc powder (2.45 g, 37.41 mmol) and a slurriy of ammonium chloride (3.20 g, 59.9 mmol) in water (10 mL). The resulting mixture was rapidly stirred for 7 h at RT. The mixture was filtrated through Celite and the filtrate was concentrated in vacuo. The residue was taken up in ethyl acetate and washed with sat. NaHCC>3 solution, brine, dried over MgS04, filtrated and concentrated in vacuo. Purification by chromatography on silica gel afforded the title compound (1.69 g, 7.12 mmol) as yellow oil.
1H NMR (400 MHz, CDC ): δ 7.43-7.49 (m, 2H), 7.28-7.36 (m, 3H), 6.94-7.00 (m, 1 H), 6.38-6.43 (m, 2H), 4.86 (s, 2H), 3.64 (bs, 2H), 2.12 (s, 3H).
Preparation of 6-methyl-4-phenyl-2H-chromen-7-amine
To a solution of 2-methyl-5-(3-phenylprop-2-ynoxy)aniline (1 .60 g, 6.7 mmol) in DCM (60 mL) was added (acetonitrile)[(2-biphenyl)di-tert-butylphosphine]gold(l)
hexafluoroantimonate (0.052 g, 0.067 mmol) in a single portion at RT. The resulting yellow solution was stirred for 60 min at RT, the solvent was evaporated and the residue purified by chromatography on silica gel to afford the title compound (1 .40 g, 5.90 mmol) as off white solid.
1H NMR (400 MHz, CDCI3): δ 7.31 -7.45 (m, 5H), 6.70 (s, 1 H), 6.28 (s, 1 H), 5.59 (t, 1 H), 4.77 (d, 2H), 3.69 (bs, 2H), 2.02 (s, 3H).
Preparation of N-ethyl-N-methyl-N'-(6-methyl-4-phenyl-chroman-7-yl)formamidine
A suspension of of 6-methyl-4-phenyl-2H-chromen-7-amine (0.045 g, 0.19 mmol) and Pd/C (10%-wt Pd, 0.01 g) in ethanol (3 mL) was hydrogenated (1 bar of H2) for 18 h at RT. The mixture was filtrated through Celite and the solvent was evaporated. The residue was dissolved in toluene (0.8 mL), p-toluenesulfonic acid (0.003 g, 0.018 mmol) and N- (dimethoxymethyl)-N-methyl-ethanamine (0.05 g, 0.38 mmol) was added, the vial was sealed, warmed to 50 °C and stirred for 18 h at this temperature. The reaction was cooled to RT and diluted with sat. NaHC03-solution. The mixture was extracted with ethyl acetate; the organic layer was washed with brine, dried over MgS04, filtrated and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (0.057 g, 0.18 mmol) as colorless oil.
1H N MR (400 MHz, CDCI3): δ 7.46 (bs, 1 H), 7.12-7.36 (m, 5H), 6.59 (s, 1 H), 6.31 (s, 1 H), 4.13 (t, 3H), 3.16-3.62 (m, 2H), 2.99 (s, 3H), 2.23-2.39 (m, 1 H), 2.09 (s, 3H), 1 .96-2.07 (m, 1 H), 1 .20 (t, 3H).
Table E: Physical data of compounds of formula (I)
The compounds of formula (I) in Table E were prepared using techniques analogous to those described above and/or common synthetic techniques generally known to the person skilled in the art.
Figure imgf000074_0001
Figure imgf000075_0001
Figure imgf000076_0001
76
Figure imgf000077_0001
Figure imgf000078_0001

Figure imgf000079_0001

Figure imgf000080_0001
80
Figure imgf000081_0001
81
Figure imgf000082_0001
82
Figure imgf000083_0001
83
Figure imgf000084_0001
84
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
[M+H]
Entry STRUCTURE RT (min) Method MP °C
(measured)
E1.71 335
E1.72 0.81 317 A
I
Biological Examples
Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) I wheat / leaf disc preventative (Powdery mildew on wheat)
Wheat leaf segments cv. Kanzler were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks were incubated at 20 °C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate chamber and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application).
The following compounds gave at 200 ppm give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development: E1 .01 , E1 .02 , E1.03 , E1.04 , E1.05 , E1.07 , E1.18 , E1 .19 , E1.20 , E1 .22 , E1 .23 , E1 .24 , E1 . 25 , E1.26 , E1 .27 , E1 .28 , E1 .29 , E1 .30 , E1. 31 , E1.32 , E1.33 , E1.34 , E1.35 , E1.36 , E1.37 , E1.38 , E1.39 , E1.40 , E1.41 , E1.44 , E1.45 , E1.46 , E1.47 , E1.48 , E1.49 , E1.50 , E1.51 , E1.52 , E1.53 , E1.54 , E1.55 , E1.56 , E1.57, E1 .58, E1.59, E1.61 , E1 .62, E1 .63, E1.64, E1 .65, E1 .67, E1.68, E1.69, E1 .70, E1 .71 , E1 .72 Puccinia recondita f. sp. tritici / wheat / leaf disc preventative (brown rust)
Wheat leaf segments cv. Kanzlerwere placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7-9 days after application).
The following compounds gave at 200 ppm gave at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development: E1.01, E1.03, E1.04, E1.05, E1.06, E1.07, E1.18, E1.19, E1.20, E1.21, E1.22, E1.23, E1.24, E1.25, E1.26, E1.27, E1.28, E1.29, E1.30, E1.31, E1.32, E1.33, E1.34, E1.35, E1.36, E1.37, E1.38 , E1.39 , E1.40 , E1.41 , E1.42 , E1.43 , E1.44 , E1.45 , E1.46 , E1.47 , E1.48 , E1.49 , E1.50 , E1.51 , E1.52 , E1.53 , E1.54 , E1.55 , E1.56 , E1.57, E1.58, E1.59, E1.61, E1.62, E1.63, E1.64, E1.65, E1.67, E1.68, E1.69, E1.70, E1.71, E1.72
Puccinia recondita f. sp. tritici / wheat / leaf disc curative (Brown rust)
Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. Plates were stored in darkness at 19°C and 75% rh. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6-8 days after application).
The following compounds gave at 200 ppm gaive at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development: : E1.01, E1.03, E1.04, E1.05, E1.06, E1.07, E1.18, E1.19, E1.20, E1.21, E1.22, E1.23, E1.24, E1.25, E1.26, E1.27, E1.28, E1.29, E1.30, E1.31, E1.32, E1.33, E1.34, E1.35, E1.36, E1.37, E1.38 , E1.39 , E1.40 , E1.41 , E1.42 , E1.43 , E1.44 , E1.45 , E1.46 , E1.47 , E1.48 , E1.49 , E1.50 , E1.51 , E1.52 , E1.53 , E1.54 , E1.55 , E1.56 , E1.57, E1.58, E1.59, E1.61, E1.62, E1.63, E1.64, E1.65, E1.66 , E1.67, E1.68, E1.69, E1.70, E1.71, E1.72
Phakopsora pachyrhizi / soybean / leaf disk preventative (soybean rust) Four-week old soybean plants are sprayed in a spray chamber with the formulated test compound diluted in water. Leaf disks are cut from treated plants and placed on agar into 24-well plates one day after application. Leaf disks are inoculated by spraying them with a spore suspension on their lower leaf surface. After an incubation period in a climate cabinet of 24-36 hours in darkness at 20 °C and 75% rh, the leaf disks are then kept at 20 °C with 12 h light/day and 75% rh. The percentage leaf disk area covered by disease is assessed when an appropriate level of disease appears on untreated check plants (12 - 14 days after application).
The following compounds gave at 200 ppm gave at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development: E1 .01 , E1 .03 , E1.05 , E1.06 , E1.07 , E1.23 , E1.24 , E1 .25 , E1.26 , E1 .27 , E1 .28 , E1 .29 , E1 .30 , E1.31 , E1.32 , E1.33 , E1.34 , E1.35 , E1.36 , E1 .37 , E1.38 , E1 .39 , E1 .40 , E1 .42 , E1 .44 , E1.46 , E1.47 , E1.48 , E1.49 , E1.50 , E1.51 , E1 .53 , E1.54 , E1 .56 , E1.57, E1 .59, E1.61 , E1.62, E1 .63, E1 .64, E1.65, E1.67, E1 .68, E1 .72

Claims

A compound of formula (I):
Figure imgf000091_0001
wherein
R1 and R2 each independently represent hydrogen, Ci-C4 alkyl, Ci-C4 fluoroalkyl, C2- C4 alkenyl, C2-C4 alkynyl or C3-C6 cycloalkyl; or
R1 and R2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom;
R3 represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C3 fluoroalkoxy or C3-C6 cycloalkyl;
Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein the -Q1 - Q2-Q3- linkage does not contain contiguous oxygen atoms;
R4 and R5 each independently represents hydrogen, cyano, aryl (which may be substituted with one to three R8 groups), heteroaryl (which may be substituted with one or two R8 groups), heterocyclyl (which may be substituted with one or two R8 groups), hydroxy, Ci-Cs alkyl, C2-C8 alkenyl, C2-C8 alkynyl, Ci-Cs haloalkyl, Ci-Cs alkoxy, C3-C8 cycloalkyl (which may be substituted with one to three R8 groups);
or R4 and R5 together with the carbon atom to which they are attached form a three to eight- membered saturated or partially-unsaturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain one or two oxygen atoms, one or two sulphur atoms or NR9, wherein R9 is hydrogen, C1-C4 alkoxy, C2-C4 alkynyl or C1-C4 alkyl);
R6 and R7 each independently represent hydrogen, fluoro, C1-C3 alkyl, Ci-Csfluoroalkyl or C3-C5 cycloalkyl; or R6 and R7 together with carbon atom to which they are attached to form a three to six membered saturated cyclic group which may optionally contain an oxygen or sulfur atom; and
Each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C3 fluoroalkoxy, C2-C4 alkynyl or C3-C6 cycloalkyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-O-C1- C4alkyl; or a salt or N-oxide thereof.
2. A compound according to claim 1 wherein R1 and R2 each independently represent hydrogen, Ci-C4 alkyl, Ci-C4fluoroalkyl, or C3-C6 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group.
3. A compound according to claim 1 or 2 wherein R3 represents fluoro, chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, or C1-C3 fluoroalkoxy. 4. A compound according to any one of claims 1 , 2 or 3 wherein R4 and R5 each
independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl, pyrimidinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, thiazolyl, or quinolinyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R8 groups), C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a three to eight- membered saturated or partially-unsaturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain one or two oxygen atoms, one or two sulphur atoms or NR9, wherein R9 is hydrogen, C1-C4 alkoxy or C2-C4 alkynyl);
wherein each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-O-C1- C4alkyl.
5. A compound according to any one of claims 1 , 2, 3 or 4 wherein Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein only one of Q1 , Q2 and Q3 can be -O- or alternatively both of Q1 and Q3 are -0-, and wherein R6 and R7 each independently represent hydrogen, fluoro, C1-C2 alkyl or C1-C2 fluoroalkyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group. 6. A compound according to any one of claims 1 , 2, 3, 4, or 5 wherein R1 and R2 each independently represent hydrogen, C1-C4 alkyl or C3-C6 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a five to six- membered saturated cyclic group..
A compound according to any one of claims 1 , 2, 3, 4, 5 or 6 wherein R3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, or C1-C2 alkoxy.
A compound according to any one of claims 1 , 2, 3, 4, 5, 6 or 7 wherein R4 and R5 each independently represents hydrogen, cyano, phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl, thiophenyl, oxazolyl or thiazolyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two R8 groups), C1-C6 alkyl, C2-C6 alkenyl, C1-C3 fluoroalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain an oxygen atom, a sulphur atom or NR9, wherein R9 is C1-C4 alkoxy or C2-C4 alkynyl); wherein each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl.
A compound according to claim 1 wherein R1 and R2 each independently represent hydrogen, C1-C4 alkyl or cyclopropyl; R3 represents chloro, bromo, cyano, C1-C3 alkyl, C1-C2 fluoroalkyl, or C1-C2 alkoxy; Q1 , Q2 and Q3 each independently represent - C(R6)(R7)- or -0-, wherein only one of Q1 , Q2, Q3 can be -0-; R4 represents hydrogen or C1-C6 alkyl; R5 represents phenyl (which may be substituted with one to three R8 groups), heteroaryl (wherein the heteroaryl is pyridyl or thiophenyl, and wherein the heteroaryl may be substituted with one or two R8 groups), heterocyclyl (wherein the heterocyclyl is tetrahydropyranyl or thianyl, and wherein the heterocyclyl may be substituted with one or two methyl groups), C1-C6 alkyl, C1-C3 fluoroalkyl, Ci- C4 alkoxy or C3-C6 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with one or two groups independently selected from C1-C4 alkyl and C1-C3 alkoxy, and which may contain an oxygen atom or NR9, wherein R9 is C1-C4 alkoxy); R6 and R7 each independently represent hydrogen, fluoro or methyl; or R6 and R7 together with carbon atom to which they are attached to form a cyclopropyl group; and each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C1-C2 fluoroalkyl, C1-C3 alkoxy, C1-C2 fluoroalkoxy, C2-C4 alkynyl or cyclopropyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, 5 wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl; or a salt or N-oxide thereof.
10. A compound according to claim 1 wherein R1 represents methyl; R2 represents ethyl or isopropyl; R3 represents chloro or methyl; Q1 , Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein Q2 is -C(R6)(R7)- and wherein only one of Q1
10 and Q3 can be -0-; R4 represents hydrogen, methyl or ethyl; R5 represents phenyl
(which may be substituted with one to three R8 groups) or C1-C6 alkyl; or R4 and R5 together with the carbon atom to which they are attached form a five to eight- membered saturated carbocyclic group (which may be substituted with C1-C4 alkyl or C1-C3 alkoxy); R6 and R7 each independently represent hydrogen; and each R8
15 independently represents fluoro, chloro, cyano, methyl, trifluoromethyl, C1-C3 alkoxy, trifluoromethoxy or difluoromethoxy; or a salt or N-oxide thereof.
1 1 . A compound according to any preceding claim wherein Q1 is -0-, Q2 is -CH2 - and Q3
20
12. A compound according any of claims 1 - 10 wherein Q1 is -CH2-, Q2 is -CH2 - and Q3 is -0-.
13. A composition comprising a fungicidally effective amount of a compound of formula 25 (I) as defined in any of claims 1 - 12.
14. A composition according to claim 13, wherein the composition further comprises at least one additional active ingredient and/or a diluent.
30 15. A method of combating, preventing or controlling phytopathogenic diseases which comprises applying to a phytopathogen, to the locus of a phytopathogen, or to a plant susceptible to attack by a phytopathogen, or to propagation material thereof, a fungicidally effective amount of a compound of formula (I) as defined in any of claims 1 - 12 or a composition comprising a fungicidally effective amount of a compound of
35 formula (I) as defined in any of claims 1 - 12.
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EP3643175A1 (en) 2018-10-24 2020-04-29 Basf Se Ternary pesticidal mixtures containing metyltetraprole and fenpropimorph

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WO2018193385A1 (en) 2017-04-20 2018-10-25 Pi Industries Ltd. Novel phenylamine compounds
US11524934B2 (en) 2017-04-20 2022-12-13 Pi Industries Ltd Phenylamine compounds
WO2018211442A1 (en) 2017-05-18 2018-11-22 Pi Industries Ltd. Formimidamidine compounds useful against phytopathogenic microorganisms
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EP3643175A1 (en) 2018-10-24 2020-04-29 Basf Se Ternary pesticidal mixtures containing metyltetraprole and fenpropimorph

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