EP2120560A1 - Phenoxyphenylamidines a substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides - Google Patents

Phenoxyphenylamidines a substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides

Info

Publication number
EP2120560A1
EP2120560A1 EP08716376A EP08716376A EP2120560A1 EP 2120560 A1 EP2120560 A1 EP 2120560A1 EP 08716376 A EP08716376 A EP 08716376A EP 08716376 A EP08716376 A EP 08716376A EP 2120560 A1 EP2120560 A1 EP 2120560A1
Authority
EP
European Patent Office
Prior art keywords
groups
formula
ethyl
substituted
methylimidoformamide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08716376A
Other languages
German (de)
English (en)
Inventor
Klaus Kunz
Ralf Dunkel
Jörg Nico GREUL
Oliver Guth
Kerstin Ilg
Darren James Mansfield
Wahed Ahmed Moradi
Thomas Seitz
Peter Dahmen
Ulrike Wachendorff-Neumann
Arnd Voerste
Jean-Pierre Vors
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP08716376A priority Critical patent/EP2120560A1/fr
Publication of EP2120560A1 publication Critical patent/EP2120560A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Definitions

  • the present invention relates to 4-cycloalkyl- or 4-aryl-substituted phenoxyphenylamidines of the general formula (F), to a process for their preparation, to the use of the amidines according to the invention for controlling unwanted microorganisms, and to an agent for this purpose comprising the phenoxyphenylamidines according to the invention. Furthermore, the invention relates to a method for controlling unwanted microorganisms by applying the compounds of the invention to the microorganisms and / or in their habitat.
  • WO-A-00/046184 discloses the use of amidines, including N, N-dimethyl-N '- [4- (biphenyl-4-yloxy) -2,5-xylyl] -formamidine, as fungicides.
  • WO-A-03/093 224 discloses the use of arylamidine derivatives as fungicides.
  • WO-A-03/024 219 discloses fungicidal compositions comprising at least one N2-phenylamidine derivative in combination with another selected known active ingredient.
  • WO-A-04/037239 discloses antifungicidal drugs based on N2-phenylamidine derivatives.
  • WO-A-05/089 547 discloses fungicide mixtures comprising at least one arylamidine derivative in combination with another known fungicidal active ingredient.
  • WO-A-05/120 234 discloses fungicide mixtures comprising at least one phenylamidine derivative and another selected known fungicide.
  • the object of the present invention is therefore to provide amidines having improved fungicidal activity.
  • R 1 is selected from hydrogen; linear, branched, C M2 alkyl, C 2 .i 2 alkenyl, C 2- 12 alkynyl groups; cyclic C 3 . 8 alkyl, C 4-8 alkenyl, C 4 . 8 alkynyl groups, wherein in the ring system of all the aforementioned cyclic groups, one or more carbon atoms may be replaced by heteroatoms selected from N, O, P and S, and all of the aforementioned groups having one or more groups selected from -R ', -X,
  • R ' is hydrogen or a Ci. ⁇ -alkyl group which may be substituted with one or more heteroatoms selected from N, O, P and S;
  • R is a Ci. ⁇ -alkyl group, wherein in the ring system of all the aforementioned cyclic groups, one or more C atoms may be replaced by heteroatoms selected from N, O, P and S, and all previously groups with one or more groups selected from -R ', -X, -OR', -SR ', -NR' 2 , -SiR ' 3 , -COOR', -CN and -CONR 2 'substituted where R 'is the above
  • R 2 is selected from linear, branched Ci.i 2 alkyl, C 2, i 2 alkenyl, C 2, i 2 alkynyl groups, cyclic C 3 . 8 alkyl, C 4 . 8 alkenyl, C 4-8 alkynyl groups, C 5-I8 -A ⁇ l, C 7-I9 - aralkyl or C 7 .i 9 alkaryl groups wherein the ring system of all the cyclic groups mentioned above one or more C atoms through heteroatoms selected from N,
  • R ' has the above meanings;
  • R 1 and R 3 together with the atoms to which they are attached or with further atoms selected from N, O, P and S, can form a four- to seven-membered ring which is replaced by R ', OR', SR R ', NR' 2 , SiR ' 3 groups may be substituted, wherein R' has the above meanings;
  • Groups one or more C atoms can be replaced by heteroatoms selected from N, O, P and S, and all the abovementioned groups having one or more groups which are selected from -R ', -X, -OR', - SR ', -NR' 2 , -SiR ' 3 , -COOR', -CN and -CONR 2 ', where R' and R "are as defined above;
  • R 6 is selected from hydrogen, halogen atoms and Ci-6-haloalkyl groups
  • R 7 is selected from alicyclic C 3-12 alkyl, C 4 _ 12 alkenyl, C 2 4- i alkynyl groups or C 5 _i 8 aryl, C 7 .i 9 aralkyl or C 7- 9 i alkaryl groups which may be substituted with one or more groups selected from -R ', -X, -OR', -SO 2 -R ', -SR', -NR '2, -SiR ' 3 , -COOR', -CN and -CONR 2 ', wherein R' has the above meanings - A -
  • a further subject of the present invention relates to a process for preparing the phenoxyphenylamidines according to the invention comprising at least one of the following steps (a) to 0):
  • R 1 to R 7 have the above meanings
  • R 8 and R 9 are independently selected from the group consisting of hydrogen, Ci. ⁇ -alkyl, C 2 _i 2 alkenyl-C 2 -i 2 -alkynyl or C 5 _i S -aryl- or C 7- i 9 arylalkyl groups and together with the O atoms to which they are attached can form a five, six or seven-membered ring;
  • R 10 to R 12 are independently selected from the group consisting of hydrogen, Qn alkyl, C 2 i 2 alkenyl, C 2 i 2 alkynyl or C 5 .i 8 -aryl or C 7 , I9 arylalkyl, C 7 .i 9 -Alkylaryl groups and each R 10 with R 12 , R 10 with R 11 or R 11 with R 12 together with the O atoms to which they are attached and optionally with further C -, N, O, P or S atoms can form a five-, six- or seven-membered ring.
  • a third aspect of the invention relates to 4-cycloalkyl- or 4-aryl-substituted nitrophenyl ethers of the formula (VI)
  • a fourth subject of the invention are 4-cycloalkyl- or 4-aryl-substituted anilin ethers of the formula (VIII)
  • a fifth object of the invention is the use of the 4-cycloalkyl- or 4-aryl-substituted phenoxyphenylamidines according to the invention or mixtures thereof for controlling unwanted microorganisms.
  • a sixth aspect of the present invention is an agent for controlling unwanted microorganisms comprising at least one 4-cycloalkyl- or 4-aryl-substituted phenoxyphenylamidine according to the present invention.
  • Another object of the invention relates to a method for controlling unwanted microorganisms, characterized in that the phenoxyphenylamidines according to the invention are applied to the microorganisms and / or in their habitat. Moreover, the invention relates to a seed which has been treated with at least one of the amidines according to the invention.
  • a final object of the invention relates to a method of protecting seed from undesirable microorganisms by using a seed treated with at least one phenoxyphenylamidine of the present invention.
  • halogens includes those elements selected from the group consisting of fluorine, chlorine, bromine and iodine, with fluorine, chlorine and bromine being preferred and fluorine and chlorine being particularly preferred preferably used.
  • Optionally substituted groups may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • the group -X denotes a halogen atom which is selected from fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine, more preferably from fluorine and chlorine.
  • Alkyl groups substituted by one or more halogen atoms are for example selected from trifluoromethyl (CF 3 ), difluoromethyl (CHF 2 ), CF 3 CH 2 , ClCH 2 , CF 3 CCl 2 .
  • alkyl groups are, unless otherwise defined, linear, branched or cyclic hydrocarbon groups which optionally have one, two or more single or double unsaturations or one, two or more heteroatoms which are selected from O, N, P and S may have.
  • R' is hydrogen or a Ci.i 2 alkyl group, preferably C 2 .io-alkyl group, particularly preferably C 3-8 alkyl group containing one or more heteroatoms selected from N , O, P and S, may have.
  • Ci-C ] 2 alkyl comprises the largest range defined herein for an alkyl group. Specifically, this definition includes, for example, the meanings methyl, ethyl, n-, iso -propyl, n-, iso-, sec- and t-butyl, n-pentyl, n-hexyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl, n-heptyl, n-nonyl, n- Decyl, n-undecyl, n-dodecyl.
  • Alkenyl groups are in the context of the present invention, unless otherwise defined, linear, branched or cyclic hydrocarbon groups containing at least one simple unsaturation (double bond) and optionally one, two or more single or double unsaturations or one, two or may have a plurality of heteroatoms selected from O, N, P and S.
  • R' is hydrogen or a C -] 2 alkyl group, preferably C 2- io alkyl group, more preferably C. 3 8- alkyl group which may have one or more heteroatoms selected from N, O, P and S.
  • C 2 -C 12 alkenyl includes the largest range defined herein for an alkenyl group. Specifically, this definition includes, for example, the meanings vinyl;
  • Oct-5-enyl, oct-6-enyl, oct-7-enyl Non-1-enyl, non-2-enyl, non-3-enyl, non-4-enyl, non-5-enyl, non-6-enyl, non-7-enyl, non-8-enyl; Dec-1-enyl, Dec-2-enyl, Dec-3-enyl, Dec-4-enyl,
  • Alkynyl groups are in the context of the present invention, unless otherwise defined, linear, branched or cyclic hydrocarbon groups containing at least two-fold unsaturation (triple bond) and optionally one, two or more single or double unsaturations or one, two or may have a plurality of heteroatoms selected from O, N, P and S.
  • R' is hydrogen or a linear, branched or cyclic C M2 - alkyl group which may have one or more heteroatoms selected from N, O, P and S.
  • alkynyl includes the largest range defined herein for an alkynyl group. Specifically, this definition includes, for example, the meanings ethynyl (acetylenyl); Prop-1-ynyl and prop-2-ynyl.
  • Cs.ig-aryl includes the largest range defined herein for an aryl group of 5 to 18 atoms. Specifically, this definition includes, for example, the meanings cyclopentadienyl, phenyl, cycloheptatrienyl, cyclooctatetraenyl, naphthyl and anthracenyl.
  • Arylalkyl groups are in the context of the present invention, unless otherwise defined, substituted by aryl groups substituted alkyl groups, which
  • Alkyl group preferably C 2- I 0-alkyl group, more preferably C. 3 8- alkyl group which may have one or more heteroatoms selected from N, O, P and S.
  • C 7 .i 9 aralkyl group includes the largest range defined herein for an arylalkyl group having a total of 7 to 19 atoms in the backbone and alkylene chain. Specifically, this definition includes, for example, the meanings benzyl and phenylethyl.
  • alkylaryl group includes the largest range defined herein for an alkylaryl group having a total of 7 to 19 atoms in the backbone and alkylene chain. Specifically, this definition includes, for example, the meanings tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylphenyl.
  • alkyl, alkenyl, alkynyl, aryl, alkaryl and aralkyl groups may have one or more heteroatoms which, unless otherwise defined, are selected from N, O, P and S.
  • the heteroatoms replace the numbered carbon atoms ,
  • the compounds of the invention may be prepared as mixtures of various possible isomeric forms, particularly stereoisomers, e.g. E and Z, threo and erythro, as well as optical isomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, as well as the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms disclosed and claimed.
  • the 4-cycloalkyl- or 4-aryl-substituted amidines according to the invention are compounds of the formula (I)
  • R 1 is selected from:
  • R ' is hydrogen or a Ci .n-alkyl group, preferably C 2 -alkyl group, more preferably C 3 _ 8 -alkyl group, containing one or more
  • Heteroatoms selected from N, O, P and S, may be substituted;
  • R is a Qn-alkyl group, preferably C 2 -io-alkyl group, particularly preferably C 3-8 alkyl group, wherein im Ring system of all of the abovementioned cyclic groups, one or more C atoms can be replaced by heteroatoms selected from N, O, P and S, and all the abovementioned groups having one or more groups which are selected from -R ', halogen- -X), alkoxy (-OR '), thioether or mercapto (-SR'), amino (-NR ' 2 ), silyl (-SiR' 3 ), carboxyl (-COOR '), cyano - (-CN) and amide groups (-CONR 2 ') may be substituted, wherein R' has the above meanings.
  • R 2 is selected from:
  • R 3 is selected from:
  • R 1 and R 3 together with the atoms to which they are attached or with further atoms selected from N, O, P and S, form a four- to seven-membered, preferably a five- to six-membered ring, denoted by -R ' .
  • R 4 is selected from:
  • R 5 is selected from:
  • R 6 is selected from hydrogen, halogen atoms and CI_ 6 -haloalkyl groups.
  • R 7 is selected from alicyclic C 3 i 2 alkyl, C 4- i 2 alkenyl, C 2 4- i alkynyl groups or C 5 .IG aryl, C 7 .i 9 -aralkyl or C 7 i 9 alkaryl groups which may be substituted with one or more groups selected from -R ', -X, -OR', -SO 2 -R ', -SR', -NR ' 2 , -SiR ' 3) -COOR', -CN and -CONR 2 ', wherein R' has the above meanings and wherein the C 5 .i 8 -aryl, C 7-19 -aralkyl or C 7 _i 9 -Alkaryl groups with one or more heteroatoms selected from N, O, P and S, may be substituted.
  • R 1 is preferably selected from the group consisting of hydrogen, a mercapto group (-SH) or Ci -8 alkyl groups.
  • R 2 is preferably selected from linear or branched, Ci -8 alkyl groups.
  • R 3 is preferably selected from linear, branched and alicyclic C 2 -g -alkyl groups.
  • R 2 and R 3 together with the N atom to which they are attached or with further atoms selected from N and O, form a five- or six-membered ring.
  • R 4 is preferably selected from -X, linear or branched, Ci -8 alkyl groups and Ci. 5 haloalkyl groups.
  • R 5 is preferably selected from -X, linear or branched, Ci -8 alkyl groups and Ci. 5 haloalkyl groups.
  • R 6 is preferably selected from hydrogen, fluorine, chlorine, bromine, -CF 3 , -CFlF 2 .
  • R 7 is preferably selected from phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl groups which may be substituted by one or more groups selected from -R ', -X, - OR ', -SR', -SO 2 -R ', -NR' 2 » -SiR ' 3 , -COOR', -CN and -CONR 2 ', wherein R' has the above meanings.
  • R 1 is more preferably selected from hydrogen, methyl and ethyl.
  • R 2 is more preferably selected from methyl and ethyl.
  • R 3 is more preferably selected from ethyl and cyclopropyl
  • R 2 and R 3 particularly preferably together can form a piperidyl or pyrrolidyl ring.
  • R 4 is particularly preferably selected from Cl and F atoms and -CF 3 , -CF 2 H and methyl groups.
  • R 5 is independently of R 4 particularly preferably selected from Cl and F atoms and -CF 3 , -CF 2 H and methyl groups.
  • R 6 is particularly preferably selected from -CF 3 , -CHF 2 .
  • R 7 is particularly preferably selected from phenyl, 4-chlorophenyl, 4-ethylsulfonylphenyl, 4-trifluoromethylphenyl, 4-dimethylaminophenyl, 4-methoxyphenyl, 4-tert-butylphenyl,
  • amidines according to the invention have acidic or basic properties and can form salts with inorganic or organic acids or with bases or with metal ions, if appropriate also with internal salts or adducts.
  • the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others into consideration. Particularly preferred are the metal ions of the elements of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (C 1 -C 4 ) -alkyl groups, mono-, , Di- and trialkanolamines of (C r C 4 ) -alkanols, choline and chlorocholine.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid and acid salts such as NaHSO 4 and KHSO 4 .
  • organic acids are, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl groups having 1 to 20 carbon atoms ), Arylsulfonic acids or disulfonic acids (aromatic groups such as phenyl and naphthyl bearing one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl groups having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic groups such as phenyl and Naphthyl which carry one or two phosphonic acid groups), the alkyl or aryl groups being able
  • the salts thus obtainable also have fungicidal properties.
  • Amidines particularly preferred in the context of the present invention are selected from the group consisting of N '- ⁇ 4 - [(4'-chlorobiphenyl-4-yl) oxy] -2,5-dimethylphenyl ⁇ -N-ethyl-N- methylimidoformamide (1), N-ethyl-N '- (4 - ⁇ [4' - (ethylsulfonyl) -biphenyl-4-yl] oxy ⁇ -2,5-dimethylphenyl) -N-methylimidoformamide (2), N'- (2,5-dimethyl-4 - ⁇ [4'- (trifluoromethyl) biphenyl-4-yl] oxy ⁇ phenyl) -N-ethyl-N-methylimidoformamide (3), N '- (4 - ⁇ [4'- (Dimethylamino) biphenyl-4-yl] oxy ⁇ -2,5-di
  • amidines according to the invention can be obtained by the process shown in the following scheme (I):
  • nitrobenzene derivatives of the formula (III) are reacted with 4-substituted phenols of the formula (II) or the phenolates formed therefrom according to the reaction scheme below to give nitrophenyl ethers of the formula (VI):
  • leaving group (Z) all substituents are suitable which have sufficient nucleofugicity under the prevailing reaction conditions.
  • halogens, triflate, mesylate, tosylate or SO 2 Me may be mentioned as suitable leaving groups.
  • the reaction is optionally carried out in the presence of a base.
  • bases are organic and inorganic bases commonly used in such reactions.
  • bases are used, which are selected for example from the group consisting of hydrides, hydroxides, amides, alcoholates, acetates, fluorides, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
  • bases are selected for example from the group consisting of hydrides, hydroxides, amides, alcoholates, acetates, fluorides, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
  • bases are selected for example from the group consisting of hydrides, hydroxides, amides, alcoholates, acetates, fluorides, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
  • Particular preference is given to sodium amide, sodium hydride, lithium diisopropylamide, sodium methoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium
  • tertiary amines such as e.g. Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylpyrrolidone, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclo-nonene (DBN) and diazabicycloundecene (DBU) ,
  • DABCO diazabicyclooctane
  • DBN diazabicyclo-nonene
  • DBU diazabicycloundecene
  • a catalyst selected from the group consisting of palladium, copper and their salts or complexes can be used.
  • the reaction of the nitrobenzene derivative with the phenol can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent, which is selected from conventional, inert in the prevailing reaction conditions solvents.
  • aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g.
  • Chlorobenzene dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane
  • Ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1, 2-diethoxyethane or anisole
  • Nitriles such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile
  • Amides such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone (NMP) or hexamethylenephosphoric triamide; or mixtures of these with water and pure water.
  • DMF N-dimethylformamide
  • the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of -20 to 200 ° C., preferably the reaction is carried out at normal pressure and at temperatures of 50 to 150 ° C.
  • nitrophenol derivatives of the formula (V) or the phenolates formed therefrom are reacted with 4-substituted phenyl derivatives of the formula (IV) according to the following reaction scheme to give nitrophenyl ethers of the formula (VI):
  • Step (c) With regard to reaction conditions, solvents, catalysts and suitable leaving groups, reference is made to step (a). Step (c)
  • anilines of the formula (VII) are reacted with 4-substituted phenols of the formula (II) or the phenolates formed therefrom according to the following reaction scheme to give aminophenyl ethers of the formula (VIII):
  • step (a) With regard to reaction conditions, solvents, catalysts and suitable leaving groups, reference is made to step (a).
  • aminophenols of the formula (XII) are reacted with 4-substituted phenyl derivatives of the formula (IV) according to the following reaction scheme to give aminophenyl ethers of the formula (VHT):
  • step (c) With regard to reaction conditions, solvents, catalysts and suitable leaving groups, reference is made to step (c).
  • step (e) can be carried out by all methods described in the prior art for the reduction of nitro groups.
  • the reduction is carried out with stannous chloride in concentrated hydrochloric acid as described in WO 0046184.
  • the reduction may also be carried out with hydrogen gas, preferably in the presence of suitable hydrogenation catalysts, e.g. Raney nickel, Pd / C done.
  • suitable hydrogenation catalysts e.g. Raney nickel, Pd / C done.
  • the reaction should take place in a solvent which is inert to the prevailing reaction conditions.
  • a solvent which is inert to the prevailing reaction conditions.
  • Such is, for example, toluene.
  • step (f) The conversion of the aniline ethers of the formula (VIII) into the amidines of the formula (I) according to the invention in step (f) can, as previously shown in scheme (I), be carried out by various alternative methods using
  • the anilin ethers of formula (VIII) are defined with amino acetals of formula (X ⁇ i) in which R 2 and R 3 are as previously defined and R 8 and R 9 are selected from Ci. 8 alkyl groups, preferably from C 2 ⁇ -AIkyl groups, more preferably from C 3 . 5- alkyl groups and which together with the O atoms to which they are attached, can form a five- or six-membered carbocyclic ring, to give the phenoxyphenylamidines of the formula (I) according to the invention.
  • amino acetals of formula (XIII) are prepared from the formamides described in JACS, 65, 1566 (1943) by reaction with alkylating reagents such as e.g. Dimethylsulfate, available.
  • reaction according to step (i) is optionally carried out in the presence of an acid.
  • Suitable acids are, for example, selected from the group consisting of organic and inorganic acids, p-toluenesulfonic acid, methanesulfonic acid, hydrochloric acid (gaseous, aqueous or in organic solution) or sulfuric acid.
  • step (ii) In an alternative embodiment of the invention shown in Scheme (I) as step (ii), the anilin ethers of formula (VIII) are reacted with amides of formula (XIV) in which the groups R 1 to R 3 are as before are converted to the phenoxyphenylamidines according to the invention.
  • the reaction according to step (ii) is optionally carried out in the presence of a halogenating agent.
  • Suitable halogenating agents are, for example, selected from the group consisting of PCl 5 , PCl 3 , POCl 3 or SOCl 2 .
  • the reaction may alternatively be in the presence of a condensing agent.
  • Suitable condensing agents are those commonly used to form amide bonds, by way of example acid halide formers such as e.g. Phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide or thionyl chloride; Anhydride formers such as e.g. Chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; Carbodiimines such as e.g. N, N'-dicyclohexylcarbodiimine (DCC) or other conventional condensing agents, e.g.
  • acid halide formers such as e.g. Phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide or thionyl chloride
  • Phosphorus pentoxide polyphosphoric acid, N, N'-carbodiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane or Bromtripyrrolidinophosphoniumhexafluorophosphat called.
  • step (ii) is optionally carried out in a solvent which is selected from the usual, inert in the prevailing reaction conditions solvents.
  • a solvent which is selected from the usual, inert in the prevailing reaction conditions solvents.
  • Alcohols such as methanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert-butanol, ethanediol, propane-l, 2-diol, ethoxiethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether or mixtures thereof used.
  • the reaction according to step (iii) is preferably carried out in a solvent which is selected from the usual, inert in the prevailing reaction conditions solvents.
  • a solvent which is selected from the usual, inert in the prevailing reaction conditions solvents.
  • aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g. Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether,
  • aminophenols of the formula (XII) may already be
  • step (f) With regard to the reaction conditions, solvents, catalysts, reference is made to step (f).
  • step (f) With regard to the reaction conditions, solvents, catalysts, reference is made to step (f).
  • the further reaction of the amidines of the formula (XI) to the target molecules of the formula (I) according to the invention can be carried out, for example, as described in step (i).
  • the amidines of formula (XI) obtainable from step (h) can be reacted with 4-substituted phenols of formula (II) or the phenolates formed therefrom to form the target molecules of formula (I) according to the invention according to the following reaction scheme :
  • step (a) With regard to the reaction conditions, solvents and catalysts, reference is made to step (a).
  • the amidines of the formula (X) obtainable from step (g) can be reacted with 4-substituted phenyl derivatives of the formula (IV) to give the target molecules of the formula (I) according to the invention in accordance with the following reaction scheme:
  • step (b) With regard to the reaction conditions, solvents and catalysts, reference is made to step (b).
  • phenoxyphenylamidines according to the invention is preferably carried out without intermediate isolation of the intermediates.
  • the final purification of phenoxyphenylamidines can be carried out by customary purification methods.
  • the purification is carried out by crystallization.
  • amidines according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Hemileia species such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as Puccinia recondita
  • Uromyces species such as Uromyces appendiculatus
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Pythium species such as Pythium ultimum
  • Cercospora species such as Cercospora beticola
  • Cladosporium species such as Cladosporium cucumerinum
  • Cochliobolus species such as Cochliobolus sativus
  • Drechslera Syn: Helminthosporium
  • Colletotrichum species such as Colletotrichum lindemuthanium
  • Cycloconium species such as cycloconium oleaginum
  • Diaporthe species such as Diaporthe citri;
  • Elsinoe species such as Elsinoe fawcettii
  • Gloeosporium species such as, for example, Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata;
  • Guignardia species such as Guignardia bidwelli;
  • Leptosphaeria species such as Leptosphaeria maculans
  • Magnaporthe species such as Magnaporthe grisea
  • Mycosphaerella species such as Mycosphaerella graminicola and Mycosphaerella fljiensis
  • Mycosphaerella species such as Mycosphaerella graminicola and Mycosphaerella fljiensis
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Corticium species such as Corticium graminearum
  • Fusarium species such as Fusarium oxysporum
  • Gaeumannomyces species such as Gaeumannomyces graminis
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis
  • Thielaviopsis species such as Thielaviopsis basicola
  • Ear and panicle diseases caused by e.g.
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium cladosporioides
  • Claviceps species such as Claviceps purpurea
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gibberella zeae
  • Monographella species such as Monographella nivalis; Diseases caused by fire fungi, e.g.
  • Sphacelotheca species such as Sphacelotheca reiliana
  • Tilletia species such as Tilletia caries
  • Urocystis species such as Urocystis occulta; Ustilago species such as Ustilago nuda; Fruit rot caused, for example, by Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Penicillium species such as Penicillium expansum and Penicillium pu ⁇ urogenum; Sclerotinia species, such as Sclerotinia sclerotiorum; Verticilium species such as Verticilium alboatrum;
  • Aphanomyces species such as Aphanomyces euteiches
  • Ascochyta species such as Ascochyta lentis
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium herbarum Cochliobolus species, such as Cochliobolus sativus
  • Colletotrichum species such as Colletotrichum coccodes
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gibberella zeae
  • Macrophomina species such as Macrophomina phaseolina
  • Monographella species such as Monographella nivalis
  • Penicillium species such as Penicillium expansum
  • Phomopsis species such as Phomopsis sojae
  • Phytophthora species such as Phytophthora cactorum
  • Pyrenophora species such as Pyrenophora graminea
  • Pyricularia species such as Pyricularia oryzae
  • Pythium species such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species such as Rhizopus oryzae Sclerotium species such as Sclerotium rolfsii; Septoria species such as Septoria nodorum; Typhula species, such as Typhula incarnata;
  • Verticillium species such as, for example, Verticillium dahliae cancers, galls and witches brooms, caused by e.g. Nectria species, such as Nectria galligena; Wilt diseases caused by e.g. Monilinia species such as Monilinia laxa;
  • Esca species such as Phaeomoniella chlamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;
  • Botrytis species such as Botrytis cinerea
  • Rhizoctonia species such as Rhizoctonia solani
  • Helminthosporium species such as Helminthosporium solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as Erwinia amylovora
  • the following diseases of soybean beans can be controlled:
  • Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and Blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Pod and Star Blight (Phomopsis sojae), Powdery Mildew (
  • Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var.
  • Phytophthora red (Phytophthora megasperma), Brown Star Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Star Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Star Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • the active compounds according to the invention also have a strong restorative effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
  • Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
  • the substances of the invention can therefore be used to plants within a certain period of time after treatment against the
  • the period within which protection is generally from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
  • the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
  • the active compounds according to the invention can be used with particularly good success for controlling cereal diseases, such as, for example, against Puccinia species and diseases in the wine, fruit and vegetable growing, such. against Botrytis, Venturia or Alternaria species.
  • the active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the active compounds according to the invention may optionally also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, spraying, evaporating, atomizing, spreading, brushing and propagating material, in particular in the case of seeds single or multi-layer coating.
  • mycotoxins include: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 and HT2 toxin, fumonisins, zearalenone, moniliformin, fusarin, diaceotoxyscirpenol (DAS) , Beauvericin, enniatine, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins, which may be caused, for example, by the following fungi: Fusarium spec., Such as Fusarium acuminatum, F.
  • the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • technical materials to be protected from microbial change or destruction by the active compounds of the invention may be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastics, coolants, and other materials that may be infested or degraded by microorganisms .
  • materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms.
  • the technical materials which may be mentioned are preferably adhesives, glues, papers and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • microorganisms that can cause degradation or a change in the technical materials
  • bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • fungi in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Basidiomycetes wood-discolouring and wood-destroying fungi
  • slime organisms and algae There may be mentioned, for example, microorganisms of the following genera:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus like Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia like Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus. formulations
  • the present invention relates to an agent for controlling undesirable microorganisms comprising at least one of the phenoxyphenylamidines according to the invention.
  • the phenoxyphenylamidines according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in seed coating compositions, as well as ULV KaIt and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foaming agents means.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foaming agents means.
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated acrylates, maten or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated acrylates such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohe
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
  • solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • Suitable dispersants are: for example, lignin liquors and methylcellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
  • the formulations described above can be used in a method according to the invention for controlling unwanted microorganisms, in which the phenoxyphenylamidines according to the invention are applied to the microorganisms and / or in their habitat.
  • the present invention therefore more particularly relates to a method of protecting seeds and germinating plants from the infestation of phytopathogenic fungi by treating the seed with an agent according to the invention.
  • the invention also relates to the use of the seed treatment agents of the invention for protecting the seed and the germinating plant from phytopathogenic fungi.
  • the invention relates to seed which has been treated with an agent according to the invention for protection against phytopathogenic fungi.
  • One of the advantages of the present invention is that because of the particular systemic properties of the compositions of the invention, treatment of the seed with these agents not only protects the seed itself, but also the resulting plants after emergence from phytopathogenic fungi. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • compositions according to the invention are suitable for the protection of seeds of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (such as wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, bean, coffee, turnip (eg sugarbeet and fodder), peanut, vegetables ( like tomato, cucumber, onions and lettuce), lawn and ornamental plants.
  • cereals such as wheat, barley, rye, millet and oats
  • corn cotton, soy, rice, potatoes, sunflower, bean, coffee, turnip (eg sugarbeet and fodder), peanut, vegetables ( like tomato, cucumber, onions and lettuce), lawn and ornamental plants.
  • turnip eg sugarbeet and fodder
  • peanut like tomato, cucumber, onions and lettuce
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a condition that is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used which has been harvested, cleaned and dried to a moisture content below 15% by weight.
  • seed may also be used which, after drying, e.g. treated with water and then dried again.
  • the agents according to the invention can be applied directly, ie without containing further components and without being diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
  • the active compound combinations that can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • These formulations are prepared in a known manner by mixing the active ingredients or combinations of active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also Water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, CI. Pigment Red 112 and CI. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • antifoams all can be used in the seed dressing formulations which can be used according to the invention.
  • Formulation of agrochemical active ingredients usual foam-inhibiting substances to be contained.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers and beets or even vegetable seeds of various nature.
  • the seed dressing formulations which can be used according to the invention or their diluted preparations can also be used for pickling seeds of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.
  • the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
  • all mixing devices which can usually be used for the dressing can be considered. Specifically, in the pickling procedure, the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the respective content of the active ingredients in the formulations and on the seed.
  • the application rates of active fabric combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • phenoxyphenylamidines of the invention can be used as such or in their formulations also in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, e.g. to broaden the spectrum of action or to prevent development of resistance.
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphtheria (for example against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character.
  • the active compounds according to the invention can therefore be used both in medical and in non-medical applications.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.
  • the application rates can be varied within a wide range depending on the type of application.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the treatment method of the invention may be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds are used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially refers to a gene which is provided or assembled outside the plant and which, when introduced into the nuclear genome, chloroplast genome or hypochondriacal genome, imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide or that it is downregulating or shutting down another gene present in the plant or other genes present in the plant (for example by antisense technology, cosuppression technology or RNAi technology [RNA Interference]).
  • a heterologous gene present in the genome is also referred to as a transgene.
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
  • the following effects are possible, which go beyond the expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to dryness or water or soil salinity, increased flowering, crop relief, maturation acceleration, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher Sugar concentration in fruits, better shelf life and / or processability of harvested products.
  • the active compound combinations according to the invention can also exert a strengthening effect on plants. They are therefore suitable for mobilizing the plant defense system against attack by undesirable phytopathogenic fungi and / or microorganisms and / or viruses. This may optionally be one of the reasons for the increased effectiveness of the combinations according to the invention, for example against fungi.
  • Plant-strengthening (resistance-inducing) substances in the present context should also mean those substances or combinations of substances which are able to stimulate the plant defense system such that the treated plants, when subsequently inoculated with undesirable phytopathogenic fungi and / or microorganisms and / or viruses a considerable degree of resistance to these unwanted phytopathogenic fungi and / or microorganisms and / or viruses.
  • phytopathogenic fungi, bacteria and viruses are understood to be undesirable phytopathogenic fungi and / or microorganisms and / or viruses.
  • the substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the treatment.
  • the period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active substances.
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).
  • Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors.
  • Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife.
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, internode count and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability.
  • improved plant architecture under stress and non-stress conditions
  • Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
  • Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or of the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • cytoplasmic male sterility have been described, for example, for Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072).
  • pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
  • a particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 1991/002069).
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants that have been tolerated to the herbicide glyphosate or its salts.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • AroA gene mutant CT7 of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371)
  • the CP4 gene of the bacterium Agrobacterium sp. Barry et al., Curr Topics Plant Physiol.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants may also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described, for example, in US Pat. As WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782 is encoded.
  • Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described, for example, in WO 2001/024615 or WO 2003/013226.
  • Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • Such an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
  • a phosphinotricin acetyltransferase such as the bar or pat protein from Streptomyces species.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenases
  • HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO 1996/038567, WO 1999/024585 and WO 1999 / 024586, are transformed.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants in addition to a gene coding for an HPPD tolerant enzyme with a gene coding for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
  • ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • plants which are tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 1997/41218, for the sugar beet in US 5,773,702 and WO 1999/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention are insect-resistant transgenic plants, i. Plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • insect-resistant transgenic plant includes any plant containing at least one transgene comprising a coding sequence encoding:
  • an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins described by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac. uk / Home / Neil Crickrnore / Bt /), or insecticidal parts thereof, e.g. Proteins of the cry protein classes CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
  • a crystal protein from Bacillus thuringiensis or a part thereof which is insecticidal in the presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006), 71, 1765-1774); or 3) an insecticidal hybrid protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or
  • VEP3Aa an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative insecticidal proteins (VIPs) available at http://www.lifesci.sussex.ac.uk/home/ Neil Crickmore / Bt / vip. html are listed, z. B. Proteins of protein class VEP3Aa; or
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 1994/21795).
  • a hybrid insecticidal protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
  • insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8.
  • an insect-resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following:
  • Plants which contain a transgene capable of reducing the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5 is described.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering
  • Plants or plant varieties which can also be treated according to the invention, have a modified amount, quality and / or shelf life of the harvested product and / or altered properties of certain components of the crop, such as:
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering, which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include:
  • plants such as cotton plants, which contain an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219;
  • plants such as cotton plants having increased expression of sucrose phosphate synthase as described in WO 2001/017333;
  • plants such as cotton plants with an increased expression of sucrose synthase, as described in WO 02/45485;
  • plants such as cotton plants with modified reactivity fibers, e.g. B. by
  • N-acetylglucosamine transferase gene including nodC, and of chitin synthase genes, as described in WO 2006/136351.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be through genetic transformation or through Selection of plants containing a mutation conferring such altered oil properties; these include:
  • plants such as rape plants producing oil of high oleic acid content, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947;
  • plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755.
  • plants such as oilseed rape plants which produce oil with a low saturated fatty acid content, such as e.g. As described in US 5,434,283.
  • transgenic plants which can be treated according to the invention are plants with one or more genes coding for one or more toxins, the transgenic plants offered under the following commercial names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, Soybeans
  • KnockOut® for example corn
  • BiteGard® for example maize
  • BT-Xtra® for example corn
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example corn
  • Protecta® and NewLeaf® pot
  • Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn.
  • the herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfeld® (for example corn).
  • transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in the files of various national or regional authorities (see, for example, http: // /gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
  • the listed plants can be used particularly advantageously according to the invention with the compounds of the general formula (I) or the active substance mixtures according to the invention be treated.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • Example 1 Podosphaera test (apple) / protective
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Example 2 Sphaerotheca test (cucumber) / protective
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the compounds of the invention show 32, 38, 33, 35, 41, 1, 2, 3, 8, 7, 11, 5, 6, 19, 13, 14, 15, 16, 17, 18, 20, 22 , 23, 24, 25, 26 and 27 (see Tab.II) at an active ingredient concentration of 100 ppm, an efficiency of 70% or more.
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the compounds of the invention 32, 38, 33, 35, 41, 1, 3, 7, 11, 5, 6, 19, 13, 14, 15, 16, 17, 18, 20, 22, 23, 24 , 25, 26 and 27 (see Table II) with an active ingredient concentration of 250 ppm an efficiency of 70% or more.
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at about 21 0 C and a relative humidity of about 90%.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • compounds 32, 36, 11, 19, 27 and 31 according to the invention exhibit an efficacy of 70% or more at a concentration of active ingredient of 500 ppm.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at a temperature of about 20 0 C and a relative humidity of 80% to promote the development of rust pustules.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

L'invention concerne des phénoxyphénylamidines à substitution 4-cycloalkyle ou 4-aryle de formule générale (I), un procédé de production de ces amidines, leur utilisation pour lutter contre des micro-organismes indésirables, et un agent conçu à cet effet comprenant les phénoxyphénylamidines selon l'invention. Cette invention concerne également un procédé pour lutter contre des micro-organismes indésirables par application des composés selon l'invention sur les micro-organismes et/ou introduction desdits composés dans leur biotope.
EP08716376A 2007-03-12 2008-03-08 Phenoxyphenylamidines a substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides Withdrawn EP2120560A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08716376A EP2120560A1 (fr) 2007-03-12 2008-03-08 Phenoxyphenylamidines a substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07005005A EP1969934A1 (fr) 2007-03-12 2007-03-12 Phénoxyphénylamidine substituée par 4 cycloalkyl ou 4 aryl et son utilisation en tant que fongicide
PCT/EP2008/001864 WO2008110315A1 (fr) 2007-03-12 2008-03-08 Phénoxyphénylamidines à substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides
EP08716376A EP2120560A1 (fr) 2007-03-12 2008-03-08 Phenoxyphenylamidines a substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides

Publications (1)

Publication Number Publication Date
EP2120560A1 true EP2120560A1 (fr) 2009-11-25

Family

ID=38037430

Family Applications (2)

Application Number Title Priority Date Filing Date
EP07005005A Ceased EP1969934A1 (fr) 2007-03-12 2007-03-12 Phénoxyphénylamidine substituée par 4 cycloalkyl ou 4 aryl et son utilisation en tant que fongicide
EP08716376A Withdrawn EP2120560A1 (fr) 2007-03-12 2008-03-08 Phenoxyphenylamidines a substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP07005005A Ceased EP1969934A1 (fr) 2007-03-12 2007-03-12 Phénoxyphénylamidine substituée par 4 cycloalkyl ou 4 aryl et son utilisation en tant que fongicide

Country Status (6)

Country Link
US (2) US8299302B2 (fr)
EP (2) EP1969934A1 (fr)
JP (1) JP2010520906A (fr)
CN (1) CN101631459A (fr)
BR (1) BRPI0808796A2 (fr)
WO (1) WO2008110315A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0808846A2 (pt) * 2007-03-12 2019-09-24 Bayer Cropscience Ag fenoxifenilamidinas 3-substituídas e seu uso como fungicidas
CA2680617A1 (fr) * 2007-03-12 2008-09-18 Bayer Cropscience Ag Utilisation de n2-phenylamidines en tant qu'herbicides
CA3006745C (fr) 2010-11-05 2021-03-30 Oat Agrio Co., Ltd. Ethynylphenylamidine ou l'un de ses sels, son procede de production et fongicide pour applications agricoles et horticoles
EP3307707B1 (fr) 2015-06-15 2020-10-07 Bayer CropScience Aktiengesellschaft Phenoxyphenylamidines substitués et leur utilisation comme fongicides
EP3307706B1 (fr) 2015-06-15 2019-07-24 Bayer CropScience AG Phenoxyphenylamidines substitués et leur utilisation comme fongicides
CA2991436A1 (fr) 2015-07-08 2017-01-12 Bayer Cropscience Aktiengesellschaft Phenoxyhalogenophenylamidines et leur utilisation comme fongicides
WO2018109002A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
MX2019007137A (es) 2016-12-14 2019-09-05 Bayer Ag Fenilamidinas y su uso como fungicidas.
EA201991354A1 (ru) * 2016-12-14 2019-12-30 Байер Кропсайенс Актиенгезельшафт Феноксифениламидины и их применение в качестве фунгицидов
EP3335559A1 (fr) 2016-12-14 2018-06-20 Bayer CropScience Aktiengesellschaft Combinaisons de composés actifs
EP3612514B1 (fr) 2017-04-20 2022-03-30 PI Industries Ltd Nouveaux composés de phénylamine
EP3625215B1 (fr) 2017-05-18 2023-09-13 PI Industries Ltd Composés de formimidamidine utile contre les microorganismes phytopathogeniques
CN112778230A (zh) * 2019-11-07 2021-05-11 浙江省化工研究院有限公司 一类含芳基脒结构的化合物、其制备方法及应用
EP3708565A1 (fr) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphénylamidines et leur utilisation comme fongicides
EP3915971A1 (fr) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phényl-s(o)n-phénylamidines et leur utilisation comme fongicides

Family Cites Families (200)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1241832B (de) * 1963-02-23 1967-06-08 Hoechst Ag Verfahren zur Herstellung von Pyrimidiniumverbindungen
JPS5724761B2 (fr) * 1973-12-19 1982-05-26
DE2502786A1 (de) * 1975-01-24 1976-07-29 Merck Patent Gmbh Diphenylaether-derivate und verfahren zu ihrer herstellung
US4272417A (en) * 1979-05-22 1981-06-09 Cargill, Incorporated Stable protective seed coating
US4245432A (en) * 1979-07-25 1981-01-20 Eastman Kodak Company Seed coatings
US5304732A (en) * 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
US5331107A (en) * 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
US4761373A (en) * 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
EP0242236B2 (fr) * 1986-03-11 1996-08-21 Plant Genetic Systems N.V. Cellules végétales résistantes aux inhibiteurs de la synthétase de glutamine, produites par génie génétique
US5273894A (en) * 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) * 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5637489A (en) * 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5605011A (en) * 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) * 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5378824A (en) * 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US4808430A (en) * 1987-02-27 1989-02-28 Yazaki Corporation Method of applying gel coating to plant seeds
US5638637A (en) * 1987-12-31 1997-06-17 Pioneer Hi-Bred International, Inc. Production of improved rapeseed exhibiting an enhanced oleic acid content
GB8810120D0 (en) * 1988-04-28 1988-06-02 Plant Genetic Systems Nv Transgenic nuclear male sterile plants
US5084082A (en) * 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
US6013861A (en) * 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
HU214927B (hu) 1989-08-10 1998-07-28 Plant Genetic Systems N.V. Eljárás módosított virággal rendelkező növények előállítására
US5908810A (en) * 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
US5739082A (en) * 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
ATE152572T1 (de) * 1990-04-04 1997-05-15 Pioneer Hi Bred Int Herstellung von rapssamen mit verringertem gehalt an gesättigten fettsäuren
US5198599A (en) * 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
JP3173784B2 (ja) * 1990-06-25 2001-06-04 モンサント カンパニー グリホセート耐性植物
FR2667078B1 (fr) 1990-09-21 1994-09-16 Agronomique Inst Nat Rech Sequence d'adn conferant une sterilite male cytoplasmique, genome mitochondrial, mitochondrie et plante contenant cette sequence, et procede de preparation d'hybrides.
DE4104782B4 (de) * 1991-02-13 2006-05-11 Bayer Cropscience Gmbh Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide
US5731180A (en) * 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
US6270828B1 (en) * 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
DE4227061A1 (de) 1992-08-12 1994-02-17 Inst Genbiologische Forschung DNA-Sequenzen, die in der Pflanze die Bildung von Polyfructanen (Lävanen) hervorrufen, Plasmide enthaltend diese Sequenzen sowie Verfahren zur Herstellung transgener Pflanzen
GB9218185D0 (en) 1992-08-26 1992-10-14 Ici Plc Novel plants and processes for obtaining them
EP0664835B1 (fr) 1992-10-14 2004-05-19 Syngenta Limited Nouvelles plantes et leurs procedes d'obtention
US5286506A (en) * 1992-10-29 1994-02-15 Bio-Technical Resources Inhibition of food pathogens by hop acids
GB9223454D0 (en) 1992-11-09 1992-12-23 Ici Plc Novel plants and processes for obtaining them
US5370863A (en) * 1992-12-16 1994-12-06 Miller Brewing Company Oral care compositions containing hop acids and method
AU695940B2 (en) * 1993-04-27 1998-08-27 Cargill Incorporated Non-hydrogenated canola oil for food applications
WO1995004826A1 (fr) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Enzymes de deramification et sequences d'adn les codant, utilisables dans la modification du degre de ramification de l'amidon amylopectinique dans des plantes
DE4330960C2 (de) * 1993-09-09 2002-06-20 Aventis Cropscience Gmbh Kombination von DNA-Sequenzen, die in Pflanzenzellen und Pflanzen die Bildung hochgradig amylosehaltiger Stärke ermöglichen, Verfahren zur Herstellung dieser Pflanzen und die daraus erhaltbare modifizierte Stärke
CN1066487C (zh) * 1993-10-01 2001-05-30 三菱商事株式会社 鉴定植物不育细胞质的基因及用其生产杂交植物的方法
AU692791B2 (en) * 1993-10-12 1998-06-18 Agrigenetics, Inc. Brassica napus variety AG019
CA2176109A1 (fr) 1993-11-09 1995-05-18 Perry Girard Caimi Cultures transgeniques a accumulation de fructosane et procedes pour leur production
EP0754235A1 (fr) 1994-03-25 1997-01-22 National Starch and Chemical Investment Holding Corporation Procede pour produire une fecule modifiee a partir de plants de pommes de terre
AU699552B2 (en) 1994-05-18 1998-12-10 Bayer Cropscience Aktiengesellschaft DNA sequences coding for enzymes capable of facilitating the synthesis of linear alpha-1,4 glucans in plants, fungi and microorganisms
JPH10507622A (ja) 1994-06-21 1998-07-28 ゼネカ・リミテッド 新規植物およびその入手法
US5824790A (en) * 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
NL1000064C1 (nl) 1994-07-08 1996-01-08 Stichting Scheikundig Onderzoe Produktie van oligosacchariden in transgene planten.
DE4441408A1 (de) 1994-11-10 1996-05-15 Inst Genbiologische Forschung DNA-Sequenzen aus Solanum tuberosum kodierend Enzyme, die an der Stärkesynthese beteiligt sind, Plasmide, Bakterien, Pflanzenzellen und transgene Pflanzen enhaltend diese Sequenzen
DE4447387A1 (de) 1994-12-22 1996-06-27 Inst Genbiologische Forschung Debranching-Enzyme aus Pflanzen und DNA-Sequenzen kodierend diese Enzyme
US6057494A (en) 1995-01-06 2000-05-02 Centrum Voor Plantenveredelings-En Reproduktieonderzoek DNA sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants
DE19509695A1 (de) 1995-03-08 1996-09-12 Inst Genbiologische Forschung Verfahren zur Herstellung einer modifizieren Stärke in Pflanzen, sowie die aus den Pflanzen isolierbare modifizierte Stärke
CA2218526C (fr) * 1995-04-20 2012-06-12 American Cyanamid Company Produits resistant a des herbicides elabores a partir de structures
US5853973A (en) * 1995-04-20 1998-12-29 American Cyanamid Company Structure based designed herbicide resistant products
WO1996034968A2 (fr) 1995-05-05 1996-11-07 National Starch And Chemical Investment Holding Corporation Ameliorations apportees a une composition a base d'amidon de plante
FR2734842B1 (fr) * 1995-06-02 1998-02-27 Rhone Poulenc Agrochimie Sequence adn d'un gene de l'hydroxy-phenyl pyruvate dioxygenase et obtention de plantes contenant un gene de l'hydroxy-phenyl pyruvate dioxygenase, tolerantes a certains herbicides
US5712107A (en) * 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US6284479B1 (en) * 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
GB9513881D0 (en) * 1995-07-07 1995-09-06 Zeneca Ltd Improved plants
FR2736926B1 (fr) * 1995-07-19 1997-08-22 Rhone Poulenc Agrochimie 5-enol pyruvylshikimate-3-phosphate synthase mutee, gene codant pour cette proteine et plantes transformees contenant ce gene
ATE332382T1 (de) 1995-09-19 2006-07-15 Bayer Bioscience Gmbh Pflanzen, die eine modifizierte stärke synthetisieren, verfahren zu ihrer herstellung sowie modifizierte stärke
GB9524938D0 (en) 1995-12-06 1996-02-07 Zeneca Ltd Modification of starch synthesis in plants
DE19601365A1 (de) 1996-01-16 1997-07-17 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle aus Pflanzen codierend Enzyme, die an der Stärkesynthese beteiligt sind
DE19608918A1 (de) 1996-03-07 1997-09-11 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle, die neue Debranching-Enzyme aus Mais codieren
US5773704A (en) * 1996-04-29 1998-06-30 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
DE19618125A1 (de) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle, die neue Debranching-Enzyme aus Kartoffel codieren
DE19619918A1 (de) 1996-05-17 1997-11-20 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend lösliche Stärkesynthasen aus Mais
DE19620600C2 (de) 1996-05-22 2000-05-11 Wilhelm Reisacher Vorrichtung und Verfahren zum Einbringen von Wärmedämmstoff in Hohlräume
EP0904452A1 (fr) 1996-06-12 1999-03-31 Pioneer Hi-Bred International, Inc. Substituts de l'amidon modifie utilises dans la fabrication du papier
JP2000512349A (ja) 1996-06-12 2000-09-19 パイオニア ハイ―ブレッド インターナショナル，インコーポレイテッド 製紙における改変澱粉の代用品
WO1997047807A1 (fr) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substituts de l'amidon modifie utilises dans la fabrication du papier
US5876739A (en) * 1996-06-13 1999-03-02 Novartis Ag Insecticidal seed coating
AUPO069996A0 (en) 1996-06-27 1996-07-18 Australian National University, The Manipulation of plant cellulose
US5850026A (en) * 1996-07-03 1998-12-15 Cargill, Incorporated Canola oil having increased oleic acid and decreased linolenic acid content
US5773702A (en) * 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
DE69732780T2 (de) * 1996-10-02 2006-04-06 Novartis Ag Pyrimiderivate und verfahren zu ihrer herstellung
GB9623095D0 (en) 1996-11-05 1997-01-08 Nat Starch Chem Invest Improvements in or relating to starch content of plants
US6232529B1 (en) 1996-11-20 2001-05-15 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
DE19653176A1 (de) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh Neue Nucleinsäuremoleküle aus Mais und ihre Verwendung zur Herstellung einer modifizierten Stärke
CA2193938A1 (fr) * 1996-12-24 1998-06-24 David G. Charne Oleagineux du genre brassica renfermant un gene restaurateur de la fertilite ameliore encodant la sterilite male cytoplasmique ogura
US5981840A (en) 1997-01-24 1999-11-09 Pioneer Hi-Bred International, Inc. Methods for agrobacterium-mediated transformation
DE19708774A1 (de) 1997-03-04 1998-09-17 Max Planck Gesellschaft Nucleinsäuremoleküle codierend Enzyme die Fructosylpolymeraseaktivität besitzen
DE19709775A1 (de) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend Stärkephosphorylase aus Mais
ATE242245T1 (de) * 1997-03-19 2003-06-15 Basf Ag Pyrrolo(2,3-d)pyrimidine und ihre verwendung als tyrosinkinase-inhibitoren
GB9718863D0 (en) 1997-09-06 1997-11-12 Nat Starch Chem Invest Improvements in or relating to stability of plant starches
US6251461B1 (en) * 1997-10-10 2001-06-26 S. S. Steiner, Inc. Antimicrobial activity of hops extract against Clostridium botulinum, Clostridium difficile and Helicobacter pylori
DE19749122A1 (de) 1997-11-06 1999-06-10 Max Planck Gesellschaft Nucleinsäuremoleküle codierend Enzyme, die Fructosyltransferaseaktivität besitzen
FR2770854B1 (fr) 1997-11-07 2001-11-30 Rhone Poulenc Agrochimie Sequence adn d'un gene de l'hydroxy-phenyl pyruvate dioxygenase et obtention de plantes contenant un tel gene, tolerantes aux herbicides
FR2772789B1 (fr) * 1997-12-24 2000-11-24 Rhone Poulenc Agrochimie Procede de preparation enzymatique d'homogentisate
BR9908858A (pt) 1998-04-09 2000-12-19 Du Pont Fragmento de ácido nucléico isolado, gene quimérico, célula hospedeira transformada, polipeptìdio, método de alteração do nìvel de expressão de uma proteìna, método de obtenção de um fragmento de ácido nucléico e produto.
DE19820608A1 (de) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh Nucleinsäuremoleküle codierend Enzyme aus Weizen, die an der Stärkesynthese beteiligt sind
DE19820607A1 (de) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh Nucleinsäuremoleküle codierend Enzyme aus Weizen, die an der Stärkesynthese beteiligt sind
EP1078088B1 (fr) 1998-05-13 2006-07-26 Bayer BioScience GmbH Vegetaux transgeniques presentant l'activite modifiee d'un translocateur d'adp/atp plastidien
DE19821614A1 (de) 1998-05-14 1999-11-18 Hoechst Schering Agrevo Gmbh Sulfonylharnstoff-tolerante Zuckerrübenmutanten
US6635756B1 (en) 1998-06-15 2003-10-21 National Starch And Chemical Investment Holding Corporation Starch obtainable from modified plants
US6693185B2 (en) * 1998-07-17 2004-02-17 Bayer Bioscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
DE19836098A1 (de) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Pflanzen, die eine modifizierte Stärke synthetisieren, Verfahren zur Herstellung der Pflanzen, ihre Verwendung sowie die modifizierte Stärke
DE19836099A1 (de) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Nukleinsäuremoleküle kodierend für eine ß-Amylase, Pflanzen, die eine modifizierte Stärke synthetisieren, Verfahren zur Herstellung der Pflanzen, ihre Verwendung sowie die modifizierte Stärke
CA2341078A1 (fr) 1998-08-25 2000-03-02 Pioneer Hi-Bred International, Inc. Acides nucleiques de glutamine vegetale: fructose-6-phosphate amidotransferase
CA2342124A1 (fr) 1998-09-02 2000-03-16 Planttec Biotechnologie Gmbh Molecules d'acide nucleique codant une amylosucrase
DE19924342A1 (de) 1999-05-27 2000-11-30 Planttec Biotechnologie Gmbh Genetisch modifizierte Pflanzenzellen und Pflanzen mit erhöhter Aktivität eines Amylosucraseproteins und eines Verzweigungsenzyms
CZ20011125A3 (cs) 1998-10-09 2001-10-17 Planttec Biotechnologie Gmbh Forschung & Entwicklung Molekuly nukleových kyselin, které kódují rozvětvovací enzym z bakterie rodu Neisseria, a způsob výroby alfa-1,6- rozvětvených alfa-1,4 glukanů
AU773808B2 (en) 1998-11-09 2004-06-10 Bayer Cropscience Aktiengesellschaft Nucleic acid molecules from rice and their use for the production of modified starch
US6503904B2 (en) * 1998-11-16 2003-01-07 Syngenta Crop Protection, Inc. Pesticidal composition for seed treatment
US6531648B1 (en) 1998-12-17 2003-03-11 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
GB9902592D0 (en) * 1999-02-06 1999-03-24 Hoechst Schering Agrevo Gmbh Fungicides
DE19905069A1 (de) 1999-02-08 2000-08-10 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend Alternansucrase
US6323392B1 (en) * 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
WO2000057877A1 (fr) * 1999-03-26 2000-10-05 Euro-Celtique S.A. Pyrazoles, imidazoles, oxazoles, thiazoles et pyrroles aryle substitues et leurs utilisations
BR0010169A (pt) * 1999-04-29 2002-02-05 Syngenta Ltd Polinucleotìdeo isolado, vetor, material de planta, plantas completas férteis, morfologicamente normais, plantas de milho, trigo e arroz, métodos para controlar seletivamente ervas daninhas no campo, para produzir plantas que são substancialmente tolerantes ou substancialmente resistentes a glifosato, para selecionar material biológico e para regenerar uma planta transformada fértil para conter dna estranho, e, uso do polinucleotìdeo
CZ20013856A3 (cs) * 1999-04-29 2002-04-17 Syngenta Ltd. Herbicidně rezistentní rostliny
DE19926771A1 (de) 1999-06-11 2000-12-14 Aventis Cropscience Gmbh Nukleinsäuremoleküle aus Weizen, transgene Pflanzenzellen und Pflanzen und deren Verwendung für die Herstellung modifizierter Stärke
US6451365B1 (en) * 2000-07-14 2002-09-17 Rhodia Inc. Antibacterial composition for control of gram positive bacteria in food applications
US6475537B1 (en) * 2000-07-27 2002-11-05 Rhodia Inc. Hops acid antibacterial compositions
DE19937348A1 (de) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nukleinsäuremoleküle aus Pflanzen codierend Enzyme, die an der Stärkesynthese beteiligt sind
DE19937643A1 (de) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgene Zellen und Pflanzen mit veränderter Aktivität des GBSSI- und des BE-Proteins
WO2001014569A2 (fr) 1999-08-20 2001-03-01 Basf Plant Science Gmbh Augmentation de la teneur en polysaccharides dans des plantes
US6423886B1 (en) * 1999-09-02 2002-07-23 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
US6472588B1 (en) 1999-09-10 2002-10-29 Texas Tech University Transgenic cotton plants with altered fiber characteristics transformed with a sucrose phosphate synthase nucleic acid
GB9921830D0 (en) 1999-09-15 1999-11-17 Nat Starch Chem Invest Plants having reduced activity in two or more starch-modifying enzymes
AR025996A1 (es) * 1999-10-07 2002-12-26 Valigen Us Inc Plantas no transgenicas resistentes a los herbicidas.
US6803501B2 (en) 2000-03-09 2004-10-12 Monsanto Technology, Llc Methods for making plants tolerant to glyphosate and compositions thereof using a DNA encoding an EPSPS enzyme from Eleusine indica
US6822146B2 (en) * 2000-03-09 2004-11-23 E. I. Du Pont De Nemours And Company Sulfonylurea-tolerant sunflower line M7
US8293258B2 (en) * 2000-05-18 2012-10-23 John I. Hass, Inc. Pesticide treatments made from hop extracts
US6379720B1 (en) * 2000-07-18 2002-04-30 Nalco Chemical Company Compositions containing hops extract and their use in water systems and process streams to control biological fouling
EP1178038A1 (fr) * 2000-08-04 2002-02-06 Aventis Cropscience S.A. Dérivés de phenylamidine fongicides
AU8786201A (en) * 2000-09-29 2002-04-08 Syngenta Ltd Herbicide resistant plants
US6660690B2 (en) * 2000-10-06 2003-12-09 Monsanto Technology, L.L.C. Seed treatment with combinations of insecticides
US6734340B2 (en) 2000-10-23 2004-05-11 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
UA86918C2 (ru) 2000-10-30 2009-06-10 Вердиа, Инк. Изолированный или рекомбинантный полинуклеотид, кодирующий полипептид, имеющий активность глифосат-n-ацетилтрансферазы (gat)
FR2815969B1 (fr) * 2000-10-30 2004-12-10 Aventis Cropscience Sa Plantes tolerantes aux herbicides par contournement de voie metabolique
AU2004260931B9 (en) 2003-04-29 2012-01-19 E.I. Du Pont De Nemours And Company Novel glyphosate-N-acetyltransferase (GAT) genes
BR0115782A (pt) 2000-12-08 2004-01-20 Commonwealh Scient And Ind Res Modificação de expressão de gene de sacarose sintase em tecido de planta e usos
US6352726B1 (en) * 2001-01-09 2002-03-05 S. S. Steiner, Inc. Method of killing protozoa
US7078062B2 (en) * 2001-01-17 2006-07-18 S.S. Steiner, Inc. Hop-based udder and teat dips and washes
US20020134012A1 (en) 2001-03-21 2002-09-26 Monsanto Technology, L.L.C. Method of controlling the release of agricultural active ingredients from treated plant seeds
US20040107461A1 (en) 2001-03-30 2004-06-03 Padma Commuri Glucan chain length domains
ATE394497T1 (de) 2001-06-12 2008-05-15 Bayer Cropscience Ag Transgene pflanzen die stärke mit hohem amylosegehalt herstellen
WO2003013226A2 (fr) * 2001-08-09 2003-02-20 Cibus Genetics Plantes non transgeniques resistant aux herbicides
FR2829362B1 (fr) * 2001-09-10 2003-11-07 Aventis Cropscience Sa Composition fongicide a base de derives d'arylamidine et de composes fongicides connus
CN100509853C (zh) 2001-10-17 2009-07-08 巴斯福种植科学有限公司 淀粉
DE10208132A1 (de) 2002-02-26 2003-09-11 Planttec Biotechnologie Gmbh Verfahren zur Herstellung von Maispflanzen mit erhöhtem Blattstärkegehalt und deren Verwendung zur Herstellung von Maissilage
WO2003092360A2 (fr) 2002-04-30 2003-11-13 Verdia, Inc. Nouveaux genes de la glyphosate-n-acetyltransferase (gat)
EP1501789A1 (fr) 2002-05-03 2005-02-02 E.I. Du Pont De Nemours And Company Composes amidinylphenyle et utilisations de ceux-ci comme fongicides
AUPS280402A0 (en) * 2002-06-07 2002-06-27 Barrack Combustion Process Pty Ltd Diesel combustion enhancer & fuel conditioner
FR2844142B1 (fr) 2002-09-11 2007-08-17 Bayer Cropscience Sa Plantes transformees a biosynthese de prenylquinones amelioree
EP1413301A1 (fr) * 2002-10-24 2004-04-28 Bayer CropScience SA Médicaments antifongiques à base de dérivés d'arylamidine
WO2004040012A2 (fr) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions et procedes permettant d'identifier des plantes presentant une meilleure tolerance aux herbicides imidazolinones
US20040110443A1 (en) 2002-12-05 2004-06-10 Pelham Matthew C. Abrasive webs and methods of making the same
ATE405653T1 (de) 2002-12-19 2008-09-15 Bayer Cropscience Ag Pflanzenzellen und pflanzen, die eine stärke mit erhöhter endviskosität synthetisieren
CA2517879A1 (fr) 2003-03-07 2004-09-16 Basf Plant Science Gmbh Production d'amylose amelioree dans les plantes
WO2004090140A2 (fr) 2003-04-09 2004-10-21 Bayer Bioscience N.V. Procedes et elements destines a augmenter la tolerance de plantes par rapport a des conditions de stress
BRPI0410544A (pt) 2003-05-22 2006-06-20 Syngenta Participations Ag amido modificado usos, processos para a produção do mesmo
CA2527115C (fr) 2003-05-28 2019-08-13 Basf Aktiengesellschaft Plantes de ble presentant une tolerance accrue aux herbicides d'imidazolinone
EP1493328A1 (fr) * 2003-07-04 2005-01-05 Institut National De La Recherche Agronomique Production des lignées B. napus double zéro restauratrices avec une bonne qualité agronomique
DE602004030345D1 (de) 2003-07-31 2011-01-13 Toyo Boseki Hyaluronsäure produzierende pflanze
WO2005017157A1 (fr) 2003-08-15 2005-02-24 Commonwealth Scientific And Industrial Research Organisation (Csiro) Procedes et moyens d'alteration des caracteristiques des fibres dans des plantes produisant des fibres
WO2005020673A1 (fr) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Plants de riz presentant une tolerance accrue aux herbicides imidazolinone
DE602004030613D1 (de) 2003-09-30 2011-01-27 Bayer Cropscience Ag Pflanzen mit reduzierter aktivität eines klasse-3-verzweigungsenzyms
WO2005030941A1 (fr) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plantes presentant une activite augmentee d'une enzyme de ramification de classe 3
EP1725666B1 (fr) 2004-03-05 2012-01-11 Bayer CropScience AG Plantes presentant une activite reduite de l'enzyme de phosphorylation de l'amidon phosphoglucane dikinase
AR048024A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Plantas con actividad aumentada de distintas enzimas fosforilantes del almidon
AR048026A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Procedimientos para la identificacion de proteinas con actividad enzimatica fosforiladora de almidon
EP1570736A1 (fr) * 2004-03-05 2005-09-07 Bayer CropScience S.A. Composition fongicide comprenant une arylamidine et des composés fongicides connus
AR048025A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Plantas con actividad aumentada de una enzima fosforilante del almidon
US7432082B2 (en) * 2004-03-22 2008-10-07 Basf Ag Methods and compositions for analyzing AHASL genes
CA2558057A1 (fr) 2004-03-22 2005-10-13 Basf Aktiengesellschaft Melanges fongicides
EA200602287A1 (ru) 2004-06-03 2007-04-27 Е. И. Дюпон Де Немур Энд Компани Фунгицидные смеси амидинилфенильных соединений
AU2005262525A1 (en) 2004-06-16 2006-01-19 Basf Plant Science Gmbh Polynucleotides encoding mature AHASL proteins for creating imidazolinone-tolerant plants
DE102004029763A1 (de) 2004-06-21 2006-01-05 Bayer Cropscience Gmbh Pflanzen, die Amylopektin-Stärke mit neuen Eigenschaften herstellen
TR200900517T2 (tr) * 2004-07-30 2009-03-23 Basf Agrochemical Products B.V. Herbisitlere dayanıklı ayçiçeği bitkileri herbisitlere dayanıklı asetohidroksiasit sintaz geniş altünite proteinlerini kodla yan polinükleotidler ve kullanma metotları.
EP1776462A4 (fr) 2004-08-04 2010-03-10 Basf Plant Science Gmbh Séquences ahass de monocotylédone et leurs méthodes d'utilisation
RU2007109207A (ru) * 2004-08-13 2008-09-20 Прикис Фамэсьютикэлс, Инк. (US) Соединения-модуляторы активности рецептора сфингозин-1-фосфата (варианты), фармацевтическая композиция, содержащая указанные соединения, и способ лечения нарушения, ассоциированного со сфингозин-1-фосфатом
PT1786908E (pt) 2004-08-18 2010-04-29 Bayer Cropscience Ag Plantas com um aumento da actividade da enzima de fosforilação do amido r3 nos plastídeos
CA2578187C (fr) * 2004-08-26 2015-08-04 Dhara Vegetable Oil And Foods Company Limited Nouveau systeme de sterilite cytoplasmique pour especes de brassicees et utilisation pour production de graines hybrides de moutarde indienne brassica juncea a base de graines oleagineuses
DE602005015473D1 (de) 2004-09-23 2009-08-27 Bayer Cropscience Ag Verfahren und mittel zur herstellung von hyaluronan
ES2338443T3 (es) 2004-09-24 2010-05-07 Bayer Bioscience N.V. Plantas resistentes al estres.
ZA200704247B (en) 2004-10-29 2008-09-25 Bayer Bioscience Nv Stress tolerant cotton plants
AR051690A1 (es) * 2004-12-01 2007-01-31 Basf Agrochemical Products Bv Mutacion implicada en el aumento de la tolerancia a los herbicidas imidazolinona en las plantas
EP1672075A1 (fr) 2004-12-17 2006-06-21 Bayer CropScience GmbH Plantes transformées exprimant un dextrane sucrase et synthétisant un amidon modifie
EP1679374A1 (fr) 2005-01-10 2006-07-12 Bayer CropScience GmbH Plantes transformées exprimant un mutane sucrase et synthétisant un amidon modifie
JP2006304779A (ja) 2005-03-30 2006-11-09 Toyobo Co Ltd ヘキソサミン高生産植物
EP1707632A1 (fr) 2005-04-01 2006-10-04 Bayer CropScience GmbH Amidon de pomme de terre cireux phosphorylé
EP1710315A1 (fr) 2005-04-08 2006-10-11 Bayer CropScience GmbH Amidon à forte teneur en phosphate
PT1893759E (pt) * 2005-06-15 2009-10-29 Bayer Bioscience Nv Métodos para aumentar a resistência de plantas a condições hipóxicas
ES2461593T3 (es) 2005-06-24 2014-05-20 Bayer Cropscience Nv Métodos para alterar la reactividad de paredes de células vegetales
AR054174A1 (es) 2005-07-22 2007-06-06 Bayer Cropscience Gmbh Sobreexpresion de sintasa de almidon en vegetales
EA201000757A1 (ru) * 2005-08-24 2010-12-30 Пайонир Хай-Бред Интернэшнл, Инк. Способы борьбы с сорными растениями на возделываемой посевной площади
CA2617803C (fr) * 2005-08-31 2012-05-29 Monsanto Technology Llc Sequences nucleotidiques codant des proteines insecticides
JP5261181B2 (ja) * 2005-09-13 2013-08-14 バイエル・クロップサイエンス・アーゲー 殺虫剤フェニルオキシ置換フェニルアミジン誘導体
AR056869A1 (es) * 2005-09-13 2007-10-31 Bayer Cropscience Ag Composicion fungicida que comprende un derivado arilamidina y dos compuestos fungicidas conocidos
AU2006298962A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with an increased production of hyaluronan II
EP1951878B1 (fr) 2005-10-05 2015-02-25 Bayer Intellectual Property GmbH Vegetaux a production d'hyaluronan accrue
AU2006298963A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Improved methods and means for producings hyaluronan
CA2646476A1 (fr) * 2006-03-21 2007-09-27 Bayer Bioscience N.V. Vegetaux resistant au stress
CA2651734A1 (fr) 2006-05-12 2007-11-22 Bayer Bioscience N.V. Nouvelles molecules de micro-arn liees au stress et leurs utilisations
EP1887079A1 (fr) 2006-08-09 2008-02-13 Bayer CropScience AG Plante genetiquement modifié pour synthetiser d'amidon avec un pouvoir de gonfler elevé
AR064557A1 (es) 2006-12-29 2009-04-08 Bayer Cropscience Ag Almidon de maiz y harinas y alimentos de maiz que comprenden este almidon de maiz
AR064558A1 (es) 2006-12-29 2009-04-08 Bayer Cropscience Sa Proceso para la modificacion de las propiedades termicas y de digestion de almidones de maiz y harinas de maiz
EP1950303A1 (fr) 2007-01-26 2008-07-30 Bayer CropScience AG Plantes génétiquement modifiées synthétisant un amidon à teneur réduite en amylose et à capacité de gonflement augmentée
EP2120558B1 (fr) * 2007-03-12 2016-02-10 Bayer Intellectual Property GmbH Dérivés de phénoxyphenylamidine 3,4 disubstituée et son utilisation en tant que fongicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008110315A1 *

Also Published As

Publication number Publication date
BRPI0808796A2 (pt) 2014-08-12
US8748662B2 (en) 2014-06-10
US20130012742A1 (en) 2013-01-10
WO2008110315A1 (fr) 2008-09-18
US8299302B2 (en) 2012-10-30
EP1969934A1 (fr) 2008-09-17
US20100120615A1 (en) 2010-05-13
CN101631459A (zh) 2010-01-20
JP2010520906A (ja) 2010-06-17

Similar Documents

Publication Publication Date Title
EP2136629B1 (fr) Phenoxyphenylamidines utilisées comme fongicides
EP2134170B1 (fr) Fluoroalkylphenylamidines et leur utilisation comme fongicides
EP2146975B1 (fr) Thiadiazolyloxyphénylamidines et leur utilisation comme fongicides
EP2120559B1 (fr) Phenylamidines substituees et utilisation en tant que fongicides
EP2307391B1 (fr) Thiadiazolyloxyphénylamidines et utilisation comme fongicides
EP2136628B1 (fr) Dérivés de phénoxyphénylamidine substituée et leur utilisation en tant que fongicides
EP2307390B1 (fr) Thiadiazolyloxyphénylamidines et leur utilisation comme fongicides
EP2120560A1 (fr) Phenoxyphenylamidines a substitution 4-cycloalkyle ou 4-aryle et leur utilisation en tant que fongicides
US9199922B2 (en) Dihalophenoxyphenylamidines and use thereof as fungicides
WO2008110281A2 (fr) Phénoxyphénylamidines 3,4-disubstituées et leur utilisation comme fongicides
EP2223917A1 (fr) Isothiazolyloxyphénylamidine et son utilisation en tant que fongicide
EP2072506A1 (fr) Thiazolyloxyphenylamidine ou thiadiazolyloxyphenylamidine et son utilisation en tant que fongicide
EP2264012A1 (fr) Hétéroarylamidine et son utilisation en tant que fongicide
EP1969933A1 (fr) Phénoxyphenlamidine dihalogénée et son utilisation en tant que fongicide
WO2011082941A1 (fr) Sels de thiadiazolyloxyphénylamidinium substitués par un benzyle en tant que fongicides
EP2264011A1 (fr) Hétéroarylamidine et son utilisation en tant que fongicide

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20091012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

17Q First examination report despatched

Effective date: 20100212

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20120731