Fungicidal combinations of active substances
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6 claims: 6 independent, 0 dependent
- 1Claims of equivalent WO 0144215 A2 Translation of claims of equivalent WO 0144215 A2 Active substance combinations, containing at least one compound of the formula and (1) a triazole derivative of the formula in which X is chlorine or phenyl, and -C- - CH-II IY is o or OH, and / or ( Patentansprüche Wirkstoffkombinationen, enthaltend mindestens eine Verbindung der Formel und (1) ein Triazol-Derivat der Formel in welcher X für Chlor oder Phenyl steht, und -C— — CH- II I Y für o oder OH steht, und/oder (
- 22) das Triazol-Derivat der Formel le) und/oder (3) ein Anilin-Derivat der Formel in welcher R1 für Wasserstoff oder Methyl steht, und/oder (4) N-[ 1 -(4-Chlor-phenyl)-ethyl]-2,2-dichlor- 1 -ethyl-3-methyl- cyclopropan-carbonsäureamid der Formel (Carpropamid) und/oder (5) das Zink-propylen- 1 ,2-bis-(dithiocarbamidat) der Formel n > = 1 (Propineb) und oder (6) mindestens ein Thiocarbamat der Formel Me = Zn oder Mn oder Gemisch aus Zn und Mn und/oder (7) das Anilin-Derivat der Formel (Fenhexamid) und/oder (8) die Verbindung der Formel (Iprovalicarb) und/oder (9) das Benzothiadiazol-Derivat der Formel (Acibenzolar-S-methyl) und/oder (10) das 8-t-Butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-l,4-dioxa- spiro[5,4]-decan der Formel (Spiroxamine) und/oder (11) die Verbindung der Formel und/oder (12) die Verbindung der Formel (Trifloxystrobin) und/oder (13) die Verbindung der Formel und/oder ( 14) das Cyanoxim-Deri vat der Formel (Cymoxanil) und/oder (15) ein Pyrimidin-Derivat der Formel in welcher R2 für Methyl, — CzzzC — CH3 (Mepanipyrim) oder Cyclopropyl (Cyprodinyl) steht, und/oder (16) ein Anilin-Derivat der Formel (Metalaxyl bzw. Metalaxyl M) und/oder (17) das Morpholin-Derivat der Formel (XVIII) und/oder (18) das Phthalimid-Derivat der Formel O N-S— CCI, (XIX) o II (Folpet) und/oder (19) die Phosphor- Verbindung der Formel und/oder (20) das Hydroxyethyl-triazol-Derivat der Formel und/oder (21) das l-[(6-Chlor-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimin der Formel und/oder (22) das Oxazolidindion der Formel (XXIII) (Famoxadone) und/oder (23) das Benzamid-Derivat der Formel (Zoxamide) und/oder (24) das Guanidin-Derivat der Formel x (2 + m) CH3COOH in welcher m für ganze Zahlen von 0 bis 5 steht und R3 für Wasserstoff (17 bis 23 %) oder den Rest der Formel -C=NH (77 bis 83 %) NH, steht, und/oder (25) das Triazol-Derivat der Formel und/oder (26) das Halogen-benzimidazol der Formel (XXVII) und/oder (27) das Halogenpyrimidin der Formel (XXVIII) und/oder (28) das Tetrachlor-isophthalo-dinitril der Formel (Chlorothalonil) und/oder (29) die Verbindung der Formel (Propamocarb) und/oder (30) das Pyridinamin der Formel (Fluazinam) und/oder (31) das Thiazolcarboxamid der Formel I) (Ethaboxam) und/oder (32) das Sulfonamid der Formel (XXXIII) (Cyamidazosulfamid) und/oder (33) der Verbindung der Formel (XXXIV) und/oder (34) die Verbindung der Formel (Iprodione) und/oder (35) die Verbindung der Formel (XXXVI) (Procymidone) und/oder (36) dem Diamid der Formel (Thiram) und/oder (37) das Methoxyacrylat-Derivat der Formel (XXXVIII) (Picoxystrobin) und/oder (38) das Chinolin-Derivat der Formel (XXXIX) (Quinoxyfen) und/oder (39) das Phenylamid-Derivat der Formel (Oxadixyl) und/oder (40) das Phenylamid-Derivat der Formel (XXXXI) (Benalaxyl) und/oder (41) das Dicarboxim-Derivat der Formel (XXXXIIa) (Captan) und oder (42) die Phosphonsäure der Formel H — P— OH (XXXXIII) OH (Phosphonsäure) und/oder (43) das Pyπol-Derivat der Formel (XXXXIV) (Fludioxonil) und/oder (44) das Phenylcarbonat der Formel (XXXXV) (Diethofencarb) und/oder (45) die Kupferverbindungen a) Kupferoxychlorid (XXXXVIa) b) Kupferhydroxid (XXXXVIb) und/oder (46) das Imidazol-Derivat der Formel (XXXXVII) (Prochloraz) und/oder (47) das Triazolderivat der Formel a) (XXXXVIIIa) (Difenconazole) und/oder b) (XXXXVIIIb) (Hexaconazole) und/oder c) (XXXXVIIIe) (Cyproconazole) und oder d) (XXXXVlIId) (Flusilazole) und/oder e) (XXXXVII le) (Propiconazole) und/oder f) (XXXXVIIIf) (Myclobutanil) und/oder g) (XXXXVIIIg) (Fenbuconazole) und/oder h) (XXXXVIIIh) (Tetraconazole) und/oder (48) eine Verbindung der allgemeinen Formel (XXXXIX) in welcher R für unsubstituiertes oder durch Fluor, Chlor, Brom, Methyl oder Ethyl substituiertes Phenyl, 2-Naphthyl, 1,2,3,4-Tetrahydronaphthyl oder Indanyl steht, und/oder (49) N-Methyl-2-(methoxyimino)-2-[2-([ 1 -(3-tri-fluoro-methyl- phenyl)ethoxy]iminomethyl)phenyl]acetamid der Formel (XXXXX) und/oder (50) 2,4-Dihydro-5-methoxy-2-methyl-4-[2-([([l-(3-tri-fluoro- methylphenyl)ethylidene]amino)oxy]methyl)phenyl]-3H-l,2,4-triazol- 3-one der Formel (XXXXXI) und/oder (51 ) die Verbindung der Formel (XXXXXII) 2. Wirkstoffkombinationen, gemäß Anspruch 1, enthaltend mindestens eine Verbindung der Formel (I) wie in Anspruch 1 definiert und (3) ein Anilin-Derivat der Formel und/oder (5) das Zink-propylen-l,2-bis-(dithiocarbamidat) der Formel n > = 1 (Propineb) und/oder (6) mindestens ein Thiocarbamat der Formel Me = Gemisch aus Zn und Mn und/oder (7) das Anilin-Derivat der Formel (Fenhexamid) und oder (8) die Verbindung der Formel (Iprovalicarb) und/oder (11) die Verbindung der Formel und/oder (12) die Verbindung der Formel (Trifloxystrobin) und oder (13) die Verbindung der Formel und/oder (18) das Phthalimid-Derivat der Formel und/oder (20) das Hydroxyethyl-triazol-Derivat der Formel und oder (26) das Halogen-benzimidazol der Formel (XXVII) und/oder (27) das Halogenpyrimidin der Formel (XXVIII) und oder (28) das Tetrachlor-isophthalo-dinitril der Formel (Chlorothalonil) und/oder (30) das Pyridinamin der Formel (Fluazinam) und/oder (45) die Kupferverbindungen a) Kupferoxychlorid (XXXXVIa) b) Kupferhydroxid (XXXXVIb). 2) the triazole derivative of the formula le) and / or (3) an aniline derivative of the formula in which R1 is hydrogen or methyl, and / or (4) N- [1- (4-chloro-phenyl) -ethyl] -2,2-dichloro-1-ethyl-3-methyl-cyclopropane-carboxamide of the formula (Carpropamid) and / or (5) the zinc propylene-1,2-bis (dithiocarbamidate) of the formula n> = 1 (propineb) and / or (6) at least one thiocarbamate of the formula Me = Zn or Mn or mixture of Zn and Mn and / or (7) the aniline derivative of the formula (Fenhexamide) and / or (8) the compound of the formula (Iprovalicarb) and / or (9) the benzothiadiazole derivative of the formula (Acibenzolar-S-methyl) and / or (10) the 8-t-butyl-2- (N-ethyl-Nn-propyl-amino) -methyl-1,4-dioxaspiro [5,4] -decane the formula (Spiroxamine) and / or (11) the compound of formula and / or (12) the compound of the formula (Trifloxystrobin) and / or (13) the compound of the formula and / or (14) the cyanoxime derivative of the formula (Cymoxanil) and / or (15) a pyrimidine derivative of the formula in which R2 for methyl, - CzzzC - CH3 (Mepanipyrim) or cyclopropyl (cyprodinyl), and / or (16) an aniline derivative of the formula (Metalaxyl or metalaxyl M) and / or (17) the morpholine derivative of the formula (XVIII) and / or (18) the phthalimide derivative of the formula O NS-CCI, (XIX) o II (folpet) and / or (19) the phosphorus compound of the formula and / or (20) the hydroxyethyl-triazole derivative of the formula and / or (21) the l - [(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidinimine of the formula and / or (22) the oxazolidinedione of formula (XXIII) (famoxadone) and / or (23) the benzamide derivative of the formula (Zoxamide) and / or (24) the guanidine derivative of the formula x (2 + m) CH3COOH in which m stands for integers from 0 to 5 and R3 for hydrogen (17 to 23%) or the radical of the formula -C = NH (77 to 83%) NH, and / or (25) the triazole derivative of the formula and / or (26) the halobenzimidazole of the formula (XXVII) and / or (27) the halopyrimidine of the formula (XXVIII) and / or (28) the tetrachloro-isophthalo-dinitrile of the formula (Chlorothalonil) and / or (29) the compound of the formula (Propamocarb) and / or (30) the pyridinamine of the formula (Fluazinam) and / or (31) the thiazolecarboxamide of the formula I) (Ethaboxam) and / or (32) the sulfonamide of the formula (XXXIII) (Cyamidazosulfamide) and / or (33) the compound of the formula (XXXIV) and / or (34) the compound of the formula (Iprodione) and / or (35) the compound of formula (XXXVI) (Procymidone) and / or (36) the diamide of the formula (Thiram) and / or (37) the methoxyacrylate derivative of the formula (XXXVIII) (Picoxystrobin) and / or (38) the quinoline derivative of the formula (XXXIX) (Quinoxyfen) and / or (39) the phenylamide derivative of the formula (Oxadixyl) and / or (40) the phenylamide derivative of the formula (XXXXI) (Benalaxyl) and / or (41) the dicarboxime derivative of the formula (XXXXIIa) (Captan) and or (42) the phosphonic acid of the formula H - P - OH (XXXXIII) OH (phosphonic acid) and / or (43) the pyrazole derivative of the formula (XXXXIV) (Fludioxonil) and / or (44) the phenyl carbonate of the formula (XXXXV) (Diethofencarb) and / or (45) the copper compounds a) copper oxychloride (XXXXVIa) b) copper hydroxide (XXXXVIb) and / or (46) the imidazole derivative of the formula (XXXXVII) (Prochloraz) and / or (47) the triazole derivative of the formula a) (XXXXVIIIa) (Difenconazole) and / or b) (XXXXVIIIb) (Hexaconazole) and / or c) (XXXXVIIIe) (Cyproconazole) and or d) (XXXXVIIII) (Flusilazole) and / or e) (XXXXVII le) (Propiconazole) and / or f) (XXXXVIIIf) (Myclobutanil) and / or g) (XXXXVIIIg) (Fenbuconazole) and / or h) (XXXXVIIIh) (Tetraconazole) and / or (48) a compound of general formula (XXXXIX) in which R is unsubstituted or substituted by fluorine, chlorine, bromine, methyl or ethyl phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl, and / or (49) N-methyl-2- (methoxyimino ) -2- [2 - ([1- (3-trifluoromethylphenyl) ethoxy] iminomethyl) phenyl] acetamide of the formula (XXXXX) and / or (50) 2,4-dihydro-5-methoxy-2-methyl-4- [2 - [([([1- (3-trifluoromethylphenyl) ethylidene] amino) oxy] methyl) phenyl. 3H-l, 2,4-triazol-3-ones of the formula (XXXXXI) and / or (51) the compound of the formula (XXXXXII) 2. active substance combinations, according to claim 1, containing at least one compound of formula (I) as defined in claim 1 and (3) an aniline derivative of the formula and / or (5) the zinc propylene 1,2-bis (dithiocarbamidate) of the formula n> = 1 (propineb) and / or (6) at least one thiocarbamate of the formula Me = mixture of Zn and Mn and / or (7) the aniline derivative of the formula (Fenhexamide) and or (8) the compound of the formula (Iprovalicarb) and / or (11) the compound of the formula and / or (12) the compound of the formula (Trifloxystrobin) and or (13) the compound of the formula and / or (18) the phthalimide derivative of the formula and / or (20) the hydroxyethyl-triazole derivative of the formula and or (26) the halobenzimidazole of the formula (XXVII) and / or (27) the halopyrimidine of the formula (XXVIII) and or (28) the tetrachloro-isophthalo-dinitrile of the formula (Chlorothalonil) and / or (30) the pyridinamine of the formula (Fluazinam) and / or (45) the copper compounds a) copper oxychloride (XXXXVIa) b) copper hydroxide (XXXXVIb).
- 3Mittel gemäß Anspruch 1, dadurch gekennzeichnet, dass in den Wirkstoffkombinationen das Gewichtsverhältnis von Wirkstoff der Formel (I) zu Wirkstoff der Gruppe (1) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (2) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (3) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe (4) zwischen 1:0,1 und 1:10 liegt, Wirkstoff der Gruppe (5) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe (6) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe (7) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (8) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (9) zwischen 1:0,02 und 1:50 liegt, Wirkstoff der Gruppe (10) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (11) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (12) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (13) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (14) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (15) zwischen 1:0,2 und 1:50 liegt, Wirkstoff der Gruppe (16) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (17) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (18) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe (19) zwischen 1:0,1 und 1:150 liegt, Wirkstoff der Gruppe (20) zwischen 1:0,02 und 1:50 liegt, Wirkstoff der Gruppe (21) zwischen 1:0,05 und 1:20 liegt, Wirkstoff der Gruppe (22) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (23) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (24) zwischen 1:0,1 und 1:150 liegt, Wirkstoff der Gruppe 25) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 26) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 27) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 28) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe 29) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe 30) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 31) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 32) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 33) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 34) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 35) zwischen 1:1 und 1:50 liegt, Wirkstoff der Gruppe 36) zwischen 1 : 1 und 1:150 liegt, Wirkstoff der Gruppe 37) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 38) zwischenl:0,l und 1:50 liegt, Wirkstoff der Gruppe 39) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 40) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 41) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe 42) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe 43) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 44) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 45a) zwischen 1 : 1 und 1 : 150 liegt, Wirkstoff der Gruppe 45b) zwischen 1:1 und 1:150 liegt, Wirkstoff der Gruppe 46) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 47a) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 47b) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 47c) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 47d) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 47e) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 47f) zwischen 1 :0,1 und 1:50 liegt, Wirkstoff der Gruppe 47g) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe 47h) zwischen 1:0,1 und 1:50 liegt, - Wirkstoff der Gruppe (48) zwischen 1 :0,1 und 1:50 liegt, - Wirkstoff der Gruppe (49) zwischen 1:0,1 und 1 :50 liegt, - Wirkstoff der Gruppe (50) zwischen 1 :0,1 und 1 :50 liegt, - Wirkstoff der Gruppe (51) zwischen 1 :0,1 und 1 :50 liegt. Third Means according to claim 1, characterized, in the active substance combinations the weight ratio of active ingredient of the formula (I) to active ingredient of the group (1) is between 1: 0.1 and 1:50, Active ingredient of group (2) is between 1: 0.1 and 1:50 Active ingredient of group (3) is between 1: 1 and 1: 150, Active ingredient of group (4) is between 1: 0.1 and 1:10, Active ingredient of group (5) is between 1: 1 and 1: 150, Active ingredient of group (6) is between 1: 1 and 1: 150, Active ingredient of group (7) is between 1: 0.1 and 1:50 Active ingredient of group (8) is between 1: 0.1 and 1:50 Active ingredient of group (9) is between 1: 0.02 and 1:50, Active ingredient of the group (10) is between 1: 0.1 and 1:50 Active ingredient of group (11) is between 1: 0.1 and 1:50 Active ingredient of the group (12) is between 1: 0.1 and 1:50 Active ingredient of the group (13) is between 1: 0.1 and 1:50 Active ingredient of the group (14) is between 1: 0.1 and 1:50 Active ingredient of group (15) is between 1: 0.2 and 1:50 Active ingredient of the group (16) is between 1: 0.1 and 1:50 Active ingredient of group (17) is between 1: 0.1 and 1:50 Active ingredient of group (18) is between 1: 1 and 1: 150, Active ingredient of group (19) is between 1: 0.1 and 1: 150, Active ingredient of the group (20) is between 1: 0.02 and 1:50, Active ingredient of the group (21) is between 1: 0.05 and 1:20, Active ingredient of the group (22) is between 1: 0.1 and 1:50 Active ingredient of the group (23) is between 1: 0.1 and 1:50, Active ingredient of the group (24) is between 1: 0.1 and 1: 150, Active ingredient of group 25) is between 1: 0.1 and 1:50, Active ingredient of group 26) is between 1: 0.1 and 1:50, Active ingredient of group 27) is between 1: 0.1 and 1:50, Active ingredient of group 28) is between 1: 1 and 1: 150, Active ingredient of group 29) is between 1: 1 and 1: 150, Agent of group 30) is between 1: 0.1 and 1:50, Active ingredient of group 31) is between 1: 0.1 and 1:50, Active ingredient of group 32) is between 1: 0.1 and 1:50, Active ingredient of group 33) is between 1: 0.1 and 1:50, Active ingredient of group 34) is between 1: 0.1 and 1:50, Active ingredient of group 35) is between 1: 1 and 1:50, Active ingredient of group 36) is between 1: 1 and 1: 150, Group 37) is between 1: 0.1 and 1:50, Active ingredient of group 38) lies between 0: 1 and 1:50, Active ingredient of group 39) is between 1: 0.1 and 1:50, Active ingredient of group 40) is between 1: 0.1 and 1:50, Active ingredient of group 41) is between 1: 1 and 1: 150, Active ingredient of group 42) is between 1: 1 and 1: 150, Active ingredient of group 43) is between 1: 0.1 and 1:50, Active ingredient of group 44) is between 1: 0.1 and 1:50, Agent of group 45a) is between 1: 1 and 1: 150, Active ingredient of group 45b) is between 1: 1 and 1: 150, Group 46) is between 1: 0.1 and 1:50, Active ingredient of group 47a) is between 1: 0.1 and 1:50, Active ingredient of group 47b) is between 1: 0.1 and 1:50, Active compound of group 47c) is between 1: 0.1 and 1:50 Active compound of group 47d) is between 1: 0.1 and 1:50, Agent of group 47e) is between 1: 0.1 and 1:50, Active ingredient of group 47f) is between 1: 0.1 and 1:50, Active ingredient of group 47g) is between 1: 0.1 and 1:50, Active ingredient of group 47h) is between 1: 0.1 and 1:50 The active substance of the group (48) lies between 1: 0.1 and 1:50, The active substance of the group (49) is between 1: 0.1 and 1:50, The active substance of the group (50) is between 1: 0.1 and 1:50, - Active ingredient of the group (51) is between 1: 0.1 and 1: 50.
- 4Verfahren zur Bekämpfung von Pilzen, dadurch gekennzeichnet, daß man Wirkstoffkombinationen gemäß mindestens einem der Ansprüche 1 bis 3 auf die Pilze und/oder deren Lebensraum ausbringt. 4th Method of combating fungi, characterized in that active compound combinations according to at least one of claims 1 to 3 are applied to the fungi and / or their habitat.
- 6Verfahren zur Herstellung von fungiziden Mitteln, dadurch gekennzeichnet, daß man Wirkstoffkombinationen gemäß mindestens einem der Ansprüche 1 bis 3 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt. 6th A process for the preparation of fungicidal agents, which comprises mixing active compound combinations according to at least one of claims 1 to 3 with extenders and / or surface-active substances.
Independent claims6
587 paragraphs in 41 sections, as filed
Translation of description of equivalent WO 0144215 A2
Fungicides drug combinations
The present invention relates to novel active compound combinations, on the one hand and other known active compounds on the other hand consist of a known fluorine-benzothiazole derivative and are highly suitable for controlling phytopathogenic fungi.
It is already known that isopropyl l - ({[l- (6-fluoro-l, 3-benzothiazol-2-yl) ethyl] - amino} carbonyl) -2-methylpropylcarbamat fungicidal properties (cf. EP-AI. - 775 696). The activity of this substance is good; however, at low application rates it is sometimes unsatisfactory.
Furthermore, it is already known that numerous triazole derivatives, aniline derivatives, Dicarb- oximide and other heterocycles can be employed for combating fungi (cf.. EP-A 0,040,345, DE-A 22 01 063, DE-A 23 24 010, Pesticide Manual,
9th. Edition (1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0515901). The action of these substances is, however, at low application rates is not always sufficient.
Finally, it is also known that l - [(6-chloro-3-pyridinyl) methyl] azolidinimin for controlling animal pests, such as insects, is -N-nitro-2-imide used (cf. Pesticide Manual, 9th Edition.. (1991), page 491). Fungicides properties of this substance have hitherto not been described.
Furthermore, it is already known that L- (3,5-dimethyl-isoxazol-4-sulfonyl) -2-chloro-6,6-difluoro [l, 3] -dioxolo- [4,5f] -benzimidazole has fungicidal properties (see FIG. WO 97-06171).
Furthermore already known that substituted Azadioxacycloalkenc show a fungicidal activity (see. EP-B-712 396). Finally, it is known that substituted halogenopyrimidines fungicidal properties (cf.. DE-Al-196 46 407, EP-B-712 396).
It has now been found that the novel active ingredient combinations made of a fluorine-benzothiazole derivative of formula
<img id="imgf000003_0001" he="28" wi="103" file="imgf000003_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and
(1) a triazole derivative of the formula
<img id="imgf000003_0002" he="27" wi="83" file="imgf000003_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> in which
X represents chlorine or phenyl, and
- C - CH
II I
Y ° or <sup>0H</sup> stands,
and or (2) the triazole derivative of the formula
<img id="imgf000004_0001" he="38" wi="90" file="imgf000004_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(3) an aniline derivative of the formula
<img id="imgf000004_0002" he="14" wi="86" file="imgf000004_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> in which
R<sup>1</sup> is hydrogen or methyl,
and or
(4) N- [1 - (4-chloro-phenyl) -ethyl] -2,2-dichloro- 1 -ethyl-3-methyl-cyclopropane-carboxylic bonsäureamid of formula
<img id="imgf000004_0003" he="25" wi="95" file="imgf000004_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Carpropamid) and / or (5) the zinc propylene-l, 2-bis- (dithiocarbamidat) of the formula
S CH. S
- [Zn S- C ll- NH- CH- C H ι <sup>3</sup>- NH- C π-S] -
(VI) n> = 1 (propineb) and / or
(6) at least one thiocarbamate of formula
<img id="imgf000005_0001" he="25" wi="55" file="imgf000005_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Me = Zn or Mn or mixture of Zn and Mn
and or
(7) the aniline derivative of the formula
<img id="imgf000005_0002" he="23" wi="79" file="imgf000005_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Fenhexamid) and / or (8) the compound of formula
<img id="imgf000006_0001" he="22" wi="119" file="imgf000006_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Iprovalicarb)
and or
(9) the benzothiadiazole derivative of the formula
<img id="imgf000006_0002" he="24" wi="59" file="imgf000006_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Acibenzolar-S-methyl) and / or
(10) the 8-t-butyl-2- (N-ethyl-Nn-propyl-amino) -methyl-1, 4-dioxaspiro [5.4] - decane of the formula
<img id="imgf000006_0003" he="20" wi="92" file="imgf000006_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Spiroxamine) and / or (11) the compound of formula
<img id="imgf000007_0001" he="32" wi="88" file="imgf000007_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(12) the compound of formula
<img id="imgf000007_0002" he="41" wi="94" file="imgf000007_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Trifloxystrobin)
and or
(13) the compound of formula
<img id="imgf000007_0003" he="36" wi="90" file="imgf000007_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
and or (14) the Cyanoxim derivative of the formula
<img id="imgf000008_0001" he="14" wi="96" file="imgf000008_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Cymoxanil) and / or
(15) a pyrimidine derivative of the formula
<img id="imgf000008_0002" he="25" wi="75" file="imgf000008_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> in which
R<sup>2</sup> methyl, - C-nC - CH<sub>3</sub> (Mepanipyrim) or cyclopropyl (Cyprodinyl) is,
and or
(16) an aniline derivative of the formula
<img id="imgf000008_0003" he="28" wi="88" file="imgf000008_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Metalaxyl or metalaxyl M) and / or (17) the morpholine derivative of the formula
(XVIII)
<img id="imgf000009_0001" he="39" wi="64" file="imgf000009_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(18) the phthalimide derivative of the formula
<img id="imgf000009_0002" he="32" wi="70" file="imgf000009_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(19) the phosphorus compound of the formula
<img id="imgf000009_0003" he="21" wi="74" file="imgf000009_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or (20) the hydroxyethyl-triazole derivative of the formula
<img id="imgf000010_0001" he="39" wi="82" file="imgf000010_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(21) the l - [(6-chloro-3-pyridinyl) methyl] -N-nitro-2-imidazolidinimine of the formula
<img id="imgf000010_0002" he="21" wi="87" file="imgf000010_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(22) the oxazolidinedione of formula
e) <img id="imgf000010_0003" he="31" wi="96" file="imgf000010_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or (23) the benzamide derivative of the formula
<img id="imgf000011_0001" he="25" wi="103" file="imgf000011_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Zoxamide) unαVoder
(24) a guanidine derivative of the formula
<img id="imgf000011_0002" he="17" wi="86" file="imgf000011_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> x (2 + m) CH OOH
in which m represents integers from 0 to 5, and
R<sup>3</sup> represents hydrogen (17 to 23%) or the radical of the formula
-C = NH | (77-83%)
NH<sub>2</sub>
stands,
and or (25) the triazole derivative of the formula
<img id="imgf000012_0001" he="36" wi="86" file="imgf000012_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(26) the halogen-benzimidazole of formula
(XXVII)
<img id="imgf000012_0002" he="35" wi="47" file="imgf000012_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(27) the halogenopyrimidine of formula
(XXVIII)
<img id="imgf000012_0003" he="35" wi="90" file="imgf000012_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or (28) the tetrachloro-isophthalo-dinitrile of formula
<img id="imgf000013_0001" he="32" wi="56" file="imgf000013_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Chlorothalonil) and / or
(29) the compound of formula
<img id="imgf000013_0002" he="23" wi="92" file="imgf000013_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Propamocarb) and / or
(30) the pyridinamine of formula
<img id="imgf000013_0003" he="30" wi="85" file="imgf000013_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Fluazinam) and / or (1) the thiazolecarboxamide of formula
<img id="imgf000014_0001" he="40" wi="80" file="imgf000014_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Ethaboxam)
and or
(32) the sulfonamide of the formula
(XXXIII)
<img id="imgf000014_0002" he="50" wi="53" file="imgf000014_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Cyamidazosulfamid)
and or
(33) the compound of formula
(XXXIV)
<img id="imgf000014_0003" he="34" wi="66" file="imgf000014_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(34) the compound of formula
<img id="imgf000015_0001" he="31" wi="94" file="imgf000015_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Iprodione), and / or
(35) the compound of formula
(XXXVI) <img id="imgf000015_0002" he="41" wi="51" file="imgf000015_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Procymidone) and / or
(36) the diamide of formula
(XXXVII) <img id="imgf000015_0003" he="23" wi="55" file="imgf000015_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Thiram), and / or (37) the methoxyacrylate derivative of the formula
(XXXVIII) <img id="imgf000016_0001" he="34" wi="73" file="imgf000016_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Picoxystrobin) and / or
(38) the quinoline derivative of the formula
(XXXIX) <img id="imgf000016_0002" he="30" wi="63" file="imgf000016_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Quinoxyfen) and / or
(39) the phenylamide derivative of the formula
<img id="imgf000016_0003" he="32" wi="90" file="imgf000016_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Oxadixyl) and / or (40) the phenylamide derivative of the formula
(XLI) <img id="imgf000017_0001" he="41" wi="58" file="imgf000017_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Benalaxyl) and / or
(41) the Dicarboxim derivative of the formula
(XXXXIIa) <img id="imgf000017_0002" he="32" wi="48" file="imgf000017_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Captan)
and or
(42) the phosphonic acid of the formula
H- OH
(XLIII)
OH (phosphonic)
and or (43) the pyrrole derivative of the formula
(XLIV) <img id="imgf000018_0001" he="37" wi="38" file="imgf000018_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Fludioxonil) and / or
(44) the phenyl carbonate of formula
(XXXXV) <img id="imgf000018_0002" he="32" wi="68" file="imgf000018_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Diethofencarb) and / or
(45) the copper compounds a) copper oxychloride (XXXXVIa) b) copper hydroxide (XXXXVIb) and / or
(46) the imidazole derivative of the formula
(XLVII) <img id="imgf000018_0003" he="32" wi="71" file="imgf000018_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Prochloraz) and or
(47) a triazole derivative of the formula a)
(XXXXVIIIa) <img id="imgf000019_0001" he="34" wi="76" file="imgf000019_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Difenconazole) and / or
b)
(XXXXVIIIb) <img id="imgf000019_0002" he="25" wi="57" file="imgf000019_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Hexaconazole) and / or
c)
(XXXXVIIIe) <img id="imgf000019_0003" he="29" wi="54" file="imgf000019_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Cyproconazole) and / or d)
(XXXXVlIId) <img id="imgf000020_0001" he="34" wi="58" file="imgf000020_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Flusilazole)
and or
e)
(XXXXVIIIe) <img id="imgf000020_0002" he="31" wi="55" file="imgf000020_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Propiconazole) and / or
f)
(XXXXVIIIf) <img id="imgf000020_0003" he="43" wi="51" file="imgf000020_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Myclobutanil) and / or G)
(XXXXVIIIg) <img id="imgf000021_0001" he="43" wi="66" file="imgf000021_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(Fenbuconazole)
and or
h) F,
(XXXXVIIIh) <img id="imgf000021_0002" he="33" wi="55" file="imgf000021_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Tetraconazole)
and or
(48) a compound of general formula
(XLIX)
<img id="imgf000021_0003" he="30" wi="68" file="imgf000021_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> in which R<sup>1</sup> is unsubstituted or substituted by fluorine, chlorine, bromine, methyl or ethyl-substituted phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl,
and or
(49) N-methyl-2- (methoxyimino) -2- [2 - ([1 - (3-tri-fluoro-methylphenyl) ethoxy] iminomethyl) -phenyl] acetamide of the formula
(XXXXX)
<img id="imgf000022_0001" he="36" wi="74" file="imgf000022_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(50) 2,4-dihydro-5-methoxy-2-methyl-4- [2 - ([([l- (3-tri-fluoro-methylphenyl) ethylidene] amino) oxy] methyl) phenyl] -3H- l, 2,4-triazol-3-ones of the formula
(XXXXXI)
<img id="imgf000022_0002" he="41" wi="65" file="imgf000022_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and or
(51) the compound of formula
(XXXXXII)
<img id="imgf000022_0003" he="34" wi="83" file="imgf000022_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> have very good fungicidal properties.
Surprisingly, the fungicidal action of the active ingredient according to the invention combinations is substantially higher than the sum of the effects of the individual active ingredients. It is therefore, an unforeseeable, true synergistic effect and not just an addition.
From the structural formula of the active compound of the formula (I) it is evident that the connection is two asymmetrically substituted carbon atoms. The product may be present as a mixture of different isomers or else in the form of a single isomer.
Preferred compounds of formula (I) are compounds in which the A is formed ino- acid part of i-propyloxycarbonyl-L-valine and the fluoro-benzothiazol is ethylaminteil racemic, but in particular (R) has -Konfιguration.
The formula (II) comprises the compounds
l- (4-chloro-phenoxy) -3,3-dimethyl-l- (l, 2,4-triazol-l-yl) -butan-2-one of the formula
<img id="imgf000023_0001" he="33" wi="97" file="imgf000023_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> l- (4-chloro-phenoxy) -3,3-dimethyl-l- (l, 2,4-triazol-l-yl) -butan-2-ol of the formula
<img id="imgf000024_0001" he="33" wi="80" file="imgf000024_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and
1 - (4-phenyl-phenoxy) -3,3-dimethyl-1 - (1, 2,4-triazol-1-yl) -butan-2-ol of the formula
<img id="imgf000024_0002" he="33" wi="105" file="imgf000024_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
The formula (IV) includes the aniline derivatives of the formulas
<img id="imgf000024_0003" he="15" wi="94" file="imgf000024_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
and
<img id="imgf000024_0004" he="15" wi="61" file="imgf000024_0004.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (Tolylfluanid)
From the structural formula of the active compound of the formula (V) it is apparent that the compound has three asymmetrically substituted carbon atoms. The product may be present as a mixture of different isomers or else in the form of a single component. Particularly preferred compounds are N- (R) - [1 - (4-chloro-phenyl) -ethyl] - (1 S) -2,2-dichloro-1-ethyl 3t-methyl-1 R-cyclopropyl pancarbonsäureamid of formula
<img id="imgf000025_0001" he="25" wi="107" file="imgf000025_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
(S) (R)
and
N- (R) - [1 - (4-chloro-phenyl) -ethyl] - (1 R) -2,2-dichloro-1-ethyl-3t-methyl-1R-cyclopropane of formula pancarbonsäureamid
<img id="imgf000025_0002" he="35" wi="107" file="imgf000025_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
The formula (VII) includes the compounds
(VIIa) Me - Zn (Zineb)
(VIIb) Me = Mn (maneb) and
(VIIc) mixture of (VIIa) and (VIIb) (mancozeb).
The formula (XVI) includes the compounds
(XV la) R<sup>2</sup> = CH, (Pyrimethanil) and (XVIb) R<sup>2</sup> = - <] (Cyprodinyl)
(XVIc) R<sup>2</sup> = -C≡C-CH<sub>3</sub> (Mepanipyrim)
The compound of formula (XVII) may be used as methyl N- (2,6-dimethylphenyl) -N- (methoxyacetyl) -DL-alaninate (metalaxyl, XVIIa) or as methyl N- (2,6-dimethylphenyl) -N- ( methoxyacetyl) -D-alaninate (metalaxyl-M, XVIIb) are present.
The hydroxyethyl-triazole derivative of the formula (XXI) may be in the "thiono" form of the formula
<img id="imgf000026_0001" he="41" wi="88" file="imgf000026_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
or in the tautomeric "mercapto" form of the formula
<img id="imgf000026_0002" he="41" wi="90" file="imgf000026_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
present. For simplicity, each listed only the "thiono" form.
The guanidine derivative of the formula (XXV) is a mixture of substances with the common name guazatine.
From the structural formula for the active compounds of the formula (XXXXIX) can be seen that the compounds may exist as E or Z isomers. The product can therefore exist as a mixture of different isomers or else in the form of a single isomer. Preferred compounds of formula (XLIX) in which there are the compounds of formula (XLIX) as the E isomer are. Particularly preferred are the compounds of the formulas
(XXXXIXa)
<img id="imgf000027_0001" he="30" wi="88" file="imgf000027_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
and
(XXXXIXb)
<img id="imgf000027_0002" he="30" wi="89" file="imgf000027_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and
(XXXXIXc)
<img id="imgf000027_0003" he="30" wi="87" file="imgf000027_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
and
(XXXXIXd)
<img id="imgf000027_0004" he="30" wi="86" file="imgf000027_0004.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> and
(XXXXIXe)
<img id="imgf000028_0001" he="30" wi="89" file="imgf000028_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
and
(XXXXIXf)
<img id="imgf000028_0002" he="30" wi="96" file="imgf000028_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
and isomers thereof.
Suitable mixture partners of the compounds of formula (I), the following active compounds are particularly preferred:
(3) tolylfluanid (IVb),
(5) propineb (VI),
(6) mancozeb (VIIc)
(7) fenhexamid (VIII),
(8) iprovalicarb (VIII), (1 1) azoxystrobin (XII),
(12) trifloxystrobin (XIII),
(13) Compound of formula (XIV), (18) folpet (XIX),
(20) Compound of formula (XXI), (26) Compound of formula (XXVII),
(27) Compound of formula (XXVIII), (28) chlorothalonil (XXIX), (30) fluazinam (XXXI), and (45) copper compounds a) copper oxychloride (XXXXVIa) b) copper (XXXXVIb).
Present in the active compound combinations according to the invention in addition to a halogen-benzimidazole of the formula (XXVII) components are also known.
In particular, the active compounds are described in the following publications:
(1) Compounds of formula (II)
DE-A 22 01 063. DE-A 23 24 010
(2) Compound of formula (III)
EP-A 0040345
(3) Compounds of formula (IV) Pesticide Manual, 9th. Ed. (1991), pages 249 and 827
(4) Compound of formula (V) and their derivatives single
EP-A 0341475
(5) Compound of formula (VI)
Pesticide Manual, 9th. Ed. (1991), page 726
(6) Compounds of formula (VII)
Pesticide Manual, 9th. Ed. (1991), pages 529, 531 and 866 (7) Compound of formula (VIII)
EP-A 0339418
(8) the compound of formula (IX) EP-A 0472996
(9) Compound of formula (X)
EP-A 0313512
(10) Compound of formula (XI)
EP-A 0281842
(11) Compound of formula (XII)
EP-A 0382375
(12) Compound of formula (XIII)
EP-A-460 575
(13) the compound of formula (XIV) DE-A 196 02 095
(14) Compound of formula (XV)
Pesticide Manual, 9th. Ed. (1991), page 206
(15) Compounds of formula (XVI)
EP-A 0270111, EP-A 0310550
(16) Compound of formula (XVII) Pesticide Manual, 9th. Ed. (1991), page 554 (17) Compound of formula (XVIII)
EP-A 0219756
(18) Compound of formula (XIX) Pesticide Manual, 9th. Ed. (1991), page 431
(19) Compound of formula (XX)
Pesticide Manual, 9th. Ed. (1991), page 443
(20) Compound of formula (XXI)
WO 96-16048
(21) Compound of formula (XXII)
Pesticide Manual, 9th. Ed. (1991), page 491
(22) Compound of formula (XXIII)
EP-A 0393911
(23) Compound of formula (XXIV) EP-A 0600629
(24) substance of the formula (XXV)
Pesticide Manual, 9th. Ed. (1991), page 461
(25) Compound of formula (XXVI)
Pesticide Manual, 9th. Ed. (1991), page 654
(26) Compound of formula (XXVII) WO 97-06171 (27) Compound of formula (XXVIII)
DE-Al-196 46 407, EP-B-0712396
(28) Compound of formula (XXIX)
US 3290353
(29) Compound of formula (XXX)
DE-A- 156 7169
(30) Compound of formula (XXXI)
EP-A-0031257
(31) Compound of formula (XXXII) EP-A-0639547
(32) Compound of formula (XXXIII)
EP-A-0298196
(33) Compound of formula (XXXIV)
EP-A-600 629
(34) Compound of formula (XXXV)
DE-A-2149923
(35) Compound of formula (XXXVI)
DE-A-2012656
(36) Compound of formula (XXXVU) US 1,972,961 (37) Compound of formula (XXXVIII) EP-A-326 330
(38) Compound of formula (XXXIX) EP-A 278 595
(39) the compound of formula (XXXX) DE-A-3030026
(40) Compound of formula (XXXXI)
DE-A-2903612
(41) Compound of formula (XXXXII)
US 2553770
(42) the compound of formula (XLIII) known and commercially available
(43) Compound of formula (XXXXIV) EP-A-206 999
(44) Compound of formula (XXXXV)
EP-A-78663
(45) a) compound of formula (XXXXVIa) known and commercially available
b) compound of formula (XXXXVIb) known and commercially available (46) the compound of formula (XLVII) DE-A-2429523
(47) a) compound of formula (XXXXVIIIa)
EP-A-112 284 b) compound of formula (XXXXVIIIb) DE-A-3042303
c) compound of formula (XXXXVIIIc)
DE-A-3406993
d) compound of formula (XXXXVlIId) EP-A-68813
e) the compound of formula (XXXXVIIIe) DE-A-2551560
f) compound of formula (XXXXVIIIf) EP-A- 145 294
g) the compound of formula (XXXXVIIIg) DE-A-3721786
h) compound of formula (XXXXVIIIh)
EP-A-234 242
(48) Compound of formula (XXXXIX) WO 96/23763 (49) the compound of formula (XXXXX)
EP-A-596 254
(50) compound of the formula (XXXXXI) WO 98/23155
(51) compound of the formula (XXXXXII)
EP-A-569 384th
The active compound combinations according to the invention in addition to an active compound of the formula (I) at least one active compound from the compounds of groups (1) to (51). You can moreover contain further fungicidally active components Zumischkom-.
If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active compounds can be varied in the active substance combinations in a relatively wide range. Generally, for every 1 part by weight of active compound of formula (I)
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (1),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (2),
1 to 150 parts by weight, preferably 1 to 100 parts by weight of active compound of group (3),
0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight of active compound of
Group (4) 1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound from the group (5),
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of
Group (6),
0.1 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound of group (7),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (8),
0.02 to 50 parts by weight, preferably 0.1 to 10 parts by weight of active compound of group (9),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (10),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of
Group (11),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (12).
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from the group (13),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (14), 0.2 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound of group (15),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (16),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (17),
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound from
Group (18),
0.1 to 150 parts by weight, preferably 1 to 100 parts by weight of active compound of group (19),
0.02 to 50 parts by weight, preferably 0.2 to 10 parts by weight of active compound of group (20),
0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight of active compound of group (21),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (22),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from
Group (23),
0.01 to 150 parts by weight, preferably 1 to 100 parts by weight of active compound of group (24), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (25),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (26),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (27),
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of
Group (28),
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (29),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (30),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (31),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (32),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of
Group (33),
0.1 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound from the group (34), 0.1 to 50 parts by weight, preferably 1 to 10 parts by weight of active compound of group (35),
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (36),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (37).
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of
Group (38),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (39),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (40),
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (41),
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (42),
0.1 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound of
Group (43),
0.1 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound from the group (44), 1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (45a)
1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (45b),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (46),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of
Group (47a)
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (47b)
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (47c),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (47d),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (47e)
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of
Group (47f)
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from the group (47g) 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (47h)
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from the group (48),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (49),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of
Group (50),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (51).
The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodium, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc..
The active compound combinations of the invention are particularly suitable for controlling Phytophthora infestans and Plasmopara viticola.
The good plant tolerance of the active compound combinations in the concentrations required for combating plant diseases, permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. The active compound combinations according to the invention can be used for foliar application or else as seed dressings. The active compound combinations according to the invention are also suitable for increasing the crop yield. They have reduced toxicity and are well tolerated by plants.
According to the invention all plants and plant parts can be treated. Among
Plants are understood here all plants and plant populations such as desired and undesired wild plants or Kultuφflanzen (including naturally occurring Kultuφflanzen). Kultuφflanzen 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 protectable by varietal property rights or not protectable plant varieties. Plant parts all aerial and subterranean parts and organs of plants such as shoot, leaf, flower and root are to be understood, for example, leaves, needles, stalks, stems, flowers, Fruchtköφer, fruits and
Seeds, roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.
The inventive treatment of the plants and plant parts with the active compounds is carried out directly or by action on their environment, habitat or storage space by the customary treatment methods, for example by dipping, spraying, evaporation, fogging, scattering, painting on and with propagation material, especially seeds, also by applying one or more coats.
The active compound combinations according to the invention can be converted into the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seed, and ULV formulations. These formulations are produced in known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surfactants, that is emulsifiers and / or dispersants and / or foam-forming agents.
In the case of the use of water as stretching means eg also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or Alkylnaphtha- line, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, meth ylisobutylketon or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such 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 highly disperse silica, alumina and silicates. As solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. As emulsifying and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty holether, for example alkylaryl ether, alkyl sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose. It can be used in the formulations adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latexf-shaped polymers such as polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.
Colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, 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 in general contain between 0.1 and 95 wt .-% active ingredients, preferably between 0.5 and 90%.
The active compound combinations according to the invention, as such or in their
Formulations are used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, for example so as to widen the spectrum of action or prevent development of resistance. In many cases, synergistic effects, ie the activity of the mixture exceeds the activity of the individual components.
A mixture with other known active compounds such as herbicides or with fertilizers and growth regulators is also possible.
The active compound combinations, as such, in the form of their formulations or the use forms prepared as ready-emulsified gi newable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules, are applied. They are used in the customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, dry dressing, moist dressing, wet dressing, slurry dressing or encrusting. When using the active compound combinations according to the invention, the application rates can be varied depending on the type of application within a substantial range. In the treatment of plant parts, the application rates of active compound combination are generally from 0.1 to 10,000 g / ha, preferably between 10 and 1 000 grams / ha. For seed treatment, the application rates of active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. When treating the soil, the application rates of active compound combination are generally from 0.1 to 10,000 g / ha, preferably 1-5000 g / ha.
The good fungicidal activity of the active compound combinations according to the invention is illustrated by the following examples. While the individual active compounds in the fungicidal action weaknesses, the combinations show an action which exceeds a simple additive effect.
A synergistic effect in fungicides is always present when the fungicidal activity of the active compound combinations is greater than the sum of the effects of the active ingredients applied individually.
The expected activity for a given combination of two active compounds can SR Colby ( "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1_5 (1967), 20-22) are calculated as follows:
If
X is the efficacy when employing active compound A at an application rate of mg / ha,
Y is the efficacy when applying active compound B at an application rate of ng / ha and E is the efficacy when employing active compounds A and B at application rates of m and ng / ha,
then
X - Y
E = X + Y
100
Here, the efficacy is determined in%. 0% means an efficacy which corresponds to the control, while an efficacy of 100% means that no infection is observed.
If the actual fungicidal activity exceeds the calculated value, the combination is superadditive, ie there is a synergistic effect. In this case, the actually observed efficacy must exceed the value calculated using the above formula for the expected efficacy (E).
The invention is illustrated by the following examples. The invention is not limited to the examples.
Beispicl 1
Phytophthora test (tomato) / protective
Solvent: 47 parts by weight of acetone Emulsifier: 3 parts by weight of alkylaryl
To produce a suitable preparation of active compound, 1 part by weight of active ingredient or combination of active ingredients with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration or diluting a commercial formulation of active ingredient or
Combination of active ingredients with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. the plants are After drying the spray coating inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at about 20 ° C and 100% relative humidity.
3 days after the inoculation evaluation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of
100% means that no infection is observed.
The activity found for the active compound combination according to the invention is greater than the calculated activity, ie a synergistic effect exists. . The combination of compound of formula (I) and the halogen-benzimidazole of the formula No. XXVII has at a mixing ratio of 1: 1 and an application rate of 0.1 g / ha, an actual efficiency of 73%. Calculated according to the Colby formula expectation is with 63% significantly less.
Active compounds, application rates and test results are shown in the following tables. Table 1
Phytophthora test (tomato) / protective
Active Application rate efficiency of drug in in%
Noted: g / ha
Compound of formula (XXVII) 0.1 30
<img id="imgf000048_0001" he="35" wi="46" file="imgf000048_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Compound of formula (I) 0.1 47
<img id="imgf000048_0002" he="26" wi="81" file="imgf000048_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
Drug mixture expenses Actual expectation ratio quantity to effect value calculated
Drug grad Colby research in g / ha mel
<img id="imgf000048_0003" he="23" wi="135" file="imgf000048_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="yes" /> Table 2
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000049_0001" he="26" wi="81" file="imgf000049_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Propineb (VI) 20 19
<img id="imgf000049_0002" he="13" wi="89" file="imgf000049_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> n> = 1 (propineb)
Inventive mixture:
Mixing application rates of actual expectancy-value,
Ratio quantity of efficiency calculated with
Active degree Colby formula in g / ha
<img id="imgf000049_0003" he="23" wi="133" file="imgf000049_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 3
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000050_0001" he="26" wi="81" file="imgf000050_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Chlorothalonil (XXIX) 20 12
<img id="imgf000050_0002" he="32" wi="34" file="imgf000050_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
Mixture expenses Actual expectation ratio quantity to effect value calculated
Drug grad Colby in g / ha formula
<img id="imgf000050_0003" he="23" wi="136" file="imgf000050_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 4
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000051_0001" he="26" wi="80" file="imgf000051_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Dichlofluanid (IVa) 20
<img id="imgf000051_0002" he="14" wi="48" file="imgf000051_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
Mixture expenses Actual expectation ratio quantity to effect value calculated
Drug grad Colby in g / ha formula
<img id="imgf000051_0003" he="23" wi="136" file="imgf000051_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (IVa) Table 5
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000052_0001" he="27" wi="80" file="imgf000052_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Tolylfluanid (IVb) 20 21
<img id="imgf000052_0002" he="12" wi="49" file="imgf000052_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
worth mixing application rates of actual expectancy ratio amount of efficiency, calculated drug grad Colby in g / ha - Formula
<img id="imgf000052_0003" he="23" wi="136" file="imgf000052_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="yes" /> (IVa) Table 6
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000053_0001" he="26" wi="80" file="imgf000053_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Folpet (XIX) 20
<img id="imgf000053_0002" he="32" wi="48" file="imgf000053_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
worth mixing application rates of actual expectancy ratio amount of efficiency, calculated in drug grad Colby g / ha formula
<img id="imgf000053_0003" he="24" wi="136" file="imgf000053_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 7
Phytophthora test (tomato) / protective
Active Application rate% Wirkungsan compound in g / ha degree
Known:
Compound of formula (I) 39
<img id="imgf000054_0001" he="26" wi="81" file="imgf000054_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Mancozeb (VIIc) 20 28
Inventive mixture:
Mixture expenses Actual expectation ratio quantity to effect value calculated
Drug grad Colby in g / ha formula
<img id="imgf000054_0002" he="25" wi="152" file="imgf000054_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 8
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000055_0001" he="26" wi="80" file="imgf000055_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Bitertanol (IIc) 10
Inventive mixture:
MischungsAufwand- Expectations worth proportionate amount of actual on efficiency charged
Active degree Colby formula in g / ha
73 49 <img id="imgf000055_0002" he="23" wi="101" file="imgf000055_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 9
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000056_0001" he="27" wi="80" file="imgf000056_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Tebuconazole (III) 10
<img id="imgf000056_0002" he="34" wi="59" file="imgf000056_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
MischungsAufwand- Expectations worth proportionate amount of actual on efficiency charged
Agent in grade Colby formula g / ha
<img id="imgf000056_0003" he="23" wi="131" file="imgf000056_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (III) Table 10
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000057_0001" he="26" wi="80" file="imgf000057_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Triadimenol (IIb) 10
<img id="imgf000057_0002" he="30" wi="63" file="imgf000057_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
Mixing application rates of actual expectancy-value,
Ratio quantity of efficiency calculated with
Active degree Colby formula in g / ha
<img id="imgf000057_0003" he="23" wi="128" file="imgf000057_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (IIb) Table 11
Phytophthora test (tomato) / protective
<img id="imgf000058_0002" he="99" wi="152" file="imgf000058_0002.tif" img-format="tif" img-content="table" orientation="portrait" inline="no" />
Inventive mixture:
MischungsAufwand- Expectations worth proportionate amount of actual on efficiency charged
Agent in grade Colby formula g / ha
<img id="imgf000058_0001" he="24" wi="130" file="imgf000058_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 12
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of Foπnel (I) 47
<img id="imgf000059_0001" he="26" wi="81" file="imgf000059_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Compound of the formula (XXI) (20) 10
<img id="imgf000059_0002" he="39" wi="81" file="imgf000059_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Erf indungsgemäße mixture:
Mixture expenses Actual expectation ratio quantity to effect value calculated
Active in grad Colby g / ha formula
<img id="imgf000059_0003" he="23" wi="135" file="imgf000059_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 13
Phytophthora test (tomato) / protective
<img id="imgf000060_0002" he="103" wi="152" file="imgf000060_0002.tif" img-format="tif" img-content="table" orientation="portrait" inline="no" />
Inventive mixture:
MischungsAufwand- actual expected value, relationship to quantitative efficiency. charged
Active degree Colby formula in g / ha
<img id="imgf000060_0001" he="23" wi="133" file="imgf000060_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> (VIII) Table 14
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000061_0001" he="26" wi="80" file="imgf000061_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Caφropamid (V) 10
<img id="imgf000061_0002" he="32" wi="56" file="imgf000061_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
MischungsAufwand- actual - value ratio expectation amount of efficiency, calculated in drug grad Colby g / ha formula
<img id="imgf000061_0003" he="23" wi="136" file="imgf000061_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 15
Phytophthora test (tomato) / protective
Active Application rate% Wirkungsan compound in g / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000062_0001" he="27" wi="81" file="imgf000062_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Spiroxamine (XI) 10
<img id="imgf000062_0002" he="20" wi="70" file="imgf000062_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
worth MischungsAufwand- actual expectancy ratio amount of efficiency, calculated drug grad Colby in g / ha formula
<img id="imgf000062_0003" he="23" wi="133" file="imgf000062_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 16
Phytophthora test (tomato) / protective
<img id="imgf000063_0002" he="109" wi="152" file="imgf000063_0002.tif" img-format="tif" img-content="table" orientation="portrait" inline="no" />
Inventive mixture:
worth mixing application rates of actual expectancy ratio amount of efficiency, calculated in drug grad Colby g / ha formula
87 73 <img id="imgf000063_0001" he="23" wi="103" file="imgf000063_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 17
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000064_0001" he="26" wi="80" file="imgf000064_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Compound of formula (XXVIII) (27)
<img id="imgf000064_0002" he="33" wi="80" file="imgf000064_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
worth mixing application rates of actual expectancy ratio amount of efficiency, calculated in drug grad Colby g / ha formula
72 52 <img id="imgf000064_0003" he="24" wi="99" file="imgf000064_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 18
Phytophthora test (tomato) / protective
Application rate of active agent in% Wirkungsg / ha degree
Known:
Compound of formula (I) 47
<img id="imgf000065_0001" he="27" wi="81" file="imgf000065_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Compound of the formula (XIV) (13)
<img id="imgf000065_0002" he="36" wi="67" file="imgf000065_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
worth mixing application rates of actual expectancy ratio amount of efficiency, calculated drug grad Colby in g / ha formula
<img id="imgf000065_0003" he="23" wi="132" file="imgf000065_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 19
Phytophthora test (tomato) / protective
<img id="imgf000066_0002" he="92" wi="149" file="imgf000066_0002.tif" img-format="tif" img-content="table" orientation="portrait" inline="no" />
Inventive mixture:
MischungsAufwand- Expectations worth proportionate amount of actual on efficiency charged
Active degree Colby formula in g / ha
82 56
<img id="imgf000066_0001" he="20" wi="98" file="imgf000066_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> a) Table 20
Phytophthora test (tomato) / protective
<img id="imgf000067_0002" he="147" wi="149" file="imgf000067_0002.tif" img-format="tif" img-content="table" orientation="portrait" inline="no" />
Inventive mixture:
MischungsAufwand- tatsäch Licher expectancy ratio quantity to effect degree value calculated in drug with Colby g / ha formula
95 80
<img id="imgf000067_0001" he="19" wi="99" file="imgf000067_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" /> Table 21
Phytophthora test (tomato) / protective
Active Application rate% Wirkungsan agent in grade Noted: g / ha
Formula (I) 56
<img id="imgf000068_0001" he="27" wi="81" file="imgf000068_0001.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Compound of formula (XIII) (12) trifloxystrobin
<img id="imgf000068_0002" he="66" wi="55" file="imgf000068_0002.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Inventive mixture:
Mixing application rates actually Expectations worth proportionate amount calculated at Licher with
Drug efficiency Colby formula in g / ha degree
68 56
<img id="imgf000068_0003" he="19" wi="96" file="imgf000068_0003.tif" img-format="tif" img-content="drawing" orientation="portrait" inline="no" />
Contents41
47 members in 26 offices
Priority claims14
| Document | Office | Kind | Date |
|---|---|---|---|
| 19959947 | Germany | A | |
| 19959947 | Germany | A | |
| 19959947 | Germany | – | |
| 10021412 | Germany | A | |
| 10021412 | Germany | A | |
| 10021412 | Germany | – | |
| 0011989 | European Patent Office (EPO) | W | |
| 0011989 | European Patent Office (EPO) | W | |
| 10021412 | – | – | – |
| 19959947 | – | – | – |
| DE1999159947 | – | – | – |
| DE2000121412 | – | – | – |
| EP0011989 | – | – | – |
| WO2000EP11989 | – | – | – |
Members47
| Document | Office | Kind | |
|---|---|---|---|
| CA2393988A1 | Canada | A1 | |
| DE10021412A1 | Germany | A1 | |
| WO0144215A2 | World Intellectual Property Organization (WIPO) | A2 | |
| AU2164101A | Australia | A | |
| WO0144215A3 | World Intellectual Property Organization (WIPO) | A3 | |
| KR20020059759A | Republic of Korea | A | |
| BR0016336A | Brazil | A | |
| EP1239733A2This record | European Patent Office (EPO) | A2 | |
| CZ20022079A3 | Czechia | A3 | |
| IL149554D0 | Israel | D0 | |
| TR200201544T2 | Türkiye | T2 | |
| CO5221089A1 | Colombia | A1 | |
| MXPA02005835A | Mexico | A | |
| HU0203563A2 | Hungary | A2 | |
| HUP0203563A2 | Hungary | A2 | |
| AR026938A1 | Argentina | A1 | |
| HU0203563A3 | Hungary | A3 | |
| HUP0203563A3 | Hungary | A3 | |
| CN1409596A | China | A | |
| ZA200203650B | South Africa | B | |
| JP2003516979A | Japan | A | |
| US2003105146A1 | United States of America | A1 | |
| EP1239733B1 | European Patent Office (EPO) | B1 | |
| AT243933T | Austria | T | |
| ATE243933T1 | Austria | T1 | |
| DE50002776D1 | Germany | D1 | |
| US6624183B2 | United States of America | B2 | |
| DK1239733T3 | Denmark | T3 | |
| NZ519460A | New Zealand | A | |
| PT1239733E | Portugal | E | |
| ES2197124T3 | Spain | T3 | |
| RU2002119003A | Russian Federation | A | |
| US2004029840A1 | United States of America | A1 | |
| PL355756A1 | Poland | A1 | |
| TW590741B | Taiwan Province of China | B | |
| CN1547911A | China | A | |
| CN1212768C | China | C | |
| US2006172981A1 | United States of America | A1 | |
| KR100613238B1 | Republic of Korea | B1 | |
| US7115593B2 | United States of America | B2 | |
| US7208510B2 | United States of America | B2 | |
| US2007161688A1 | United States of America | A1 | |
| IL149554A | Israel | A | |
| PL200668B1 | Poland | B1 | |
| CZ301233B6 | Czechia | B6 | |
| CN101627772A | China | A | |
| US7956009B2 | United States of America | B2 |
67 legal events, as 11 offices reported them to INPADOC
Over the term
Point at a mark for the eventEvents
| Event | Code | Office | |
|---|---|---|---|
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Announcement of lapse in spainLapsedFD2A | FD2A | ES | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal feeWithdrawnR119 | R119 | DE | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Patent lapsedLapsedMM4A | MM4A | IE | |
| Notification of lapseLapsedST | ST | FR | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Gb: european patent ceased through non-payment of renewal feeCeasedGBPC | GBPC | EP | |
| Lapse due to non-payment of feesLapsedML | ML | GR | |
| Patent ceasedCeasedPL | PL | CH | |
| Lapsed because of non-payment of the annual feeLapsedV1 | V1 | NL | |
| Annulment/lapse due to non-payment of fees, searched and examined patentLapsedLAPSE DUE TO NON-PAYMENT OF FEESMM4A | MM4A | PT | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Ep patent lapsedLapsedEBP | EBP | DK | |
| Be: lapsedLapsedBERE | BERE | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP | PGFP | EP | |
| Name/firm changedPFA | PFA | CH | |
| No opposition filedOpposition26N | 26N | EP | |
| No opposition filed within time limitOppositionORIGINAL CODE: 0009261PLBE | PLBE | EP | |
| Information on the status of an ep patent application or granted ep patentGrantedSTATUS: NO OPPOSITION FILED WITHIN TIME LIMITSTAA | STAA | EP | |
| Fr: translation filedET | ET | EP | |
| Definitive protectionFG2A | FG2A | ES | |
| Lt: invalidation of european patent or patent extensionLTIE | LTIE | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Ep patent validated in greeceEP | EP | GR | |
| Gb: translation of ep patent filed (gb section 77(6)(a)/1977)GBT | GBT | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Corresponds to:REF | REF | EP | |
| European patents granted designating irelandGrantedGERMANFG4D | FG4D | IE | |
| New agentNV | NV | CH | |
| European patent takes effect as a national patent in ch/liEP | EP | CH | |
| Designated contracting statesAK | AK | EP | |
| European patent grantedGrantedNOT ENGLISHFG4D | FG4D | GB | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25 | PG25 | EP | |
| (expected) grantORIGINAL CODE: 0009210GRAA | GRAA | EP | |
| Despatch of communication of intention to grant a patentORIGINAL CODE: EPIDOS IGRAGRAH | GRAH | EP | |
| Despatch of communication of intention to grant a patentORIGINAL CODE: EPIDOS IGRAGRAH | GRAH | EP | |
| Party data changed (applicant data changed or rights of an application transferred)RAP1 | RAP1 | EP | |
| Request for examination filed17P | 17P | EP | |
| Designated contracting statesAK | AK | EP | |
| Request for extension of the european patentAL;LT;LV;MK;RO;SIAX | AX | EP | |
| Public reference made under article 153(3) epc to a published international application that has entered the european phaseORIGINAL CODE: 0009012PUAI | PUAI | EP |
Numbers
- Publication
- 1239733
- Publication, DOCDB
- 1239733
- Publication, EPODOC
- EP1239733
- Application
- 985119
- Application, DOCDB
- 00985119
- Application, EPODOC
- EP20000985119
Titles3
- German
- FUNGIZIDE WIRKSTOFFKOMBINATIONEN
- English
- FUNGICIDAL COMBINATIONS OF ACTIVE SUBSTANCES
- French
- COMBINAISONS FONGICIDES DE SUBSTANCES ACTIVES
Classification
- CPC, 1
- A01N47/12
- IPC, 30
- A01N37 18
- A01N37 22
- A01N37 24
- A01N37 34
- A01N37 50
- A01N41 06
- A01N43 28
- A01N43 36
- A01N43 38
- A01N43 40
- A01N43 42
- A01N43 50
- A01N43 54
- A01N43 653
- A01N43 76
- A01N43 78
- A01N43 80
- A01N43 828
- A01N43 84
- A01N43 88
- A01N47 12
- A01N47 14
- A01N47 20
- A01N47 34
- A01N47 44
- A01N51 00
- A01N53 12
- A01N55 00
- A01N57 12
- A01N59 26
Designated states26
- Contracting states, 20
- Austria
- Belgium
- Switzerland
- Cyprus
- Germany
- Denmark
- Spain
- Finland
- France
- United Kingdom
- Greece
- Ireland
- Italy
- Liechtenstein
- Luxembourg
- Monaco
- Netherlands (Kingdom of the)
- Portugal
- Sweden
- Türkiye
- Extension states, 6
- Albania
- Lithuania
- Latvia
- North Macedonia
- Romania
- Slovenia