MX2008007856A - Biphenyl carboxamides for controlling micro-organisms - Google Patents
Biphenyl carboxamides for controlling micro-organismsInfo
- Publication number
- MX2008007856A MX2008007856A MXMX/A/2008/007856A MX2008007856A MX2008007856A MX 2008007856 A MX2008007856 A MX 2008007856A MX 2008007856 A MX2008007856 A MX 2008007856A MX 2008007856 A MX2008007856 A MX 2008007856A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- halogen
- atoms
- carbonyl
- Prior art date
Links
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical class NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 244000005700 microbiome Species 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 534
- 239000001257 hydrogen Substances 0.000 claims description 158
- 229910052739 hydrogen Inorganic materials 0.000 claims description 158
- -1 carbon atoms halogen Chemical class 0.000 claims description 153
- 125000000217 alkyl group Chemical group 0.000 claims description 140
- 150000002431 hydrogen Chemical class 0.000 claims description 133
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 132
- 229910052731 fluorine Inorganic materials 0.000 claims description 132
- 239000011737 fluorine Substances 0.000 claims description 132
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 130
- 239000000460 chlorine Substances 0.000 claims description 130
- 229910052801 chlorine Inorganic materials 0.000 claims description 130
- 125000001188 haloalkyl group Chemical group 0.000 claims description 107
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 83
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 83
- 229910052794 bromium Inorganic materials 0.000 claims description 83
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 80
- 229910052736 halogen Inorganic materials 0.000 claims description 75
- 150000002367 halogens Chemical class 0.000 claims description 73
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 73
- 125000003545 alkoxy group Chemical group 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 52
- 125000001246 bromo group Chemical group Br* 0.000 claims description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
- YMEHWISYYMKMFO-WOMRJYOTSA-N methyl N-[(12E,15S)-15-[(4S)-4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2(7),3,5,12,16-hexaen-5-yl]carbamate Chemical compound COC(=O)Nc1ccc2-c3cnc([nH]3)[C@H](C\C=C\CCC(=O)Nc2c1)N1CC[C@@H](CC1=O)c1cccc(Cl)c1 YMEHWISYYMKMFO-WOMRJYOTSA-N 0.000 claims description 11
- 125000006413 ring segment Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 230000009261 transgenic effect Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000004967 formylalkyl group Chemical group 0.000 claims description 5
- 230000007480 spreading Effects 0.000 claims description 5
- 238000003892 spreading Methods 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 239000013067 intermediate product Substances 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 102
- 241000196324 Embryophyta Species 0.000 description 86
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 79
- 150000001875 compounds Chemical class 0.000 description 47
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 47
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 45
- 239000000047 product Substances 0.000 description 35
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 29
- 239000003112 inhibitor Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 20
- 201000010099 disease Diseases 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 235000005822 corn Nutrition 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 241000233866 Fungi Species 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 235000013399 edible fruits Nutrition 0.000 description 9
- 241000894007 species Species 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 230000017074 necrotic cell death Effects 0.000 description 8
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- 241000223218 Fusarium Species 0.000 description 7
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- 241001361634 Rhizoctonia Species 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 7
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- 241000223600 Alternaria Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000221300 Puccinia Species 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
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- 238000000576 coating method Methods 0.000 description 6
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
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- 235000015103 Malus silvestris Nutrition 0.000 description 5
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- 125000002877 alkyl aryl group Chemical group 0.000 description 5
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 5
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- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
The invention relates to novel biphenyl carboxamides of formula (I), wherein R1, R8, R9, R10and A have the meanings cited in the description. The invention relates to several methods for producing said substances, to the use thereof for controlling undesired micro-organisms, to novel intermediate products and to the use thereof.
Description
BIFENYLCARBOXAMIDES FOR THE FIGHT AGAINST MICROORGANISMS Field of the invention The present invention relates to new biphenylcarboxamides, various processes for their preparation and their use for the control of harmful microorganisms in the protection of plants and materials. BACKGROUND OF THE INVENTION It has already been known that certain biphenylcarboxamides have fungicidal properties (see, for example, WO 03/07075 and EP-A 0 545 099). The activity of the compounds, described there, is good but, nevertheless, leaves much to be desired in some cases. DETAILED DESCRIPTION OF THE INVENTION New biphenylcarboxamides of the formula (I) have now been found
wherein R 1 signifies hydrogen, alkyl having 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4
REF .: 194017 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 up to 4 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-alkyl with 1 to 3 carbon atoms, (alkyl with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms, (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms; halogen- (alkyl having 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (alkyl with 1 to 8 carbon atoms) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 8 alkylthio) carbonyl, (C 1 -C 4 alkoxy-alkyl with 1 to 4 carbon atoms) carbonyl, (alkenyloxy with 3 to 6 carbon atoms) carbonyl, (alkynyloxy with 3 to 6 carbon atoms) carbonyl, (cycloalkyl with 3 to 8 carbon atoms) carbonyl; (haloalkyl with
1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogenalkylthio with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4) carbon atoms) carbonyl, (halogenoalkenyloxy with 3 to 6 carbon atoms) carbonyl, (halogenoalkynyloxy with 3 to 6 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 carbon atoms fluorine, chlorine and / or bromine; or -CH2-C = C-R1"A, -CH2-CH = CH-R1_A, -CH = C = CH-R1-A, -C (= 0) C (= 0) R2, -CONR3R4 or -CH2NR5R6 , R1_A means hydrogen, alkyl with 1 to 6 carbon atoms, halogenalkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with
2 to 6 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, (alkoxy with 1 to 4 carbon atoms) carbonyl, (alkenyloxy with 3 to 6 carbon atoms) carbonyl, (alkynyloxy with 3 to 6 carbon atoms) carbonyl or cyano, R2 means hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 atoms of carbon; halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R3 and R4 mean, independently of each other, respectively, hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine atoms and / or of bromine, R3 and R4 also form, together with the nitrogen atom, with which they are bound, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if appropriate, once or several times, in the same or in different forms, by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, which may be noncontiguous, may be contained in the series formed by - oxygen, sulfur or NR7, R5 and R6 mean , independently of one another, hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R5 and R6 also form, together with the nitrogen atom, with which they are linked, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if appropriate, one or more times, in the same or in different ways, by halogen or by alkyl with 1 to 4 carbon atoms , the heterocycle comprising 1 or 2 more heteroatoms, not contiguous, of the series consisting of oxygen, sulfur or NR7, R7 means hydrogen or alkyl having 1 to 6 carbon atoms, R8 means hydrogen or fluorine, R9 means -SOmR11, - S02NR12R13, -C (= X) R14, -Si (R15) 3, NR12R13, -CH2-NR12R13, R10 means fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl, R11 means alkyl with 1 to 6 carbon atoms or haloalkyl with 1 to 6 carbon atoms with 1 to 13 halogen atoms, m means 1 or 2, R12 means hydrogen, alkyl with 1 to 4 carbon atoms or -C (= X) R14, R13 means hydrogen, alkyl having 1 to 4 carbon atoms or -C (= X) R14, R12 and R13 also form, together with the nitrogen atom, with which they are bound, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if appropriate, once or several times, in the same or in different ways, by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 more heteroatoms, non-contiguous, of the series consisting of oxygen, sulfur or NR7, X means O (oxygen) or S (sulfur), R14 means hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or -NR16R17,
R 15 is hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 6 carbon atoms, whereby the three radicals R15 can be the same or different, respectively, R16 is hydrogen or alkyl having 1 to 4 carbon atoms, R17 is hydrogen or alkyl is 1 up to 4 carbon atoms, R16 and R17 also form, together with the nitrogen atom, with which they are bound, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if appropriate, once or several times, in the same or in different forms, by halogen or alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, which are not contiguous, may be contained in the series formed by oxygen, sulfur or NR7, A means one of the residues Up to A Next 19
To A2 A3 A4 A5
Ala A17 A18 A19 R18 means hydrogen, cyano, halogen, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-alkyl with 1 to 4 carbon atoms, R 19 is hydrogen, halogen, cyano, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or alkylthio having 1 to 4 carbon atoms, R 20 is hydrogen, alkyl having 1 to 4 carbon atoms, hydroxy alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-to uyl with 1 to 4 carbon atoms, halogen to 1 to 4 carbon atoms, halogen to alkyl with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogen to alkoxy with 1 to 4 atoms carbon-alkyl with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or phenyl, R21 and R signify, independently of each other, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogen alkyl with 1 up to 4 carbon atoms with 1 to 5 halogen atoms, R23 means halogen, cyano or alkyl with 1 to 4 carbon atoms, or halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R24 and R25 mean, independently of each other, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 carbon atoms halogen, R26 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R27 means hydrogen, halogen, hydroxy, cyano, alkyl with 1 to 6 carbon atoms carbon, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R28 means halogen, hydroxy, cyano, alkyl with 1 up to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R29 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, alkylsulfinyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 carbon atoms, R30 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R31 means alkyl with 1 to 4 carbon atoms, Q1 means S (sulfur), SO, S02 or CH2, p means 0, 1 or 2, where R22 is identical or different, when p means 2, R32 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R33 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 atoms of halogen, R34 and R35 mean, independently of each other, hydrogen, halogen, amino, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R36 means hydrogen Oxygen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, with 1 to 5 halogen atoms, R37 and R38 mean, independently of each other, hydrogen, halogen, amino, nitro, alkyl with 1 up to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R39 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 atoms of halogen, R40 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) amino, cyano, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R41 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, with 1 to 5 halogen atoms, R42 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) amino, cyano, alkyl with 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R43 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R44 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R45 means hydrogen or alkyl with 1 to 4 carbon atoms, R46 means halogen or alkyl with 1 to 4 carbon atoms. R47 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R48 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R49 means halogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R50 means alkyl with 1 to 4 carbon atoms, R51 means hydrogen, cyano, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, hydroxy-alkyl with 1 h up to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms) aminosulfonyl, alkylcarbonyl with 1 to 6 carbon atoms or phenylsulfonyl or benzoyl respectively substituted, if any, R52 means hydrogen , halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R53 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R54 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms. Furthermore, it has been found that the biphenylcarboxamides of the formula (I) are obtained, if (a) halogenides of carboxylic acids of the formula (II) v_A (II) are reacted in which A has the meanings indicated above , X 1 means halogen or hydroxy, with amines of the formula (III)
wherein R1, R8, R9 and R10 have the meanings indicated above, optionally in the presence of a coupling reagent, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent, or (b) biphenylcarboxamides of the formula (Ia) are reacted
wherein R8, R9, R10 and A have the meanings given above, with halides of the formula (IV) R1-Hal (IV)) in which R1 'means alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 up to 4 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-alkyl with 1 to 3 carbon atoms, (alkyl with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms, (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms; halogen- (alkyl having 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms;
(alkyl with 1 to 8 carbon atoms) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 8 alkylthio) carbonyl, (C 1 -C 4 alkoxy-alkyl with 1 to 4 carbon atoms) carbonyl, (alkenyloxy with 3 to 6 carbon atoms) carbonyl, (alkynyloxy with 3 to 6 carbon atoms) carbonyl, (cycloalkyl with 3 to 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogenalkylthio with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms) carbonyl,
(halogenoalkenyloxy with 3 to 6 carbon atoms) carbonyl, (halogenoalkynyloxy with 3 to 6 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or or bromine; or -CH2-C = C-R1_A, -CH2-CH = CH-R1_A, CH = C = CH-R1"A, -C (= 0) C (= 0) R2, -CONR3R4 or -CH2NR5R6, R1_A, R2, R3, R4, R5 and R6 have the meanings indicated above, Hal means chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent Finally, it has been found that the new biphenylcarboxamides of the formula (I) they have very good microbicidal properties and can be used for the control of undesirable microorganisms both in the protection of plants and also in the protection of materials.The compounds, according to the invention, can be presented, if appropriate. , in the form of mixtures of the various possible isomeric forms, especially of stereoisomers, such as the E and Z isomers, threo and erythro, as well as of the optical isomers, but also, where appropriate, also of the tautomers. both the E isomers and, also, Z, as well as the threo and erythro isomers, as well as the optical isomers s, the arbitrary mixtures of these isomers, as well as the possible tautomeric forms. The biphenylthiazolecarboxamides, according to the invention, are generally defined by the formula (I). Next, the preferred definitions of the remains of the formulas mentioned above have been given and will be cited below. These definitions are valid, in an equivalent way, both for the final products of the formula (I) as well as for the intermediate products. R 1 is preferably hydrogen, alkyl having 1 to 6 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms-alkyl with 1 up to 3 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-alkyl with 1 to 3 carbon atoms, (alkyl with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms, (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms; halogen- (alkyl having 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 6 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 4 alkylthio) carbonyl, (C 1 -C 3 -alkoxy with 1 to C) 3 carbon atoms) carbonyl, (alkenyloxy with 3 to 4 carbon atoms) carbonyl, (alkynyloxy with 3 to 4 carbon atoms) carbonyl, (cycloalkyl with 3 to 6 carbon atoms) carbonyl; (halogenalkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms) carbonyl, (halogenalkylthio with 1 to 4 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 3 carbon atoms - alkyl with 1 to 3 carbon atoms) carbonyl, (halogenalkenyloxy with 3 to 4 carbon atoms) carbonyl, (halogenoalkynyloxy with 3 to 4 carbon atoms) carbonyl,
(halogencycloalkyl with 3 to 6 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -CH2-C = C-R1_A, -CH2- CH = CH-R1"A, -CH = C = CH-R1_A,
-C (= 0) C (= 0) R2, -CONR3R4 or -CH2NR5R6. means, particularly preferably, hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere. -butyl, pentyl or hexyl, methylsulphinyl, ethylsulphinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulphonyl, n- or iso-propylsulphonyl, n-, iso-, sec- or tere. -butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethyl-sulphonyl, trifluoromethyl-sulfonyl, trifluoromethoxymethyl; formyl, -CH2-CHO, - (CH2) 2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3,
-CH 2 -CO-CH (CH 3) 2, - (CH 2) 2 -CO-CH 3, - (CH 2) 2 -CO-CH 2 CH 3, - (CH 2) 2 -CO-CH (CH 3) 2, -CH 2 -C 0 2 CH 3, -CH2-C02CH2CH3, -CH2-C02CH (CH3) 2, - (CH2) 2-C02CH3, - (CH2) 2-C02CH2CH3, - (CH2) 2-C02CH (CH3) 2, -CH2-CO-CF3, - CH2-C0-CC13, -CH2-CO-CH2CF3, -CH2-C0-CH2CC13, - (CH2) 2-CO-CH2CF3, - (CH2) 2-C0-CH2CC13, -CH2-C02CH2CF3, -CH2-C02CF2CF3, -CH2-C02CH2CC13, -CH2-C02CC12CC13, - (CH2) 2-C02CH2CF3, - (CH2) 2-C02CF2CF3, - (CH2) 2-C02CH2CC13, - (CH2) 2-C02CCl2CCl3; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tere. -butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, iso-propoxycarbonyl, tert-butoxycarbonyl, methylthiocarbonyl, ethylthiocarbonyl, iso-propylthiocarbonyl, tere. butylthiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, cyclopropylcarbonyl; trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, or CH2-C = C-R1_A, -CH2-CH = CH-R1"A,
-CH = C = CH-R1_A, -C (= 0) C (= 0) R2, -C0NR3R4 or -CH2NR5R6. R 1 signifies, very particularly preferably, hydrogen, methyl, methoxymethyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, formyl, -CH 2 -C = CH,
-CH2-CH = CH2, -CH = C = CH2, -CH2-CHO, - (CH2) 2 -CH0, -CH2-CO-CH3,
-CH2-CO-CH2CH3, -CH2-CO-CH (CH3) 2, -C (= 0) CHO, -C (= 0) C (= 0) CH3,
-C (= 0) C (= 0) CH2OCH3, -C (= 0) C02CH3, -C (= 0) C02CH2CH3. R 1-A is preferably hydrogen, alkyl having 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, cycloalkyl with 3 up to 6 carbon atoms, (alkoxy with 1 to 4 carbon atoms) carbonyl, or cyano. R1_A means, particularly preferably, hydrogen, methyl or ethyl. R 2 signifies, preferably, hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl having 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms - alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms. R 2 signifies, particularly preferably, hydrogen, methyl, ethyl, n- or iso-propyl, tere. -butyl, methoxy, ethoxy, n- or iso-propoxy, tere. -butoxy, methoxymethyl, cyclopropyl; trifluoromethyl, trifluoromethoxy. R3 and R4 signify, independently of one another, preferably hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl having 1 to 3 carbon atoms, cycloalkyl having 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine atoms and / or bromine. R3 and R4 also form, together with the nitrogen atom, with which they are linked, preferably a heterocycle, saturated, with 5 or 6 atoms in the substituted ring, if appropriate, of one to four times, in the same or in different ways, by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, not contiguous, of the series consisting of oxygen, sulfur or NR7. R3 and R4 mean, independently of one another, particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere. -butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R3 and R4 also form, together with the nitrogen atom, with which they are bonded, particularly preferably a saturated heterocycle, of the series consisting of morpholine, thiomorpholine or substituted piperazine, optionally from one to four times , in the same or in different ways, by fluorine, chlorine, bromine or methyl, the piperazine, in the second nitrogen atom, may be substituted by R7. R5 and R6 stand for, independently of one another, preferably hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms. R5 and R6 also form, together with the nitrogen atom, with which they are bonded, preferably a saturated heterocycle, with 5 or 6 ring atoms, optionally substituted one or more times, Likewise or in different forms, by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle may contain 1 or 2 more heteroatoms, non-contiguous, of the series consisting of oxygen, sulfur or NR7. R5 and R6 mean, independently of one another, particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere. -butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R5 and R6 also form, together with the nitrogen atom, with which they are linked, particularly preferably a saturated heterocycle, of the series consisting of morpholine, thiomorpholine or piperazine, optionally substituted four times, in the same or in different ways, by fluorine, by chlorine, by bromine or by methyl, the piperazine, in the second nitrogen atom, may be substituted by R7. R 7 is preferably hydrogen or alkyl with 1 to 4 carbon atoms. R7 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere. - Butyl R8 signifies, preferably, hydrogen. R8 signifies, particularly preferably, fluorine. R9 signifies, preferably, -SOmR11.
R9 also signifies, preferentially, -S02NR12R13. R9 further denotes, preferentially, -C (= X) R14. R9 also means, preferably, -Si (R15) 3. R9 further denotes, preferentially, -NR12R13. R9 further denotes, preferentially, -CH2-NR12R13. R 10 is preferably fluorine, chlorine or bromine. R10 further denotes, preferably, methyl or trifluoromethyl. R 10 is particularly preferably fluorine. R 10 also means, in a particularly preferred manner, chlorine. R 10 also means, especially preferably, methyl. R 10 is also, especially preferably, trifluoromethyl. R 11 is preferably alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 9 fluorine, chlorine and / or bromine atoms. R 11 is particularly preferably methyl, ethyl, n-, iso-propyl, n-, i-, s-, t-butyl, trifluoromethyl, -CH 2 CF 3, -C 2 F 5 or trichloromethyl. R 11 signifies, very particularly preferably, methyl, trifluoromethyl, -CH 2 CF 3 or -C 2 F 5.
m means, preferably, 1. m also preferably means 2.m means, particularly preferably 2. R12 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. -butyl or - C (= X) R14. R 12 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or -C (= X) R 14. R12 signifies, very particularly preferably, hydrogen or methyl. R 13 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. -butyl or - C (= X) R14. R 13 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or -C (= X) R 14. R 13 signifies, very particularly preferably, hydrogen or methyl. R12 and R13 also form, together with the nitrogen atom, with which they are bonded, preferably a heterocycle with 5 or 6 ring atoms, saturated, substituted, if appropriate, once or several times, in such a way that same or in different forms, by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 more heteroatoms, not contiguous, of the series formed by oxygen, sulfur or NR7.
R12 and R13 also form, together with the nitrogen atom, with which they are linked, particularly preferably a saturated heterocycle of the series consisting of morpholine, thiomorpholine or substituted piperazine, optionally from one to four times, in the same or in different forms by fluorine, chlorine, bromine or methyl, the piperazine in the second nitrogen atom being replaced by R7. X preferably means 0 (oxygen). X also means, preferably, S (sulfur). R 14 signifies, preferably, hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. -butyl, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec.- or tere. -butoxy or -NR16R17. R 14 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy O-NR 16 R 17. R 14 signifies, very particularly preferably, hydrogen, methyl, ethyl, methoxy, ethoxy or -NR 16 R 17. R15 means, preferably, it means alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms or alkylthio with 1 to 3 atoms of carbon-alkyl with 1 to 3 carbon atoms, the three residues R 15 may be the same or different, respectively. R 15 is particularly preferably methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or ethylthioethyl, wherein the three radicals R 15 may be identical or different. R 15 is very particularly preferably methyl, methoxy, methoxymethyl or methylthiomethyl, whereby the three radicals R 15 can be identical or different, respectively. R 15 means, particularly preferably, methyl.
R16 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. -butyl. R16 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl. R16 signifies, very particularly preferably, hydrogen or methyl. R 17 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec.- or tere. -butyl. R 17 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl. R 17 signifies, very particularly preferably, hydrogen or methyl. R16 and R17 also form, together with the nitrogen atom, with which they are linked, preferably a heterocycle with 5 or 6 ring atoms, saturated, substituted, if appropriate, once or several times, in such a way that same or in different forms, by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 more heteroatoms, not contiguous, of the series formed by oxygen, sulfur or NR7. R16 and R17 also form, together with the nitrogen atom, with which they are bonded, particularly preferably a saturated heterocycle of the series consisting of morpholine, thiomorpholine or piperazine, optionally substituted up to four times , in the same or different ways by fluorine, chlorine, bromine or methyl, the piperazine being substituted on the second nitrogen atom by R7. A preferably means one of the residues Al, A2, A3, A4, A5, A6, A9, A10, All, A12 or A17. A means, particularly preferably, one of the residues Al, A2, A4, A5, A6, A9, All, A16, A17. A means, very particularly preferably, the rest Al. A also signifies, very particularly preferably, the residue A2. A also means, very particularly preferably, the remainder A4. A also signifies, very particularly preferably, the rest A5. A also signifies, very particularly preferably, the rest A6. A also signifies, very particularly preferably, the rest A9. A also signifies, very particularly preferably, the remainder All. A also signifies, very particularly preferably, the residue A16. A also signifies, very particularly preferably, residue A17. R18 is preferably hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, haloalkyl with 1 to 2 carbon atoms, haloalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl atoms. R18 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio. R18 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R18 is particularly preferably methyl, difluoromethyl, trifluoromethyl or l-fluoroethyl. R 19 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio. R 19 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine or methyl. R19 signifies, very particularly preferably, hydrogen, fluorine, chlorine or methyl. R20 is preferably hydrogen, methyl, ethyl, n-propyl, iso-propyl, halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl. , cyclopentyl, cyclohexyl or phenyl. R20 is particularly preferably hydrogen, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl. R20 means, very particularly preferably, hydrogen, methyl, trifluoromethyl or phenyl. R20 means, particularly preferably, methyl.
R21 and R22 signify, independently of one another, preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R21 and R22 mean, independently of each other, particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R21 and R22 mean, independently of one another, very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R21 and R22 mean, respectively, particularly preferably, hydrogen. R 23 is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, halogenalkyl having 1 to 2 carbon atoms or halogenalkoxy having 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine. R 23 is particularly preferably fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R 23 is particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy. R 23 is particularly preferably methyl or trifluoromethyl. R 24 and R 25 signify, independently of one another, preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 24 and R 25 mean, independently of each other, particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R 24 and R 2 B mean, independently of one another, very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 24 and R 25 mean, respectively, particularly preferably, hydrogen. R 26 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 26 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl. R 26 signifies, very particularly preferably, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
R 27 is preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, halogen with 1 to 2 carbon atoms, halogen with 1 to 2 carbon atoms or halogenalkylthio with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms. R 27 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio. R 27 signifies, very particularly preferably, hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 27 is particularly preferably iodo, methyl, difluoromethyl or trifluoromethyl. R 28 is preferably fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or haloalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms. R28 is particularly preferably fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R28 signifies, very particularly preferably, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 29 is preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms. carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, alkylsulfinyl with 1 to 2 carbon atoms or alkylsulfonyl with 1 to 2 carbon atoms. R 29 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulfinyl or methylsulfonyl. R29 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulfinyl or methylsulfonyl. R29 signifies, particularly preferably, hydrogen. R 30 is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 30 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R31 is preferably methyl or ethyl. R31 signifies, especially preferably, methyl. Q1 signifies, preferably, S (sulfur), S02 or CH. Q1 means, particularly preferably, S (sulfur) or CH2. Q1 means, very particularly preferably, S(sulfur). p means, preferably, 0 or 1. p means, particularly preferably, 0.
R 32 is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R32 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R32 signifies, very particularly preferably, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R33 is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 33 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R33 signifies, very particularly preferably, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R34 and R35 signify independently, preferably, hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms . R34 and R35 mean, independently of each other, particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R34 and R35 mean, independently of one another, very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R34 and R35 mean, respectively, particularly preferably, hydrogen. R36 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or haloalkyl with 1 to
2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 36 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R36 signifies, very particularly preferably, hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R36 signifies, particularly preferably, methyl. R 37 and R 38 stand for, independently of one another, preferably hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or of bromine. R37 and R38 signify, independently of each other, particularly preferably hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R37 and R38 mean, independently of one another, very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 37 and R 38 mean, respectively, particularly preferably, hydrogen. R39 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R39 means, particularly preferably , hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R39 signifies, very particularly preferably, hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R39 signifies, particularly preferably, methyl. R 40 is preferably hydrogen, fluorine, chlorine, bromine, amino, alkylamino having 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms), amino, cyano, methyl, ethyl or haloalkyl with 1 to 2. carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R40 is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R40 signifies, very particularly preferably, hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 40 is particularly preferably amino, methylamino, dimethylamino, methyl or trifluoromethyl. R41 is preferably fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R41 is particularly preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R41 signifies, very particularly preferably, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R41 signifies, particularly preferably, methyl, trifluoromethyl or difluoromethyl. R 42 is preferably hydrogen, fluorine, chlorine, bromine, amino, alkylamino with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms), amino, cyano, methyl, ethyl or haloalkyl with 1 to 2. carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 42 is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R42 signifies, very particularly preferably, hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R42 is particularly preferably amino, methylamino, dimethylamino, methyl or trifluoromethyl. R43 is preferably fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 43 is particularly preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R43 is particularly preferably fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R43 is particularly preferably methyl, trifluoromethyl or difluoromethyl. R44 is preferably fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R44 is particularly preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R44 means, very particularly preferably, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 45 signifies, preferably, hydrogen, methyl or ethyl. R 45 signifies, especially preferably, methyl. R46 is preferably fluorine, chlorine, bromine, methyl or ethyl. R46 is particularly preferably fluorine, chlorine or methyl. R47 is preferably methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R47 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R47 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R47 is particularly preferably methyl or trifluoromethyl. R 48 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 48 is particularly preferably hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl. R49 is preferably fluorine, chlorine, bromine, iodine, hydroxy, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl having 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms. up to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms. R49 means, especially preferably, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R49 denotes, very particularly preferably, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R50 is preferably methyl, ethyl, n-propyl or iso-propyl. R 50 is particularly preferably methyl or ethyl. R 51 is preferably hydrogen, methyl, ethyl, haloalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 carbon atoms, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl. R51 is particularly preferably hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl. R51 signifies, very particularly preferably, methyl or methoxymethyl. R52 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R52 is particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R52 signifies, very particularly preferably, hydrogen or methyl. R53 is preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms .
R53 is particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R53 is particularly preferably hydrogen, methyl, difluoromethyl or trifluoromethyl. R54 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R54 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl. R54 signifies, very particularly preferably, hydrogen. Preferred are those compounds of the formula (I) in which all the radicals have, respectively, the abovementioned preferred meanings. Especially preferred are those compounds of the formula (I) in which all the radicals have, respectively, the especially preferred meanings indicated above. In addition, preferred are compounds of the formula (I-b) in which R 1, R 8, R 9, R 10 and A have the meanings indicated above. In addition, the compounds of the formula (I-c) are preferred
wherein R1, R8, R9, R10 and A have the meanings indicated above. In addition, the compounds of the formula (I-d) are preferred
wherein R1, R8, R9, R10 and A have the meanings indicated above.
In addition, the compounds of the formula (I-e) are preferred.
wherein R1, R8, R9, R10 and A have the meanings indicated above. In addition, the compounds of the formula (I-f) are preferred
wherein R1, R8, R9, R10 and A have the meanings indicated above. In the same way, the compounds of the formulas (I) and (I-b) to (I-f), in which R 1 denotes hydrogen, are preferred. In the same way, the compounds of the formulas (I) and (I-b) to (I-f), wherein R8 means hydrogen, are preferred. In the same way, the compounds of the formulas (I) and (1-b) to (I-f), in which R 8 denotes fluorine, are preferred. However, the definitions of the radicals or the definitions according to the invention, indicated above in a general manner or in the preferred ranges, can be combined arbitrarily with each other, ie between the respective ranges and the preferred ranges. These are valid for the final products as well as, correspondingly, for the starting products and for the intermediate products. If, for example, l-methyl-3- (trifluoromethyl) -lH-pyrazole-4-carbonyl chloride and methyl 2'-amino-3, 5 '-difluorobiphenyl-4-carboxylate are used as starting materials, for example, , as well as a basis, the development of the procedure (a), according to the invention, can be represented by means of the following reaction equation:
The halides of carboxylic acids, which are necessary as starting materials for carrying out the process
(a), according to the invention, are defined, in general, by means of formula (II). In this formula (II), A preferably has, particularly preferably, very particularly preferably or particularly preferably, those meanings which have already been indicated for this remainder as preferred, especially preferred, etc. in relation to the description of the products of the formula (I) according to the invention. Preferably X1 means fluorine, chlorine or hydroxy, particularly preferably chlorine or hydroxy. The halides of the carboxylic acids of the formula (II) are known and / or can be prepared according to known processes (see, for example, EP-A 0 545 099, JP-A 01-290662 and US 5,093,347). The amines, which are also necessary as starting materials for carrying out the process (a), according to the invention, are defined, in general, by means of formula (III). In this formula (III), R.sub.1, R.sub.8, R.sub.9 and R.sub.10 are preferably, very particularly preferably, very particularly preferably or particularly preferably those meanings which have already been indicated for these radicals as preferred, and especially preferred, etc. in relation to the description of the products of the formula (I) according to the invention. The amines of the formula (III) are new.
The amines of the formulas (III-1), (III-2) and (III-3) can be prepared according to known procedures (see, for example, WO 01/53259 and WO 01/49664, see, also , the obtaining examples). If 3, 5 '-difluor-2' - ( { [L-methyl-3- (trifluoromethyl) -lH-pyrazol-4-yl] carbonyl}. Amino) biphenyl-4-carboxylic acid methyl ester is used. and the acetyl chloride as starting products, the development of the process (b), according to the invention, can be represented by means of the following formula scheme:
The biphenylcarboxamides, which are necessary as starting materials for carrying out process (b), according to the invention, are defined, in general, by means of formula (I-a). In this formula (I-a), R8, R9, R10 and A have preferably, particularly preferably, very particularly preferably or particularly preferably those meanings which have already been indicated as preferred, especially preferred, etc. in relation to the description of the compounds of the formula (I), according to the invention. The compounds of the formula (I-a) are compounds according to the invention and can be prepared according to process (a). The halides, which are also necessary as starting materials for carrying out process (b), are defined, in general, by means of formula (IV). In this formula (IV), R1_B preferably has, particularly preferably, very particularly preferably or particularly preferably those meanings which have already been indicated above for the radical R1 as preferred, especially preferred, etc., without R1_B ever meaning hydrogen. Hal means chlorine, bromine or iodine. The halides of the formula (IV) are known. Suitable diluents for carrying out process (a), according to the invention, are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, ketones such as acetone, butanone, ethyl isobutyl ketone or cyclohexanone, nitriles, such as acetonitrile, propionitrile, not i-butyronitrile or benzonitrile; the amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide; their mixtures with water or pure water. Process (a), according to the invention, is carried out, if appropriate, in the presence of a suitable acid acceptor. As such, all usual inorganic or organic bases are suitable. These include, preferably, the hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of the alkaline earth metals or alkali metals, such as, for example, sodium hydride, amide sodium, lithium diisopropylamide, sodium methylate, sodium ethylate, tere. - potassium butylate, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN), or diazabicycloundecene (DBU). Process (a), according to the invention, is carried out, if appropriate, in the presence of a suitable coupling agent (when X 1 means hydroxy). As such, all the usual carbonyl activators are suitable. To these belong, preferably, N- [3- (dimethylamino) propyl] -N? Hydrochloride. -ethyl-carbodiimide, N, N'-di-sec. -butyl-carbodiimide, N, N * -dicicium hexylcarbodiimide,
N, N'-diisopropylcarbodiimide, l- (3- (dimethylamino) propyl) -3-ethyl-carbodiimide methoiodide, 2-bromo-3-ethyl-4-methyl-thiazolium tetrafluoroborate, N, N chloride -bis [2-oxo-3-oxazolidinyl] phosphorodiamide, chloro-tripyrrolidin-phosphonium hexafluorophosphate, bromo-tripyrrolidin-phosphonium hexafluorophosphate, 0- (1H-benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate , O- (lH-benzotriazol-1-yl) -N, N, N ', N' -tetramethyluronium hexafluorophosphate, O- (lH-benzotriazol-1-yl) -N, N, NX jN 'hexafluorophosphate - is (tetramethylene) uronium, the tetrafluoroborate of 0- (lH-benzotriazol-1-yl) -N, N, N ', N? -bis (tetramethylene) uronium, the tetrafluoroborate of N, N, N ', Nl-bis (tetramethylene) chloruronium, the hexafluorophosphate of 0- (7-azabenzotriazol-1-yl) -N, N, N, N-tetramethyluronium and 1-hydroxybenzotriazole These reagents can be used separately as well as in combination. The reaction temperatures in carrying out the process (a), according to the invention, can vary within wide limits. In general, temperatures are from 02C to 150C, preferably at temperatures from 20aC to 110SC. For carrying out the process (a) according to the invention, for the preparation of the compounds of the formula (I), per mole of the carboxylic acid halide of the formula (II), in general, from 0, 2 to 5 moles, preferably from 0.5 to 2 moles of the aniline derivative of the formula (III). The processing is carried out in accordance with the usual methods. Suitable diluents for carrying out process (b), according to the invention, are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; the ethers, such as diethyl ether, diisopropyl ether, methyl tert. -butyl ether, methyl-tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide. Process (b), according to the invention, is carried out in the presence of a base. As such, all usual inorganic or organic bases are suitable. These include, preferably, the hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of the alkaline earth metals or alkali metals, such as, for example, sodium hydride, amide sodium, sodium methylate, sodium ethylate, tere. -potassium butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, bicarbonate of potassium, sodium bicarbonate or cesium carbonate, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine , N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). The reaction temperatures in carrying out the process (b), according to the invention, can vary within wide limits. In general, temperatures are from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 110 ° C. For carrying out the process (b) according to the invention, for the preparation of the compounds of the formula (I), per mol of the biphenylcarboxamide of the formula (Ia), in general, from 0.2 to 5 moles, preferably from 0.5 to 2 moles of halide of the formula (IV). The processes (a) and (b), according to the invention, will be carried out, in general, under normal pressure.
However, it is also possible to work under higher pressure or at lower pressure - generally between
0.1 bar and 10 bars -. The products according to the invention have a potent microbicidal effect and can be used to combat unwanted microorganisms, such as fungi and bacteria, in the protection of plants and in the protection of materials. Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes,
Basidiomycetes and Deuteromycetes. Bactericides can be used in the protection of plants for the control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and
Streptomycetaceae. Mention may be made, by way of example, but without any limiting character, of some pathogens of fungal and bacterial diseases, which fall within the general definitions listed above: diseases, caused by pathogens of mildew, such as, for example, Blumeria, such as, for example, Blumeria graminis; Podosphaera species, such as, for example, Podosphaera leucotricha; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Uncinula species, such as, for example, Uncinula necator; diseases caused by pathogens of rust diseases such as, for example, Gymnosporangium species, such as, for example,
Gymnosporangium sabinae Hemileia species, such as, for example, Hemileia vastatrix; Phakopsora species, such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as, for example, Puccinia recóndita or puccinia graminis; Uromyces species, such as, for example, Uromyces appendiculatus; diseases caused by pathogens of the group of
Oomycetes such as, for example, Bremia species, such as, for example, Bremia laccucae; Peronospora species, such as, for example, Peronospora pisi or P. brassicae; Phytophthora species, such as, for example, Phytophthora infestans; Plasmopara species, such as, for example, Plasmopara viticola; Pseudoperonospora species, such as, for example,
Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, such as, for example, Pythium ultimum; the diseases of leaf spots and withered leaves, caused, for example, by Alternaria species, such as, for example, Alternaria solani; Cercospora species, such as, for example, Cercospora beticola; Cladiosporum species, such as, for example, Cladiosporiu cucumerinum;
- Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, synonym: Helminthosporium); species of Colletotrichum, such as, for example, Colletotrichum lindemuthanium; Cycloconium species, such as, for example, Cycloconium oleaginum; Diaporthe species, such as, for example, Diaporthe citri; Elsinoe species, such as, for example, Elsinoe fawcettii; Gloeosporium species, such as, for example, Gloeosporium laeticolor; Glomerella species, such as, for example, Glomerella cingulata; Guignardia species, such as, for example, Guignardia bidwelli; Leptosphaeria species, such as, for example, Leptosphaeria maculans; Magnaporthe species, such as, for example, Magnaporthe grísea; ycosphaerella species, such as, for example,
Mycosphaerelle graminicola and Mycodphaerella fijiensis; Phaeosphaeria species, such as, for example, Phaeosphaeria nodoru; Pyrenophora species, such as, for example, Pyrenophora teres;
Ramularia species, such as, for example, Ramularia collo-cygni; Rhynchosporium species, such as, for example,
Rhynchosporium secalis; Septoria species, such as, for example, Septoria apii; Typhula species, such as, for example, Typhula incarnata; Venturia species, such as, for example, Venturia inaequalis; root and stem diseases, caused, for example, by Corticium species, such as, for example, Corticium graminearum; Fusarium species, such as, for example, Fusarium oxysporum; species of Gaeumannomyces, such as, for example,
Gaeumannomyces graminis; Rhizoctonia species, such as, for example, Rhizoctonia solani; Tapesia species, such as, for example, Tapesia acuformis or Tapesia yallundae; Thielaviopsis species, such as, for example, Thielaviopsis basicola, -the diseases of spikes and panicles (including corn cobs), caused, for example, by Alternaria species, such as, for example, , Alternate spp .; Aspergillus species, such as, for example, Aspergillus flavus; Cladosporium species, such as, for example, Cladosporium cladosporioides; Claviceps species, such as, for example, Claviceps purpurea; Fusarium species, such as, for example, Fusarium culmorum; Gibberella species, such as, for example, Gibberella zeae; Monographella species, such as, for example, Monographella nivalis; the diseases caused by the ustilaginales, such as, for example, Sphacelotheca species, such as, for example, Sphacelotheca reiliana; Tilletia species, such as, for example, Tilletia caries; Urocystis species, such as, for example, Urocystis occulta; Ustilago species, such as, for example, Ustilago nuda; the rotting of fruits caused, for example, by Aspergillus species, such as, for example, Aspergillus flavus; Botrytis species, such as, for example, Botrytis cinerea; Penicillium species, such as, for example, Penicillium expansum and Penicillium purpurogenu;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Verticilium species, such as, for example, Verticilium alboatrum; rotting and wilting of seeds and from the soil, as well as diseases of seedlings, caused, for example, by Fusarium species, such as, for example, Fusarium culmorum; Phytophthora species, such as, for example, Phytophthora cactorum; Pythium species, such as, for example, Pythium ultimum; Rhizoctonia species, such as, for example, Rhizoctonia solani; Sclerotium species, such as, for example, Sclerotium rolfsii; the verrucous, vesicular and witch's broom diseases, caused, for example, by Nectria species, such as, for example, Nectria galligena; wilt diseases caused, for example, by Monilinia species, such as, for example, Monilinia laxa; deformations of leaves, flowers and fruits, caused, for example, by Taphrina species, such as, for example, Taphrina deformans; the degenerative diseases of woody plants, caused, for example, by Esca species, such as, for example, Phaemoniella clamydospora and Phaeoacrenonium aleophilum and Fomiespecieria mediterránea; diseases of flowers and seeds, caused, for example, by Botrytis species, such as, for example, Botrytis cinerea; diseases of the tubers of plants, caused, for example, by Rhizoctonia species, such as, for example, Rhizoctonia solani; Helminthosporium species, such as, for example,
Helminthosporium solani; diseases, caused by bacterial pathogens, such as, for example, Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia species, such as, for example, Erwinia amylovora. Preferably, the following soybean diseases can be combated: the fungal diseases of leaves, stems, pods and seeds caused, for example, by leaf stains by Alternaria (Alternaria leaf spot -Alternataria spec atrans tenuissima-), anthracnose (Anthracnose -Colletotrichum gloeosporoides dematium var. truncatum-), brown spots (Septoria glycines-), leaf spots and Cercospora necrosis (Cercospora leaf spot and blight -Cercospora kikuchii-), the necrosis of the leaves by Choanephora (Choanephora leaf blight -Choanephora infundibulifera trispora (synonym)), the spots on the leaves by Dactuliophora (Dactuliophora leaf spot Dactuliophora glycines-), the downy mildew (Downy Mildew -Peronospora manshurica- ), necrosis by Drechslera
(Drechslera blight -Drechslera glycini-), leaf spots by cercosporosis (Frogeye Leaf spot -Cercospora sojina-), leaf spots by Leptosphaerulina
(Leptosphaerulina Leaf Spot -Leptosphaerulina trifolii-), the spots on the leaves by Phyllostica (Phyllostica Leaf Spot -Phyllosticta sojaecola-), the blight of the pod and the stem (Pod and Stem Blight -Phomopsis sojae), the oidium of the apple tree ( Powdery Mildew -Microsphaera diffusa-), the spots on the leaves by Pyrenochaeta (Pyrenochaeta Leaf Spot -Pyrenochaeta glycines-), the aerial necrosis of foliage and tissue by Rhizoctonia (Rhizoctonia Aerial, Foliage, and Web Blight Rhizoctonia solani-), rust (Rust -Phakopsora pachyrhizi-), the scab (Scab -Sphaceloma glycines-), the necrosis of the leaves by Stemphylium (Stemphylium Leaf Blight -Stemphylium botryosum-), the cercosporosis of the cucurbits (Target Spot -Corynespora cassiicola-). Fungal diseases in the roots and at the base of the stems caused by, for example root rot (Black Root Rot-Calonectria crotalariae-), stem rot (Charcoal Rot -Macrophomina phaseolina-), necrosis or wilting, root blacking and pod and neck rot by Fusarium (Fusarium Blight or Wilt, Root Rot, and Pod and Rot Collar -Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti-), root rot by Mycoleptodiscus (Mycoleptodiscus Root
Rot - Mycoleptodiscus terrestris-), the neocosmospora
(Neocosmospora vasinfecta), the necrosis of the pod and the stem
(Pod and Stem Blight -Diaporthe phaseolorum), the canker of the stems (Stem Canker -Diaporthe phaseolorum var. Caulivora-), the rot by Phytophthora (Phytophthora Rot -Phytophthora megasperma-), the brown rot of the stems (Brown Stem Rot -Phialophora gregata-), Pythium rot (Pythium Rot -Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), root rot due to Rhizoctonia, rot of stems, and rot of seedlings
(Rhizoctonia Root Rot, Stem Decay and Damping-Off -Rhizoctonia solani-), the rot of the stems by Sclerotinia (Sclerotinia Stem Decay -Sclerotinia sclerotiorum-), the necrosis by Sclerotinia meridional (Sclerotinia Southern Blight -Sclerotinia rolfsii-), the root rot by Thielaviopsis (Thielaviopsis Root Rot -Thielaviopsis basicola-) • The active products, according to the invention, also have a potent reinforcing effect on plants. These are suitable, therefore, to mobilize the resistance forces of plants against the attack of unwanted microorganisms. Plant-reinforcing products (resistance inducers) will be understood in this context as those substances that are capable of stimulating the immune system of plants in such a way that the treated plants develop a broad resistance against microorganisms when a subsequent inoculation occurs. with these unwanted microorganisms. It should be understood by unwanted microorganisms, in the present case, phytopathogenic fungi, bacteria and viruses. Thus, the products according to the invention can be used to protect the plants, within a certain period of time from the treatment, against the attack due to the aforementioned pathogens. The lapse of time, within which protection is caused, generally extends from 1 to 28 days, preferably from 1 to 14 days, especially preferably from 1 to 7 days, from the treatment of the plants with the active products The good compatibility with the plants of the active products at the concentrations necessary for the fight against plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds as well as soil. In this case, the active compounds according to the invention can be used with particularly good success for the control of cereal diseases, such as, for example, against Puccinia species and against diseases of vineyard plantations. , of fruit trees and vegetables, such as, for example, against species of Botrytis, Venturia, or Alternaria. Likewise, the active products, according to the invention, are suitable for increasing the yield of the crops. Likewise, they have a low toxicity and have a good compatibility with plants. The active compounds according to the invention can be used, if appropriate, in certain concentrations and amounts of application, also as herbicides, to influence the growth of plants, as well as for the control of animal pests. These can also be used, if appropriate, as intermediates and as starting materials for the synthesis of other active products. In accordance with the invention, all plants and parts of plants can be treated. By plants, all plants and plant populations, such as desired and unwanted wild plants or crop plants (including crop plants of natural origin), will be understood in this case. Crop plants can be plants that can be obtained by conventional methods of cultivation and optimization or by means of biotechnological and genetic engineering methods or by combinations of these methods, including transgenic plants and including plants. varieties of plants that can be protected or not by means of the right of protection of plant varieties. By parts of the plants should be understood all parts and aerial and underground organs of plants, such as buds, leaves, flowers and roots, being able to indicate, as examples, leaves, needles, stems, trunks, flowers, bodies of fruits, fruits and seeds as well as roots, tubers and rhizomes. The harvests as well as vegetative and generative reproductive material, for example seedlings, tubers, rhizomes, layering and seeds, also belong to the parts of the plants. The treatment, according to the invention, of the plants and parts of the plants with the active products is carried out directly or by action on the environment, the biotope or the storage enclosure in accordance with the methods of conventional treatments, for example by means of dipping, spraying, evaporation, fogging, spreading, application by brush and, in the case of the reproduction material, especially in the case of seeds, also by coating with one or more layers. The products according to the invention can be used in the protection of industrial materials against attack and destruction due to unwanted microorganisms. Industrial materials in the present context will be understood as non-living materials, which have been made for use in the art. By way of example, the industrial materials, which would be protected against microbial destruction or destruction by means of the active products according to the invention, are glues, glues, paper and cardboard, textiles, leather, wood. , paints and articles of synthetic material, cold lubricants and other materials, which can be attacked or destroyed by microorganisms. In the field of the materials to be protected, parts of production facilities, for example closed cooling water circuits, which may be adversely affected by the multiplication of microorganisms may also be mentioned. Within the scope of the present invention, the adhesives, the glues, can preferably be mentioned as industrial materials., paper and cardboard, leather, wood, paints, cold lubricants and heat transfer liquids, especially wood. As microorganisms, which can cause the decomposition or modification of industrial materials, there may be mentioned by way of example bacteria, fungi, yeasts, algae and mucilaginous organisms. Preferably, the active compounds according to the invention act against fungi, especially against molds, fungi coloring and destroying the wood (Basidiomycetes) as well as against mucilaginous organisms and algae. By way of example, microorganisms of the following species may be cited: Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus. Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microencapsules. in polymer materials and in masses for the coating of the seeds, as well as the formulations of cold fogging and hot in ultralow volume (ULV). These formulations are prepared in a known manner, for example by mixing the active agents with spreading agents, ie liquid solvents, liquefied gases, which are under pressure and / or solid support materials, optionally with the use of surfactants, that is, emulsifiers and / or dispersants and / or foam generating agents. When water is used as an extender agent, organic solvents can also be used as auxiliary solvents, for example. Suitable liquid solvents are: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, as well as ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethisulfoxide as well as water. By liquefied gaseous support materials or extender agents are meant those liquids which are gaseous at normal temperature and under normal pressure, for example propellant gases for aerosols, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid support materials are, for example, natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic mineral flours, such as highly dispersed silicic acid, aluminum oxide and silicates. Suitable solid support materials for granules are, for example, broken and fractionated natural minerals such as calcite, pumice, marble, sepiolite, dolomite, as well as synthetic granules, constituted from inorganic flours and mixtures thereof. organic, as well as granulates, made from organic material such as wood sawdust, the husks of coconut nuts, the corn ears and the tobacco stalks. Suitable emulsifying agents and / or foaming agents are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, ethers of polyoxyethylenated fatty alcohols, for example alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulphates, aryl sulfonates, as well as albumin hydrolysates. Suitable dispersing agents are, for example, sulphite lignin bleach and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers, powders, granules or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate as well as natural phospholipids, such as cephalignan may be used in the formulations. and synthetic lecithin and phospholipids. Other additives can be mineral and vegetable oils. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanide blue and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and nutrient materials in traces, such as the salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
7
The formulations generally contain between 0.1 and 95 weight percent active product, preferably between 0.5 and 90%. The active compounds, according to the invention, can be present as such or in their formulations, also, in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order to extend, for example, the spectrum of activity or to avoid the development of resistance. In many cases, synergistic effects are obtained, ie, the activity of the mixture is greater than the activity of the individual components. Examples of suitable mixing components are the following compounds: Fungicides: 1) inhibitors of nucleic acid synthesis: for example Benalaxyl, Benalaxyl-M, Bupirimate, Clozylacon, Dimethirimol, Ethyrimol, Furalaxyl, Hymexazole, Mefenoxam , Metalaxyl, Metalaxyl-M, Ofurace, Oxadixyl, Oxolinic acid; 2) inhibitors of mitosis and cell division: for example Benomyl, Carbendazim, Diethofencarb, Ethaboxam,
Fuberidazole, Pencycuron, Thiabendazole, Thiophanate-methyl, Zoxamide; 3) inhibitors of respiration (inhibitors of the chain of respiration): 3.1) inhibitors of complex I of the chain of respiration: for example Diflumetorim; 3.2) inhibitors of the complex II chain of respiration: for example Boscalid / Nicobifen, Carboxin, Fenfuram, Flutolanil, Furametpyr, Furmecyclox, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide; 3.3) Inhibitors of the complex III chain of respiration: for example Amisulbrom, Azoxystrobin, Cyazofa id, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidone, Fluoxastrobin, Kresoxim-methyl, Methominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin; 4) decouplers: for example Dinocap, Fluazinam, Meptyldinocap; 5) inhibitors of ATP production: for example Fentin acetate, Fentin chloride, Fentin hydroxide, Silthiofam; 6) inhibitors of the synthesis of amino acids and proteins: for example Andoprim, Blasticidin-S, Cyprodinil, Kasugamycin, Kasugamycin hydrochloride hydrate, Mepanipyrim, Pyrimethanil; 7) inhibitors of signal transduction: for example Fenpiclonil, Fludioxonil, Quinoxyfen; 8) inhibitors of lipid and membrane synthesis: for example Biphenyl, Chlozolinate, Edifenphos, Iodocarb, Iprobenfos, Iprodione, Isoprothiolane, Procymidone, Propamocarb, Propamocarb hydrochloride, Pyrazophos, Tolclofos-methyl, Vinclozolin;
9) inhibitors of ergosterol synthesis: for example Aldimorph, Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazole, Difenoconazole, Diniconazole, Diniconazole-M, Dodemorph, Dodemorph acetate, Epoxiconazole, Etaconazole, Fenarimol, Fenbuconazole, Fenhexamid, Fenpropidin, Fenpropimorph , Fluquinconazole, Flurprimidol, Flusilazole, Flutriafol, Furconazole, Furconazole-cis, Hexaconazole, Imazalil, Imazalil sulfate, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Naftifine, Nuarimol, Oxpoconazole, Paclobutrazol, Pefurazoate, Penconazole, Prochloraz, Propiconazole, Prothioconazole, Pyributicarb, Pyrifenox, Simeconazole, Spiroxamine, Tebuconazole, Terbinafine, Tetraconazole, Triadimefon, Triadimenol, Tridemorph, Triflumizole, Triforine, Triticonazole, Uniconazole, Viniconazole, Voriconazole; 10) inhibitors of cell wall synthesis: for example Benthiavalicarb, Dimethomorph, Flumorph, Iprovalicarb, Polyoxins, Polyoxorim, Validamycin A; 11) inhibitors of melanin biosynthesis: for example Carpropamid, Diclocymet, Fenoxanil, Phthalide,
Pyroquilon, Tricyclazole; 12) resistance inducers: for example Acibenzolar-S-methyl, Probenazole, Tiadinil; 13) compounds with multi-point activity: for example Bordeaux Mixture, Captafol, Captan, Chlorothalonil, copper naphthenate, copper oxide, copper oxychloride, copper preparations such as, for example, copper hydroxide, copper sulfate, Dichlofluanid, Dithianon , Dodine, Dodine free base, Ferbam, Fluorofolpet, Folpet, Guazatine, Guazatine acetate, Iminoctadine, Iminoctadine albesilate, Iminoctadine triacetate, Mancopper, Mancozeb, Maneb, Metiram, Metiram Zinc, Copper Oxina, Propineb, Sulfur and sulfur preparations such as , for example calcium polysulfide, Thiram, Tolylfluanid, Zineb, Ziram; 14) a compound from the following list: (2E) -2- (2- {[[6- (3-chloro-2-methylphenoxy) -5-flucorpirimidin-4-yl] oxy} phenyl) -2 - (methoxyimino) -N-methylacetamide, (2E) -2-. { 2- [( { [(1E) -1- (3. {[[(E) -l-fluoro-2-phenylvinyl] oxy} phenyl) ethylidene] amino.} Oxy] methyl] phenyl } -2- (methoxyimino) -N-methylacetamide, 1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol, 2,2-dimethylpropyl-1H-imidazole-1- 1- [(4-methoxyphenoxy) methyl], 2- (4-chlorophenyl) -N- carboxylate. { 2- [3-methoxy-4- (prop-2-yn-l-yloxy) phenyl] ethyl} -2- (prop-2-yn-l-yloxy) acetamide, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2-butoxy-6-iodo-3-propyl-4H-chromen-4 -one, 2-chloro-N- (1,1,3-trimethyl-2,3-dihydro-lH-inden-4-yl) nicotinamide, 2-phenylphenol and salts thereof, 3,4,5-trichloropyridine- 2,6-dicarbonitrile, 3,4-dichloro-N- (2-cyanophenyl) isothiazole-5-carboxamide, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine, 5- chloro-6- (2,4,6-trifluorophenyl) -N- [(IR) -1,2,2-trimethylpropyl] [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1, 2, 4] triazolo [1, 5-a] pyrimidine, 5-chloro-N- [(1 R) -l, 2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine, 8-hydroxyquinoline sulfate, Benthiazole, Bethoxazin, Capsimycin, Carvone, Chinomethionat, Cufraneb, Cyflufenamid, Cymoxanil, Dazomet, Debacarb, Dichlorophen, Diclomezine, Dicloran, Difenzoquat, Diphenzoquat sulfate, Diphenylamine, Ferimzone, Flumetover, Fluopicolide, Fluoroimid e, Flusulfamide, Fosetyl-aluminum, Fosetyl-calcium, Fosetyl-sodium, hexachlorobenzene, Irumamycin, Methasulfocarb, (2-chloro-5-. { (1E) -N- [(6-methylpyridin-2-yl) methoxy] ethanimidoyl} benzyl) methyl carbamate, (2E) -2-. { 2- [( { Cyclopropyl [(4-methoxyphenyl) iminojmethyl] thio) methyl] phenyl} Methyl-3-methoxyacrylate, 1- (2, 2-dimethyl-2,3-dihydro-lH-inden-l-yl) -lH-imidazole-5-carboxylic acid methyl, 3- (4-chlorophenyl) -3 -. { [N- (isopropoxycarbonyl) valyl] amino} methyl propanoate, methyl isothiocyanate, Metrafenone, Mildiomycin, N- (3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, N- (3-ethyl-3,5,5,5-trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, N- [( 5-bromo-3-chloropyridin-2-yl) methyl] -2,4-dichloronicotinamide, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodonicotinamide, N- [2- (4- { [3- (4-chlorophenyl) prop-2 in-l-yl] oxy} - 3-methoxyphenyl) ethyl] -N2- (methylsulfonyl) valinamide, N-. { (Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2, 3-difluorophenyl] methyl} -2-phenylacetamide, N-. { 2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, Natamycin, nickel dimethyldithiocarbamate, Nitrothal-isopropyl, 0-. { l- [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl} lH-imidazole-l-carbothioate, Octhilinone,
Oxamocarb, Oxyfenthiin, pentachlorophenol and salts, phosphoric acid and its salts, piraline, Propamocarb Fosetylate, Propanosine-sodium, Proquinazid, Pyrrolnitrine, Quintozene, Tecloftalam, Tecnazene, Triazoxide, Trichlamide, Zarilamide. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, Probenazole, Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides: 1. Acetylcholinesterase inhibitors (AChE) 1.1 carbamates (eg Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Chloethocarb, aphos, Cyanofenphos, Cyanophos, Dimetilan, Ethiophencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb); 1.2 the organophosphates (eg Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiophos, Cadusafos, Carbophenothion, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl / -ethyl), aphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulfone, Dialiphos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimphos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazophos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazophos, Isofenphos, O-Isopropyl salicylate, Isoxathion, Malathion, Mecarbam,
Methacrifos, Methamidophos, Methidathion, Mevinphos,
Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion
(-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet,
Phosphamidon, Phosphocarb, Phoxi, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, Propetamphos, Prothiophos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulphophos, Tebupyrimphos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos , Trichlorfon, Vamidothion). 2. Modulators of the sodium channel / blockers of the sodium channel as a function of the tension 2.1 the pyrethroids (for example Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifenthrin, Bioallethrin, Bioallethrin- S-cyclopentyl isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, Chlovaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalo hrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Deltamethrin, Empenthrin (IR isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma-Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (cis-, trans-), Phenothrin (lR-trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (IR isomer), Tralo methrin, Transfluthrin, ZXI 8901, Pyrethrins (pyrethrum)); 2.2 the oxadiazines (for example Indoxacarb). 3. The agonists / antagonists of the acetylcholine receptors 3.1 the chloronicotinyl / neonicotinoids (for example Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Nithiazine, Thiacloprid, Thiamethoxam); 3.2 Nicotine, Bensultap, Cartap.
Four . Modulators of acetylcholine receptor 4.1 spinosides (for example Spinosad). 5. Chiral channel antagonists controlled by GABA
. 1 Cyclodienic organochlorines (for example Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane,
Methoxychlor) 5.2 fiproles (for example Acetoprole, Ethiprole, Fipronil, Vaniliprole). 6. Activators of chloride channel 6.1 mectins (for example Abamectin, Avermectin, Emamectin, Emamectin-benzoate, Ivermectin, Milbemectin, Milbemycin). 7. The mimetics of the juvenile hormone (for example Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene). 8. The agonists / disrupters of ecdysone 8.1 diacylhydrazines (for example Chromafenozide,
Halofenozide, Methoxyfenozide, Tebufenozide). 9. The inhibitors of the biosynthesis of the qutina 9.1 the benzoylureas (for example Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron,
Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Triflumuron); 9.2 Buprofezin; 9.3 Cyromazine. 10. Inhibitors of oxidative phosphorylation, disruptors of ATP 10.1 Diafenthiuron; 10.2 the organotins (for example Azocyclotin, Cyhexatin, Fenbutatin-oxide). 11. The decouplers of oxidative phosphorylation by interruption of the protonic gradient of H 11.1 the pyrroles (for example Chlorfenapyr); 11.2 the dinitrophenols (for example Binapacyrl, Dinobuton, Dinocap, DNOC). 12. Inhibitors of electronic transport location I
12. 1 the METI (for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad); 12.2 Hydramethylnone; 12.3 Dicofol. 13. Inhibitors of electronic transport location II 13.1 Rotenone 14. Loe inhibitors of electronic transport location III 14.1 Acequinocyl, Fluacrypyrim. 15. The microbial disruptors of the intestinal membrane of insects strains of Bacillus thuringiensis. 16. Inhibitors of synthesis of fats 16.1 tetronic acids (for example Spirodiclofen, Spiromesifen); 16.2 the tetramic acids [eg 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3 - (2, 5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS-Reg. -No .: 382608-10-8) and Carbonic acid, cis -3- (2, 5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS-Reg.-No .: 203313 -25-1)]. 17. The biphenylcarboxamides (for example Flonicamid). 18. Octopaminergic agonists (for example Amitraz). 19. Inhibitors of ATPase stimulated by magnesium (for example Propargite). 20. The ryanodine receptor agonists, 20.1 the benzoic acid dicarboxamides [for example N2- [l, l-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N1- [2-methyl-4- [ 1, 2, 2, 2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS-Reg .No .: 272451-65-7),
Flubendiamide]; 20.2 the anthranilamides (for example DPX E2Y45 = 3-bromo-N-. {4-chloro-2-methyl-6- [(methylamino) carbonyl] phenyl} - l- (3-chloropyridin-2-yl) -lH-pyrazole-5-carboxamide). twenty-one . Analogs of nereistoxin (for example Thiocyclam hydrogen oxalate, Thiosultap-sodium). 22. Loe biological products, lae hormonae or lae feroe onae (for example Azadirachtin, Bacillus spec., Beauveria spec, Codlemone, Metarrhizium spec., Paecilomyces spec., Thuringiensin, Verticillium spec.). 23. Loe active products with unknown or non-specific action mechanism 23.1 agents for gassing (eg aluminum phosphide, methyl bromide, sulfuryl fluoride). 23.2 Selective Inhibitors of Intake (eg Cryolite, Flonicamid, Pymetrozine). 23.3 mite growth inhibitors (for example Clofentezine, Etoxazole, Hexythiazox). 23.4 Amidoflumet, Benclothiaz, Benzoxitate, Bifenazate, Bromopropylate, Buprofezin, Chinomethionat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, in addition, the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) ) -8- (2, 2, 2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS-Reg .-- No. 185982-80-3) and the corresponding 3-endo isomer (CAS) -Reg .-- No. 185984-60-5) (see publications WO 96/37494, WO 98/25923), as well as preparations, containing plant extracts with insecticidal activity, nematodes, fungi or viruses.
A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, protective or semi-chemical products is also possible. In the same way, the compounds according to the invention of the formula (I) also have very good antifungal effects. They have a very broad spectrum of antifungal activity, especially against dermatophytes and blastomycetes, molds and against diphasic fungi (for example against Candida species, such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigae, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species, such as Microsporon canis and Audouinii. The enumeration of these fungi does not represent in any way a limitation of the fungal spectrum to be considered but it has only an orientative character. The active compounds can be used in the form of their formulations or in the application forms prepared therefrom, such as solutions, suspensions, sprayable powders, pastes, soluble powders, powdering agents and ready granules. for its use. The application is carried out in a conventional manner, for example by means of irrigation, by spraying, by dusting, by spreading, by dipping, by foaming, by brush application, etc. In the same way, it is possible to apply the active products in accordance with the ultra-low volume process or to inject into the soil the preparation of the active product or the active product itself. The seeds of the plants can also be treated. When the active products are used as fungicides, according to the invention, the application quantities can vary within wide limits in accordance with the type of the application. When the parts of the plants are treated, the application quantities of active product are, in general, between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of the treatment of the seeds, the application amounts of the active compound are, in general, between 0.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seeds. In the case of the treatment of the land, the application quantities of active product are, in general, between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha. As already indicated above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plants and plant varieties as well as parts thereof of wild origin or that are obtained by conventional methods of biological cultivation, such as crossing or fusion of protoplasts, are treated. In another preferred embodiment, the plants and the varieties of transgenic plants, which have been obtained in accordance with genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms -Genetically Modified Organisms-) and their parts, are treated. . The expressions of "parts" or "parts of plants" or "components of plants" have been explained above. Particularly preferred are plants, according to the invention, of the plant varieties customary in the market or which are in use. Plant varieties are understood as plants with new properties ("characteristics"), which have been cultivated either by conventional culture, by mutagenesis or by recombinant DNA techniques. These can be varieties, races, biospecies or genospecies. In accordance with the plant species or the plant varieties, their location and the growth conditions (soil, climate, vegetation period, feeding), additional effects can also be produced by means of the treatment according to the invention. "synergistic"). In this way they are possible, for example, lower amounts of application and / or enlargements of the activity spectrum and / or a reinforcement of the effect of the products and agents employable according to the invention, better growth of the plants, more developed root systems, a greater stability of Vegetable spices or plant varieties, a greater growth of the stalks, a greater vitality of the plants, a greater tolerance to high or low temperatures, a greater tolerance against drought or against the salt content of water or of the land, a greater floral yield, an easier harvest, an acceleration of the maturation, greater yields of the harvests, bigger fruits, bigger sizes of the plants, greener leaves, an earlier infloración, a greater quality and / or a higher nutritional value of the products harvested, higher concentration of sugar in the fruits, greater storage capacity and / or transformation tion of the products collected, which go beyond the expected effect itself. To plants or varieties of transgenic plants
(Genetically engineered) to be treated preferably according to the invention, belong all plants, which have acquired genetic material by modification by genetic engineering, which provide these plants with particularly advantageous valuable properties
("characteristics"). Examples of such properties are, better plant growth, greater tolerance to high or low temperatures, greater tolerance to drought or against the salt content of water or soil, greater floral yield, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, greater storage capacity and / or transformation of the products harvested. Other examples, especially noteworthy for such properties are the greater resistance of plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as a greater tolerance of plants against certain active herbicide products. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit tree plantations.
(with the fruits apple, pear, citrus and grape), should be noted especially corn, soybeans, potatoes, cotton, tobacco and rapeseed. As properties ("characteristics"), the greater resistance of plants to insects, arachnids, nematodes and snails will be pointed out by means of the toxins generated in plants, especially those generated in plants by genetic material from Bacillus Thuringiensis (for example by means of genes
Cry? A (a), Cry? A (b), Cry? A (c), CrylIA, CrylIIA, CryIIIB2, Cry9c,
Cry2Ab, Cry3Bb and CrylF as well as their combinations),
(hereinafter referred to as "Bt plants"). As properties
("characteristics") should also be noted, especially, the greater resistance of plants against fungi, bacteria and viruses through systemic acquired resistance
(SAR), systemin, phytoalexin, elicitors as well as resistance genes and corresponding expressed proteins and toxins.
As properties ("characteristics"), in particular, the greater tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or Phosphinothricin, should be pointed out.
(for example "PAT" gene). The genes that provide the respective desired properties ("characteristics") may also be present in combinations with each other in the transgenic plants. Examples of "Bt plants" include corn varieties, cotton varieties, soya varieties and potato varieties, which are marketed under the trademarks YIELD GARD® (for example corn, cotton, soybean), KnockOut® (for example corn), StarLinkO (for example corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®
(dad) . Examples of herbicide tolerant plants include corn varieties, cotton varieties and soybean varieties, which are marketed under the trademarks Roundup Ready® (tolerance against Glyphosate, for example corn, cotton, soybean), Liberty Link®. { olerance against
Phosphinothricin, for example rapeseed), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas for example corn). As herbicide-resistant plants (conventionally grown in relation to herbicide tolerance), the varieties marketed for the name Clearfield® (eg corn) can also be cited. Obviously, these manifestations are valid also for the varieties of plants developed in the future or that are marketed in the future with these genetic properties or with those that are developed in the future ("characteristics"). The stated plants can be treated in a particularly advantageous manner according to the invention with the compounds of the general formula (I) or mixtures of the active compounds according to the invention. The preferred ranges, previously mentioned, in the case of active products or mixtures, are also valid for the treatment of these plants. It should be noted in a special way the treatment of the plants with the compounds or with the mixtures indicated especially in the present text. The obtaining and use of the active products according to the invention are apparent from the following examples.
Preparation examples Example 1
They are added to a suspension consisting of 155.3 mg (0.8 mmol) of 1-methyl-3- (trifluoromethyl) -lH-pyrazole-4-carboxylic acid in 5 ml of dichloromethane and 30 μl of dimethylformamide, 0, 08 ml (0.88 mmol) of oxalic acid dichloride. The reaction mixture is stirred for 2 hours at room temperature as a step prior to the addition, dropwise, of a solution consisting of 210.6 mg (0.8 mmol) of the 2'-amino-3, 5 '- Methyl difluorbiphenyl-4-carboxylate and 0.16 ml (1.1 mmol) of triethylamine in 5 ml of dichloromethane. The reaction mixture is stirred for 16 hours at room temperature, poured into 4 ml of water, the organic phase is dried over sodium sulfate and concentrated in vacuo. 308 mg (0.7 mmol, 87% of theory) of 3,5 '-difluor-2' - ( { [L-methyl-3- (trifluoromethyl) -lH-pyrazol-4-yl] are obtained. carbonyl.}. amino) biphenyl-4-carboxylic acid [logP (pH 2.3) 2.64]. Analogously to that of Example 1, as well as, according to the general descriptions of the processes according to the invention, the compounds of the formula (I) mentioned in Table 1 below can be obtained. Table 1
Obtaining the starting materials of the formula (III) Example (III-l)
Under an atmosphere of inert gas (argon) 4.5 ml of a saturated solution of sodium carbonate and 0.1 g (0.1 mmol) of tetrakis (triphenylphosphine) palladium (0) are added to a suspension consisting of 0, 9 g (4.8 mmol) of 2-bromo-4-fluoroaniline and 1.0 g (5.1 mmol) of [3-fluoro-4- (methoxycarbonyl) phenyl] boronic acid in 5 ml of toluene and , 5 ml of ethanol. The reaction mixture is stirred for 16 hours at 80 ° C., then it is poured into 10 ml of water and extracted with 20 ml of toluene. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography (cyclohexane / ethyl acetate gradient) provides 0.5 g (1.76 mmol, 37% of theory) of methyl 2'-amino-3, 5 '-difluorobiphenyl-4-carboxylate [logP ( pH 2.3) 2.73]. Analogously to that of example (III-1), as well as, according to the general descriptions of the processes according to the invention, the compounds of the formula (III) mentioned in table 2 below can be obtained.
Table 2
The determination of the logP values indicated in the preceding tables and in the preparation examples is carried out in accordance with EEC directive 79/831 annex V.A8 by means of HPLC (High Performance Liquid Chromatography - High Performance Liquid Chromatography) in a column with phase inversion (C 18). Temperature: 43 eC. The determination is carried out in the acid range at pH 2.3 with 0.1% aqueous phosphoric acid and with acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile.
The calibration is carried out with unbranched alcan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two successive alkanones ). The maximum values of lambda are determined by means of the UV spectra from 200 nm to 400 nm at the maximums of the chromatographic signals. Application examples Example A Test with Venturia (apple tree) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are inoculated with an aqueous suspension of conidia of the pathogen of anthracnose of the apple tree Venturia inaequalis and then remain for 1 day at approximately 20 ° C and with a relative humidity of 100% in an incubation cabin. The plants are arranged, then, in the greenhouse, at approximately 21 aC and with a relative humidity of 90% approximately. The evaluation is carried out 10 days after inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed. Table A Test with Venturia (apple tree) / protector
Example B Test with Botrytis (beans) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, 2 pieces of agar coated with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in an obscured chamber at approximately 20SC and with a relative humidity of 100%. The evaluation is carried out 2 days after the inoculation by means of the magnitude of the spots produced by the attack. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed.
Table B Test with Botrytis (beans) / protector
Example C Test with Uromyces (beans) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are inoculated with an aqueous suspension of spores of the rust pathogen of the beans Uromyces appendiculatus and the plants then remain for 1 day at approximately 20 ° C and with a relative humidity of the air of the 100% in an incubation cabin. The plants are then placed in the greenhouse at approximately 21SC and with a relative humidity of approximately 90%. The evaluation is carried out 10 days after inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed. Table C Test with Uromyces (beans) / protector
Test with Uromyces (beans) / protector
Example D Puccinia (wheat) / protector test Solvent: 50 parts by weight of N, N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are sprayed with a conidial suspension of Puccinia recóndi ta. The plants remain in an incubation cabin for 48 hours at 20 ° C and with a relative humidity of 100%. The plants are then placed in a greenhouse at a temperature of about 20 ° C and with a relative humidity of about 80%. The evaluation is carried out 10 days after inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack has been observed. Table D Puccinia (wheat) / protective assay
It is noted that, in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (4)
- CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1.- Biphenylcarboxamides of the formula (I) characterized in that R 1 is hydrogen, alkyl having 1 to 8 carbon atoms, alkylsulfinyl having 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms , cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms -alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-alkyl with 1 to 3 carbon atoms, (alkyl with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms, (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms; halogen- (alkyl having 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (alkyl with 1 to 8 carbon atoms) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 8 alkylthio) carbonyl, (C 1 -C 4 alkoxy-alkyl with 1 to 4 carbon atoms) carbonyl, (alkenyloxy with 3 to 6 carbon atoms) carbonyl, (alkynyloxy with 3 to 6 carbon atoms) carbonyl, (cycloalkyl with 3 to 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogenalkylthio with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkenyloxy with 3 to 6 carbon atoms) carbonyl, (halogenoalkynyloxy with 3 to 6 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C ^ -C = C-R1"*", -CH2- CH = CH-R1_A, -CH = C = CH-R1"A, -C (= 0) C (= 0) R2, -CONR3R4 or -CH2NR5R6, R1_A means hydrogen, alkyl with 1 to 6 carbon atoms, halogenalkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, alkynyl with 2 to 6 carbon atoms, cycloalkyl with 3 to 7 carbon atoms carbon, (C 1 -C 4 alkoxy) carbonyl, (C 3 -C 6 alkenyloxy) carbonyl, (C 3 -C 6 alkynyloxy) carbonyl or cyano, R 2 means hydrogen, alkyl with 1 to 8 atoms carbon, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, halogenalkyl with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogen-cycloalkyl with 3 to 8 carbon atoms With respectively 1 to 9 fluorine, chlorine and / or bromine atoms, R.sub.3 and R.sub.4 are independently, respectively, hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms. - alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine atoms and / or bromine, R3 and R4 formin addition, together with the nitrogen atom, with which they are bonded, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if appropriate, one or more times, in the same or in different forms, by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle comprising 1 or 2 more heteroatoms, non-contiguous, of the series formed by oxygen, sulfur or NR7, R5 and R6 mean, independently of each other, hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R5 and R6 also form, together with the nitrogen atom, with which they are linked, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if appropriate, one or more times, in the same or in different ways, by halogen or by alkyl with 1 to 4 carbon atoms , the heterocycle comprising 1 or 2 more heteroatoms, not contiguous, of the series consisting of oxygen, sulfur or NR7, R7 means hydrogen or alkyl having 1 to 6 carbon atoms, R8 means hydrogen or fluorine, R9 means -SOmR11, - S02NR12R13, -C (= X) R14, -NR12R13, -CH2-NR12R13, R10 means fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl, R11 means alkyl with 1 to 6 carbon atoms or halogenalkyl with 1 to 6 carbon atoms. carbon with 1 to 13 halogen atoms, m signifi ca 1 or 2, R12 means hydrogen, alkyl with 1 to 4 carbon atoms or -C (= X) R14, R13 means hydrogen, alkyl with 1 to 4 carbon atoms or -C (= X) R14, R12 and R13 they also form, together with the nitrogen atom, with which they are bound, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if necessary, once or several times, in the same or in different ways, by halogen or alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 more heteroatoms, non-contiguous, of the series formed by oxygen, sulfur or NR7, X means 0 (oxygen) or S (sulfur), R14 means hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or -NR16R17, R 15 is hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms or halogen alkyl with 1 to 6 carbon atoms, the three radicals R 15 may be the same or different, respectively, R 16 denotes hydrogen or alkyl having 1 to 4 carbon atoms, R 17 is hydrogen or alkyl with 1 to 4 carbon atoms, R16 and R17 also form, together with the nitrogen atom, to which they are bound, a heterocycle with 5 to 8 ring atoms, saturated, substituted, if necessary, once or several times , in the same or in different forms, by halogen or alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 more heteroatoms, not contiguous, of the series formed by oxygen, sulfur or NR 'may mean one of the remains Up to A19 following Al l A12 A13 A14 A15 Al A17 A18 Al9 means hydrogen, cyano, halogen, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms carbon or halogenoalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-alkyl with 1 to 4 carbon atoms, R19 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms , alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms, R20 means hydrogen, alkyl with 1 to 4 carbon atoms, hydroxy-alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 6 carbon atoms carbon, cycloalkyl with 3 to 6 carbon atoms, alkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogen alkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or phenyl, R21 and R22 mean, independently of one another, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogen alkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R23 means halogen, cyano or alkyl with 1 to 4 carbon atoms, or halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R24 and R25 mean, independently of each other, hydrogen , halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R26 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms; carbon or halogen alkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R27 means hydrogen, halogen, hydroxy, cyano, alkyl with 1 to 6 carbon atoms, halogen alkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 up to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R28 means halogen, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms , alkylthio with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R29 means hydrogen , halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms , haloalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, alkylsulfinyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 carbon atoms, R30 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R31 means alkyl with 1 to 4 carbon atoms, Q1 means S (sulfur), SO, S02 or CH2, p means 0, 1 or 2, where R22 is identical or different, when p means 2, R32 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R33 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 atoms of halogen, R34 and R35 mean, independently of each other, hydrogen, halogen, amino, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R36 means hydrogen or, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, with 1 to 5 halogen atoms, R37 and R38 mean, independently of each other, hydrogen, halogen, amino, nitro, alkyl with 1 up to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R39 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 atoms of halogen, R40 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) amino, cyano, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R41 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, with 1 to 5 halogen atoms, R42 means hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) amino, cyano, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 4 carbon atoms with 1 to 5 carbon atoms halogen, R43 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R44 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 atoms carbon with 1 to 5 halogen atoms, R45 means hydrogen or alkyl with 1 to 4 carbon atoms, R46 means halogen or alkyl with 1 to 4 carbon atoms, R47 means alkyl with 1 to 4 carbon atoms or haloalkyl with 1 up to 4 carbon atoms with 1 to 5 halogen atoms, R48 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R4 9 means halogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, R50 means alkyl with 1 to 4 carbon atoms, R51 means hydrogen, cyano, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, hydroxy-alkyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, di (C 1 -C 4 -alkyl) aminosulfonyl, alkylcarbonyl with 1 to 6 carbon atoms or phenylsulphonyl or benzoyl subuted respectively, optionally, R 52 means hydrogen, halogen, alkyl with 1 up to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R53 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R54 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms.
- 2. Process for obtaining biphenylcarboxamides of the formula (I), according to claim 1, characterized in that (a) halogenides of carboxylic acids of the formula (II) are reacted wherein A has the meanings indicated in claim 1, X 1 means halogen or hydroxy, with amines of the formula (III) in which R 1, R 8, R 9 and R 10 have the meanings indicated in claim 1, where appropriate the presence of a coupling reagent, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent, or (b) biphenylcarboxamides of the formula < I-a) wherein R8, R9, R10 and A have the meanings indicated in claim 1, with halides of the formula (IV) R1B-Hal (IV) in which R1_B means alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 up to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 up to 4 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-alkyl with 1 to 3 carbon atoms, (alkyl with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms, (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms; halogen- (alkyl having 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl having 1 to 3 carbon atoms with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (alkyl with 1 to 8 carbon atoms) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 8 alkylthio) carbonyl, (C 1 -C 4 alkoxy-alkyl with 1 to 4 carbon atoms) carbonyl, (alkenyloxy with 3 to 6 carbon atoms) carbonyl, (alkynyloxy with 3 to 6 carbon atoms) carbonyl, (cycloalkyl with 3 to 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogenalkylthio with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkenyloxy with 3 to 6 carbon atoms) carbonyl, (halogenoalkynyloxy with 3 to 6 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -CH2-C = C-R1_A, -CH2-CH = CH-R1_A, CH = C = CH-R1 ~ A, -C (= 0) C (= 0) R2, -CONR3R4 or -CH2NR5R6, R1_A, R2, R3, R4, R5 and R6 have the meanings indicated in claim 1, Hal means chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
- 3. Agents for the fight against unwanted microorganisms, characterized in that they have a content in at least one biphenylcarboxamide of the formula (I), in accordance with claim 1, in addition to spreading agents and / or surfactant products.
- 4. Use of biphenylcarboxamides of the formula (I) according to claim 1, for the control against unwanted microorganisms. 5. - Procedure for the control against unwanted microorganisms, characterized in that a biphenylcarboxamide of the formula (I) is applied according to claim 1 on the microorganisms and / or on their environment. 6. - Procedure for obtaining agents for the fight against unwanted microorganisms, characterized in that biphenylcarboxamides of the formula (I) are mixed, according to claim 1, with spreading agents and / or surfactant products. 1 . - Use of the biphenylcarboxamides of the formula (I), according to claim 1, for the treatment of the seeds. 8. Use of the biphenylcarboxamides of the formula (I), according to claim 1, for the treatment of transgenic plants. 9. Use of the biphenylcarboxamides of the formula (I), according to claim 1, for the treatment of the seeds of the transgenic plants. 10.- Amines of the formulas (in-l), (III-2) and (III-3) 10 15 20 25
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005060462.5 | 2005-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2008007856A true MX2008007856A (en) | 2008-09-02 |
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