CA2622796A1 - Fungicide mixtures based on pyridine carboxamides - Google Patents
Fungicide mixtures based on pyridine carboxamides Download PDFInfo
- Publication number
- CA2622796A1 CA2622796A1 CA002622796A CA2622796A CA2622796A1 CA 2622796 A1 CA2622796 A1 CA 2622796A1 CA 002622796 A CA002622796 A CA 002622796A CA 2622796 A CA2622796 A CA 2622796A CA 2622796 A1 CA2622796 A1 CA 2622796A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl
- formula
- halogen
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000000855 fungicidal effect Effects 0.000 title claims abstract 7
- 239000000203 mixture Substances 0.000 title claims abstract 7
- 239000000417 fungicide Substances 0.000 title abstract 2
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title 1
- -1 amide compound Chemical class 0.000 claims abstract 8
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract 2
- ZTONKKHCXJTROW-UHFFFAOYSA-N n-(2-oxopropyl)benzamide Chemical compound CC(=O)CNC(=O)C1=CC=CC=C1 ZTONKKHCXJTROW-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 241000233866 Fungi Species 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000001143 conditioned effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 abstract 3
- 239000013543 active substance Substances 0.000 abstract 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 abstract 2
- 239000011701 zinc Substances 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- 239000012990 dithiocarbamate Substances 0.000 abstract 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 abstract 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to fungicide mixtures containing, as active components, a) an amide compound of formula (I) A-CO-NR1R2 and b) a dithiocarbamate (II) selected from the group: manganese-ethylene bis(dithiocarbamate) (zinc complex) (IIa); manganese-ethylene bis(dithiocarbamate) (IIb); zinc ammoniate-ethylene bis(dithiocarbamate) (IIc) and zinc-ethylene bis(dithiocarbamate) (IId), and/or c) a carbamate of formula (III) (CH3)2N-CH2CH2CH2-NH-CO2-CH2CH2CH3 and/or b) a N-acetonyl--benzamide of formula (IV) or one of the salts thereof or adducts, and/or b) an active substance of formula (V), and/or an active substance of formula (VI), and/or e) an active substance of formula (VII), whereby the substituents have the meanings given in the description. The active components are provided in a synergistically effective quantity.
Claims (5)
1. A fungicidal mixture comprising as active components:
a) an amide compound I having the formula Ia:
in which R10 is C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio or halogen, and A is X is methylene, sulfur, sulfynyl or sulfonyl (SO2), R3 is methyl, difluoromethyl, trifluoromethyl, chlorine, bromine or iodine, R4 is trifluoromethyl or chlorine, R5 is hydrogen or methyl, R6 is methyl, difluoromethyl, trifluoromethyl or chlorine, R7 is hydrogen, methyl or chlorine, R8 is methyl, difluoromethyl or trifluoromethyl, R9 is hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine, or the amide compound and b) a carbamate of the formula III
(CH3)2N-CH2CH2CH2-NH-CO2-CH2CH2CH3 (III) and/or c) an N-acetonylbenzamide of the formula IV
where the substituents have the following meaning:
R12, R14 independently of one another are halogen or C1-C4-alkyl;
R13 is cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C1-C4-alkoxy;
R15 is hydrogen or C1-C4-alkyl;
R16 is C2-C4-alkyl;
R17 is thiocyanato, isothiocyanato or halogen;
or a salt or adduct thereof;
and/or d) an active ingredient of the formula V
where the substituents have the following meaning:
Y is hydrogen, a metal atom of the first to the third main group of the Periodic Table of the Elements or a group NR19R20R21;
R18 is hydrogen, a C1-C18-alkyl group which may be substituted by halogen or a nitro group, a C2-C8-alkenyl or C2-C8-alkynyl group which may be substituted by halogen or a nitro group, a C1-C8-alkoxy-C1-C8-alkyl or a C2-C8-alkenyl-C1-C8-alkyl group, an unsubstituted or substituted aryl group having 6 to 14 carbon atoms, a C3-C7-cycloalkyl group, a C1-C4-alkylaryl group or a heterocyclic group having 5 or 6 ring atoms and a hetero atom selected from the group consisting of N, O and S, where the heterocyclic group is attached directly or via an aliphatic chain to the oxygen atom, and R19-R21 independently of one another are a C1-C4-alkyl group or a C1-C4-hydroxyalkyl group, and/or e) an active ingredient of the formula VI
and/or f) an active ingredient of the formula VII
where the substituents R23 to R26 have the following meanings.
H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, formyl, C3-C7-cycloalkyl, C6-C10-aryl, unsubstituted or C1-C4-alkyl-, C1-C4-alkoxy-, nitro- or halogen-substituted, C1-C6-alkoxy, C2-C6-alkoxyalkyl, C2-C6-alkylthioalkyl, di-C1-C4-alkylaminoalkyl, pyridyl, thiazolyl, furyl or thienyl and W is O, S or S=O;
in a synergistically effective amount.
a) an amide compound I having the formula Ia:
in which R10 is C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio or halogen, and A is X is methylene, sulfur, sulfynyl or sulfonyl (SO2), R3 is methyl, difluoromethyl, trifluoromethyl, chlorine, bromine or iodine, R4 is trifluoromethyl or chlorine, R5 is hydrogen or methyl, R6 is methyl, difluoromethyl, trifluoromethyl or chlorine, R7 is hydrogen, methyl or chlorine, R8 is methyl, difluoromethyl or trifluoromethyl, R9 is hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine, or the amide compound and b) a carbamate of the formula III
(CH3)2N-CH2CH2CH2-NH-CO2-CH2CH2CH3 (III) and/or c) an N-acetonylbenzamide of the formula IV
where the substituents have the following meaning:
R12, R14 independently of one another are halogen or C1-C4-alkyl;
R13 is cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl or C1-C4-alkoxy;
R15 is hydrogen or C1-C4-alkyl;
R16 is C2-C4-alkyl;
R17 is thiocyanato, isothiocyanato or halogen;
or a salt or adduct thereof;
and/or d) an active ingredient of the formula V
where the substituents have the following meaning:
Y is hydrogen, a metal atom of the first to the third main group of the Periodic Table of the Elements or a group NR19R20R21;
R18 is hydrogen, a C1-C18-alkyl group which may be substituted by halogen or a nitro group, a C2-C8-alkenyl or C2-C8-alkynyl group which may be substituted by halogen or a nitro group, a C1-C8-alkoxy-C1-C8-alkyl or a C2-C8-alkenyl-C1-C8-alkyl group, an unsubstituted or substituted aryl group having 6 to 14 carbon atoms, a C3-C7-cycloalkyl group, a C1-C4-alkylaryl group or a heterocyclic group having 5 or 6 ring atoms and a hetero atom selected from the group consisting of N, O and S, where the heterocyclic group is attached directly or via an aliphatic chain to the oxygen atom, and R19-R21 independently of one another are a C1-C4-alkyl group or a C1-C4-hydroxyalkyl group, and/or e) an active ingredient of the formula VI
and/or f) an active ingredient of the formula VII
where the substituents R23 to R26 have the following meanings.
H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, formyl, C3-C7-cycloalkyl, C6-C10-aryl, unsubstituted or C1-C4-alkyl-, C1-C4-alkoxy-, nitro- or halogen-substituted, C1-C6-alkoxy, C2-C6-alkoxyalkyl, C2-C6-alkylthioalkyl, di-C1-C4-alkylaminoalkyl, pyridyl, thiazolyl, furyl or thienyl and W is O, S or S=O;
in a synergistically effective amount.
2. The fungicidal mixture as claimed in claim 1, which comprises as amide compound I:
in which R4 is trifluoromethyl or chlorine, and R11 is phenyl which is substituted by halogen.
in which R4 is trifluoromethyl or chlorine, and R11 is phenyl which is substituted by halogen.
3. The fungicidal mixture as claimed in claim 1, which comprises as amide compound I, a compound of the formula:
4. The fungicidal mixture as claimed in any one of claims 1 to 3, which is conditioned in two parts, one part comprising the amide compound I in a solid or liquid carrier and the other part comprising the compounds III and/or IV to VII in a solid or liquid carrier.
5. A method for controlling harmful fungi, which comprises treating the fungi, their habitat, or the materials, plants, seeds, soils, areas or spaces to be protected against fungal attack with the fungicidal mixture as claimed in any one of claims 1 to 4, where the application of the active components is carried out simultaneously, that is either jointly or separately, or in succession.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2704256A CA2704256A1 (en) | 1997-12-18 | 1998-12-15 | Fungicide mixtures based on pyridine carboxamides |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19756378.3 | 1997-12-18 | ||
| DE19756378 | 1997-12-18 | ||
| CA002313333A CA2313333C (en) | 1997-12-18 | 1998-12-15 | Fungicide mixtures based on pyridine carboxamides |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002313333A Division CA2313333C (en) | 1997-12-18 | 1998-12-15 | Fungicide mixtures based on pyridine carboxamides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2704256A Division CA2704256A1 (en) | 1997-12-18 | 1998-12-15 | Fungicide mixtures based on pyridine carboxamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2622796A1 true CA2622796A1 (en) | 1999-07-01 |
| CA2622796C CA2622796C (en) | 2010-08-17 |
Family
ID=39537692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2622796A Expired - Fee Related CA2622796C (en) | 1997-12-18 | 1998-12-15 | Fungicide mixtures based on pyridine carboxamides |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2622796C (en) |
-
1998
- 1998-12-15 CA CA2622796A patent/CA2622796C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2622796C (en) | 2010-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20121217 |