CH650253A5 - Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe. - Google Patents

Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe. Download PDF

Info

Publication number: CH650253A5
Authority: CH; Switzerland
Prior art keywords: oxide; pyrazinyl; compounds; general formula; acid addition
Prior art date: 1982-03-26

Application number

CH1881/82A

Other languages

German (de)

English (en)

Inventor

Franz Dr Dorn

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-03-26

Filing date

1982-03-26

Publication date

1985-07-15

1982-03-26 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1982-03-26 Priority to CH1881/82A priority Critical patent/CH650253A5/de

1983-02-25 Priority to IT19818/83A priority patent/IT1205296B/it

1983-03-16 Priority to DE19833309466 priority patent/DE3309466A1/de

1983-03-22 Priority to FR8304658A priority patent/FR2523966B1/fr

1983-03-25 Priority to JP58050279A priority patent/JPS58174364A/ja

1983-03-25 Priority to GB08308341A priority patent/GB2117768B/en

1985-07-15 Publication of CH650253A5 publication Critical patent/CH650253A5/de

Links

230000000855 fungicidal effect Effects 0.000 title claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 5
239000013543 active substance Substances 0.000 title description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 58
239000002253 acid Substances 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
239000004480 active ingredient Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
-1 O-substituted hydroxylamine Chemical class 0.000 claims description 14
238000009472 formulation Methods 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 8
241000233866 Fungi Species 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
238000003898 horticulture Methods 0.000 claims description 4
239000000417 fungicide Substances 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
150000003216 pyrazines Chemical class 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
125000000068 chlorophenyl group Chemical group 0.000 claims 1
239000000463 material Substances 0.000 claims 1
239000002904 solvent Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
239000002270 dispersing agent Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
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CGZQCZNRBCLEOH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-pyridin-3-ylethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CC1=CC=CN=C1 CGZQCZNRBCLEOH-UHFFFAOYSA-N 0.000 description 2
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 2
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XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
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XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
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229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
150000008366 benzophenones Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000012043 crude product Substances 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical class CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
ZBBGAUHWTZKKQQ-UHFFFAOYSA-N ethyl 2,4-dichlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1Cl ZBBGAUHWTZKKQQ-UHFFFAOYSA-N 0.000 description 1
RPWXYCRIAGBAGY-UHFFFAOYSA-N ethyl 2-pyridin-3-ylacetate Chemical compound CCOC(=O)CC1=CC=CN=C1 RPWXYCRIAGBAGY-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000012010 growth Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000006028 limestone Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000151 polyglycol Chemical class 0.000 description 1
239000010695 polyglycol Chemical class 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000417 polynaphthalene Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229960001866 silicon dioxide Drugs 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH1881/82A 1982-03-26 1982-03-26 Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe. CH650253A5 (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH1881/82A CH650253A5 (de)	1982-03-26	1982-03-26	Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe.
IT19818/83A IT1205296B (it)	1982-03-26	1983-02-25	Derivati piridinici e pirazinici
DE19833309466 DE3309466A1 (de)	1982-03-26	1983-03-16	Pyridin- und pyrazin-derivate
FR8304658A FR2523966B1 (fr)	1982-03-26	1983-03-22	Derives de pyridine et de pyrazine, leur preparation et leur application en tant qu'agents fongicides
JP58050279A JPS58174364A (ja)	1982-03-26	1983-03-25	新規オキシム誘導体、それらの製造法、ならびにそれらからなる植物病原菌防除剤
GB08308341A GB2117768B (en)	1982-03-26	1983-03-25	Fungicidal pyridine and pyrazine derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1881/82A CH650253A5 (de)	1982-03-26	1982-03-26	Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe.

Publications (1)

Publication Number	Publication Date
CH650253A5 true CH650253A5 (de)	1985-07-15

Family

ID=4220764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1881/82A CH650253A5 (de)	1982-03-26	1982-03-26	Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe.

Country Status (6)

Country	Link
JP (1)	JPS58174364A (it)
CH (1)	CH650253A5 (it)
DE (1)	DE3309466A1 (it)
FR (1)	FR2523966B1 (it)
GB (1)	GB2117768B (it)
IT (1)	IT1205296B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0445069A1 (de) *	1990-02-16	1991-09-04	Ciba-Geigy Ag	Heterocyclische Verbindungen

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3205234A (en) *	1961-06-30	1965-09-07	Upjohn Co	Nu-oxides of pyridyl ketone omicron-hydrocarbonoximes
US4171214A (en) *	1977-01-06	1979-10-16	Imperial Chemical Industries Limited	Pyrazine-2-ylmethyl-ketones and their fungicidal use
GB2015524A (en) *	1978-03-06	1979-09-12	Ici Ltd	Pyridine derivatives
US4297359A (en) *	1978-07-25	1981-10-27	Acf Chemiefarma Nv	Anti-ulcer compositions containing certain pyridyl oxime ethers
CA1225092A (en) *	1980-10-10	1987-08-04	Franz Dorn	Pyridine and pyrazine derivatives
IT1172404B (it) *	1982-03-31	1987-06-18	Hoffmann La Roche	Composti eterociclici

1982
- 1982-03-26 CH CH1881/82A patent/CH650253A5/de not_active IP Right Cessation
1983
- 1983-02-25 IT IT19818/83A patent/IT1205296B/it active
- 1983-03-16 DE DE19833309466 patent/DE3309466A1/de not_active Withdrawn
- 1983-03-22 FR FR8304658A patent/FR2523966B1/fr not_active Expired
- 1983-03-25 JP JP58050279A patent/JPS58174364A/ja active Pending
- 1983-03-25 GB GB08308341A patent/GB2117768B/en not_active Expired

Also Published As

Publication number	Publication date
IT1205296B (it)	1989-03-15
FR2523966B1 (fr)	1986-12-05
JPS58174364A (ja)	1983-10-13
GB2117768A (en)	1983-10-19
GB2117768B (en)	1985-10-09
DE3309466A1 (de)	1983-10-06
FR2523966A1 (fr)	1983-09-30
IT8319818A0 (it)	1983-02-25
GB8308341D0 (en)	1983-05-05

Legal Events

Date	Code	Title	Description
1987-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0049854B1 (de)	1985-01-16	Pyridin- und Pyrazin-Derivate, Herstellung dieser Verbindungen, fungizide Mittel, die diese Verbindungen als Wirkstoffe enthalten sowie Verwendung solcher Verbindungen bzw. Mittel zur Bekämpfung von Fungi in der Landwirtschaft und im Gartenbau
CH618583A5 (en)	1980-08-15	Fungicidal composition
EP0040744B1 (de)	1984-02-08	Aminopropiophenon-oxime, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0074018B1 (de)	1986-09-24	Pyridin- und Pyrazin-Derivate, Herstellung dieser Verbindungen, fungizide Mittel, die diese Verbindungen als Wirkstoffe enthalten, Verwendung solcher Verbindungen bzw. Mittel zur Bekämpfung von Fungi in der Landwirtschaft und im Gartenbau sowie Ketone und diese enthaltende fungizide Mittel
EP0209854A2 (de)	1987-01-28	Pyridinderivate und deren Verwendung als fungizide Wirkstoffe
EP0117485A2 (de)	1984-09-05	Pyridin-, Pyrazin- und Pyrimidinderivate und deren Verwendung als fungizide Wirkstoffe
EP0001751B1 (de)	1980-09-17	N-(Imidazolylmethyl)-acetanilide, ihre Verwendung als Herbizide und Verfahren zur Bekämpfung unerwünschten Pflanzenwuchses
DE2943631A1 (de)	1980-05-14	Azolylketale, verfahren zu ihrer herstellung und ihre verwendung als mikrobizide
CH650253A5 (de)	1985-07-15	Pyridin- und pyrazin-derivate und ihre verwendung als fungizide wirkstoffe.
CH651552A5 (en)	1985-09-30	Heterocyclic compounds
DE3310148A1 (de)	1983-10-06	Heterocyclische verbindungen
EP0056125B1 (de)	1984-09-05	Keten-O,N-acetale, Verfahren zu ihrer Herstellung, diese enthaltende Fungizide und ihre Verwendung zur Bekämpfung von Pilzen
EP0022531B1 (de)	1983-03-02	1-(2,4-Dichlorphenyl)-1-(2,6-dihalogenbenzylmercapto)-2-(1,2,4-triazol-1-yl)-ethane, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0019133B1 (de)	1983-07-20	Fungizide Mittel, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DD236869A5 (de)	1986-06-25	Fungizide mittel
DE3505869A1 (de)	1985-08-22	2-((arylthio)phenyl)-2-(1h-azolylmethyl)-diox(ol)ane als mikrobizide
EP0119572A2 (de)	1984-09-26	Substituierte Phenethyl-triazolyl-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EP0040367A1 (de)	1981-11-25	Substituierte Phenyl-triazolyl-vinyl-ketone, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EP0385267A2 (de)	1990-09-05	Pyridinderivate, deren Herstellung und Verwendung als Fungizide
DD221343A5 (de)	1985-04-24	Fungizide mittel
DD298392A5 (de)	1992-02-20	Fungizide mittel auf basis von 1,3,5-triaryl-2-pyrazolin-derivaten, neue 1,3,5-triaryl-2-pyrazoline und ein verfahren zu ihrer herstellung
EP0102517A2 (de)	1984-03-14	Fungizide Mittel
EP0197322A2 (de)	1986-10-15	Triazol-Derivate
DE3315806A1 (de)	1984-10-31	Phenoxytriazolyl-ketone und -carbinole, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0228607A1 (de)	1987-07-15	Substituierte Cyclopropyl-oximether