DE1793502C3 - 2-Methyl-5,6-dihydropyran-3-carbonsäureanilide und diese Verbindungen enthaltende Pflanzenschutzmittel - Google Patents
2-Methyl-5,6-dihydropyran-3-carbonsäureanilide und diese Verbindungen enthaltende PflanzenschutzmittelInfo
- Publication number
- DE1793502C3 DE1793502C3 DE1793502A DE1793502A DE1793502C3 DE 1793502 C3 DE1793502 C3 DE 1793502C3 DE 1793502 A DE1793502 A DE 1793502A DE 1793502 A DE1793502 A DE 1793502A DE 1793502 C3 DE1793502 C3 DE 1793502C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- carboxylic acid
- dihydropyran
- compounds
- crop protection
- 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.)
- Expired
Links
- NPTRDZWZSUYBAG-UHFFFAOYSA-N 6-methyl-n-phenyl-3,6-dihydro-2h-pyran-5-carboxamide Chemical class CC1OCCC=C1C(=O)NC1=CC=CC=C1 NPTRDZWZSUYBAG-UHFFFAOYSA-N 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title description 21
- 239000011814 protection agent Substances 0.000 title description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 241000209140 Triticum Species 0.000 description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- -1 aluminum silicates Chemical class 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 238000005554 pickling Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QSYWYGWXCVQLAP-UHFFFAOYSA-N 6-methyl-3,6-dihydro-2h-pyran-5-carboxylic acid Chemical compound CC1OCCC=C1C(O)=O QSYWYGWXCVQLAP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000415582 Puccinia striiformis f. sp. tritici Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- 241001163841 Albugo ipomoeae-panduratae Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000221561 Ustilaginales Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013532 brandy Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| OA53484A OA02979A (fr) | 1968-01-22 | 1968-01-22 | Anilides dérivant de l'acide pyrane-3-carboxylique et leurs applications comme produits phytosanitaires. |
| DE1793502A DE1793502C3 (de) | 1968-01-22 | 1968-09-27 | 2-Methyl-5,6-dihydropyran-3-carbonsäureanilide und diese Verbindungen enthaltende Pflanzenschutzmittel |
| IE56/69A IE32958B1 (en) | 1968-01-22 | 1969-01-15 | Pyrancarboxylic acid anilides,process for their manufacture and their use as pesticides |
| IL31427A IL31427A (en) | 1968-01-22 | 1969-01-15 | Pyrancarboxylic acid anilides,process for their manufacture and their use as plant fungicides |
| NL6900825A NL6900825A (enrdf_load_stackoverflow) | 1968-01-22 | 1969-01-17 | |
| ES362655A ES362655A1 (es) | 1968-01-22 | 1969-01-18 | Un procedimiento para la obtencion de anilidas piracarboxi-licas y su utilizacion como agentes protectores de plantas. |
| RO58797A RO55546A (enrdf_load_stackoverflow) | 1968-01-22 | 1969-01-18 | |
| SE00716/69A SE355807B (enrdf_load_stackoverflow) | 1968-01-22 | 1969-01-20 | |
| CH77769A CH509751A (de) | 1968-01-22 | 1969-01-20 | Pflanzenschutzmittel und Verfahren zu seiner Herstellung |
| AT55569A AT290914B (de) | 1968-01-22 | 1969-01-20 | Pflanzenschlutzmittel |
| CS38969*#A CS154610B2 (enrdf_load_stackoverflow) | 1968-01-22 | 1969-01-21 | |
| DK33469AA DK125504B (da) | 1968-01-22 | 1969-01-21 | Fungicid. |
| YU129/69A YU34422B (en) | 1968-01-22 | 1969-01-21 | Process for preparing anilides of 2-methyl-5,6-dihydropyran-3-carboxylic acid |
| PL1969131313A PL80882B1 (enrdf_load_stackoverflow) | 1968-01-22 | 1969-01-21 | |
| GB3313/69A GB1194526A (en) | 1968-01-22 | 1969-01-21 | Pyrancarboxylic Acid Anilides, process for their manufacture and their use as Pesticides |
| FI690178A FI48831C (fi) | 1968-01-22 | 1969-01-21 | Kasvinsuojeluaineina käytettävät 2-metyyli-5,6-dihydropyraani-3-karbon ihappoanilidit. |
| CA040698A CA931153A (en) | 1968-01-22 | 1969-01-21 | Pyran-carboxylic acid anilides and their use as pesticides |
| BE727245D BE727245A (enrdf_load_stackoverflow) | 1968-01-22 | 1969-01-22 | |
| FR6901119A FR2000552A1 (en) | 1968-01-22 | 1969-01-22 | 2-Methyl-5,6-dihydropyran-3-carboxylic acid anilides - fungicidal anti-parasitic |
| YU2896/74A YU34423B (en) | 1968-01-22 | 1974-10-29 | Process for preparing anilides of 2-methyl-5,6-dihydropyran-3-carboxylic acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1968F0054602 DE1668899B1 (de) | 1968-01-22 | 1968-01-22 | 2-Methyl-5,6-dihydropyran-3-carbonsaeureanilid und dieses enthaltende Pflanzenschutzmittel |
| DE1793502A DE1793502C3 (de) | 1968-01-22 | 1968-09-27 | 2-Methyl-5,6-dihydropyran-3-carbonsäureanilide und diese Verbindungen enthaltende Pflanzenschutzmittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1793502A1 DE1793502A1 (de) | 1972-03-09 |
| DE1793502B2 DE1793502B2 (de) | 1979-06-13 |
| DE1793502C3 true DE1793502C3 (de) | 1980-04-03 |
Family
ID=25756057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1793502A Expired DE1793502C3 (de) | 1968-01-22 | 1968-09-27 | 2-Methyl-5,6-dihydropyran-3-carbonsäureanilide und diese Verbindungen enthaltende Pflanzenschutzmittel |
Country Status (19)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4078070A (en) | 1973-01-16 | 1978-03-07 | Hoechst Aktiengesellschaft | Fungicidal dispersions |
| DE2301922C3 (de) * | 1973-01-16 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Fungizide Dispersionen von 2-Methyl5,6-dihydropyran-3-carbonsäureanilid |
| NL7412787A (nl) * | 1973-10-04 | 1975-04-08 | Hoechst Ag | Fungicide dispersies van carbonzuuramiden. |
| DE4131311A1 (de) * | 1991-09-20 | 1993-04-01 | Basf Ag | Dihydropyranderivate und diese enthaltende pflanzenschutzmittel |
| WO2000012495A1 (de) * | 1998-09-01 | 2000-03-09 | Basf Aktiengesellschaft | Verwendung von dihydropyrancarbonsäureamiden als herbizide und neue dihydropyrancarbonsäureamide |
-
1968
- 1968-01-22 OA OA53484A patent/OA02979A/xx unknown
- 1968-09-27 DE DE1793502A patent/DE1793502C3/de not_active Expired
-
1969
- 1969-01-15 IL IL31427A patent/IL31427A/en unknown
- 1969-01-15 IE IE56/69A patent/IE32958B1/xx unknown
- 1969-01-17 NL NL6900825A patent/NL6900825A/xx unknown
- 1969-01-18 RO RO58797A patent/RO55546A/ro unknown
- 1969-01-18 ES ES362655A patent/ES362655A1/es not_active Expired
- 1969-01-20 CH CH77769A patent/CH509751A/de not_active IP Right Cessation
- 1969-01-20 SE SE00716/69A patent/SE355807B/xx unknown
- 1969-01-20 AT AT55569A patent/AT290914B/de not_active IP Right Cessation
- 1969-01-21 DK DK33469AA patent/DK125504B/da unknown
- 1969-01-21 CS CS38969*#A patent/CS154610B2/cs unknown
- 1969-01-21 GB GB3313/69A patent/GB1194526A/en not_active Expired
- 1969-01-21 FI FI690178A patent/FI48831C/fi active
- 1969-01-21 YU YU129/69A patent/YU34422B/xx unknown
- 1969-01-21 PL PL1969131313A patent/PL80882B1/pl unknown
- 1969-01-21 CA CA040698A patent/CA931153A/en not_active Expired
- 1969-01-22 BE BE727245D patent/BE727245A/xx unknown
- 1969-01-22 FR FR6901119A patent/FR2000552A1/fr not_active Withdrawn
-
1974
- 1974-10-29 YU YU2896/74A patent/YU34423B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT290914B (de) | 1971-06-25 |
| DE1793502B2 (de) | 1979-06-13 |
| DK125504B (da) | 1973-03-05 |
| RO55546A (enrdf_load_stackoverflow) | 1974-03-01 |
| PL80882B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| YU12969A (en) | 1978-12-31 |
| OA02979A (fr) | 1970-12-15 |
| CA931153A (en) | 1973-07-31 |
| CH509751A (de) | 1971-07-15 |
| CS154610B2 (enrdf_load_stackoverflow) | 1974-04-30 |
| FI48831C (fi) | 1975-01-10 |
| NL6900825A (enrdf_load_stackoverflow) | 1969-07-24 |
| FR2000552A1 (en) | 1969-09-12 |
| GB1194526A (en) | 1970-06-10 |
| YU34422B (en) | 1979-07-10 |
| IL31427A0 (en) | 1969-03-27 |
| YU34423B (en) | 1979-07-10 |
| ES362655A1 (es) | 1971-02-01 |
| IE32958B1 (en) | 1974-02-06 |
| BE727245A (enrdf_load_stackoverflow) | 1969-07-22 |
| IL31427A (en) | 1972-02-29 |
| YU289674A (en) | 1978-12-31 |
| SE355807B (enrdf_load_stackoverflow) | 1973-05-07 |
| DE1793502A1 (de) | 1972-03-09 |
| IE32958L (en) | 1969-07-22 |
| FI48831B (enrdf_load_stackoverflow) | 1974-09-30 |
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| C3 | Grant after two publication steps (3rd publication) | ||
| 8340 | Patent of addition ceased/non-payment of fee of main patent |