DE2724786C2 - Cyclopropancarbonsäure-[N-(2-oxoperhydro-3-furyl)-anilide], Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende fungizide Mittel - Google Patents
Cyclopropancarbonsäure-[N-(2-oxoperhydro-3-furyl)-anilide], Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende fungizide MittelInfo
- Publication number
- DE2724786C2 DE2724786C2 DE2724786A DE2724786A DE2724786C2 DE 2724786 C2 DE2724786 C2 DE 2724786C2 DE 2724786 A DE2724786 A DE 2724786A DE 2724786 A DE2724786 A DE 2724786A DE 2724786 C2 DE2724786 C2 DE 2724786C2
- Authority
- DE
- Germany
- Prior art keywords
- anilide
- oxoperhydro
- cyclopropanecarboxylic acid
- furyl
- acid
- 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
- 150000001875 compounds Chemical class 0.000 title description 20
- 238000002360 preparation method Methods 0.000 title description 8
- 238000000034 method Methods 0.000 title description 6
- CCMUXDKGKNRNKV-UHFFFAOYSA-N O=C1OCCC1N(C1=CC=CC=C1)C(=O)C1CC1 Chemical compound O=C1OCCC1N(C1=CC=CC=C1)C(=O)C1CC1 CCMUXDKGKNRNKV-UHFFFAOYSA-N 0.000 title description 5
- 239000000417 fungicide Substances 0.000 title description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 27
- -1 dimethylphenyl Chemical group 0.000 description 29
- 239000004480 active ingredient Substances 0.000 description 22
- 230000000694 effects Effects 0.000 description 19
- 150000003931 anilides Chemical class 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- 206010061217 Infestation Diseases 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000002538 fungal effect Effects 0.000 description 10
- 241000233866 Fungi Species 0.000 description 9
- 240000004713 Pisum sativum Species 0.000 description 9
- 235000010582 Pisum sativum Nutrition 0.000 description 9
- 240000003768 Solanum lycopersicum Species 0.000 description 8
- 230000000855 fungicidal effect Effects 0.000 description 8
- 230000017074 necrotic cell death Effects 0.000 description 8
- 244000061456 Solanum tuberosum Species 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000233622 Phytophthora infestans Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- GJMONPSULDEHGJ-UHFFFAOYSA-N CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C(=CC=C1)C GJMONPSULDEHGJ-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 235000000292 Gouania lupuloides Nutrition 0.000 description 4
- 244000299452 Gouania lupuloides Species 0.000 description 4
- 241000918584 Pythium ultimum Species 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003032 phytopathogenic effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- KGVDHPKIECPMKY-UHFFFAOYSA-N CC=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 Chemical compound CC=1C=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC1 KGVDHPKIECPMKY-UHFFFAOYSA-N 0.000 description 2
- 241000371644 Curvularia ravenelii Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZBQMDZKAYOBWBW-UHFFFAOYSA-N C(C)(C)C1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 Chemical compound C(C)(C)C1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 ZBQMDZKAYOBWBW-UHFFFAOYSA-N 0.000 description 1
- WQMRIGLEHRHANC-UHFFFAOYSA-N C(C)C1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 Chemical compound C(C)C1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 WQMRIGLEHRHANC-UHFFFAOYSA-N 0.000 description 1
- NTLPYAXIGVIIBS-UHFFFAOYSA-N C(C)OC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 Chemical compound C(C)OC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 NTLPYAXIGVIIBS-UHFFFAOYSA-N 0.000 description 1
- WFIJLXJAATWFJD-UHFFFAOYSA-N C(C)OC1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 Chemical compound C(C)OC1=CC=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C1 WFIJLXJAATWFJD-UHFFFAOYSA-N 0.000 description 1
- JCJQYWUPDCLNNR-UHFFFAOYSA-N C1=CC(Cl)=CC=C1N(C(=O)C1CC1)C1C(=O)OCC1 Chemical compound C1=CC(Cl)=CC=C1N(C(=O)C1CC1)C1C(=O)OCC1 JCJQYWUPDCLNNR-UHFFFAOYSA-N 0.000 description 1
- BKYFNNMXSIPLID-UHFFFAOYSA-N C1CC1C(=O)N(C2CCOC2=O)C3=CC=CC(=C3)C(F)(F)F Chemical compound C1CC1C(=O)N(C2CCOC2=O)C3=CC=CC(=C3)C(F)(F)F BKYFNNMXSIPLID-UHFFFAOYSA-N 0.000 description 1
- WPIGCLSPMBOMMQ-UHFFFAOYSA-N CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C(C=C1)C Chemical compound CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=C(C=C1)C WPIGCLSPMBOMMQ-UHFFFAOYSA-N 0.000 description 1
- ACWNSQYNWQANLI-UHFFFAOYSA-N CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC(=C1)C Chemical compound CC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC(=C1)C ACWNSQYNWQANLI-UHFFFAOYSA-N 0.000 description 1
- LGOYBDKCFHJDOO-UHFFFAOYSA-N COC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 Chemical compound COC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1 LGOYBDKCFHJDOO-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- CHPYXJXCEADFQC-UHFFFAOYSA-N ClC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1Cl Chemical compound ClC1=C(N(C(=O)C2CC2)C2C(OCC2)=O)C=CC=C1Cl CHPYXJXCEADFQC-UHFFFAOYSA-N 0.000 description 1
- GKLKISMJWCRVSX-UHFFFAOYSA-N ClC=1C=C(N(C(=O)C2CC2)C2C(OC(C2)C)=O)C=CC1 Chemical compound ClC=1C=C(N(C(=O)C2CC2)C2C(OC(C2)C)=O)C=CC1 GKLKISMJWCRVSX-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- ZCEQTRBOJBOALR-UHFFFAOYSA-N N-(4-methoxyphenyl)-N-(2-oxooxolan-3-yl)cyclopropanecarboxamide Chemical compound C1=CC(OC)=CC=C1N(C(=O)C1CC1)C1C(=O)OCC1 ZCEQTRBOJBOALR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233629 Phytophthora parasitica Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002552 anti-phytopathogenic effect Effects 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 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
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 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
- 239000004571 lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-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
- C07D307/30—Heterocyclic compounds containing five-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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (40)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2724786A DE2724786C2 (de) | 1977-05-27 | 1977-05-27 | Cyclopropancarbonsäure-[N-(2-oxoperhydro-3-furyl)-anilide], Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende fungizide Mittel |
| FI781264A FI68397C (fi) | 1977-05-27 | 1978-04-24 | Saosom fungicid anvaendbara cyklopropankarboxylsyraanilider |
| YU1102/78A YU40192B (en) | 1977-05-27 | 1978-05-09 | Process for obtaining cyclopropane carboxylic aci anilides |
| MX787079U MX5224E (es) | 1977-05-27 | 1978-05-11 | Procedimiento para preparar anilidas de acido ciclopropanocarboxilico |
| CA303,250A CA1108161A (en) | 1977-05-27 | 1978-05-12 | Fungicidally active cyclopropanecarboxylic acid anilides |
| PH21136A PH15700A (en) | 1977-05-27 | 1978-05-15 | Fungicidally active furancarboxylic acid anilides and their use |
| IL54719A IL54719A (en) | 1977-05-27 | 1978-05-16 | 2-oxoperhydrofuryl anilides of cyclopropanecarboxylic acid having fungicidal activity and their manufacture and use |
| NL7805404A NL7805404A (nl) | 1977-05-27 | 1978-05-18 | Cyclopropaancarbonzuuraniliden, werkwijze voor het be- reiden van fungiciden op basis van deze verbindingen, alsmede werkwijze voor het bereiden van de genoemde a- niliden. |
| TR20568A TR20568A (tr) | 1977-05-27 | 1978-05-18 | Fungisit olarak aktif siklopropankarboksilik asit anilitleri ve bunlarin imali ve kullanilmasi |
| GB21326/78A GB1603730A (en) | 1977-05-27 | 1978-05-23 | Fungicidally active cyclopropanecarboxylic acid analides and their manufacture and use |
| CY1163A CY1163A (en) | 1977-05-27 | 1978-05-23 | Fungicidally active cyclopropanecarboxylic acid analides and their manufacture and use |
| PT68075A PT68075B (de) | 1977-05-27 | 1978-05-23 | Ciclopropansaureanilide fungizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| AT380578A AT360803B (de) | 1977-05-27 | 1978-05-24 | Fungizide mittel |
| PL1978207069A PL110646B1 (en) | 1977-05-27 | 1978-05-24 | Fungicide |
| ES470195A ES470195A1 (es) | 1977-05-27 | 1978-05-24 | Procedimiento para la preparacion de anilidas de acido ci- clopropancarboxilico |
| EG333/78A EG13373A (en) | 1977-05-27 | 1978-05-24 | Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and use |
| AR272308A AR220710A1 (es) | 1977-05-27 | 1978-05-24 | Nuevos derivados de n-(2-oxoperhidro-3-furil)-anilidas del acido ciclopropanocarboxilico;composiciones fungicidas que contienen estos compuestos,y procedimientos para producirlos |
| JP6212278A JPS53147061A (en) | 1977-05-27 | 1978-05-24 | Cyclopropanic acid anilide process for preparing same and mouldicide containing same |
| IE1029/78A IE46923B1 (en) | 1977-05-27 | 1978-05-24 | Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and use |
| DD78205587A DD136093A5 (de) | 1977-05-27 | 1978-05-25 | Fungizide mittel |
| LU79711A LU79711A1 (de) | 1977-05-27 | 1978-05-25 | Cyclopropancarbonsaeureanilide,fungizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| IT23774/78A IT1096326B (it) | 1977-05-27 | 1978-05-25 | Anilidi dell'acido ciclopropancarbossilico mezzi funghicidi contenenti tali composti e procedimento per la loro preparazione |
| RO7894166A RO75072A (ro) | 1977-05-27 | 1978-05-25 | Procedeu pentru prepararea unor anilide ale acizilor ciclopropancarboxilici |
| SE7805994A SE442868B (sv) | 1977-05-27 | 1978-05-25 | Cyklopropankarbonsyraanilider med fungicid verkan samt deras anvendning i fungicida medel |
| CS783406A CS203192B2 (en) | 1977-05-27 | 1978-05-25 | Fungicide and method of producing its active components |
| AU36529/78A AU520353B2 (en) | 1977-05-27 | 1978-05-26 | Fungicidally active cyclopropanecarboxylic acid anilides |
| BE188101A BE867556A (fr) | 1977-05-27 | 1978-05-26 | Anilides d'acide cyclopropanecarboxylique, leur procede de preparation et leur utilisation |
| FR7815747A FR2392019A1 (fr) | 1977-05-27 | 1978-05-26 | Cyclopropane-carboxamides utilisables comme matieres actives de produits fongicides |
| NO781838A NO149430C (no) | 1977-05-27 | 1978-05-26 | Cyclopropancarboxylsyreanilider med fungicid virkning |
| SU782621101A SU784770A3 (ru) | 1977-05-27 | 1978-05-26 | Способ получени анилидов циклопропанкарбоновой кислоты |
| CH580678A CH633784A5 (en) | 1977-05-27 | 1978-05-26 | Cyclopropanecarboxanilides, fungicides containing these compounds, and a process for the preparation of the new compounds |
| HU78SCHE646A HU184201B (en) | 1977-05-27 | 1978-05-26 | Fungicide compositions containing anilides of cyclopropane-carboxylic acid and process for producing these compounds |
| BR7803382A BR7803382A (pt) | 1977-05-27 | 1978-05-26 | Anilidas de acido ciclopropanocarboxilico,processo para sua fabricacao e composicoes fungicidas contendo esses compostos |
| SU782621053A SU727107A3 (ru) | 1977-05-27 | 1978-05-26 | Фунгицидное средство |
| DK233878A DK233878A (da) | 1977-05-27 | 1978-05-26 | Cyklopropancarboxylsyreanilider til anvendelse som fungcider samt fremgangsmaade til fremstilling deraf |
| ZA00783036A ZA783036B (en) | 1977-05-27 | 1978-05-26 | Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and use |
| GR56344A GR72966B (enrdf_load_stackoverflow) | 1977-05-27 | 1978-05-26 | |
| BG039862A BG28688A3 (bg) | 1977-05-27 | 1978-05-26 | Фунгицидно средство |
| KE3241A KE3241A (en) | 1977-05-27 | 1982-10-28 | Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and use |
| MY210/83A MY8300210A (en) | 1977-05-27 | 1983-12-30 | Fungicidally active cyclopropanecarboxylic acid anilides and their manufacture and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2724786A DE2724786C2 (de) | 1977-05-27 | 1977-05-27 | Cyclopropancarbonsäure-[N-(2-oxoperhydro-3-furyl)-anilide], Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende fungizide Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2724786A1 DE2724786A1 (de) | 1978-12-14 |
| DE2724786C2 true DE2724786C2 (de) | 1986-07-24 |
Family
ID=6010435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2724786A Expired DE2724786C2 (de) | 1977-05-27 | 1977-05-27 | Cyclopropancarbonsäure-[N-(2-oxoperhydro-3-furyl)-anilide], Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende fungizide Mittel |
Country Status (39)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440780A (en) * | 1979-06-01 | 1984-04-03 | Chevron Research Company | Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones |
| EP0016985A1 (de) * | 1979-03-16 | 1980-10-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Substituierte Anilide, Verfahren zu deren Herstellung, fungicide Mittel enthaltend solche Verbindungen sowie Verwendung solcher Verbindungen bzw. Mittel zur Bekämpfung von Pflanzenfungi |
| DE2920435A1 (de) * | 1979-05-19 | 1980-12-04 | Basf Ag | 2-aminopropanalacetale, verfahren zu ihrer herstellung, ihre anwendung als fungizide und verfahren zur herstellung von substituierten anilinen |
| US4599351A (en) * | 1981-08-14 | 1986-07-08 | Chevron Research Company | Fungicidal 3-(N-acyl-N-arylamino) lactones |
| JPS61186735U (enrdf_load_stackoverflow) * | 1985-05-14 | 1986-11-21 |
-
1977
- 1977-05-27 DE DE2724786A patent/DE2724786C2/de not_active Expired
-
1978
- 1978-04-24 FI FI781264A patent/FI68397C/fi not_active IP Right Cessation
- 1978-05-09 YU YU1102/78A patent/YU40192B/xx unknown
- 1978-05-11 MX MX787079U patent/MX5224E/es unknown
- 1978-05-12 CA CA303,250A patent/CA1108161A/en not_active Expired
- 1978-05-15 PH PH21136A patent/PH15700A/en unknown
- 1978-05-16 IL IL54719A patent/IL54719A/xx unknown
- 1978-05-18 NL NL7805404A patent/NL7805404A/xx not_active Application Discontinuation
- 1978-05-18 TR TR20568A patent/TR20568A/xx unknown
- 1978-05-23 GB GB21326/78A patent/GB1603730A/en not_active Expired
- 1978-05-23 PT PT68075A patent/PT68075B/pt unknown
- 1978-05-23 CY CY1163A patent/CY1163A/en unknown
- 1978-05-24 PL PL1978207069A patent/PL110646B1/pl unknown
- 1978-05-24 AR AR272308A patent/AR220710A1/es active
- 1978-05-24 ES ES470195A patent/ES470195A1/es not_active Expired
- 1978-05-24 EG EG333/78A patent/EG13373A/xx active
- 1978-05-24 JP JP6212278A patent/JPS53147061A/ja active Granted
- 1978-05-24 AT AT380578A patent/AT360803B/de not_active IP Right Cessation
- 1978-05-24 IE IE1029/78A patent/IE46923B1/en unknown
- 1978-05-25 CS CS783406A patent/CS203192B2/cs unknown
- 1978-05-25 RO RO7894166A patent/RO75072A/ro unknown
- 1978-05-25 DD DD78205587A patent/DD136093A5/xx unknown
- 1978-05-25 SE SE7805994A patent/SE442868B/sv not_active IP Right Cessation
- 1978-05-25 IT IT23774/78A patent/IT1096326B/it active
- 1978-05-25 LU LU79711A patent/LU79711A1/de unknown
- 1978-05-26 DK DK233878A patent/DK233878A/da not_active Application Discontinuation
- 1978-05-26 SU SU782621053A patent/SU727107A3/ru active
- 1978-05-26 GR GR56344A patent/GR72966B/el unknown
- 1978-05-26 BR BR7803382A patent/BR7803382A/pt unknown
- 1978-05-26 ZA ZA00783036A patent/ZA783036B/xx unknown
- 1978-05-26 BE BE188101A patent/BE867556A/xx not_active IP Right Cessation
- 1978-05-26 AU AU36529/78A patent/AU520353B2/en not_active Expired
- 1978-05-26 HU HU78SCHE646A patent/HU184201B/hu unknown
- 1978-05-26 BG BG039862A patent/BG28688A3/xx unknown
- 1978-05-26 FR FR7815747A patent/FR2392019A1/fr active Granted
- 1978-05-26 NO NO781838A patent/NO149430C/no unknown
- 1978-05-26 SU SU782621101A patent/SU784770A3/ru active
- 1978-05-26 CH CH580678A patent/CH633784A5/de not_active IP Right Cessation
-
1982
- 1982-10-28 KE KE3241A patent/KE3241A/xx unknown
-
1983
- 1983-12-30 MY MY210/83A patent/MY8300210A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |