NZ202309A - Fungicidal n-phenylcarbamates - Google Patents
Fungicidal n-phenylcarbamatesInfo
- Publication number
- NZ202309A NZ202309A NZ202309A NZ20230982A NZ202309A NZ 202309 A NZ202309 A NZ 202309A NZ 202309 A NZ202309 A NZ 202309A NZ 20230982 A NZ20230982 A NZ 20230982A NZ 202309 A NZ202309 A NZ 202309A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- methyl
- halogen
- formula
- ethyl
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 34
- -1 cyclic imide Chemical class 0.000 claims abstract description 105
- 239000000417 fungicide Substances 0.000 claims abstract description 57
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims abstract description 45
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 claims abstract description 23
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 21
- 241000233866 Fungi Species 0.000 claims abstract description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 87
- 239000003814 drug Substances 0.000 claims description 69
- 229940079593 drug Drugs 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 230000002265 prevention Effects 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 230000003449 preventive effect Effects 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 claims description 15
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 244000000004 fungal plant pathogen Species 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 6
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 6
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
- LNJNFVJKDJYTEU-UHFFFAOYSA-N diethofencarb Chemical compound CCOC1=CC=C(NC(=O)OC(C)C)C=C1OCC LNJNFVJKDJYTEU-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- RQMCRDJXPIVZJN-UHFFFAOYSA-N 1-phenylethyl n-(3,4-diethoxyphenyl)carbamate Chemical compound C1=C(OCC)C(OCC)=CC=C1NC(=O)OC(C)C1=CC=CC=C1 RQMCRDJXPIVZJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 101100125350 Candida albicans (strain SC5314 / ATCC MYA-2876) HYR3 gene Proteins 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
- IGUYEXXAGBDLLX-UHFFFAOYSA-N ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-1,3-oxazolidine-5-carboxylate Chemical compound O=C1C(C(=O)OCC)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 IGUYEXXAGBDLLX-UHFFFAOYSA-N 0.000 claims description 2
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 230000001717 pathogenic effect Effects 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 238000002474 experimental method Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000004615 ingredient Substances 0.000 description 15
- 240000008067 Cucumis sativus Species 0.000 description 14
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 14
- 239000004563 wettable powder Substances 0.000 description 14
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 239000004495 emulsifiable concentrate Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- 230000001276 controlling effect Effects 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000005842 Thiophanate-methyl Substances 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 7
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- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 6
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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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D307/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
- Materials For Medical Uses (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17404381A JPH0239503B2 (ja) | 1981-10-29 | 1981-10-29 | Nnfuenirukaabameetokeikagobutsu*sonoseizohooyobisoreojukoseibuntosurunoengeiyosatsukinzai |
| JP57007257A JPS58126856A (ja) | 1982-01-19 | 1982-01-19 | Ｎ―フェニルカーバメート系化合物を有効成分とする農園芸用殺菌剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ202309A true NZ202309A (en) | 1985-07-31 |
Family
ID=26341531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ202309A NZ202309A (en) | 1981-10-29 | 1982-10-28 | Fungicidal n-phenylcarbamates |
Country Status (21)
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605668A (en) * | 1983-05-17 | 1986-08-12 | Sumitomo Chemical Company, Limited | Fungicidal carbamate compounds |
| US4617417A (en) * | 1985-07-29 | 1986-10-14 | Ortho Pharmaceutical Corporation | Alkyl 2-carboalkoxy-3,4-dialkoxybenzenecarbamates and process for their preparation |
| US4825271A (en) * | 1986-05-20 | 1989-04-25 | Kabushiki Kaisha Toshiba | Nonvolatile semiconductor memory |
| US4797416A (en) * | 1987-01-05 | 1989-01-10 | Stauffer Chemical Co. | Fungicidal carbanilates |
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| DE10019758A1 (de) | 2000-04-20 | 2001-10-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE10141618A1 (de) * | 2001-08-24 | 2003-03-06 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| EP2255627A3 (de) | 2004-04-30 | 2012-09-26 | Basf Se | Fungizide Mischungen |
| ATE484194T1 (de) | 2005-06-09 | 2010-10-15 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
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| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| EP2410850A2 (de) | 2009-03-25 | 2012-02-01 | Bayer Cropscience AG | Synergistische wirkstoffkombinationen |
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|---|---|---|---|---|
| US3933470A (en) * | 1972-06-30 | 1976-01-20 | American Cyanamid Company | Ester of (alkynyloxy)-, (alkenyloxy)-, and (cyanoalkoxy) carbanilic acids and their use as herbicides |
| US3997325A (en) * | 1973-05-24 | 1976-12-14 | American Cyanamid Company | (Alkynyloxy)alkyl and (alkenyloxy)alkyl carbamates and their use as herbicides |
| DE2330242A1 (de) * | 1973-06-14 | 1975-01-09 | Bayer Ag | Fluorhaltige n-phenylcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| HU172341B (hu) * | 1975-05-06 | 1978-08-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija proizvodnykh karbamida |
| GR76941B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-11-07 | 1984-09-04 | Sumitomo Chemical Co | |
| NZ200242A (en) * | 1981-04-16 | 1985-08-30 | Sumitomo Chemical Co | N-phenyl carbamates and fungicidal compositions |
-
1982
- 1982-10-22 OA OA57829A patent/OA07237A/xx unknown
- 1982-10-22 US US06/436,073 patent/US4608385A/en not_active Expired - Lifetime
- 1982-10-26 GR GR69641A patent/GR76753B/el unknown
- 1982-10-27 PH PH28041A patent/PH20007A/en unknown
- 1982-10-27 DE DE8282305714T patent/DE3263156D1/de not_active Expired
- 1982-10-27 IL IL67083A patent/IL67083A/xx not_active IP Right Cessation
- 1982-10-27 EP EP82305714A patent/EP0078663B1/en not_active Expired
- 1982-10-27 BR BR8206275A patent/BR8206275A/pt unknown
- 1982-10-27 TR TR21609A patent/TR21609A/xx unknown
- 1982-10-27 AT AT82305714T patent/ATE12766T1/de not_active IP Right Cessation
- 1982-10-28 HU HU823465A patent/HU191823B/hu unknown
- 1982-10-28 NZ NZ202309A patent/NZ202309A/en unknown
- 1982-10-28 HU HU864178A patent/HU195081B/hu unknown
- 1982-10-28 KR KR8204855A patent/KR890000482B1/ko not_active Expired
- 1982-10-29 CS CS827698A patent/CS236688B2/cs unknown
- 1982-10-29 ES ES516989A patent/ES516989A0/es active Granted
- 1982-10-29 AU AU89891/82A patent/AU551861B2/en not_active Expired
- 1982-10-29 DK DK482282A patent/DK170436B1/da not_active IP Right Cessation
- 1982-10-29 CA CA000414465A patent/CA1196337A/en not_active Expired
- 1982-10-29 BG BG058442A patent/BG47643A3/xx unknown
- 1982-10-29 PT PT75765A patent/PT75765B/pt unknown
-
1983
- 1983-06-29 ES ES523698A patent/ES8403861A1/es not_active Expired
-
1984
- 1984-03-13 PH PH30389A patent/PH20034A/en unknown
-
1986
- 1986-07-25 PH PH34065A patent/PH21819A/en unknown
-
1987
- 1987-12-30 MY MY619/87A patent/MY8700619A/xx unknown
-
1988
- 1988-10-11 KR KR1019880013244A patent/KR890001531B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR8206275A (pt) | 1983-09-20 |
| CS236688B2 (en) | 1985-05-15 |
| TR21609A (tr) | 1984-11-26 |
| GR76753B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-08-30 |
| CA1196337A (en) | 1985-11-05 |
| ES8401017A1 (es) | 1983-12-01 |
| ES523698A0 (es) | 1984-04-01 |
| IL67083A0 (en) | 1983-02-23 |
| ATE12766T1 (de) | 1985-05-15 |
| ES8403861A1 (es) | 1984-04-01 |
| EP0078663B1 (en) | 1985-04-17 |
| HU191823B (en) | 1987-04-28 |
| US4608385A (en) | 1986-08-26 |
| DK482282A (da) | 1983-04-30 |
| BG47643A3 (en) | 1990-08-15 |
| PH20034A (en) | 1986-09-04 |
| PH21819A (en) | 1988-03-04 |
| KR890000482B1 (ko) | 1989-03-18 |
| KR890001531B1 (ko) | 1989-05-06 |
| MY8700619A (en) | 1987-12-31 |
| PT75765B (en) | 1985-10-04 |
| DE3263156D1 (de) | 1985-05-23 |
| AU8989182A (en) | 1983-05-05 |
| ES516989A0 (es) | 1983-12-01 |
| AU551861B2 (en) | 1986-05-15 |
| KR840001805A (ko) | 1984-06-07 |
| EP0078663A3 (en) | 1983-08-03 |
| PT75765A (en) | 1982-11-01 |
| IL67083A (en) | 1988-02-29 |
| PH20007A (en) | 1986-08-28 |
| HU195081B (en) | 1988-04-28 |
| OA07237A (en) | 1984-04-30 |
| EP0078663A2 (en) | 1983-05-11 |
| DK170436B1 (da) | 1995-09-04 |
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