DE2422977C2 - Cyclopropan-carbonsäure-α-cyanbenzylester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pestizide Mittel - Google Patents
Cyclopropan-carbonsäure-α-cyanbenzylester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pestizide MittelInfo
- Publication number
- DE2422977C2 DE2422977C2 DE2422977A DE2422977A DE2422977C2 DE 2422977 C2 DE2422977 C2 DE 2422977C2 DE 2422977 A DE2422977 A DE 2422977A DE 2422977 A DE2422977 A DE 2422977A DE 2422977 C2 DE2422977 C2 DE 2422977C2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- preparation
- alpha
- processes
- agents containing
- 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 19
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 6
- 230000000361 pesticidal effect Effects 0.000 title description 4
- POGISOCYCQEQTF-UHFFFAOYSA-N [cyano(phenyl)methyl] cyclopropanecarboxylate Chemical compound C1CC1C(=O)OC(C#N)C1=CC=CC=C1 POGISOCYCQEQTF-UHFFFAOYSA-N 0.000 title 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002946 cyanobenzyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- -1 phenoxy, tolyloxy, propargyloxy Chemical group 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000003197 gene knockdown Methods 0.000 description 4
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- 239000000575 pesticide Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- YUBCVMNXGPVXID-UHFFFAOYSA-N 2,2-dichloro-3,3-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(Cl)Cl YUBCVMNXGPVXID-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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- 241000335053 Beta vulgaris Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- 241000257226 Muscidae Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000370092 Actiniopteris Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
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- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
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- 230000008021 deposition Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
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- 150000004665 fatty acids Chemical class 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 150000002334 glycols Chemical class 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004062 sedimentation Methods 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
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2297073A GB1437815A (en, 2012) | 1973-05-15 | 1973-05-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2422977A1 DE2422977A1 (de) | 1974-12-05 |
| DE2422977C2 true DE2422977C2 (de) | 1984-01-12 |
Family
ID=10187998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2422977A Expired DE2422977C2 (de) | 1973-05-15 | 1974-05-13 | Cyclopropan-carbonsäure-α-cyanbenzylester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pestizide Mittel |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3914274A (en, 2012) |
| JP (1) | JPS5821602B2 (en, 2012) |
| AR (1) | AR215114A1 (en, 2012) |
| AT (1) | AT334136B (en, 2012) |
| BE (1) | BE814819A (en, 2012) |
| BR (1) | BR7403875D0 (en, 2012) |
| CA (1) | CA1048530A (en, 2012) |
| CH (1) | CH592409A5 (en, 2012) |
| CS (1) | CS185652B2 (en, 2012) |
| DD (1) | DD113429A5 (en, 2012) |
| DE (1) | DE2422977C2 (en, 2012) |
| DK (1) | DK136600B (en, 2012) |
| EG (1) | EG11355A (en, 2012) |
| ES (1) | ES426266A1 (en, 2012) |
| FR (1) | FR2229689B1 (en, 2012) |
| GB (1) | GB1437815A (en, 2012) |
| HU (1) | HU168107B (en, 2012) |
| IL (1) | IL44807A (en, 2012) |
| IT (1) | IT1053763B (en, 2012) |
| NL (1) | NL189040C (en, 2012) |
| OA (1) | OA04662A (en, 2012) |
| PH (1) | PH11747A (en, 2012) |
| TR (1) | TR17825A (en, 2012) |
| YU (1) | YU36370B (en, 2012) |
| ZA (1) | ZA743030B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1562908A (en) * | 1976-12-09 | 1980-03-19 | Ici Ltd | Insecticidal compostions |
| GB1595081A (en) * | 1977-02-08 | 1981-08-05 | Shell Int Research | Pesticidal composition |
| GB1594462A (en) * | 1977-02-09 | 1981-07-30 | Shell Int Research | Pesticidal composition |
| US4299843A (en) * | 1977-09-26 | 1981-11-10 | Shell Oil Company | Stabilized cyandhydrin ester |
| US4259349A (en) | 1978-10-13 | 1981-03-31 | Shell Oil Company | Halobenzyl ester pesticides |
| DE2918023A1 (de) * | 1979-05-04 | 1980-11-13 | Bayer Ag | Verfahren zur herstellung von n-alkylierten aromatischen aminen |
| JPH02123516U (en, 2012) * | 1989-03-20 | 1990-10-11 | ||
| JPH07217540A (ja) * | 1994-01-28 | 1995-08-15 | Fumio Morigami | 防水剤吹き付け用ポンプのポンピングチューブ |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794926A (fr) * | 1971-04-23 | 1973-08-02 | Shell Int Research | Compositions biologiquement actives |
| GB1331706A (en) * | 1971-04-23 | 1973-09-26 | Shell Int Research | Cyclopropane derivatives and biologicall active compositions thereof |
| JPS515450B1 (en, 2012) * | 1971-06-29 | 1976-02-20 |
-
1973
- 1973-05-15 GB GB2297073A patent/GB1437815A/en not_active Expired
-
1974
- 1974-05-10 BE BE1005941A patent/BE814819A/xx not_active IP Right Cessation
- 1974-05-10 CA CA74199487A patent/CA1048530A/en not_active Expired
- 1974-05-10 IT IT7422568A patent/IT1053763B/it active
- 1974-05-13 DE DE2422977A patent/DE2422977C2/de not_active Expired
- 1974-05-13 FR FR7416417A patent/FR2229689B1/fr not_active Expired
- 1974-05-13 DD DD178468A patent/DD113429A5/xx unknown
- 1974-05-13 AR AR253713A patent/AR215114A1/es active
- 1974-05-13 ZA ZA00743030A patent/ZA743030B/xx unknown
- 1974-05-13 CS CS7400003398A patent/CS185652B2/cs unknown
- 1974-05-13 HU HUSE1727A patent/HU168107B/hu not_active IP Right Cessation
- 1974-05-13 CH CH651274A patent/CH592409A5/xx not_active IP Right Cessation
- 1974-05-13 BR BR3875/74A patent/BR7403875D0/pt unknown
- 1974-05-13 OA OA55201A patent/OA04662A/xx unknown
- 1974-05-13 US US469134A patent/US3914274A/en not_active Expired - Lifetime
- 1974-05-13 NL NLAANVRAGE7406384,A patent/NL189040C/xx not_active IP Right Cessation
- 1974-05-13 DK DK261074AA patent/DK136600B/da not_active IP Right Cessation
- 1974-05-13 EG EG170/74A patent/EG11355A/xx active
- 1974-05-13 PH PH15830A patent/PH11747A/en unknown
- 1974-05-13 IL IL44807A patent/IL44807A/en unknown
- 1974-05-13 AT AT394274A patent/AT334136B/de not_active IP Right Cessation
- 1974-05-13 TR TR17825A patent/TR17825A/xx unknown
- 1974-05-13 JP JP49052366A patent/JPS5821602B2/ja not_active Expired
- 1974-05-13 ES ES426266A patent/ES426266A1/es not_active Expired
- 1974-05-13 YU YU01318/74A patent/YU36370B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PH11747A (en) | 1978-06-05 |
| OA04662A (fr) | 1980-07-31 |
| AU6886874A (en) | 1975-11-13 |
| HU168107B (en, 2012) | 1976-02-28 |
| EG11355A (en) | 1977-03-31 |
| FR2229689A1 (en, 2012) | 1974-12-13 |
| NL189040B (nl) | 1992-07-16 |
| CA1048530A (en) | 1979-02-13 |
| AT334136B (de) | 1976-12-27 |
| IL44807A (en) | 1977-08-31 |
| NL189040C (nl) | 1992-12-16 |
| FR2229689B1 (en, 2012) | 1977-10-21 |
| DK136600C (en, 2012) | 1978-05-16 |
| BR7403875D0 (pt) | 1974-12-24 |
| ATA394274A (de) | 1976-04-15 |
| BE814819A (nl) | 1974-11-12 |
| YU131874A (en) | 1981-11-13 |
| CS185652B2 (en) | 1978-10-31 |
| DK136600B (da) | 1977-10-31 |
| ES426266A1 (es) | 1976-11-01 |
| IT1053763B (it) | 1981-10-10 |
| NL7406384A (en, 2012) | 1974-11-19 |
| YU36370B (en) | 1983-06-30 |
| DD113429A5 (en, 2012) | 1975-06-12 |
| IL44807A0 (en) | 1974-07-31 |
| JPS5030849A (en, 2012) | 1975-03-27 |
| CH592409A5 (en, 2012) | 1977-10-31 |
| US3914274A (en) | 1975-10-21 |
| JPS5821602B2 (ja) | 1983-05-02 |
| DE2422977A1 (de) | 1974-12-05 |
| ZA743030B (en) | 1975-05-28 |
| AR215114A1 (es) | 1979-09-14 |
| TR17825A (tr) | 1976-04-13 |
| GB1437815A (en, 2012) | 1976-06-03 |
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Legal Events
| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C121/75 |
|
| 8126 | Change of the secondary classification |
Ipc: A01N 53/00 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |