CH604522A5 - (4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters - Google Patents

(4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters

Info

Publication number: CH604522A5
Authority: CH; Switzerland
Prior art keywords: sep; parts; formula; compound; larvae
Prior art date: 1975-09-26

Application number

CH1256675A

Other languages

German (de)

English (en)

Inventor

Saleem Dr Farooq

Laurenz Dr Gsell

Willy Meyer

Jozef Dr Drabek

Friedrich Dr Karrer

Original Assignee

Ciba Geigy Ag

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

1975-09-26

Filing date

1975-09-26

Publication date

1978-09-15

1975-09-26 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-09-26 Priority to CH1256675A priority Critical patent/CH604522A5/de

1976-09-17 Priority to US05/724,141 priority patent/US4072752A/en

1976-09-21 Priority to EG578/76A priority patent/EG12490A/xx

1976-09-21 Priority to FR7628295A priority patent/FR2325634A1/fr

1976-09-22 Priority to SU762403304A priority patent/SU668568A3/ru

1976-09-23 Priority to NL7610579A priority patent/NL7610579A/xx

1976-09-23 Priority to TR19268A priority patent/TR19268A/xx

1976-09-23 Priority to DE19762642850 priority patent/DE2642850A1/de

1976-09-24 Priority to ZA765732A priority patent/ZA765732B/xx

1976-09-24 Priority to BR7606368A priority patent/BR7606368A/pt

1976-09-24 Priority to BE170897A priority patent/BE846544A/fr

1976-09-24 Priority to AT711376A priority patent/AT344458B/de

1976-09-24 Priority to IL50552A priority patent/IL50552A/xx

1976-09-24 Priority to CA262,035A priority patent/CA1069921A/fr

1976-09-24 Priority to GB39785/76A priority patent/GB1555789A/en

1976-09-25 Priority to JP51115351A priority patent/JPS5242865A/ja

1978-09-15 Publication of CH604522A5 publication Critical patent/CH604522A5/de

Links

230000000895 acaricidal effect Effects 0.000 claims abstract description 8
239000000575 pesticide Substances 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 29
239000004480 active ingredient Substances 0.000 claims description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
241000258916 Leptinotarsa decemlineata Species 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
239000007921 spray Substances 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
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239000008187 granular material Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
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241000196324 Embryophyta Species 0.000 claims description 6
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
241000256250 Spodoptera littoralis Species 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
235000013601 eggs Nutrition 0.000 claims description 5
230000000749 insecticidal effect Effects 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
240000002024 Gossypium herbaceum Species 0.000 claims description 4
235000004341 Gossypium herbaceum Nutrition 0.000 claims description 4
244000061456 Solanum tuberosum Species 0.000 claims description 4
235000002595 Solanum tuberosum Nutrition 0.000 claims description 4
241001454293 Tetranychus urticae Species 0.000 claims description 4
239000004495 emulsifiable concentrate Substances 0.000 claims description 4
239000000839 emulsion Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
TXORZOOFFDVXQY-UHFFFAOYSA-N octa-5,7-dienoic acid Chemical compound OC(=O)CCCC=CC=C TXORZOOFFDVXQY-UHFFFAOYSA-N 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
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239000013543 active substance Substances 0.000 claims description 3
239000000470 constituent Substances 0.000 claims description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
231100000614 poison Toxicity 0.000 claims description 3
239000002574 poison Substances 0.000 claims description 3
239000000741 silica gel Substances 0.000 claims description 3
229910002027 silica gel Inorganic materials 0.000 claims description 3
UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 claims description 2
206010061217 Infestation Diseases 0.000 claims description 2
240000007594 Oryza sativa Species 0.000 claims description 2
244000046052 Phaseolus vulgaris Species 0.000 claims description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
238000004440 column chromatography Methods 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000004033 plastic Substances 0.000 claims description 2
229920003023 plastic Polymers 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
235000011152 sodium sulphate Nutrition 0.000 claims description 2
239000002435 venom Substances 0.000 claims 1
231100000611 venom Toxicity 0.000 claims 1
210000001048 venom Anatomy 0.000 claims 1
239000000642 acaricide Substances 0.000 abstract description 3
239000002917 insecticide Substances 0.000 abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
-1 2,2-dichlorovinyl radical Chemical group 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
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 5
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239000010695 polyglycol Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000000654 additive Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
241000238876 Acari Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
238000006243 chemical reaction Methods 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
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
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235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241000238888 Argasidae Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
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241001466044 Delphacidae Species 0.000 description 1
241001481702 Dermanyssidae Species 0.000 description 1
241001414830 Diaspididae Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
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JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
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 1
235000013877 carbamide Nutrition 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
239000013057 ectoparasiticide Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
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238000004817 gas chromatography Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1256675A 1975-09-26 1975-09-26 (4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters CH604522A5 (en)

Priority Applications (16)

Application Number	Priority Date	Filing Date	Title
CH1256675A CH604522A5 (en)	1975-09-26	1975-09-26	(4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters
US05/724,141 US4072752A (en)	1975-09-26	1976-09-17	Pesticidal benzaspiro carboxylates
EG578/76A EG12490A (en)	1975-09-26	1976-09-21	2,2-dimethyl-4,5-benzospiro(2,4)heptane-and 2,2-dimethyl-4,5-benzospiro(2,4)hepta-4,6-diene-1-carboxylates compounds,and their used as insecticide
FR7628295A FR2325634A1 (fr)	1975-09-26	1976-09-21	Nouveaux esters derives d'acides 4,5-benzospiro(2,4)heptane-1-carboxyliques utiles dans la lutte contre les parasites
SU762403304A SU668568A3 (ru)	1975-09-26	1976-09-22	Инсектицидное средство
NL7610579A NL7610579A (nl)	1975-09-26	1976-09-23	Nieuwe esters.
TR19268A TR19268A (tr)	1975-09-26	1976-09-23	Yeni esterler
DE19762642850 DE2642850A1 (de)	1975-09-26	1976-09-23	2,2-dimethyl-4,5-benzospiro(2,4)heptan- und 2,2-dimethyl-4,5-benzospiro (2,4)hepta-4,6-dien-1-carbonsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
ZA765732A ZA765732B (en)	1975-09-26	1976-09-24	New esters
BR7606368A BR7606368A (pt)	1975-09-26	1976-09-24	Compostos organicos,processo para a preparacao destes compostos,composicoes praguicidas e seu emprego
BE170897A BE846544A (fr)	1975-09-26	1976-09-24	Nouveaux esters derives d'acides 4,5-benzospiro (2,4)heptane-1-carboxyliques utiles dans la lutte contre les parasites
AT711376A AT344458B (de)	1975-09-26	1976-09-24	Mittel zur bekaempfung von insekten
IL50552A IL50552A (en)	1975-09-26	1976-09-24	3-(2,2-dichlorovinyloxy)benzyl esters of 2,2-dimethyl-4,5-benzospiro(2,4)-hept-4-ene(or hepta4,6-diene)-1-carboxylicacids, their preparation and pesticidal compostions containing them
CA262,035A CA1069921A (fr)	1975-09-26	1976-09-24	Esters
GB39785/76A GB1555789A (en)	1975-09-26	1976-09-24	4,5 benzospiro 2,4 heptane and hepta 4 6 diene 1 carboxylates and their use aspesticides
JP51115351A JPS5242865A (en)	1975-09-26	1976-09-25	Production of carboxylic acid ester and fighting agent containing same as effective component for harmful livings

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1256675A CH604522A5 (en)	1975-09-26	1975-09-26	(4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters

Publications (1)

Publication Number	Publication Date
CH604522A5 true CH604522A5 (en)	1978-09-15

Family

ID=4384221

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1256675A CH604522A5 (en)	1975-09-26	1975-09-26	(4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters

Country Status (5)

Country	Link
AT (1)	AT344458B (fr)
BE (1)	BE846544A (fr)
CH (1)	CH604522A5 (fr)
SU (1)	SU668568A3 (fr)
ZA (1)	ZA765732B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2947209A1 (de) *	1979-11-23	1981-06-11	Bayer Ag, 5090 Leverkusen	Fluor-substituierte spirocarbonsaeure-benzylester, verfahren zu ihrer herstellung und ihre verendung in schaedlingsbekaempfungsmitteln
US4480118A (en) *	1981-01-13	1984-10-30	Sumitomo Chemical Company, Limited	Carboxylic acid ester and an insecticidal and/or acaricidal composition containing the same

1975
- 1975-09-26 CH CH1256675A patent/CH604522A5/de not_active IP Right Cessation
1976
- 1976-09-22 SU SU762403304A patent/SU668568A3/ru active
- 1976-09-24 BE BE170897A patent/BE846544A/fr unknown
- 1976-09-24 ZA ZA765732A patent/ZA765732B/xx unknown
- 1976-09-24 AT AT711376A patent/AT344458B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE846544A (fr)	1977-03-24
ZA765732B (en)	1977-09-28
AT344458B (de)	1978-07-25
SU668568A3 (ru)	1979-06-15
ATA711376A (de)	1977-11-15

Legal Events

Date	Code	Title	Description
1982-05-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0001203B1 (fr)	1980-09-03	N-phényl-N'-benzoyl-urées, procédé pour leur préparation, produits les contenant, et leur utilisation comme pesticides
EP0004030B1 (fr)	1981-12-30	N-phényl-N'-fluorobenzoyl urées substituées, leurs procédés de préparation et leur utilisation comme pesticides
DE2731033A1 (de)	1978-01-26	2,2-dimethyl-3-isobutylcyclopropansaeureester
DE2706222A1 (de)	1977-08-18	Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2642850A1 (de)	1977-04-07	2,2-dimethyl-4,5-benzospiro(2,4)heptan- und 2,2-dimethyl-4,5-benzospiro (2,4)hepta-4,6-dien-1-carbonsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
CH604522A5 (en)	1978-09-15	(4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters
DE2727614A1 (de)	1978-01-05	N,n'-bis-carbaminsaeure-sulfid-derivate, verfahren zu ihrer herstellung sowie schaedlingsbekaempfungsmittel
CH643563A5 (en)	1984-06-15	1,3-Diaza-2-phosphacyclohexane derivatives
DE2642861A1 (de)	1977-04-07	2,2-dimethyl-4,5-benzospiro(2,4)heptan- und -hepta-4,6-dien-1-carbonsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
DE2719561A1 (de)	1977-11-17	Chrysanthemumsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
CH604521A5 (en)	1978-09-15	Dimethyl-benzo-spiro-heptane carboxylic esters
CH602010A5 (en)	1978-07-14	Alkynyloxy-benzyl-cyclopropane-carboxylates
DE2713651A1 (de)	1977-10-13	Spiro-(2,4)-hepta-1-carboxylate, verfahren zu ihrer herstellung und ihre verwendung
CH623985A5 (en)	1981-07-15	A pesticide
DE2654293A1 (de)	1977-06-08	Cyclopropancarbonsaeure-3-alkinyloxy- benzylester, verfahren zu ihrer herstellung und ihre verwendung
DE2642814A1 (de)	1977-04-07	2,2-dimethyl-4,5-benzospiro(2,4)heptan- und 2,2-dimethyl-4,5-benzospiro(2,4) hepta-4,6-dien-1-carbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
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CH627621A5 (en)	1982-01-29	Pesticide containing thio-substituted carbamic acid derivatives
CH575717A5 (en)	1976-05-31	S-Arylthioalkyl-O,S-dialkyl dithiophosphates - with insecticidal, acaricidal, fungicidal, nematocidal activity, etc.
CH573206A5 (en)	1976-03-15	Pesticidal 5-halo-1,2,4-triazol-3-yl carbamates - e.g. 1-isopropyl-5-chloro-1,2,4-triazol-3-yl dimethylcarbamate
CH602006A5 (en)	1978-07-14	Cyclopropane carboxylic esters
CH563120A5 (en)	1975-06-30	Benztriazinonylmethyl organophosphorus esters - insecticides acaricides, fungicides, bactericides and nematocides
CH578304A5 (en)	1976-08-13	S-(1-benzotriazolyl) dithiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity
CH576226A5 (en)	1976-06-15	Aralkyl phenyl ethers and thioethers - with acaricidal and insecticidal activity
CH571810A5 (en)	1976-01-30	N,N-dimethyl-N'-subst. formamidines - prepd. by reacting subst. S-methyl formamidinates with dimethylformamide dialkyl acetals