CH597754A5 - Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes - Google Patents

Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes

Info

Publication number: CH597754A5
Authority: CH; Switzerland
Prior art keywords: formula; larvae; test; parts; active substance
Prior art date: 1974-06-21

Application number

CH854274A

Other languages

German (de)

English (en)

Inventor

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.)

1974-06-21

Filing date

1974-06-21

Publication date

1978-04-14

1974-06-21 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1974-06-21 Priority to CH854274A priority Critical patent/CH597754A5/de

1975-06-16 Priority to CS422375A priority patent/CS185692B2/cs

1975-06-16 Priority to US05/587,446 priority patent/US4007280A/en

1975-06-18 Priority to DE19752526982 priority patent/DE2526982A1/de

1975-06-19 Priority to FR7519210A priority patent/FR2275475A1/fr

1975-06-19 Priority to DD186766A priority patent/DD119520A5/xx

1975-06-19 Priority to CA229,685A priority patent/CA1051010A/fr

1975-06-20 Priority to ZA00753981A priority patent/ZA753981B/xx

1975-06-20 Priority to BE157520A priority patent/BE830458A/fr

1975-06-20 Priority to AT477075A priority patent/AT344448B/de

1975-06-20 Priority to BR5000/75D priority patent/BR7503889A/pt

1975-06-20 Priority to SU752149358A priority patent/SU686597A3/ru

1975-06-20 Priority to NL7507414A priority patent/NL7507414A/xx

1975-06-20 Priority to IL7547532A priority patent/IL47532A/xx

1975-06-20 Priority to GB26384/75A priority patent/GB1509005A/en

1975-06-21 Priority to JP50076429A priority patent/JPS5115615A/ja

1978-04-14 Publication of CH597754A5 publication Critical patent/CH597754A5/de

Links

230000000895 acaricidal effect Effects 0.000 title claims abstract description 6
230000000749 insecticidal effect Effects 0.000 title abstract description 3
HIXGTRAZUVJNHQ-UHFFFAOYSA-N 3-methyl-3-phenoxy-2h-1,4-benzodioxine Chemical class C1OC2=CC=CC=C2OC1(C)OC1=CC=CC=C1 HIXGTRAZUVJNHQ-UHFFFAOYSA-N 0.000 title abstract 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 23
239000004480 active ingredient Substances 0.000 claims description 21
230000000694 effects Effects 0.000 claims description 20
241001465754 Metazoa Species 0.000 claims description 13
239000013543 active substance Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
239000007921 spray Substances 0.000 claims description 5
241000256118 Aedes aegypti Species 0.000 claims description 4
241001127120 Dysdercus fasciatus Species 0.000 claims description 4
241000630736 Ephestia Species 0.000 claims description 4
244000046052 Phaseolus vulgaris Species 0.000 claims description 4
241001454293 Tetranychus urticae Species 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
235000013601 eggs Nutrition 0.000 claims description 4
235000013312 flour Nutrition 0.000 claims description 4
241000196324 Embryophyta Species 0.000 claims description 3
241000607479 Yersinia pestis Species 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
238000004587 chromatography analysis Methods 0.000 claims description 3
239000000428 dust Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000000575 pesticide Substances 0.000 claims description 3
229920000742 Cotton Polymers 0.000 claims description 2
241000238631 Hexapoda Species 0.000 claims description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
241000254109 Tenebrio molitor Species 0.000 claims description 2
241001454295 Tetranychidae Species 0.000 claims description 2
241000209140 Triticum Species 0.000 claims description 2
235000021307 Triticum Nutrition 0.000 claims description 2
235000005489 dwarf bean Nutrition 0.000 claims description 2
238000011156 evaluation Methods 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
-1 benzyl benzoyl phenoxy Chemical group 0.000 abstract description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
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 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000008187 granular material Substances 0.000 description 7
239000000126 substance Substances 0.000 description 6
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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000000654 additive Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
241000257226 Muscidae Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
239000004615 ingredient Substances 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
239000000843 powder Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UPRYYMANANICCT-UHFFFAOYSA-N 2,3,4,6-tetrahydropyrano[2,3-c]pyran Chemical class O1CCCC=2C1=COCC=2 UPRYYMANANICCT-UHFFFAOYSA-N 0.000 description 1
BDXDDNWSRKWZNG-UHFFFAOYSA-N 3-(phenoxymethylidene)-1,4-benzodioxine Chemical class C1OC2=CC=CC=C2OC1=COC1=CC=CC=C1 BDXDDNWSRKWZNG-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000907223 Bruchinae Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001124134 Chrysomelidae Species 0.000 description 1
241001414835 Cimicidae Species 0.000 description 1
241000255749 Coccinellidae Species 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
241000254171 Curculionidae Species 0.000 description 1
241001466044 Delphacidae Species 0.000 description 1
241000131287 Dermestidae Species 0.000 description 1
241001414830 Diaspididae Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
241000238816 Gryllidae Species 0.000 description 1
241001243087 Gryllotalpidae Species 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
241000530268 Lycaena heteronea Species 0.000 description 1
241001124557 Lymantriidae Species 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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
241001415279 Pseudococcidae Species 0.000 description 1
241000255893 Pyralidae Species 0.000 description 1
241001510071 Pyrrhocoridae Species 0.000 description 1
241001124072 Reduviidae Species 0.000 description 1
241000254062 Scarabaeidae Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000254107 Tenebrionidae Species 0.000 description 1
241000896028 Tettigoniidae Species 0.000 description 1
241000130767 Tineidae Species 0.000 description 1
241000131339 Tipulidae Species 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 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
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229920005551 calcium lignosulfonate Polymers 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
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000003054 catalyst Substances 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
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal 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
229910052757 nitrogen Inorganic materials 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
150000002903 organophosphorus compounds Chemical class 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 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
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 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
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CH854274A 1974-06-21 1974-06-21 Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes CH597754A5 (en)

Priority Applications (16)

Application Number	Priority Date	Filing Date	Title
CH854274A CH597754A5 (en)	1974-06-21	1974-06-21	Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes
CS422375A CS185692B2 (en)	1974-06-21	1975-06-16	Insecticide agent and mode of manufacture of active substances
US05/587,446 US4007280A (en)	1974-06-21	1975-06-16	1,4-Benzodioxan derivatives and pesticidal use thereof
DE19752526982 DE2526982A1 (de)	1974-06-21	1975-06-18	2-phenoxymethylen-1,4-benzodioxan- derivate
FR7519210A FR2275475A1 (fr)	1974-06-21	1975-06-19	Nouveaux derives de 2-phenoxy-methylen-1,4-benzodioxanne utiles comme agents anti-parasitaires
DD186766A DD119520A5 (fr)	1974-06-21	1975-06-19
CA229,685A CA1051010A (fr)	1974-06-21	1975-06-19	Ethers
ZA00753981A ZA753981B (en)	1974-06-21	1975-06-20	New ethers
BE157520A BE830458A (fr)	1974-06-21	1975-06-20	Nouveaux derives de 2-phenoxy-methylen-1,4-benzodioxanne utiles comme agents anti-parasitaires
AT477075A AT344448B (de)	1974-06-21	1975-06-20	Insektizide mittel
BR5000/75D BR7503889A (pt)	1974-06-21	1975-06-20	Processo para a obtencao de novos compostos,composicoes para combate aos parasitas,e aplicacao dos ditos compostos
SU752149358A SU686597A3 (ru)	1974-06-21	1975-06-20	Инсектицидное средство
NL7507414A NL7507414A (nl)	1974-06-21	1975-06-20	Werkwijze voor het bereiden van ethers, werkwijze voor het bereiden van preparaten met een werking tegen schadelijke organismen, alsmede de gevormde preparaten.
IL7547532A IL47532A (en)	1974-06-21	1975-06-20	2-(phenoxymethyl)-1,4-benzodioxane derivatives, their manufacture and insecticidal and acaricidal compositions containing them
GB26384/75A GB1509005A (en)	1974-06-21	1975-06-20	2-phenoxymethylene-1,4-benzodioxan derivatives
JP50076429A JPS5115615A (en)	1974-06-21	1975-06-21	Jugaiseibutsubojozaioyobi sonoseiho

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH854274A CH597754A5 (en)	1974-06-21	1974-06-21	Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes

Publications (1)

Publication Number	Publication Date
CH597754A5 true CH597754A5 (en)	1978-04-14

Family

ID=4341749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH854274A CH597754A5 (en)	1974-06-21	1974-06-21	Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes

Country Status (3)

Country	Link
BE (1)	BE830458A (fr)
CH (1)	CH597754A5 (fr)
ZA (1)	ZA753981B (fr)

1974
- 1974-06-21 CH CH854274A patent/CH597754A5/de not_active IP Right Cessation
1975
- 1975-06-20 ZA ZA00753981A patent/ZA753981B/xx unknown
- 1975-06-20 BE BE157520A patent/BE830458A/fr unknown

Also Published As

Publication number	Publication date
BE830458A (fr)	1975-12-22
ZA753981B (en)	1976-05-26

Legal Events

Date	Code	Title	Description
1981-02-27	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2418295C2 (de)	1986-04-03	Substituierte Benzyloxydiphenyläther, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
DE2637395C2 (fr)	1987-12-03
DE2418343A1 (de)	1974-11-07	Phenyl-aralkyl-aether, -thioaether und -amine, verfahren zu ihrer herstellung und ihre verwendung
DE2516331A1 (de)	1975-11-06	Phenylaralkyl-aether und -thioaether
DE2526982A1 (de)	1976-01-08	2-phenoxymethylen-1,4-benzodioxan- derivate
DE2516382A1 (de)	1975-11-06	Phenyl-aralkyl-aether, -thioaether und -amine
DE2547146A1 (de)	1976-05-06	4-substituierte diphenylaether-derivate, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
CH592411A5 (en)	1977-10-31	Phenoxymethyl- and phenylthiomethyl-pyridine derivs - with insecticidal, acaricidal and plant-growth regulating activity
DE2547167A1 (de)	1976-05-06	Neue diphenylemethan- und diphenylthioaether-derivate
DE2528314A1 (de)	1976-01-15	Phenylalkinylaether-derivate
DE2418572A1 (de)	1974-11-14	Neue phenoxy-benzylaether
DE2520177A1 (de)	1975-11-27	Diaether
CH597754A5 (en)	1978-04-14	Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes
DE2418571A1 (de)	1974-11-14	Phenyl-aralkyl-aether, diphenyle und benzophenone, verfahren zu ihrer herstellung und ihre verwendung
DE2616755A1 (de)	1976-10-28	Diaether, verfahren zu ihrer herstellung und ihre verwendung
DE2528345A1 (de)	1976-01-08	Phenylalkinylaether, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
DE2727614A1 (de)	1978-01-05	N,n'-bis-carbaminsaeure-sulfid-derivate, verfahren zu ihrer herstellung sowie schaedlingsbekaempfungsmittel
CH604501A5 (en)	1978-09-15	Insecticidal and acaricidal 2-phenoxy-methyl 1,4-benzodioxanes
DE2518019A1 (de)	1975-11-13	Neue diphenylaether und -thioaether
CH595044A5 (en)	1978-01-31	1-Benzyl or benzoyl-4-(omega phenoxyalkoxy)benzenes
DE2604282A1 (de)	1976-08-19	Neue acetale
DE2637912A1 (de)	1977-03-10	Neue diaether
CH600759A5 (en)	1978-06-30	4-((2-Hydrocarbyl(thi)oxy)ethoxy)diphenyl ethers
DE2637887A1 (de)	1977-03-10	Neue aether
CH593006A5 (en)	1977-11-15	Phenyl aralkyl-amines, ethers and thioethers - with insecticidal and acaricidal activity