CH552341A - Schaedlingsbekaempfungsmittel. - Google Patents

Schaedlingsbekaempfungsmittel.

Info

Publication number: CH552341A
Authority: CH; Switzerland
Prior art keywords: larvae; test; formula; days; alkyl
Prior art date: 1971-03-17

Application number

CH393071A

Other languages

German (de)

English (en)

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.)

1971-03-17

Filing date

1971-03-17

Publication date

1974-08-15

1971-03-17 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1971-03-17 Priority to CH393071A priority Critical patent/CH552341A/de

1972-02-23 Priority to IL38819A priority patent/IL38819A/xx

1972-02-28 Priority to CA135,681A priority patent/CA1008864A/en

1972-03-09 Priority to SE7202993A priority patent/SE384512B/xx

1972-03-14 Priority to DD171323*A priority patent/DD104702A5/xx

1972-03-15 Priority to DD161554A priority patent/DD100959A5/xx

1972-03-15 Priority to PL1972154081A priority patent/PL83281B1/pl

1972-03-15 Priority to EG104/72*UA priority patent/EG10609A/xx

1972-03-15 Priority to BG019974A priority patent/BG20540A3/xx

1972-03-16 Priority to ES400823A priority patent/ES400823A1/es

1972-03-16 Priority to HUCI1217A priority patent/HU164399B/hu

1972-03-16 Priority to BE780769A priority patent/BE780769A/xx

1972-03-16 Priority to IT21958/72A priority patent/IT965042B/it

1972-03-16 Priority to DE19722212797 priority patent/DE2212797A1/de

1972-03-16 Priority to NL7203521A priority patent/NL7203521A/xx

1972-03-16 Priority to TR18551A priority patent/TR18551A/xx

1972-03-16 Priority to ZA721804A priority patent/ZA721804B/xx

1972-03-16 Priority to GB1243372A priority patent/GB1384737A/en

1972-03-16 Priority to DK122572A priority patent/DK132326C/da

1972-03-16 Priority to FR7209184A priority patent/FR2130325B1/fr

1972-03-16 Priority to AT222472A priority patent/AT311120B/de

1972-03-17 Priority to AR240999A priority patent/AR193073A1/es

1973-11-20 Priority to US417697A priority patent/US3903100A/en

1974-08-15 Publication of CH552341A publication Critical patent/CH552341A/de

1975-06-11 Priority to US05/585,992 priority patent/US3973011A/en

Links

230000003115 biocidal effect Effects 0.000 title description 2
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 title 1
239000003795 chemical substances by application Substances 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
230000000895 acaricidal effect Effects 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
239000000575 pesticide Substances 0.000 claims abstract description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
239000004480 active ingredient Substances 0.000 claims description 31
-1 oxadiazolyl compound Chemical class 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 10
241000196324 Embryophyta Species 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
239000002689 soil Substances 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
241000244206 Nematoda Species 0.000 claims description 7
239000000839 emulsion Substances 0.000 claims description 7
239000008187 granular material Substances 0.000 claims description 7
239000007921 spray Substances 0.000 claims description 7
241000426497 Chilo suppressalis Species 0.000 claims description 6
230000000749 insecticidal effect Effects 0.000 claims description 6
238000010790 dilution Methods 0.000 claims description 5
239000012895 dilution Substances 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 4
241000238876 Acari Species 0.000 claims description 4
235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 4
241000243784 Meloidogyne arenaria Species 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
241000949016 Rhipicephalus bursa Species 0.000 claims description 4
241000238680 Rhipicephalus microplus Species 0.000 claims description 4
240000003768 Solanum lycopersicum Species 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
241001454293 Tetranychus urticae Species 0.000 claims description 4
241000607479 Yersinia pestis Species 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
235000013601 eggs Nutrition 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
241001425390 Aphis fabae Species 0.000 claims description 3
244000046052 Phaseolus vulgaris Species 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
238000004587 chromatography analysis Methods 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
229920000742 Cotton Polymers 0.000 claims description 2
235000009161 Espostoa lanata Nutrition 0.000 claims description 2
240000001624 Espostoa lanata Species 0.000 claims description 2
206010061217 Infestation Diseases 0.000 claims description 2
240000007594 Oryza sativa Species 0.000 claims description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
238000011156 evaluation Methods 0.000 claims description 2
239000011521 glass Substances 0.000 claims description 2
230000001069 nematicidal effect Effects 0.000 claims description 2
239000004033 plastic Substances 0.000 claims description 2
229920003023 plastic Polymers 0.000 claims description 2
238000009331 sowing Methods 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 abstract description 12
125000003545 alkoxy group Chemical group 0.000 abstract description 6
229910052801 chlorine Inorganic materials 0.000 abstract description 5
229910052794 bromium Inorganic materials 0.000 abstract description 4
125000003342 alkenyl group Chemical group 0.000 abstract description 3
125000000304 alkynyl group Chemical group 0.000 abstract description 3
239000000642 acaricide Substances 0.000 abstract description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
230000006578 abscission Effects 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
230000000507 anthelmentic effect Effects 0.000 abstract 1
229940124339 anthelmintic agent Drugs 0.000 abstract 1
239000000921 anthelmintic agent Substances 0.000 abstract 1
229940121375 antifungal agent Drugs 0.000 abstract 1
239000000022 bacteriostatic agent Substances 0.000 abstract 1
230000003385 bacteriostatic effect Effects 0.000 abstract 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
239000002837 defoliant Substances 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
239000003750 molluscacide Substances 0.000 abstract 1
230000002013 molluscicidal effect Effects 0.000 abstract 1
239000005648 plant growth regulator Substances 0.000 abstract 1
239000012873 virucide Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000001424 substituent group Chemical group 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
239000000725 suspension Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
241000233866 Fungi Species 0.000 description 3
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
241000258916 Leptinotarsa decemlineata Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
241001124076 Aphididae Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
240000002024 Gossypium herbaceum Species 0.000 description 2
235000004341 Gossypium herbaceum Nutrition 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 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
244000061456 Solanum tuberosum Species 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000009835 boiling Methods 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 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
239000002270 dispersing agent Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000000706 filtrate Substances 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
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
KWYVCFQNDPCMSX-UHFFFAOYSA-N oxadiazol-4-ol Chemical compound OC1=CON=N1 KWYVCFQNDPCMSX-UHFFFAOYSA-N 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
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
150000003015 phosphoric acid halides Chemical class 0.000 description 2
230000003032 phytopathogenic effect Effects 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
INVHTFJJZGBKTM-UHFFFAOYSA-N 5-phenyl-1,2,4-oxadiazol-3-one Chemical compound OC1=NOC(C=2C=CC=CC=2)=N1 INVHTFJJZGBKTM-UHFFFAOYSA-N 0.000 description 1
SEIGTPRKKORVMS-UHFFFAOYSA-N 5-tert-butyl-1,2,4-oxadiazol-3-one Chemical compound CC(C)(C)C1=NC(O)=NO1 SEIGTPRKKORVMS-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
241000238888 Argasidae Species 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
241000238816 Gryllidae Species 0.000 description 1
241001243087 Gryllotalpidae Species 0.000 description 1
241000256244 Heliothis virescens Species 0.000 description 1
241000238631 Hexapoda 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
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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
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241000233654 Oomycetes Species 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
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241000256248 Spodoptera Species 0.000 description 1
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240000006677 Vicia faba Species 0.000 description 1
235000010749 Vicia faba Nutrition 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
MODZVIMSNXSQIH-UHFFFAOYSA-N ethyl benzenecarboximidate;hydron;chloride Chemical compound Cl.CCOC(=N)C1=CC=CC=C1 MODZVIMSNXSQIH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000002464 fungitoxic effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
238000000034 method Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 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
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
229940072033 potash Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 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
239000007787 solid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000004385 trihaloalkyl group Chemical group 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65306—Five-membered rings containing two nitrogen atoms
- C07F9/65318—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CH393071A 1971-03-17 1971-03-17 Schaedlingsbekaempfungsmittel. CH552341A (de)

Priority Applications (24)

Application Number	Priority Date	Filing Date	Title
CH393071A CH552341A (de)	1971-03-17	1971-03-17	Schaedlingsbekaempfungsmittel.
IL38819A IL38819A (en)	1971-03-17	1972-02-23	Oxadiazolyl derivatives,their manufacture and their use as pesticides
CA135,681A CA1008864A (en)	1971-03-17	1972-02-28	Oxadiazolyl compounds
SE7202993A SE384512B (sv)	1971-03-17	1972-03-09	Oxadiazolylfosforforeningar till anvendning i pesticida medel
DD171323*A DD104702A5 (pl)	1971-03-17	1972-03-14
DD161554A DD100959A5 (pl)	1971-03-17	1972-03-15
PL1972154081A PL83281B1 (en)	1971-03-17	1972-03-15	1,2,4-oxadiazolyl)thiono)phosph(on)ates - with biocidal activity[CH552341A]
EG104/72*UA EG10609A (en)	1971-03-17	1972-03-15	Novel oxadiazolyl compound and a process for its production and use as pesticides
BG019974A BG20540A3 (bg)	1971-03-17	1972-03-15	Средство за борба с вредители
BE780769A BE780769A (fr)	1971-03-17	1972-03-16	Composes oxadiazolyliques et produits phytosanitaires
ZA721804A ZA721804B (en)	1971-03-17	1972-03-16	New esters
ES400823A ES400823A1 (es)	1971-03-17	1972-03-16	Procedimiento para la preparacion de nuevos esteres de oxa-diazolilo.
IT21958/72A IT965042B (it)	1971-03-17	1972-03-16	Ossa diafolil.derivati loro pre parazione e loro impiego per com battere organismi hocivi
DE19722212797 DE2212797A1 (de)	1971-03-17	1972-03-16	Neue Ester
NL7203521A NL7203521A (pl)	1971-03-17	1972-03-16
TR18551A TR18551A (tr)	1971-03-17	1972-03-16	Pestisidler
HUCI1217A HU164399B (pl)	1971-03-17	1972-03-16
GB1243372A GB1384737A (en)	1971-03-17	1972-03-16	Phosphorus-containing esters having pesticidal properties
DK122572A DK132326C (da)	1971-03-17	1972-03-16	Oxadiazolylforbindelser til anvendelse i pesticide midler
FR7209184A FR2130325B1 (pl)	1971-03-17	1972-03-16
AT222472A AT311120B (de)	1971-03-17	1972-03-16	Schädlingsbekämpfungsmittel
AR240999A AR193073A1 (es)	1971-03-17	1972-03-17	Nuevos compuestos de oxadiazolilo,un procedimiento para su preparacion y agentes antiparasitarios que incorporan a dichos compuestos
US417697A US3903100A (en)	1971-03-17	1973-11-20	Oxadiazolylphosphorus compounds for combatting animal and plant pests
US05/585,992 US3973011A (en)	1971-03-17	1975-06-11	Oxadiazolylphosphorus compounds for combatting insects and acarides

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH393071A CH552341A (de)	1971-03-17	1971-03-17	Schaedlingsbekaempfungsmittel.

Publications (1)

Publication Number	Publication Date
CH552341A true CH552341A (de)	1974-08-15

Family

ID=4266542

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH393071A CH552341A (de)	1971-03-17	1971-03-17	Schaedlingsbekaempfungsmittel.

Country Status (6)

Country	Link
AT (1)	AT311120B (pl)
CH (1)	CH552341A (pl)
HU (1)	HU164399B (pl)
PL (1)	PL83281B1 (pl)
TR (1)	TR18551A (pl)
ZA (1)	ZA721804B (pl)

1971
- 1971-03-17 CH CH393071A patent/CH552341A/de not_active IP Right Cessation
1972
- 1972-03-15 PL PL1972154081A patent/PL83281B1/pl unknown
- 1972-03-16 TR TR18551A patent/TR18551A/xx unknown
- 1972-03-16 HU HUCI1217A patent/HU164399B/hu unknown
- 1972-03-16 AT AT222472A patent/AT311120B/de not_active IP Right Cessation
- 1972-03-16 ZA ZA721804A patent/ZA721804B/xx unknown

Also Published As

Publication number	Publication date
ZA721804B (en)	1972-12-27
TR18551A (tr)	1977-03-24
AT311120B (de)	1973-10-25
PL83281B1 (en)	1975-12-31
HU164399B (pl)	1974-02-28

Legal Events

Date	Code	Title	Description
1980-11-28	PL	Patent ceased

Publication	Publication Date	Title
DE2360631A1 (de)	1974-06-12	1,2,4-triazolylphosphorsaeure- bzw. phosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2303185C2 (de)	1986-01-09	Thiophosphorsäurephenylester, Verfahren zu ihrer Herstellung sowie diese enthaltende Schädlingsbekämpfungsmittel
DE2412564A1 (de)	1974-10-17	N,n-dimethylcarbamoyl-1,2,4-triazolyl(3)-ester, verfahren zu ihrer herstellung und ihre verwendung
DE2451588A1 (de)	1975-05-07	Derivate des 1,2,4-oxadiazols, verfahren zu ihrer herstellung und ihre verwendung
DE2457147A1 (de)	1975-06-12	1,2,4-triazol-derivate, verfahren zu ihrer herstellung und ihre verwendung
CH580910A5 (pl)	1976-10-29
AT328795B (de)	1976-04-12	Schadlingsbekampfungsmittel
CH549942A (de)	1974-06-14	Schaedlingsbekaempfungsmittel.
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
CH579873A5 (en)	1976-09-30	Oxadiazolyls from hydroxydiazoles and phosphoric acid halides - with wide biocidal activity
CH571818A5 (en)	1976-01-30	O-Triazolyl O-alkyl (thio)phosph(on)ates - with biocidal (esp insecticidal and acaricidal)activity
DE2430758A1 (de)	1975-01-23	Oxadiazolylverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung
CH580386A5 (en)	1976-10-15	Pesticide triazolyl (thio) phosphoramidate derivs. - e.g. ethyl 1-phenyl 1,2,4-triazol-3-yl N-isopropyl thionophosphoramidate
CH571817A5 (en)	1976-01-30	Pesticidal 1,2,4-triazol-3-yl phosph(on)ates - e.g. O,O-diethyl-O-(1-methyl-5-(alpha-carbethoxybenzyl)-1,2,4-triazol-- 3-yl)-phosphate
DE2418363A1 (de)	1974-10-24	1,2,4-thiadiazolyl-phosphorverbindungen, verfahren zu ihrer herstellung und ihre verwendung
CH579347A5 (pl)	1976-09-15
CH552944A (de)	1974-08-30	Schaedlingsbekaempfungsmittel.
CH569414A5 (en)	1975-11-28	Triazolyphosphoric acid esters - prepd by reaction of hydroxytriazole and phosphoric acid halide,broad-spectrum biocides
CH571816A5 (en)	1976-01-30	O-Triazolyl O-alkyl (thio)phosph(on)ates - with biocidal (esp insecticidal) activity
CH570766A5 (en)	1975-12-31	Biocidal triazolyl dithio phosphates - prepd from dithiophosphoric acid halides and 3-hydroxy triazoles
CH571308A5 (en)	1976-01-15	Biocidal triazolyl dithio phosphates - prepd from dithio phosphoric acid halides and 3-hydroxy triazoles
CH549944A (de)	1974-06-14	Schaedlingsbekaempfungsmittel.
CH575718A5 (en)	1976-05-31	1,2,4-Thiadiazol-3-yloxy phosphorus cpds - with insecticidal, acaricidal, bactericidal, fungicidal and nematocidal activity
DE2651556A1 (de)	1977-05-26	1,2,4-triazolderivate, verfahren zu ihrer herstellung und ihre verwendung
CH620341A5 (en)	1980-11-28	Pesticides