CH580911A5 - 1-(Carbamoyloxy-trichloro-ethyl)-1,2,4-triazole derivs - prepd. e.g. by reacting 1-(hydroxy-trichloro ethyl)-cpd. with carbamoyl halide - Google Patents

1-(Carbamoyloxy-trichloro-ethyl)-1,2,4-triazole derivs - prepd. e.g. by reacting 1-(hydroxy-trichloro ethyl)-cpd. with carbamoyl halide

Info

Publication number: CH580911A5
Authority: CH; Switzerland
Prior art keywords: plants; infected; triazole; active ingredient; ethyl
Prior art date: 1974-02-19

Application number

CH227774A

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.)

1974-02-19

Filing date

1974-02-19

Publication date

1976-10-29

1974-02-19 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1974-02-19 Priority to CH227774A priority Critical patent/CH580911A5/de

1975-01-24 Priority to SE7500769A priority patent/SE7500769L/xx

1975-01-31 Priority to NL7501190A priority patent/NL7501190A/xx

1975-02-07 Priority to US05/548,052 priority patent/US4007278A/en

1975-02-12 Priority to EG62/75A priority patent/EG11925A/xx

1975-02-15 Priority to OA55413A priority patent/OA04901A/fr

1975-02-17 Priority to CA220,232A priority patent/CA1050554A/fr

1975-02-17 Priority to LU71863A priority patent/LU71863A1/xx

1975-02-17 Priority to DE19752506598 priority patent/DE2506598A1/de

1975-02-17 Priority to FR7504842A priority patent/FR2261275B1/fr

1975-02-18 Priority to ZA00751015A priority patent/ZA751015B/xx

1975-02-18 Priority to IL46656A priority patent/IL46656A/xx

1975-02-18 Priority to AU78305/75A priority patent/AU488776B2/en

1975-02-18 Priority to GB6804/75A priority patent/GB1490121A/en

1975-02-18 Priority to ES434806A priority patent/ES434806A1/es

1975-02-18 Priority to IT20380/75A priority patent/IT1049355B/it

1975-02-18 Priority to BE153455A priority patent/BE825657A/fr

1975-02-18 Priority to AT119575A priority patent/AT340201B/de

1975-02-18 Priority to DK58975AA priority patent/DK139892B/da

1975-02-19 Priority to JP50020813A priority patent/JPS50117938A/ja

1976-10-29 Publication of CH580911A5 publication Critical patent/CH580911A5/de

1977-12-01 Priority to IL53501A priority patent/IL53501A0/xx

Links

-1 carbamoyl halide Chemical class 0.000 title claims description 24
RAMHLFVEUSBXGU-UHFFFAOYSA-N [2,2,2-trichloro-1-(1,2,4-triazol-1-yl)ethyl] carbamate Chemical compound NC(=O)OC(C(Cl)(Cl)Cl)N1C=NC=N1 RAMHLFVEUSBXGU-UHFFFAOYSA-N 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
230000003032 phytopathogenic effect Effects 0.000 claims abstract description 6
241000894006 Bacteria Species 0.000 claims abstract description 5
230000009885 systemic effect Effects 0.000 claims abstract description 4
241000196324 Embryophyta Species 0.000 claims description 32
239000004480 active ingredient Substances 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 13
230000000694 effects Effects 0.000 claims description 13
241000233866 Fungi Species 0.000 claims description 10
239000007921 spray Substances 0.000 claims description 10
239000004563 wettable powder Substances 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
240000005979 Hordeum vulgare Species 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
230000002538 fungal effect Effects 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 6
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
238000009472 formulation Methods 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
241001480061 Blumeria graminis Species 0.000 claims description 3
240000007594 Oryza sativa Species 0.000 claims description 3
241000567019 Xanthomonas vesicatoria Species 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
239000000575 pesticide Substances 0.000 claims description 3
125000005592 polycycloalkyl group Polymers 0.000 claims description 3
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
240000004160 Capsicum annuum Species 0.000 claims description 2
235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
238000011534 incubation Methods 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
230000001681 protective effect Effects 0.000 claims description 2
239000002689 soil Substances 0.000 claims description 2
238000005507 spraying Methods 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000006000 trichloroethyl group Chemical group 0.000 claims description 2
241000209219 Hordeum Species 0.000 claims 4
125000005843 halogen group Chemical group 0.000 claims 1
FPHGQTGUXQZYDT-UHFFFAOYSA-N 2,2,2-trichloro-1-(1,2,4-triazol-1-yl)ethanol Chemical compound ClC(Cl)(Cl)C(O)N1C=NC=N1 FPHGQTGUXQZYDT-UHFFFAOYSA-N 0.000 abstract description 3
239000011230 binding agent Substances 0.000 abstract description 2
239000002253 acid Substances 0.000 abstract 1
244000038559 crop plants Species 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
239000000417 fungicide Substances 0.000 abstract 1
239000004009 herbicide Substances 0.000 abstract 1
150000003852 triazoles Chemical class 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000008187 granular material Substances 0.000 description 6
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
238000006243 chemical reaction Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
125000003438 dodecyl group Chemical group [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])* 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000839 emulsion Substances 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
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
150000003505 terpenes Chemical class 0.000 description 2
235000007586 terpenes Nutrition 0.000 description 2
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
241000605059 Bacteroidetes Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
241000588698 Erwinia Species 0.000 description 1
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
241000223221 Fusarium oxysporum Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241000233622 Phytophthora infestans Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000521936 Pseudomonas amygdali pv. lachrymans Species 0.000 description 1
241000589613 Pseudomonas savastanoi pv. phaseolicola Species 0.000 description 1
241000589626 Pseudomonas syringae pv. tomato Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241001123669 Verticillium albo-atrum Species 0.000 description 1
241000589634 Xanthomonas Species 0.000 description 1
241000589652 Xanthomonas oryzae Species 0.000 description 1
241000194062 Xanthomonas phaseoli Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
VOXPGLGBCQKFNV-UHFFFAOYSA-N [2,2,2-trichloro-1-(1,2,4-triazol-1-yl)ethyl] n-propylcarbamate Chemical compound CCCNC(=O)OC(C(Cl)(Cl)Cl)N1C=NC=N1 VOXPGLGBCQKFNV-UHFFFAOYSA-N 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons 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
230000000844 anti-bacterial effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000002704 decyl group Chemical group [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])* 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000001421 myristyl 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])[H] 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
125000001624 naphthyl group Chemical group 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
238000001228 spectrum Methods 0.000 description 1
125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 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
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
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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
244000045561 useful plants Species 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH227774A 1974-02-19 1974-02-19 1-(Carbamoyloxy-trichloro-ethyl)-1,2,4-triazole derivs - prepd. e.g. by reacting 1-(hydroxy-trichloro ethyl)-cpd. with carbamoyl halide CH580911A5 (en)

Priority Applications (21)

Application Number	Priority Date	Filing Date	Title
CH227774A CH580911A5 (en)	1974-02-19	1974-02-19	1-(Carbamoyloxy-trichloro-ethyl)-1,2,4-triazole derivs - prepd. e.g. by reacting 1-(hydroxy-trichloro ethyl)-cpd. with carbamoyl halide
SE7500769A SE7500769L (fr)	1974-02-19	1975-01-24
NL7501190A NL7501190A (nl)	1974-02-19	1975-01-31	Werkwijze voor de bereiding van 1-(1'-carba- moyloxy-2',2',2'-trichloorethyl)-1,2,4-tria- zoolderivaten, de daaruit vervaardigde prepa- raten, alsmede de toepassing ervan als pes- ticiden.
US05/548,052 US4007278A (en)	1974-02-19	1975-02-07	1-(1-Carbamoyloxy-2,2,2-trichloroethyl)-1,2,4-triazole derivatives as pesticides
EG62/75A EG11925A (en)	1974-02-19	1975-02-12	1-(1'carbamoyloxy-2',2'2'-trichloroethyl)-1,2,4-triazole derivatives as pesticides
OA55413A OA04901A (fr)	1974-02-19	1975-02-15	Dérives de l-(l-carbamoyloxy-2',2',2'-trichloroéthyl)-l,2,4-triazole et leur application comme agent de lutte contre les organismes nuisibles.
FR7504842A FR2261275B1 (fr)	1974-02-19	1975-02-17
LU71863A LU71863A1 (fr)	1974-02-19	1975-02-17
DE19752506598 DE2506598A1 (de)	1974-02-19	1975-02-17	1-(1'-carbamoyloxy-2',2',2'-trichloraethyl)-1,2,4-triazol-derivate als pestizide
CA220,232A CA1050554A (fr)	1974-02-19	1975-02-17	Derives pesticides de (carbamyloxy-1'trichloro-2',2',2' ethyl) triazole-1,2,4
GB6804/75A GB1490121A (en)	1974-02-19	1975-02-18	1,2,4-triazole derivatives as pesticides
IL46656A IL46656A (en)	1974-02-19	1975-02-18	1-(1'-carbamoyloxy-2'2',2',-trichloroethyl)-1-2,4-triazolederivatives,their production,pesticidal compositions containing them a method of controlling pests employing them
AU78305/75A AU488776B2 (en)	1974-02-19	1975-02-18	"1-(1'-carbamoyloxy-2',2',2' - trichloroethyl)-1,2,4-triazole derivatives as pesticides
ZA00751015A ZA751015B (en)	1974-02-19	1975-02-18	1-(1'-carbamoyloxy-2'-2'-2'-trichloroethyl)-1,2,4-triazole derivatives as pesticides
ES434806A ES434806A1 (es)	1974-02-19	1975-02-18	Procedimiento para preparar derivados de 1-(1'-carbamoiloxi-2', 2', 2'-tricloroetil)-1, 2, 4-triazol.
IT20380/75A IT1049355B (it)	1974-02-19	1975-02-18	1 1 carbammoilossi 2.2.2 triclo roetil 1.2.4 triazol derivati come pesticidi
BE153455A BE825657A (fr)	1974-02-19	1975-02-18	Nouvelles n-(3-tertiobutyl-1,2,4-thiadiazolyl-(5) urees, leur preparation et leur application comme herbicides selectifs
AT119575A AT340201B (de)	1974-02-19	1975-02-18	Pestizides fungizides und bakterizides mittel
DK58975AA DK139892B (da)	1974-02-19	1975-02-18	Fungicide og baktericide forbindelser.
JP50020813A JPS50117938A (fr)	1974-02-19	1975-02-19
IL53501A IL53501A0 (en)	1974-02-19	1977-12-01	1-(1'-hydroxy-2',2',2'-trichloreoethyl)-1,2,4-triazole and its preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH227774A CH580911A5 (en)	1974-02-19	1974-02-19	1-(Carbamoyloxy-trichloro-ethyl)-1,2,4-triazole derivs - prepd. e.g. by reacting 1-(hydroxy-trichloro ethyl)-cpd. with carbamoyl halide

Publications (1)

Publication Number	Publication Date
CH580911A5 true CH580911A5 (en)	1976-10-29

Family

ID=4229997

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH227774A CH580911A5 (en)	1974-02-19	1974-02-19	1-(Carbamoyloxy-trichloro-ethyl)-1,2,4-triazole derivs - prepd. e.g. by reacting 1-(hydroxy-trichloro ethyl)-cpd. with carbamoyl halide

Country Status (3)

Country	Link
BE (1)	BE825657A (fr)
CH (1)	CH580911A5 (fr)
ZA (1)	ZA751015B (fr)

1974
- 1974-02-19 CH CH227774A patent/CH580911A5/de not_active IP Right Cessation
1975
- 1975-02-18 ZA ZA00751015A patent/ZA751015B/xx unknown
- 1975-02-18 BE BE153455A patent/BE825657A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE825657A (fr)	1975-08-18
ZA751015B (en)	1976-01-28

Legal Events

Date	Code	Title	Description
1984-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2804299A1 (de)	1978-08-10	Fungizide mittel
DE2513732A1 (de)	1975-10-16	Mikrobizide und wachstumsregulierende mittel
DE2643477A1 (de)	1977-04-07	Mikrobizide
DE2741437A1 (de)	1978-03-23	Anilinderivate, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
EP0000023B1 (fr)	1980-07-23	Pentyl-urées substituées en omega, leur procédé de préparation et leur application comme fongicides
EP0130366B1 (fr)	1991-01-30	Sels d'arylalkylimidazolium et triazolium, leur procédé de préparation et leur utilisation comme microbicides
DE2513789A1 (de)	1975-10-09	Haloacylanilide als mikrobizide wirkstoffe
EP0037971B1 (fr)	1983-12-21	Cyanoguanidines trisubstituées, procédé pour leur préparation et leur utilisation comme fongicides
DE1809385A1 (de)	1970-06-11	Oxim-O-kohlensaeure-phenylester sowie Verfahren zu ihrer Herstellung
EP0002679B1 (fr)	1981-07-15	1-Halogéno-1-propyn-3-ols, leur procédé de préparation et leur emploi comme fongicides
EP0094539B1 (fr)	1985-08-21	Halogénopropargylformamides
DD248357A5 (de)	1987-08-05	Verfahren zur herstellung von 9,10-phenonthrendion-derivaten
DE1543614C3 (de)	1975-10-30	N-(Trihalogenmethylthio)-N-trifluor-methylamino-benzamide, Verfahren zu deren Herstellung und deren Verwendung
CH635580A5 (de)	1983-04-15	Mikrobizide mittel.
EP0055442B1 (fr)	1984-08-08	Biurets N-sulfénylés, procédé pour leur préparation et leur utilisation comme fongicides
DE2902861A1 (de)	1979-08-02	Mikrobizide mittel
AT340201B (de)	1977-12-12	Pestizides fungizides und bakterizides mittel
EP0046557B1 (fr)	1984-02-22	N-sulfénylurées, procédé de préparation, compositions fongicides et utilisation
EP0003975B1 (fr)	1981-05-13	Diamides de l'acide dichloromaléique, procédé pour les préparer et leur utilisation comme fongicides
EP0101800A1 (fr)	1984-03-07	N-sulfényl hydantoines
EP0087048B1 (fr)	1985-04-17	Oximinoacétamilides substituées, leur méthode de préparation ainsi que leur utilisation comme pesticide
DE2643445A1 (de)	1977-04-07	Mikrobizide mittel
DE2623847A1 (de)	1977-12-08	Neue oximaether, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
CH586011A5 (en)	1977-03-31	1-(Carbamoyloxy-trichloro-ethyl)-1,2,4-triazole derivs - prepd. e.g. by reacting 1-(hydroxy-trichloro ethyl)-cpd. with carbamoyl halide
DE2917893A1 (de)	1980-11-13	N-(alkoxy- bzw. alkoxycarbonalalkyl)- n-hydroxyacetyl- bzw. propionyl-anilin- derivate als pflanzenfungizide