CH556862A - Procede de preparation de thiadiazoles. - Google Patents

Procede de preparation de thiadiazoles.

Info

Publication number: CH556862A
Authority: CH; Switzerland
Prior art keywords: vig; dead; compound; hydrocarbon radical; lesions
Prior art date: 1970-01-15

Application number

CH125172A

Other languages

English (en)

French (fr)

Original Assignee

Air Prod & Chem

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.)

1970-01-15

Filing date

1970-01-15

Publication date

1974-12-13

1970-01-15 Application filed by Air Prod & Chem filed Critical Air Prod & Chem

1970-01-15 Priority to CH125172A priority Critical patent/CH556862A/de

1974-12-13 Publication of CH556862A publication Critical patent/CH556862A/de

Links

239000004009 herbicide Substances 0.000 title claims abstract description 10
239000000417 fungicide Substances 0.000 title claims abstract description 8
QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical class NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 title claims description 3
CMQJDYXIZIONAP-UHFFFAOYSA-N 1,3,4-thiadiazol-2-ylurea Chemical compound NC(=O)NC1=NN=CS1 CMQJDYXIZIONAP-UHFFFAOYSA-N 0.000 title 1
229930195733 hydrocarbon Natural products 0.000 claims abstract description 18
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
229910052794 bromium Inorganic materials 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 5
240000008042 Zea mays Species 0.000 claims abstract description 4
235000002017 Zea mays subsp mays Nutrition 0.000 claims abstract description 4
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims abstract description 3
235000009973 maize Nutrition 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 34
238000000034 method Methods 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 24
241000196324 Embryophyta Species 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 18
230000003902 lesion Effects 0.000 claims description 13
230000002363 herbicidal effect Effects 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 8
239000000047 product Substances 0.000 claims description 8
231100000674 Phytotoxicity Toxicity 0.000 claims description 7
125000002015 acyclic group Chemical group 0.000 claims description 7
230000000855 fungicidal effect Effects 0.000 claims description 7
231100000208 phytotoxic Toxicity 0.000 claims description 7
230000000885 phytotoxic effect Effects 0.000 claims description 7
239000007921 spray Substances 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
-1 acyclic hydrocarbons Chemical class 0.000 claims description 5
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910015900 BF3 Inorganic materials 0.000 claims description 3
238000010790 dilution Methods 0.000 claims description 3
239000012895 dilution Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
230000005764 inhibitory process Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
238000004383 yellowing Methods 0.000 claims description 3
235000016068 Berberis vulgaris Nutrition 0.000 claims description 2
241000335053 Beta vulgaris Species 0.000 claims description 2
244000140786 Brassica hirta Species 0.000 claims description 2
235000011371 Brassica hirta Nutrition 0.000 claims description 2
244000025254 Cannabis sativa Species 0.000 claims description 2
240000008620 Fagopyrum esculentum Species 0.000 claims description 2
235000009419 Fagopyrum esculentum Nutrition 0.000 claims description 2
244000068988 Glycine max Species 0.000 claims description 2
235000010469 Glycine max Nutrition 0.000 claims description 2
230000002159 abnormal effect Effects 0.000 claims description 2
239000008280 blood Substances 0.000 claims description 2
210000004369 blood Anatomy 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
230000005080 plant death Effects 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 2
241000894007 species Species 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
239000002689 soil Substances 0.000 abstract description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
239000004202 carbamide Substances 0.000 abstract 1
239000002837 defoliant Substances 0.000 abstract 1
239000002274 desiccant Substances 0.000 abstract 1
238000002360 preparation method Methods 0.000 description 12
239000000843 powder Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
230000035613 defoliation Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229920000137 polyphosphoric acid Polymers 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
244000299507 Gossypium hirsutum Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000004927 clay Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
NRZFXNSDVJNXHZ-UHFFFAOYSA-N 1-[5-chloro-1-(difluoromethyl)-1,3,4-thiadiazol-1-ium-2-yl]-1,3,3-trimethylurea Chemical compound CN(C)C(N(C)C([S+]1C(F)F)=NN=C1Cl)=O NRZFXNSDVJNXHZ-UHFFFAOYSA-N 0.000 description 2
PTVZQOAHCSKAAS-UHFFFAOYSA-N 4-methyl-3-thiosemicarbazide Chemical compound CNC(=S)NN PTVZQOAHCSKAAS-UHFFFAOYSA-N 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
235000005775 Setaria Nutrition 0.000 description 2
241000232088 Setaria <nematode> Species 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
240000006394 Sorghum bicolor Species 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000010410 dusting Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000010440 gypsum Substances 0.000 description 2
229910052602 gypsum Inorganic materials 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
150000004867 thiadiazoles Chemical class 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SKYYTGUCWARUCL-UHFFFAOYSA-N 1-amino-3-ethylthiourea Chemical compound CCNC(=S)NN SKYYTGUCWARUCL-UHFFFAOYSA-N 0.000 description 1
ZBURDFHUFWUAJQ-UHFFFAOYSA-N 1-ethyl-3-[(2,2,2-trifluoroacetyl)amino]thiourea Chemical compound CCNC(=S)NNC(=O)C(F)(F)F ZBURDFHUFWUAJQ-UHFFFAOYSA-N 0.000 description 1
QAJVDNZHKRIXGF-UHFFFAOYSA-N 1-phenyl-3-[(2,2,2-trifluoroacetyl)amino]thiourea Chemical compound FC(F)(F)C(=O)NNC(=S)NC1=CC=CC=C1 QAJVDNZHKRIXGF-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
ZATDMJQTIYJJQM-UHFFFAOYSA-N 5-chloro-4-(difluoromethyl)-n-methyl-3h-thiadiazol-2-amine Chemical compound CNN1NC(C(F)F)=C(Cl)S1 ZATDMJQTIYJJQM-UHFFFAOYSA-N 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
235000011941 Tilia x europaea Nutrition 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000010903 husk Substances 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
239000003317 industrial substance Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000021332 kidney beans Nutrition 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000003583 thiosemicarbazides Chemical class 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000009736 wetting Methods 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
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms

Landscapes

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

CH125172A 1970-01-15 1970-01-15 Procede de preparation de thiadiazoles. CH556862A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH125172A CH556862A (de)	1970-01-15	1970-01-15	Procede de preparation de thiadiazoles.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH125172A CH556862A (de)	1970-01-15	1970-01-15	Procede de preparation de thiadiazoles.

Publications (1)

Publication Number	Publication Date
CH556862A true CH556862A (de)	1974-12-13

Family

ID=4206016

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH125172A CH556862A (de)	1970-01-15	1970-01-15	Procede de preparation de thiadiazoles.

Country Status (1)

Country	Link
CH (1)	CH556862A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2341573A1 (fr) *	1976-02-20	1977-09-16	Schering Ag	Carbamoylimino-2 thiadiazolines-1,3,4 utilisables comme matieres actives de produits herbicides
FR2352809A1 (fr) *	1976-05-24	1977-12-23	Schering Ag	Sels de dimethylcarbamoylimino-2 thiadiazoline-1,3,4 ides-3 et produits herbicides qui en contiennent
FR2460941A1 (fr) *	1979-07-09	1981-01-30	Gulf Oil Corp	Phenyliminothiadiazolines, leur procede d'obtention et leur application comme substances de croissance des plantes
EP0252474A3 (en) *	1986-07-08	1989-08-09	American Cyanamid Company	Substituted 1,2,3-thiadiazole-4-thiolates

1970
- 1970-01-15 CH CH125172A patent/CH556862A/de not_active IP Right Cessation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2341573A1 (fr) *	1976-02-20	1977-09-16	Schering Ag	Carbamoylimino-2 thiadiazolines-1,3,4 utilisables comme matieres actives de produits herbicides
FR2352809A1 (fr) *	1976-05-24	1977-12-23	Schering Ag	Sels de dimethylcarbamoylimino-2 thiadiazoline-1,3,4 ides-3 et produits herbicides qui en contiennent
FR2460941A1 (fr) *	1979-07-09	1981-01-30	Gulf Oil Corp	Phenyliminothiadiazolines, leur procede d'obtention et leur application comme substances de croissance des plantes
EP0023766A1 (de) *	1979-07-09	1981-02-11	Gulf Oil Corporation	Phenyliminothiadiazoline, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenwachstumsregulatoren
EP0252474A3 (en) *	1986-07-08	1989-08-09	American Cyanamid Company	Substituted 1,2,3-thiadiazole-4-thiolates

Legal Events

Date	Code	Title	Description
1990-03-30	PL	Patent ceased

Publication	Publication Date	Title
EP1178039B1 (de)	2007-04-11	Derivate von Phenyl(thio)harnstoff und Phenyl(thio)carbamat Fungiziden
EP0332133B1 (de)	1994-08-24	Triazolverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Zusammensetzungen
FR2484412A1 (fr)	1981-12-18	Derive de cyclohexane, composition herbicide en contenant et procede pour sa preparation
EP0000681A1 (de)	1979-02-07	Amino-2 (oder -4)-alkylthio-5-Pyrimidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Herbizide und sie enthaltende Zusammensetzungen
HK1005028B (en)	1998-12-18	Novel triazole compounds, process for producing the same, and herbicidal compositions containing the same
KR0160307B1 (ko)	1998-12-01	이미노티아졸린, 그의 제조방법 및 제초제로서의 용도, 및 그의 제조용 중간체
RU2090560C1 (ru)	1997-09-20	Производные амидов пиразолгликолевой кислоты, гербицидная композиция, способ борьбы с сорняками
US5418247A (en)	1995-05-23	3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insecticides
US4008067A (en)	1977-02-15	Oxacyclohexane derivatives
CH556862A (de)	1974-12-13	Procede de preparation de thiadiazoles.
CH554886A (fr)	1974-10-15	Procede de preparation de thiadiazoles.
FR2503706A1 (fr)	1982-10-15	Derives de pyrazole, procede pour leur preparation et herbicides les contenant
CH570391A5 (en)	1975-12-15	1,3,4-Thiadiazole herbicides and fungicides - prepd. by reaction of carbamoyl chlorides with alkali metal derivs. of 2-amino-1,3,4-thiadiazoles
FR2604174A1 (fr)	1988-03-25	Nouveaux derives de la 5-pyrazolone, leur procede de preparation et leur utilisation comme herbicides
FR2462430A1 (fr)	1981-02-13	Nouvelles 1,2,4-triazolidine-3,5-dithiones trisubstituees en positions 1, 2 et 4, composition les contenant et leur utilisation comme herbicides et comme substances de croissance des plantes
JPH0453863B2 (de)	1992-08-27
EP0021939B1 (de)	1983-01-12	Hydrazino (oder Azido)-5-alkylthio-pyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendungen als Herbizide und Fungizide
US4402732A (en)	1983-09-06	Herbicidally active dihalogenated imidazolecarboxylic acid amides, compositions and use
CH653998A5 (fr)	1986-01-31	Derives du pyrazole, procede pour leur preparation et herbicides contenant ces derives.
BE897705A (fr)	1984-03-08	Nouveaux chloroacetamides, leur preparation et leur utilisation comme herbicides
EP0016132A1 (de)	1980-10-01	Neues substituiertes phenylharnstoff-herbizid
CH541572A (fr)	1973-09-15	Procédé de préparation d'un thiadiazole
FR2751968A1 (fr)	1998-02-06	Methyltetrazolinones 1-substituees,procede et intermediaires pour leur preparation et leur utilisation comme herbicides
EA004940B1 (ru)	2004-10-28	Способ получения промежуточных продуктов, применяемых при синтезе производных фенилгидразина, обладающих инсектицидной активностью
EP0000852A1 (de)	1979-02-21	Behandlung von herbizidhaltigen Kulturen mit Di- oder Trichloracetamiden, neue Di- oder Trichloracetamide und Verfahren zu ihrer Herstellung