PL88521B1 - - Google Patents
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- Publication number
- PL88521B1 PL88521B1 PL1974169509A PL16950974A PL88521B1 PL 88521 B1 PL88521 B1 PL 88521B1 PL 1974169509 A PL1974169509 A PL 1974169509A PL 16950974 A PL16950974 A PL 16950974A PL 88521 B1 PL88521 B1 PL 88521B1
- Authority
- PL
- Poland
- Prior art keywords
- wzdr
- active substance
- harmful
- formula
- crops
- Prior art date
Links
- 239000013543 active substance Substances 0.000 claims description 12
- 235000021307 Triticum Nutrition 0.000 claims description 3
- 244000098338 Triticum aestivum Species 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 240000004296 Lolium perenne Species 0.000 claims 5
- 240000002791 Brassica napus Species 0.000 claims 3
- 235000007320 Avena fatua Nutrition 0.000 claims 2
- 241000209764 Avena fatua Species 0.000 claims 2
- 235000007319 Avena orientalis Nutrition 0.000 claims 2
- 235000011293 Brassica napus Nutrition 0.000 claims 2
- 206010011878 Deafness Diseases 0.000 claims 2
- 244000058871 Echinochloa crus-galli Species 0.000 claims 2
- 241000287828 Gallus gallus Species 0.000 claims 2
- 244000100545 Lolium multiflorum Species 0.000 claims 2
- 240000006597 Poa trivialis Species 0.000 claims 2
- 244000062793 Sorghum vulgare Species 0.000 claims 2
- 241000209140 Triticum Species 0.000 claims 2
- 235000019713 millet Nutrition 0.000 claims 2
- 241000209761 Avena Species 0.000 claims 1
- 244000075850 Avena orientalis Species 0.000 claims 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims 1
- 235000011999 Panicum crusgalli Nutrition 0.000 claims 1
- 244000292693 Poa annua Species 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000234282 Allium Species 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000002764 Apium graveolens Nutrition 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000234670 Bromeliaceae Species 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000002567 Capsicum annuum Nutrition 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 241000219104 Cucurbitaceae Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 241000220223 Fragaria Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 241000459819 Gymnodinium cucumis Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- 241000219823 Medicago Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 241000219843 Pisum Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000220222 Rosaceae Species 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 241000219315 Spinacia Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000001387 apium graveolens Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- -1 e.g. wa Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001377 petroselinum spp. Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Przedmiotem wynalazku jest srodek chwastobójczy zawierajacy jako skladnik czynny nowe karbotiolany
acetydynowe.
Znane jest stosowanie S-etylo-szesciowodoro-1H-azepino-1-karbotiolanu do zwalczania roslin niepoza¬
danych w uprawach roslin uzytkowych takich jak jeczmien, pszenica i ryz (opis patentowy RFN nr 1300947).
Dzialanie jego jest jednakze niezadowalajace.
Stwierdzono, ze karbotiolany acetydynowe o wzorze 1 w którym Rl oznacza grupe alkilowa np. metylo¬
wa, etylowa, n oznacza liczby 0—4, X oznacza atom tlenu albo siarki, posiadaja dobre dzialanie chwastobójcze.
Przy jednakowym, a czesto lepszym dzialaniu chwastobójczym, rosliny lepiej je znosza niz znane S-etylo-heksa-
hydro-1 H-azepino-1 -karbotiolany.
Substancje czynne otrzymuje sie w taki sposób, ze ester kwasu tiolochloromrówkowego poddaje sie reakcji
z ewentualnie podstawiona acetydyna. Tak samo mozna wytwarzac substancje czynne jezeli acetydyne w postaci
odpowiedniego N-chlorku kwasowego poddaje sie reakcji z merkaptanami. Wytwarzanie acetydyny znane jest
z literatury.
Przyklad I. Wytwarzanie 2-etylo-(2,2,4-trójmetyloacetydyno)-1-karbotiolanu.
Do mieszaniny 4,95 czesci wagowych 2,2,4-trójmetyloacetydyny i 6 czesci trójetyloaminy w 50 czesciach
wagowych benzenu, wkrapla sie w temperaturze 30-40°C 6,23 czesci tionochloromrówczanu etylu. Po godzi¬
nie odsacza sie chlorowodorek trójetyloaminy, a przesacz przemywa woda. Po wysuszeniu zageszcza sie go pod
zmniejszonym cisnieniem, a pozostalosc destyluje. Otrzymuje sie 6,70 czesci S-etylo-(2,2,4-trójmetyloacetydy-
no)-1-karbotiolanu o wzorze strukturalnym 2 i temperaturze wrzenia: 59°C0'01.
Takim samym sposobem mozna wytwarzac nastepujace zwiazki:
S-metylo-(2,2,4-trójmetyloacetydyno)-1-karbotiolan, temperatura wrzenia: 70°C0,05
S-propylo-(2,2,4-trójmetyloacetydyno)-1 -karbotiolan, temperatura wrzenia: 81ÓC0,052
88 521
Gossypium hirsutum, Leguminosae, np.: Medicago spp., Trifolium spp., Pisum spp., Phaseolus spp., Arachi s
spp., Glycine Max, Chenopodisceae, np.: Beta vulgaris, Spinacia spp., Solanaceae, np.: Solanum spp., Nicotiania
spp., Capsicum annuum, Linaceae, np.: Linum spp., Umbeliferae, np.: Petroselinum spp., Daucus carota, Apium
graveolens, Rosaceae, np.: Fragaria, Cucurbitaceae, np.: Cucumis spp., Cucurbita spp., Liliaceae, np. Allium spp.,
Vitaceae, np.: Vitis vinifera, Bromeliaceae, np.: Ananas sativus.
Przyklad II. W cieplarni wypelnia sie naczynia doswiadczalne gliniasto piaszczysta gleba i wysiewa
rózne nasiona. Bezposrednio potem traktuje sie substancjami czynnymi IV (wzór 4), V (wzór 5), VI (wzór 6)
i VII (wzór 7) w porównaniu ze znana substancja czynna III (wzór 3), stosujac kazdorazowo 1 kg substancji
czynnej na hektar, zdyspergowanej albo zemulgowanej w 500 I wody na hektar. W czasie doswiadczenia zrasza
sie rosliny obrficie woda. Po 4 tygodniach stwierdzono, ze substancje czynne IV, V, VI i VII sa lepiej znoszone
przez rosliny uprawne i lepsze dzialanie chwastobójcze niz porównawcza substancja czynna III. Wyniki dos¬
wiadczen przedstawiono w tablicy I.
Przyklad III. Rózne rosliny o wysokosci wzrostu 3—15 cm traktuje sie substancjami czynnymi IV
(wzór 4), V (wzór 5), VI (wzór 6) i VII (wzór 7) w porównaniu ze znana substancja III (wzór 3), stosujac kaz¬
dorazowo 1 kg substancji czynnej na hektar, zdyspergowanej, albo zemulgowanej w 500 I wody na hektar.
W czasie doswiadczenia zrasza sie rosliny obficie woda. Po 4 tygodniach ustalono, ze substancje czynne IV, V,
VI i VII wykazuja lepsza znosnosc przez rosliny uprawne przy tym samym dzialaniu chwastobójczym od po¬
równawczej substancji czynnej III.
Claims (1)
1. Zastrzezenie patentowe Srodek chwastobójczy zawierajacy substancje czynna staly albo ciekly nosnik, znamienny tym, ze jako substancje czynna zawiera karbotiolan o wzorze 1, w którym R1 oznacza grupe alkilowa, n oznacza liczby 0-4, X oznacza atom tlenu albo siarki i R2 oznacza grupe alifatyczna ewentualnie podstawiona jedno- albo wielokrotnie atomem chlorowca, grupa hydroksylowa, alkoksylowa albo cyjanowa. Substancja czynna kg/ha Rosliny uzytkowe Brassica napus (rzepak) Triticum aestivum (pszenica) Rosliny niepozadane Echinochloa crusgalli (kurze proso) Lolium multiflorum (wloski rajgras) Lolium perenne (angielski rajgras) Avena fatua (gluchy owies) Poa annua (jednoroczna wiechl ina) Poa trivialis (wiechlina zwykla) Tablica 1 III ! 1 10 5 40 20 20 0 I 30 30 IV 1 0 0 95 100 95 60 100 95 V 1 0 0 90 95 90 55 85 85 VI 1 0 0 60 80 80 40 85 85 . VII 1 0 0 80 85 90 70 100 95 0 = bez szkodliwosci 100 = pelna szkodliwosc88 521 Substancja czynna kg/ha Rosliny uzytkowe Brassica napus (rzepak) Triticum aestivum (pszenica) Rosliny niepozadane Echinochloa crus galli (kurze proso) Lolium multiflorum (wloski rajgras) Lolium perenne (angielski rajgras) Avena fatua (gluchy owies) Poa annua (jednoroczna wiechlina) Poa trivialis (wiechlina zwykla) 0 = bez szkodliwosci 100 = pelna szkodliwosc Tabl ica II III 1 10 5 40 20 20 0 30 30 IV 1 0 0 95 95 90 50 95 90 V 1 0 0 90 90 85 45 90 90 VI 1 0 0 60 70 70 40 70 65 VII 1 0 0 90 90 85 50 90 8588 521 (R1) N—C-S-R2 X WZdR 1 CH3 CH3 N—C-S—CH3 CHq WZCfR U H3CX PH3 N —C—S —C2H5 H CH3 WZÓR 2 CH3 CH3Q N —C-S-CH CH, CH, WZdR 5 Qj-C-S-C2H6 O WZdR 3 CH3 CH3 Cl ci N-C-S-CH2—C=C O Cl WZdR 6 CH3 CH3 \ N-C-S-CH-C2H5 CH3 CH3 WZdR 7 Prac. Poligraf. UP PRL Naklad 120 + 18 egz. Cena 10 zl
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2312045A DE2312045A1 (de) | 1973-03-10 | 1973-03-10 | Carbothiolate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL88521B1 true PL88521B1 (pl) | 1976-09-30 |
Family
ID=5874438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974169509A PL88521B1 (pl) | 1973-03-10 | 1974-03-08 |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS49124229A (pl) |
| AR (1) | AR213711A1 (pl) |
| AT (1) | AT331070B (pl) |
| BE (1) | BE812145A (pl) |
| CA (1) | CA1023369A (pl) |
| CH (1) | CH580914A5 (pl) |
| CS (1) | CS181753B2 (pl) |
| DD (1) | DD110160A5 (pl) |
| DE (1) | DE2312045A1 (pl) |
| DK (1) | DK142561C (pl) |
| FR (1) | FR2220521B1 (pl) |
| GB (1) | GB1453490A (pl) |
| HU (1) | HU169445B (pl) |
| IL (1) | IL44238A (pl) |
| IT (1) | IT1049272B (pl) |
| NL (1) | NL7402909A (pl) |
| PL (1) | PL88521B1 (pl) |
| RO (1) | RO67836A (pl) |
| SE (1) | SE401076B (pl) |
| SU (1) | SU580801A3 (pl) |
| ZA (1) | ZA741408B (pl) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2457688A1 (de) * | 1974-12-06 | 1976-06-10 | Basf Ag | Carbaminsaeurethiolester |
| GB2140003A (en) * | 1983-04-13 | 1984-11-21 | Shell Int Research | Azetidine derivatives suitable for inducing male sterility in plants |
| US4534787A (en) * | 1984-05-24 | 1985-08-13 | Shell Oil Company | N-L-seryl-3-azetidinecarboxylic acid |
| ATE112266T1 (de) * | 1988-07-15 | 1994-10-15 | Basf Ag | Azetidinderivate, verfahren zu ihrer herstellung und ihre verwendung zur regulierung des pflanzenwachstums. |
| DE10144872A1 (de) * | 2001-09-12 | 2003-03-27 | Bayer Cropscience Gmbh | Azetidinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
-
1973
- 1973-03-10 DE DE2312045A patent/DE2312045A1/de active Pending
-
1974
- 1974-02-19 IL IL44238A patent/IL44238A/en unknown
- 1974-03-04 NL NL7402909A patent/NL7402909A/xx not_active Application Discontinuation
- 1974-03-05 ZA ZA00741408A patent/ZA741408B/xx unknown
- 1974-03-05 DK DK116574A patent/DK142561C/da active
- 1974-03-06 AR AR252651A patent/AR213711A1/es active
- 1974-03-07 SU SU7402003152A patent/SU580801A3/ru active
- 1974-03-07 CH CH321374A patent/CH580914A5/xx not_active IP Right Cessation
- 1974-03-08 RO RO7477958A patent/RO67836A/ro unknown
- 1974-03-08 FR FR7407944A patent/FR2220521B1/fr not_active Expired
- 1974-03-08 JP JP49026448A patent/JPS49124229A/ja active Pending
- 1974-03-08 SE SE7403141A patent/SE401076B/xx unknown
- 1974-03-08 IT IT49244/74A patent/IT1049272B/it active
- 1974-03-08 DD DD177064A patent/DD110160A5/xx unknown
- 1974-03-08 AT AT194774A patent/AT331070B/de not_active IP Right Cessation
- 1974-03-08 CS CS7400001704A patent/CS181753B2/cs unknown
- 1974-03-08 CA CA194,509A patent/CA1023369A/en not_active Expired
- 1974-03-08 PL PL1974169509A patent/PL88521B1/pl unknown
- 1974-03-08 HU HUBA3043A patent/HU169445B/hu unknown
- 1974-03-08 GB GB1041874A patent/GB1453490A/en not_active Expired
- 1974-03-11 BE BE141882A patent/BE812145A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU580801A3 (ru) | 1977-11-15 |
| DK142561C (da) | 1981-07-27 |
| AR213711A1 (es) | 1979-03-15 |
| AT331070B (de) | 1976-08-10 |
| IL44238A0 (en) | 1974-05-16 |
| FR2220521A1 (pl) | 1974-10-04 |
| DD110160A5 (pl) | 1974-12-12 |
| CA1023369A (en) | 1977-12-27 |
| DK142561B (da) | 1980-11-24 |
| BE812145A (fr) | 1974-09-11 |
| ZA741408B (en) | 1975-02-26 |
| CS181753B2 (en) | 1978-03-31 |
| IL44238A (en) | 1977-06-30 |
| ATA194774A (de) | 1975-10-15 |
| SE401076B (sv) | 1978-04-24 |
| JPS49124229A (pl) | 1974-11-28 |
| AU6579974A (en) | 1975-08-21 |
| DE2312045A1 (de) | 1974-09-12 |
| GB1453490A (en) | 1976-10-20 |
| CH580914A5 (pl) | 1976-10-29 |
| FR2220521B1 (pl) | 1978-09-15 |
| RO67836A (ro) | 1981-09-24 |
| HU169445B (pl) | 1976-11-28 |
| IT1049272B (it) | 1981-01-20 |
| NL7402909A (pl) | 1974-09-12 |
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