PL88521B1 - - Google Patents
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- 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
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- PL
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- wzdr
- active substance
- harmful
- formula
- crops
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- 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
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- 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.The subject of the invention is a herbicide containing new carbothiolates as an active ingredient acetidine.
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).It is known to use S-ethyl-hexahydro-1H-azepine-1-carbothiolane to control plants other than data on crops of crops such as barley, wheat and rice (German Patent No. 1,300,947).
Dzialanie jego jest jednakze niezadowalajace.Its performance, however, is unsatisfactory.
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.It has been found that acetidine carbothiolates of formula I in which R1 is an alkyl group, e.g. wa, ethyl, n is 0-4, X is oxygen or sulfur, have good herbicidal activity.
Przy jednakowym, a czesto lepszym dzialaniu chwastobójczym, rosliny lepiej je znosza niz znane S-etylo-heksa- hydro-1 H-azepino-1 -karbotiolany.With the same, and often better, herbicidal action, plants tolerate them better than the known S-ethyl-hexa hydro-1H-azepine-1-carbothiolates.
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.The active ingredients are obtained by reacting the thiolchloroformic acid ester with optionally substituted acetidine. The same can produce active ingredients if acetidine in the form the corresponding acid N-chloride is reacted with mercaptans. The preparation of acetidine is known from literature.
Przyklad I. Wytwarzanie 2-etylo-(2,2,4-trójmetyloacetydyno)-1-karbotiolanu.Example I. Preparation of 2-ethyl- (2,2,4-trimethylacetidine) -1-carbothiolane.
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.For a mixture of 4.95 parts by weight of 2,2,4-trimethylacetidine and 6 parts of triethylamine in 50 parts by weight of benzene, 6.23 parts of ethyl thionochloroformate are added dropwise at 30-40 ° C. After an hour The triethylamine hydrochloride is not filtered off and the filtrate is washed with water. After drying, it thickens underneath reduced pressure and the residue distilled. 6.70 parts of S-ethyl- (2,2,4-trimethylacetid- no) -1-carbothiolane of structural formula 2 and boiling point: 59 ° C 0-1.
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.The same method can produce the following compounds: S-methyl- (2,2,4-trimethylacetidine) -1-carbothiolane, boiling point: 70 ° C 0.05 S-propyl- (2,2,4-trimethylacetidine) -1 -carbothiolane, boiling point: 81 ° C 0.052 88 521 Gossypium hirsutum, Leguminosae, e.g. Medicago spp., Trifolium spp., Pisum spp., Phaseolus spp., Arachi s spp., Glycine Max, Chenopodisceae, e.g. Beta vulgaris, Spinacia spp., Solanaceae, e.g. Solanum spp., Nicotiania spp., Capsicum annuum, Linaceae, e.g. Linum spp., Umbeliferae, e.g. Petroselinum spp., Daucus carota, Apium graveolens, Rosaceae, e.g. Fragaria, Cucurbitaceae, e.g. Cucumis spp., Cucurbita spp., Liliaceae, e.g. Allium spp., Vitaceae, e.g. Vitis vinifera, Bromeliaceae, e.g. 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.Example II. In the greenhouse, the test vessels are filled with loamy sandy soil and sown various seeds. The active substances are treated immediately after IV (formula 4), V (formula 5), VI (formula 6) and VII (formula 7) compared with the known active substance III (formula 3), using 1 kg of the substance at a time active per hectare, dispersed or emulsified in 500 l of water per hectare. Sprinkles during the experiment water the plants abundantly. After 4 weeks, it was found that the active substances IV, V, VI and VII were better tolerated by arable crops and better herbicidal activity than the comparative active substance III. Results of dos The services are presented in Table 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.Example III. Various plants with a growth height of 3-15 cm are treated with the active substances IV (formula 4), V (formula 5), VI (formula 6) and VII (formula 7) compared to the known substance III (formula 3) using either per hectare, 1 kg of active substance per hectare, dispersed or emulsified in 500 l of water per hectare.
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.During the experiment, the plants are watered abundantly. After 4 weeks, it was established that the active substances IV, V, VI and VII show better tolerability by crops with the same herbicidal action from the beginning equivalent to the active substance III.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2312045A DE2312045A1 (en) | 1973-03-10 | 1973-03-10 | CARBOTHIOLATES |
Publications (1)
Publication Number | Publication Date |
---|---|
PL88521B1 true PL88521B1 (en) | 1976-09-30 |
Family
ID=5874438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1974169509A PL88521B1 (en) | 1973-03-10 | 1974-03-08 |
Country Status (21)
Country | Link |
---|---|
JP (1) | JPS49124229A (en) |
AR (1) | AR213711A1 (en) |
AT (1) | AT331070B (en) |
BE (1) | BE812145A (en) |
CA (1) | CA1023369A (en) |
CH (1) | CH580914A5 (en) |
CS (1) | CS181753B2 (en) |
DD (1) | DD110160A5 (en) |
DE (1) | DE2312045A1 (en) |
DK (1) | DK142561C (en) |
FR (1) | FR2220521B1 (en) |
GB (1) | GB1453490A (en) |
HU (1) | HU169445B (en) |
IL (1) | IL44238A (en) |
IT (1) | IT1049272B (en) |
NL (1) | NL7402909A (en) |
PL (1) | PL88521B1 (en) |
RO (1) | RO67836A (en) |
SE (1) | SE401076B (en) |
SU (1) | SU580801A3 (en) |
ZA (1) | ZA741408B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2457688A1 (en) * | 1974-12-06 | 1976-06-10 | Basf Ag | CARBAMINE ETHIOLESTER |
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 |
EP0350693B1 (en) * | 1988-07-15 | 1994-09-28 | BASF Aktiengesellschaft | Azetidine derivatives, process for their preparation and their use in the regulation of plant growth |
DE10144872A1 (en) * | 2001-09-12 | 2003-03-27 | Bayer Cropscience Gmbh | New N-substituted 3-di(hetero)arylalkyl-azetidine derivatives useful as pesticides |
-
1973
- 1973-03-10 DE DE2312045A patent/DE2312045A1/en 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 DK DK116574A patent/DK142561C/en active
- 1974-03-05 ZA ZA00741408A patent/ZA741408B/en unknown
- 1974-03-06 AR AR252651A patent/AR213711A1/en active
- 1974-03-07 SU SU7402003152A patent/SU580801A3/en active
- 1974-03-07 CH CH321374A patent/CH580914A5/xx not_active IP Right Cessation
- 1974-03-08 HU HUBA3043A patent/HU169445B/hu unknown
- 1974-03-08 PL PL1974169509A patent/PL88521B1/pl unknown
- 1974-03-08 RO RO7477958A patent/RO67836A/en unknown
- 1974-03-08 CA CA194,509A patent/CA1023369A/en not_active Expired
- 1974-03-08 IT IT49244/74A patent/IT1049272B/en active
- 1974-03-08 DD DD177064A patent/DD110160A5/xx unknown
- 1974-03-08 FR FR7407944A patent/FR2220521B1/fr not_active Expired
- 1974-03-08 AT AT194774A patent/AT331070B/en not_active IP Right Cessation
- 1974-03-08 JP JP49026448A patent/JPS49124229A/ja active Pending
- 1974-03-08 GB GB1041874A patent/GB1453490A/en not_active Expired
- 1974-03-08 CS CS7400001704A patent/CS181753B2/en unknown
- 1974-03-08 SE SE7403141A patent/SE401076B/en unknown
- 1974-03-11 BE BE141882A patent/BE812145A/en unknown
Also Published As
Publication number | Publication date |
---|---|
AU6579974A (en) | 1975-08-21 |
JPS49124229A (en) | 1974-11-28 |
CA1023369A (en) | 1977-12-27 |
DK142561B (en) | 1980-11-24 |
IL44238A0 (en) | 1974-05-16 |
HU169445B (en) | 1976-11-28 |
SE401076B (en) | 1978-04-24 |
SU580801A3 (en) | 1977-11-15 |
RO67836A (en) | 1981-09-24 |
ZA741408B (en) | 1975-02-26 |
ATA194774A (en) | 1975-10-15 |
GB1453490A (en) | 1976-10-20 |
NL7402909A (en) | 1974-09-12 |
IT1049272B (en) | 1981-01-20 |
DE2312045A1 (en) | 1974-09-12 |
BE812145A (en) | 1974-09-11 |
CH580914A5 (en) | 1976-10-29 |
IL44238A (en) | 1977-06-30 |
DD110160A5 (en) | 1974-12-12 |
FR2220521A1 (en) | 1974-10-04 |
DK142561C (en) | 1981-07-27 |
FR2220521B1 (en) | 1978-09-15 |
AR213711A1 (en) | 1979-03-15 |
AT331070B (en) | 1976-08-10 |
CS181753B2 (en) | 1978-03-31 |
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