PL100036B1 - A WORMHOUSE - Google Patents
A WORMHOUSE Download PDFInfo
- Publication number
- PL100036B1 PL100036B1 PL1976188292A PL18829276A PL100036B1 PL 100036 B1 PL100036 B1 PL 100036B1 PL 1976188292 A PL1976188292 A PL 1976188292A PL 18829276 A PL18829276 A PL 18829276A PL 100036 B1 PL100036 B1 PL 100036B1
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- PL
- Poland
- Prior art keywords
- chlorine
- atom
- hydrogen
- pyrrolidinone
- radical
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
Description
Przedmiotem wynalazku jest srodek chwastobój¬ czy, który oprócz znanych nosników i/albo roz¬ cienczalników zawiera jako czynna substancje co najmniej jedna nowa pochodna acykliczna, ali- cykliczna albo aromatyczna chlorowco-2-pirolidy- nonu.The present invention relates to a herbicide or, which in addition to known carriers and / or solutions thinners contains as active substances co at least one new acyclic derivative, ali- cyclic or aromatic halo-2-pyrrolidine- nonu.
Srodki wedlug wynalazku wykazuja dzialanie chwastobójcze typu ogólnego.The agents according to the invention are effective herbicides of the general type.
Jako substancje czynna srodki wedlug wynalaz¬ ku zawieraja nowe, acykliczne alko alicykliczne chlorowco-2-pirolidynony o ogólnym wzorze 1, w którym Q oznacza atom tlenu lub siarki, R ozna¬ cza nizszy rodnik alkilowy lub chlorowcoalkilowy, rodnik alkenylowy, cykloalkilowy, cykloalkilowco- alkilowy, benzylowy albo chlorobenzylowy, X o- znacza atom wodoru albo chloru, Y oznacza atom chloru lub, bromu i Z oznacza atom chloru lub bromu, przy czym gdy R oznacza rodnik cyklo- heksylowy, wówczas X oznacza atom wodoru, albo nowe, aromatyczne chlorowco-2-pirolidynony o o- gclnym wzorze 2, w którym X oznacza atom wo¬ doru lub chloru albo rodnik metylowy, Y oznacza atom wodoru, chloru albo bromu, Z oznacza atom chloru albo bromu, Rt oznacza atom wodoru lub chloru albo rodnik alkilowy lub trójfluorometylo- wy, R2 oznacza rodnik alkilowy lub atom wodoru i R3 oznacza atom wodoru, chloru, fluoru, bromu lub jodu, rodnik alkilowy lub trójfluorometylowy albo grupe nitrowa, cyjanowa, alkoksylowa, al- kilotio, alkilosulfinylowa, alkilosulfonylowa, trój- fluorometylotio, trójfluorometylosulfinylowa, trój- fluorometylosulfonylowa, acetylowa, pieciofluoro- propionamidowa albo 3-metyloureidowa.As active ingredients, the compositions according to the invention they contain a new acyclic alicyclic alcohol halo-2-pyrrolidinones of the general formula I, v where Q is oxygen or sulfur, R is a lower alkyl or haloalkyl radical, alkenyl, cycloalkyl, cycloalkyl, alkyl, benzyl or chlorobenzyl, X o- is hydrogen or chlorine, Y is atom chlorine or, bromine, and Z is chlorine or bromine, where when R is a cyclo- hexyl, then X is hydrogen, or new, aromatic halo-2-pyrrolidinones with o- according to formula II, in which X is hydrogen hydrogen or chlorine or a methyl radical, Y is a hydrogen, chlorine or bromine atom, Z is an atom chlorine or bromine, Rt is hydrogen or chlorine or an alkyl or trifluoromethyl radical where R2 is an alkyl radical or a hydrogen atom and R3 is hydrogen, chlorine, fluorine, bromine or iodine, an alkyl or trifluoromethyl radical or a nitro, cyano, alkoxy, al- kilothio, alkylsulfinyl, alkylsulfonyl, tri fluoromethylthio, trifluoromethylsulfinyl, trifluoromethyl fluoromethylsulfonyl, acetyl, pentafluoro propionamide or 3-methylureido.
Stosowane tu okreslenie „nizszy rodnik alkilo- wy" oznacza rodniki o lancuchach prostych lub rozgalezionych, zawierajace 1—6 atomów wegla, a okreslenie „rodnik chlorowcoalkilowy" oznacza wy¬ mienione wyzej rodniki alkilowe, zawierajace je¬ den lub wieksza liczbe podstawników chlorowco- wych. Okreslenie „rodnik alkenylowy" oznacza ko¬ rzystnie rodniki zawierajace 3—6 atomów wegla i co najmniej jedno wiazanie olefinowe. Rodniki cykloalkilowe w zwiazkach o wzorze 1 zawieraja korzystnie 3—7 atomów wegla, a rodniki cyklo- alkiloalkilowe 4—8 atomów wegla.As used herein, the term "lower alkyl radical wy "refers to straight-chain radicals or branched, containing 1-6 carbon atoms, a the term "haloalkyl radical" means el the above-mentioned alkyl radicals containing them one or more halo substituents out. The term "alkenyl" means co preferably radicals containing 3 to 6 carbon atoms and at least one olefinic bond. Radicals cycloalkyl compounds of Formula 1 include preferably 3 to 7 carbon atoms, and cyclo- alkylalkyl with 4 to 8 carbon atoms.
Dzieki obecnosci niesymetrycznie podstawionych atomów wegla w pewnych zwiazkach o wzorach 1 lub 2 istnieje mozliwosc wystepowania izomerii cis-trans lub izomerii geometrycznej. Izomery cis- -trans sa izomerami przestrzennymi o strukturach rózniacych sie jedynie rozmieszczeniem pewnych atomów lub grup ustawionych „sztywno" wzgledem okreslonej plaszczyzny odniesienia. Plaszczyzna od¬ niesienia jest tutaj pierscien pirolidynowy. Przy okreslaniu konfiguracji cis-trans -w zwiazku jedno- pierscieniowym rozpatruje sie dowolna sposród po¬ zycji pierscienia posiadajacych niejednakowe gru¬ py, w celu oznaczenia konfiguracji wzglednych.Due to the presence of asymmetrically substituted carbon atoms in certain compounds with formulas 1 or 2 there is a possible isomerism cis-trans or geometric isomerism. Cis- isomers -trans are spatial isomers with structures differing only in the distribution of certain atoms or groups "rigid" with respect to a specific reference plane. Plane od carrying here is a pyrrolidine ring. At determining the cis-trans-configuration in a mono- any one of the rings is considered rings with unequal thickness py to denote relative configurations.
W przypadku oznaczenia pozycji. wzglednych we wzorach strukturalnych przy pomocy rysunków. 100 036160 036 przyjmuje sie, ze uklad pierscienia pirolidynono- wego jest plaski. Rozpatrywane atomy lub grupy okresla sie jako „cis", jezeli znajduja sie po tej samej stronie plaszczyzny i „trans" — gdy po¬ lozone sa po przeciwnych stronach plaszczyzny /Glinian „Organie Chemistry" Tom I, str. 477/.In the case of marking an item. relative we structural formulas with the help of drawings. 100 036 160 036 it is assumed that the pyrrolidinone ring system it is flat. Concerned atoms or groups is referred to as "yew" if it follows this the very side of the plane and "trans" - when on are located on opposite sides of the plane (Aluminum "Organic Chemistry" Vol. I, p. 477).
Okreslenie „srodek chwastobójczy" oznacza sro¬ dek majacy zdolnosc regulowania lub zmieniania procesu wzrostu roslin. Pod pojeciem „ilosci u- mozliwiajacej regulacje wzrostu" rozumie sie taka ilosc zwiazku, która wywoluje zmiane wzrostu roslin. Zmiany te obejmuja wszystkie odchylenia od naturalnego procesu rozwoju, np. wyniszcze¬ nie, opóznienie wzrostu, defoliacje, wysuszenie, re¬ gulacje rozrostu, zahamowanie wzrostu, krzewie¬ nie sie, karlowacenie itp. Pod okresleniem „rosli¬ ny" nalezy rozumiec kielkujace nasiona, wyra¬ stajace siewki oraz rosliny lacznie z korzeniami i czesciami nadziemnymi.The term "herbicide" means sro a deck having the ability to regulate or change plant growth process. Under the concept of "amounts of u- regulating growth "means such the amount of compound that produces a change in growth plants. These changes include all variations from the natural process of development, e.g. no, growth retardation, defoliation, drying out, re growth control, inhibition of growth, propagation not grow, stunted, etc. Under the term "grew ny "must be understood as seeds germinating, expresses standing seedlings and plants including roots and parts above ground.
Zwiazki o wzorach 1 lub 2 wytwarza sie ko¬ rzystnie przez katalityczne przegrupowywanie ami¬ dów chlorowcoacylowych podstawionych rodnikiem alkenylowym przy atomie azotu.Compounds of formulas 1 or 2 are made into a horse preferably by catalytic rearrangement of ami¬ radical substituted haloacyl dies alkenyl on the nitrogen atom.
W tablicy 1 podano przyklady zwiazków stano¬ wiacych substancje czynna srodka wedlug wyna¬ lazku, podajac równiez ich charakterystyczne ce¬ chy, a mianowicie temperature topnienia lub wrze¬ nia albo wspólczynnik zalamania nD80 Tablica I ciag dalszy tablicy I Nr zwiazku 1 l \ % 3 4 1 6 7 a. i *' > 11 : 12 Nazwa zwiazku 2 l-allilo-3-chloro-4-chloro- i metylo-2-pirolidynon l-allilo-3,3-dwuchloro-4- ( -chlorornetylo-2-pirolidynon, l-etylo-3-chloro-4-chloro- metylo-2-pirolidynon, l-etylo-3,3-dwuchloro-4- -chlorometylo-2-pirolidynon, l-cykloheksylo-3-chloro-4- -chlorometylo-2-pirolidynon, 1-allilo-3-chloro^1-chloro- metylo-2-pirolidynonoetion, l-metylo-3-chloro-4-chlo- , rometylo-2-pirolidynon, l-propylo-3-chloro-4-chloro- . metylo-2-pirolidynon, : l-aUilo-3-bromo-4-lbromo- metylo-2-pirolidynon, r N-2,3-dwu.bromopropylo-3- -chloro-4-chlorometylo-2- -pirolidynon, (- N-amylo-3-chloro-4-chloro- metylo-2-pirolidynon, : N-butylo-3-chloro-4-chloro- metylo-2-pirolidynon, nD80 lub temperatura topnienia 3 | 125°C/0,25 mm Hg 1,4938 1,4720 | 1,4735 1,4788 1,5487 1,4860 1,4748 1,5350 1,5633 1,4700 .. 1,4731 2a 40 45 50 55 60 85 1 13 14 16 17 18 19 21 22 23 24 26 27 28 29 31 32 33 34 36 2__ N-izobutylo-3-chloro-4- -chlorometylo-2-pirolidynon, N-cyklopropylometylo-3- -chloro-4-chlorometylo-2- -pirolidynon, N-benzylo-3-chloro-4-chloro- metylo-2-pirolidynon, N-p-chlorobenzylo-3-chloro- -4-chlorometylo-2-pirolidynon, l-fenylo-3-chloro-4-chloro- metylo -2-pirolidynon, l-fenylo-3,3-dwuchloro-4- -chlorometylo-2-pirolidynon, l-/2',6'-dwumetylofenylo/-3- -chloro-4-chlorometylo-2- -pirolidynon, l-m-chlorofenylo-3-chloro-4- -chlorometylo-2-pirolidynon, 1 -p-ehlorofenylo-3-chloro-4- -chlorometylo-2-pirolidynon, l-m-trójfluorometylofenylo-3- -chloro-4-chlorometylo-2- -pirolidynon, l-fenylo-3-chloro-3-metylo- -4-chlorometylo-2-pirolidynon, l/3',4'-dwuchlorofenylo/3,3- -dwuchloro-4-chlorometylo- -2-pirolidynon, l-m-trójfluorometylo-3,3- -dwuchloro-4-chlorometylo- -2-pirolidynon, N-m-trójfluorometylofenylo- metylo-2-pirolidynon, l-p-tioliIo-3-chloro-4-chloro- metylo-2-pirolidynon, l-m-fluorofenylo-3-chloro- -4-chlorometylo-2-pirolidynon, N-m-trójfluorometylo-3-bro- mo-4-bromometylo-2-piroli- dynon, N-3',4'-dwuchlorofenylo-3- -chloro-4-chlorometylo-2- -pirolidynon, N-m-nitrofenylo-3-chloro-4- -chlorometylo-2-pirolidynon, N-3',5'-dwuchlorofenylo-3- -chloro-4-chlorometylo-2- -pirolidynon, N-m-trójfluorometylofenylo- -3-chloro-4-/l-chloroetylo/- -2-pirolidynon, N-m-cyjanofenylo-3-chloro- -4-chlorometylo-2-pirolidynon, N-3,5-dwuchlorofenylo 3,3- -dwuchloro-4-chlorometylo- -2-pirolidynon, N-m-trójfluorometylofenylo- -3,3-dwuchloro-4/l-chloro- etylo/-2-pirolidynon, *_ 1,4720 1,4922 1,5387 1,5502 85—90°C 133—134°C pólstaly 93—94°C 100—102°C 1,5032 79—88°C 119—121°C 100—102°C 76—78°C ; 100—104°C 60—63°C j ciecz o ciemnej barwie 119—121°C 102—104QC 80—90°C 1,5020 1,5550 1,5759 1,5122100 036 ciag dalszy tablicy I 1 37 38 39 40 41 42 43 • 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 2 N-m-cyjanofenylo-3,3-dwu- chloro-4-chlorometylo-2- -pirolidynon, N-3'-trójfluorometylo-4'- -chlorofenylo-3-chloro-4- -chlorometylo-2-pirolidynon, N-3'-trójfluorometylo-4'- -chlorofenylo-3,3-dwuchloro- -4-chlorometylo-2-pirolidynon, N-/m-trójfluorometylotiofe- nylo/-3-chloro-4-chloro- metylo-2-pirolidynon, N/m-metylotiofenylo/-3- -chloro-4-chlorometylo-2- -pirolidynon, N/m-trójfluorometylo-sulfi- nylo/-3-chloro-4-chloro- met 3 lo-2-pirolidynon, N-/m-metylosulfinylofenylo/- -3-chloro-4-chlorometylo-2- -pirolidynon, N/m-metylosulfonylofenylo/- -3-chloro-4-chlorometylo-2- -pirolidynon, N/m-trójfluorometylosulfo- nylo-metylo-2-pirolidynon, N/3',5'-bis-trójfluorometylo- fenylo/-3-chloro-4-chloro- metylo-2-pirolidynon, N-m-metoksyfenylo-3-chloro- -4-chlorometylo-2-pirolidynon, N-m-acetylofenylo-3-chloro- -4-chlorometylo-2-pirolidynon, N-m-tolilo-3-chloro-4-chloro- metylo-2-pirolidynon, N-m-trójfluorofenylo-4- -chlorometylo-2-pirolidynon, N-m-bromofenylo-3-chloro- -4-chlorometylo-2-pirolidynon, N-o-chlorofenylo-N-3-chloro- -4-chlorometylo-2-pirolidynon, N-«m-jodofenylo-3-chloro-4- -chlorometylo-2-pirolidynon, N-p-metoksyfenylo-3-chloro- -4-chlorometylo-2-pirolidynon, o-trójfluorometylo-3-chloro- 4-chlorometylo-2-pirolidynon, N/m-pieciofluoro-propion- amido-ienylo/3-chloro-4- -clilorometylo-2-pirolidynon, N/m-metyloureidofenylo/3- -chloro-4-chlorometylo-2- -pirolidynon, cis 1-m-trójfluorometylo- fenylo-3-chloro-4-chloro- metylo-2-pirolidynon, trans 1-m-trójfluorometylo- fenylo-3-chloro-4-chloro- metylo-2-pirolidynon ¦'¦¦¦' 3 ciecz o barwie ciemno¬ czerwonej 1,5263 109—112^0 1,5328 1,5974 1,5248 1,5763 [ szkliwo 1,5228 1,4690 95—99°C 1 117—121°C 1 89—91°C 1,4993 103—105°C 1,5530 107—109°C 123—125°C 1,4910 130—132°C 170—172°C 79— 80°C 54—<55°C | 6 Srodki wedlug wynalazku wytwarza sie znanymi sposobami. Srodki te maja postac pylów, roztwo¬ rów, zawiesin, proszków lub innych preparatów, w zaleznosci od ich przeznaczenia. Stosuje sie je równiez znanymi sposobami, przed albo po wzejs- ciu roslin. Wielkosc dawki o skutecznym dziala¬ niu chwastobójczym zalezy od rodzaju .nasion lub roslin, do których srodki te sa stosowane i wy¬ nosi 0,01 do okolo 5,6 g/m2. Srodki te mozna rów- xo niez stosowac do selektywnego zwalczania niektó¬ rych roslin, dobierajac odpowiednio substancje czynna oraz ilosc jej na jednostke powierzchni te¬ renu.Examples of compounds are given in Table 1 Binding active ingredients of the agent according to the invention lazku, giving their characteristic features chy, namely the melting point or boiling point nd or the refractive index nD80 Table I continuation of table I Relationship No. 1 l \% 3 4 1 6 7 and. and * ' > 11 : 12 Relationship name 2 1-allyl-3-chloro-4-chloro and methyl-2-pyrrolidinone 1-allyl-3,3-dichloro-4- (-chloromethyl-2-pyrrolidinone, 1-ethyl-3-chloro-4-chloro methyl-2-pyrrolidinone, 1-ethyl-3,3-dichloro-4- -chloromethyl-2-pyrrolidinone, 1-cyclohexyl-3-chloro-4- -chloromethyl-2-pyrrolidinone, 1-allyl-3-chloro ^ 1-chloro methyl-2-pyrrolidinoneethione, 1-methyl-3-chloro-4-chloro- , romethyl-2-pyrrolidinone, 1-propyl-3-chloro-4-chloro . methyl-2-pyrrolidinone, : 1-aUilo-3-bromo-4-lbromo- methyl-2-pyrrolidinone, r N-2,3-di-bromopropyl-3- -chloro-4-chloromethyl-2- -pyrrolidinone, (- N-amyl-3-chloro-4-chloro methyl-2-pyrrolidinone, : N-butyl-3-chloro-4-chloro methyl-2-pyrrolidinone, nD80 or temperature melting 3 | 125 ° C / 0.25 mm Hg 1.4938 1.4720 | 1.4735 1.4788 1.5487 1.4860 1.4748 1.5350 1.5633 1.4700 .. 1.4731 2a 40 45 50 55 60 85 1 13 14 16 17 18 19 21 22 23 24 26 27 28 29 31 32 33 34 36 2__ N-isobutyl-3-chloro-4- -chloromethyl-2-pyrrolidinone, N-cyclopropylmethyl-3- -chloro-4-chloromethyl-2- -pyrrolidinone, N-benzyl-3-chloro-4-chloro methyl-2-pyrrolidinone, N-p-chlorobenzyl-3-chloro -4-chloromethyl-2-pyrrolidinone, 1-phenyl-3-chloro-4-chloro methyl -2-pyrrolidinone, 1-phenyl-3,3-dichloro-4- -chloromethyl-2-pyrrolidinone, 1- (2 ', 6'-dimethylphenyl) -3- -chloro-4-chloromethyl-2- -pyrrolidinone, 1-m-chlorophenyl-3-chloro-4- -chloromethyl-2-pyrrolidinone, 1-p-chlorophenyl-3-chloro-4- -chloromethyl-2-pyrrolidinone, l-m-trifluoromethylphenyl-3- -chloro-4-chloromethyl-2- -pyrrolidinone, 1-phenyl-3-chloro-3-methyl- -4-chloromethyl-2-pyrrolidinone, l / 3 ', 4'-dichlorophenyl / 3,3- -dichloro-4-chloromethyl- -2-pyrrolidinone, 1-m-trifluoromethyl-3,3- -dichloro-4-chloromethyl- -2-pyrrolidinone, N-m-trifluoromethylphenyl- methyl-2-pyrrolidinone, 1-p-thioli-3-chloro-4-chloro methyl-2-pyrrolidinone, 1-m-fluorophenyl-3-chloro- -4-chloromethyl-2-pyrrolidinone, N-m-trifluoromethyl-3-bromo mo-4-bromomethyl-2-pyrrole- dynon, N-3 ', 4'-dichlorophenyl-3- -chloro-4-chloromethyl-2- -pyrrolidinone, N-m-nitrophenyl-3-chloro-4- -chloromethyl-2-pyrrolidinone, N-3 ', 5'-dichlorophenyl-3- -chloro-4-chloromethyl-2- -pyrrolidinone, N-m-trifluoromethylphenyl- -3-chloro-4- (1-chloroethyl) - -2-pyrrolidinone, N-m-cyanophenyl-3-chloro -4-chloromethyl-2-pyrrolidinone, N-3,5-dichlorophenyl 3,3- -dichloro-4-chloromethyl- -2-pyrrolidinone, N-m-trifluoromethylphenyl- -3,3-dichloro-4 / l-chloro ethyl / -2-pyrrolidinone, * _ 1.4720 1.4922 1.5387 1.5502 85-90 ° C 133-134 ° C half-solid 93-94 ° C 100-102 ° C 1.5032 79-88 ° C 119-121 ° C 100-102 ° C 76-78 ° C ; 100-104 ° C 60-63 ° C liquid o dark color 119-121 ° C 102-104QC 80-90 ° C 1.5020 1.5550 1.5759 1.5122100 036 continuation of table I 1 37 38 39 40 41 42 43 • 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 2 N-m-cyanophenyl-3,3-di- chloro-4-chloromethyl-2- -pyrrolidinone, N-3'-trifluoromethyl-4'- -chlorophenyl-3-chloro-4- -chloromethyl-2-pyrrolidinone, N-3'-trifluoromethyl-4'- -chlorophenyl-3,3-dichloro -4-chloromethyl-2-pyrrolidinone, N- / m-trifluoromethylthiofe- nyl / -3-chloro-4-chloro methyl-2-pyrrolidinone, N / m-methylthiophenyl) -3- -chloro-4-chloromethyl-2- -pyrrolidinone, N / m-trifluoromethyl-sulfi nyl / -3-chloro-4-chloro meth 3lo-2-pyrrolidinone, N- (m-methylsulfinylphenyl) - -3-chloro-4-chloromethyl-2- -pyrrolidinone, N (m-methylsulfonylphenyl) - -3-chloro-4-chloromethyl-2- -pyrrolidinone, N / m-trifluoromethylsulfo- nyl-methyl-2-pyrrolidinone, N / 3 ', 5'-bis-trifluoromethyl- phenyl) -3-chloro-4-chloro- methyl-2-pyrrolidinone, N-m-methoxyphenyl-3-chloro -4-chloromethyl-2-pyrrolidinone, N-m-acetylphenyl-3-chloro -4-chloromethyl-2-pyrrolidinone, N-m-tolyl-3-chloro-4-chloro methyl-2-pyrrolidinone, N-m-trifluorophenyl-4- -chloromethyl-2-pyrrolidinone, N-m-bromophenyl-3-chloro -4-chloromethyl-2-pyrrolidinone, N-o-chlorophenyl-N-3-chloro -4-chloromethyl-2-pyrrolidinone, N- "m-iodophenyl-3-chloro-4- -chloromethyl-2-pyrrolidinone, N-p-methoxyphenyl-3-chloro -4-chloromethyl-2-pyrrolidinone, o-trifluoromethyl-3-chloro- 4-chloromethyl-2-pyrrolidinone, N / m-5-fluoro-propion- amido-ienyl / 3-chloro-4- -clyloromethyl-2-pyrrolidinone, N / m-methylureidophenyl / 3- -chloro-4-chloromethyl-2- -pyrrolidinone, cis 1-m-trifluoromethyl- phenyl-3-chloro-4-chloro- methyl-2-pyrrolidinone, trans 1-m-trifluoromethyl- phenyl-3-chloro-4-chloro- methyl-2-pyrrolidinone ¦'¦¦¦ '3 liquid o color dark red 1.5263 109-112 ^ 0 1.5328 1.5974 1.5248 1.5763 [ enamel 1.5228 1.4690 95-99 ° C 1 117-121 ° C, 89-91 ° C 1.4993 103-105 ° C 1.5530 107-109 ° C 123-125 ° C 1.4910 130-132 ° C 170-172 ° C 79-80 ° C 54- <55 ° C | 6 The compositions according to the invention are prepared as is known in the art ways. These substances are in the form of dusts, a solution ditch, suspensions, powders or other preparations, depending on their destination. They are used also known methods, before or after plants. The size of the dose with effective action the herbicide depends on the type of seed or plants to which these agents are applied and exclude it is 0.01 to about 5.6 g / m2. These funds can also xo should not be used for selective control of some of various plants, selecting the appropriate substances active and its quantity per unit of surface area rhenium.
W celu modyfikowania lub hamowania wzrostu u kielkujacych nasion lub wyrastajacych siewek na¬ nosi sie na glebe srodki wedlug wynalazku w po¬ staci pylów lub cieczy, znanymi sposobami, na glebokosc nie mniejsza niz 1,3 cm. Nie jest ko¬ niecznym, aby srodki byly zmieszane z czastka- mi gleby lub byly rozprowadzane przez spryski¬ wanie lub zraszanie powierzchni gleby, gdyz moga one byc rozprowadzane równiez przez dodawanie do wody irygacyjnej, doprowadzanej do pola pod¬ dawanego zabiegowi. Srodki wedlug wynalazku w postaci pylów, granulatów lub cieczy moga po na¬ niesieniu na powierzchnie gleby byc wprowadza¬ ne pod jej powierzchnia za pomoca znanych za¬ biegów, takich jak talerzowanie, bronowanie lub mieszanie.To modify or inhibit growth in germinating seeds or emerging seedlings on the agents according to the invention are applied to the soil in half form of dusts or liquids, by known methods, on depth not less than 1.3 cm. He's not a horse it is imperative that the agents be mixed with a particle the soil or were sprayed sprinkling or sprinkling the soil surface as they can they can also be distributed by adding to the irrigation water supplied to the subfield given to the treatment. The measures according to the invention v Forms of dusts, granules or liquids may be exposed to dust to be carried to the surface of the soil to be introduced beneath its surface with the help of known methods gears such as disking, harrowing or mixing.
Srodki wedlug wynalazku moga równiez zawie¬ rac inne dodatki, np. nawozy znane srodki szkod- nikobójcze i inne. Do innych zwiazków fitotok- sycznych dzialajacych korzystnie w kombinacji z srodkami wedlug wynalazku naleza np. kwas 2,4- ' -dwuchlorofenoksyoctowy, kwas 2,4,5-trójchlorofe- noksyoctowy, kwas 2-metylo-4-chlorofenoksyocto- wy i ich sole, estry oraz amidy pochodne triazy- ny, takie jak 2,4-bis/3-metoksypropyloamido/-6-me- tylo-tio-s-triazyna, 2-chloro-4-etyloamino-6-izopro- 40 pyloamino s-triazyna, oraz 2-etyloamino-4-izopro- pyloamino-6-metylomerkapto-s-triazyna, pochodne mocznikowe, takie jak 3-/3-4-dwuchlorofenylo/- -1,1-dwumetylomocznik oraz acetamidy, takie jak N,N-dwuallilo-a-chloroacetamid i im podobne, 45 kwasy benzoesowe, takie jak kwas 3-amino-2,5- -dwuchlorobenzoesowy, oraz tiokarbaminiany, ta¬ kie jak np. ester S-propylowy kwasu dwupropylo* tiokarbaminowego, ester S-etylowy kwasu dwu- propylotiokarbaminowego lub ester S-propylowy 50 kwasu szesciowodóro-l H-azepino-1-karbotionowe- go. Jako dodatki mozna tez stosowac kompost, mierzwe, humus, piasek itp.The agents of the invention may also fail other additives, e.g. fertilizers, known harmful substances nicicidal and others. To other phytotoxin compounds are effective in combination with The agents according to the invention include, for example, 2,4- '-dichlorophenoxyacetic acid, 2,4,5-trichlorophene noxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid you and their salts, esters and amides derived from triazines nones such as 2,4-bis (3-methoxypropylamido) -6-met- tylo-thio-s-triazine, 2-chloro-4-ethylamino-6-isopro- 40 pylamino s-triazine, and 2-ethylamino-4-isopro- pylamino-6-methylmercapto-s-triazine derivatives urea compounds such as 3- (3-4-dichlorophenyl) - -1,1-dimethylurea and acetamides such as N, N-diallyl-α-chloroacetamide and the like, 45 benzoic acids such as 3-amino-2,5- - dichlorobenzoic acid and thiocarbamates, ta such as e.g. dipropyl acid S-propyl ester * thiocarbamic acid, S-ethyl ester of di- propylthiocarbamate or S-propyl ester 50 hexahydro-1H-azepine-1-carbothioic acid- him. Compost can also be used as additives, mulch, humus, sand, etc.
W celu okreslenia chwastobójczego dzialania srodków wedlug wynalazku przeprowadzono nizej 55 opisane próby przed wzejsciem i po wzejsciu roslin.In order to determine herbicidal action The measures according to the invention are performed below 55 described pre-and post-emergence trials plants.
Próba chwastobójczego dzialania przed wzejs¬ ciem.Test of the herbicidal action before emergence moths.
Na wadze analitycznej odwaza sie 20 mg bada- 60 nego zwiazku na kawalku celofanowego papieru.On an analytical balance, 20 mg of the test is weighed 60 compound on a piece of cellophane paper.
Papier ze zwiazkiem umieszcza sie w butelce o szerokiej szyjce, majacej pojemnosc 30 ml i do¬ daje 3 ml acetonu zawierajacego l°/o preparatu Twen 20 /polioksystylenowy jednoalurynian sorbi- w tanu/. Jesli material jest nierozpuszczalny w ace-100 036 tonie, to zamiast niego stosuje sie inny rozpusz¬ czalnik, np. wode, alkohol lub dwumetyloforma- mid /DMF/. W przypadku stosowania DMF, sto¬ suje sie nie wiecej niz 0,5 ml w celu rozpuszcze¬ nia zwiazku, a nastepnie dla uzupelnienia obje¬ tosci do 3 ml dodaje sie innego rozpuszczalnika. 3 ml roztworu zrasza sie równomiernie glebe za¬ warta w malym plaskim naczyniu, w 1 dzien po wysianiu nasion chwastów do plaskiego naczynia z gleba. Do rozprowadzania srodków wedlug wy¬ nalazku stosuje sie rozpylacz zasilany powietrzem pod cisnieniem 1,3 kG/cm2. Dawka srodka wynosi 0,89 g/m2, a objetosc rozpylonego roztworu — 0,133 l/m2.The paper with the compound is placed in the bottle o wide neck, having a capacity of 30 ml and up gives 3 ml of acetone containing 10% of the preparation Twen 20 / polyoxystylene monoalurate sorbi- in tanu /. If the material is insoluble in ace-100 036 is sinking, another dissolving is used instead an solvent, for example, water, alcohol or dimethylforma mid / DMF /. When using DMF, one hundred no more than 0.5 ml is used to dissolve relationship, and then to complete the ob¬ other solvent is added to 3 ml. 3 ml of the solution is evenly sprinkled on the soil worth in a small flat dish, 1 day after sowing weed seeds into a flat dish with soil. For the distribution of agents as per excerpt The invention uses an air fed atomizer under a pressure of 1.3 kg / cm2. The dose of the remedy is 0.89 g / m2 and the volume of the sprayed solution - 0.133 l / m2.
W dniu poprzedzajacym zabieg, naczynie o dlu¬ gosci 17,8 cm, szerokosci 12,7 cm i glebokosci 7 cm napelnia sie do glebokosci 5,0 cm gliniasta gleba piaszczysta. W pojedynczych rzadkach u- mieszcza sie nasiona 7 róznych gatunków chwa¬ stów, stosujac 1 gatunek na 1 rzadek rozciagaja¬ cy sie w poprzek naczynia. Nasiona pokrywa sie ziemia tak, ze znajduja sie one na glebokosci 1,3 cm. Nasiona wysiewane sa w takich odste¬ pach, aby po wykielkowaniu w jednym rzadku znajdowalo sie 20—50 siewek, zaleznie od wymiaru roslin.On the day before surgery, the vessel was long height 17.8 cm, width 12.7 cm and depth 7 cm fills to a depth of 5.0 cm loamy sandy soil. In single rarer contains seeds of 7 different species of weed using 1 grade per 1 sparse stretch running across the vessel. The seeds are covered land so that they are at a depth 1.3 cm. The seeds are sown at such distances armpits to sprout in one sparse there were 20-50 seedlings, depending on the size plants.
Stosuje sie nastepujace nasiona nastepujacych roslin: wlosnica /Setaria spp/ — Ft, chwastnica jednostronna /Echinochloa crusgalli/ — WG, czer¬ wony owies /Avena sativa/ — RO, szarlat /Ama- ranthus retroflexus/ —PW, gorczyca /Brassica junces/ — MD, szczaw kedzierzawy /Rumex cris- pus/ — CD oraz palusznik krawawy /Digitaria sariguinalis/ — CG.The following seeds are used plant: trichinella / Setaria spp / - Ft, weed one-sided / Echinochloa crusgalli / - WG, red wony oies / Avena sativa / - RO, charlat / Ama- ranthus retroflexus / —PW, mustard / Brassica junces / - MD, sorrel kedzierzawy / Rumex cris- pus / - CD and palusznik krawawy / Digitaria sariguinalis / - CG.
Naczynia po zabiegu umieszcza sie w cieplarni w temperaturze 21—29°C i podlewa przez zra- szanie woda. Po uplywie 2 tygodni od zabiegu okresla sie stopien uszkodzenia lub skutecznosci ochronnego dzialania srodka przez porównanie z roslinami i kontrolnymi w tym samym wieku, nie poddanymi zabiegowi. Dla kazdego gatunku okres¬ la sie stopien uszkodzen w procentach 0—100%, przy czym 0% oznacza brak uszkodzen, a 100°/o — calkowite zniszczenie roslin.After the treatment, the dishes are placed in the greenhouse at a temperature of 21-29 ° C and watered through rots rushing water. After 2 weeks from the procedure the degree of damage or effectiveness is specified protective action of the agent by comparison with plants and controls of the same age, no treated. Period for each species the degree of damage is 0-100%, where 0% means no damage and 100% means no damage - complete destruction of plants.
Próba dzialania chwastobójczego w okresie po wzejsciu.Test of herbicidal action in the period after ascent.
Nasiona 6 gatunków roslin: palusznik krwawy /CG/, chwastnica jednostronna /WG/, czerwony owies /RO/, gorczyca /MD/, szczaw kedzierzawy /CD/ i fasoli /Phascolus vulgaris/ /BN/, umieszcza sie opisanym sposobem w plaskich naczyniach z ziemia/Naczynia ustawia sie w cieplarni w tempe¬ raturze 21—29°C i podlewa codziennie za pomoca zraszacza. Po uplywie 10—14 dni od momentu wy¬ siania; gdy pierwotne liscie roslin fasoli sa prawie calkowicie rozwiniete i zaczynaja sie formowac pierwsze liscie potrójne, rosliny opryskuje sie ba¬ danymi roztworami. Roztwór do , opryski¬ wania sporzadza sie przez rozpuszczenie 20 mg badanego zwiazku, w 5 ml acetonu zawieraja¬ cego l°/o Tween 20 /polioksyetylenowy jednolaury- nian sorbitanu/ i nastepnie zmieszanie z 5 ml wo¬ dy. Roztwór nanosi sie na liscie za pomoca roz¬ pylacza zasilanego sprezonym powietrzem o cis¬ nieniu 1,3 kG/cm2. Stezenie roztworu do opryski¬ wania wynosi 0,2°/o, a ilosc rozprowadzanego roz¬ tworu 0,445 litra/m2. Dawka substancji chwasto¬ bójczej wynosi 0,89 g/m2.Seeds of 6 species of plants: bloody finger / CG /, one-sided weedweed / WG /, red oats / RO /, mustard / MD /, black sorrel / CD / and beans / Phascolus vulgaris / / BN /, he places using the method described in flat dishes with ground / Dishes are placed in the greenhouse at a temperature nature 21-29 ° C and watered daily with sprinkler. After 10-14 days from the moment of departure sowing; when the primary leaves of the bean plant are almost fully developed and starting to form first leaves triple, the plants are sprayed dreaded given solutions. Solution for spraying s are prepared by dissolving 20 mg of the test compound in 5 ml of acetone contain cego l ° / o Tween 20 / polyoxyethylene monaural- sorbitan nanate and then mixing with 5 ml of water dy. The solution is applied to the leaves by dilution a compressed air-powered duster 1.3 kg / cm2. The concentration of the spray solution the spreading quantity is 0.2% and the spreading quantity is 0.445 liters / m2. The dose of the weed substance the homicide is 0.89 g / m2.
Wyniki prób podano w tablicy 2, przy czym nu¬ mery zwiazków sa takie same jak podano wyzej w tablicy 1.The test results are given in Table 2, nu the relationship units are the same as in v table 1.
Tablica Dzialanie chwastobójcze — wyniki Procent uszkodzenia przy ochrony przed chwastami dawce 0,89 g/m2 Nr zwiazku 1 . 2 3 4* * 6 7 8 9 * 11 12 13 14 16 17 18 19 | 21*** 22 Przed wyrastaniem CG 2 79 80 90 95 1 100 99 100 90 95 100 90 90 100 80 90 100 80 100 70 100 | FT 3 98 60 90 100 99 98 0 95 98 90 95 95 80 80 100 80 100 100 | 1 WG 4 100 50 90 98 80 100 100 95 95 95 80 95 95 -70 40 80 100 0 100 | RO 98 0 50 100 90 98 0 0 95 70 90 80 0 50 0 100 MD 6 100 0 100 0 ¦ 20 0 80 70 0 100 100 95 0 100 100 100 0 100 \ CD 7 50 0 0 0 0 50 0 50 80 0 50 50 100 0 100 PW 8 40 0 0 0 0 0 0 0 0 0 40 0 80 80 100 0 100 Po wyrosnieciu CG 9 90 70 98 100 80 70 90 90 95 80 98 40 40 90 90 100 100 70 100 95 100 Twe 90 70 40 70 70 80 90 40 40 90 70 80 80 80 0 60 95 0 100 RO 11 60 0 40 0 0 ' 60 0 80 70 0 0 40 0 0 50 0 80 MD 12 80 0 0 98 50 0 60 50 90 90 100 , 70 50 100 100 80 80 0 100 90 100 CD 13 100 50 0 80 , 50 0 0 0 0 70 60 40 80 80 0 80 0 100 ^40 100 PW 14 70 0 60 70 50 0 0 fi 0 0 40 40 0 0 100 0 95100 036 9 10 ciag dalszy tablicy 2 1 23 24 26 27 28 29 31 32 33 34 > 1 36 37 38 39 40 41 42 43 44 45 46 47 , 48* 49 50 51 52* 53 54* 55* 56 57 1 2 1 90 0 100 100 90 100 90 70 90 100 100 1 95 1 98 100 100 100 Too 100 100 100 100 100 100 90 100 100 100 100 100 0 100 100 | 3 0 100 100 70 100 95 93 90 98 100 93 100 95 100 100 100 95 100 100 100 100 ' 90 100 100 100 100 100 0 95 90 1 4 0 100 100 0 100 80 0 60 100 50 60 80 80 40 100 98 100 70 98 70 80 80 0 80 98 100 98 95 0 0 70 ' 0 0 0 0 70 0 0 0 0 98 0 0 95 0 0 0 0 40 0 0 0 0 0 6 0 100 100 0 100 90 40 100 80 95 80 98 80 98 80 95 90 80 50 95 60 90 100 98 99 0 0 100 95 7 0 0 100 100 0 100 40 40 0 0 100 0 0 80 40 98 40 98 0 50 60 60 40 0 95 100 98 100 0 0 50 95 8 0 0 98 100 0 100 90 0 90 90 98 0 98 95 70 95 70 95 95 60 95 100 0 98 100 100 100 0 0 98 70 9 1 80 0 90 99 60 100 80 70 95 100 100 60 90 100 100 98 100 100 100 100 100 95 100 100 0 100 100 1 00 100 00 0 95 100 0 80 99 0 100 80 60 50 50 100 100 70 60 90 70 70 70 70 50 80 100 0 100 100 100 80 98 0 0 0 u 0 0 0 50 0 100 0 0 90 0 95 60 40 0 0 70 0 0 0 0 12 90 80 100 100 100 50 50 100 100 100 100 50 95 100 100 70 100 100 100 100 100 80 80 100 90 100 100 100 100 100 100 100 13 80 ¦0 100 98 50 100 40 0 80 70 100 50 95 100 80 80 95 100 90 95 80 8 100 95 100 100 8J 100 0 0 100 100 14 60 o ¦ 100 100 0 95 100 0 80 80 1 80 * 0 1 100 100 70 100 80 100 70 80 100 100 < 0 0 100 100 40 100 0 0 100 100 1 * — procent uszkodzenia przy dawce 2,24 g/rn2 w próbie przed wzjesciem i po wzejsciu. ** — w próbach przed wzejsciem, przy dawce 2,24 g/m2. '** — w próbach po wzejsciu, przy dawce 2,24 g/m2.Blackboard Herbicidal action - results Damage Percentage at protection against weeds 0.89 g / m2 Relationship No. 1. 2 3 4 * * 6 7 8 9 * 11 12 13 14 16 17 18 19 | 21 *** 22 Before rising CG 2 79 80 90 95 1 100 99 100 90 95 100 90 90 100 80 90 100 80 100 70 100 | FT 3 98 60 90 100 99 98 0 95 98 90 95 95 80 80 100 80 100 100 | 1 WG 4 100 50 90 98 80 100 100 95 95 95 80 95 95 -70 40 80 100 0 100 | RO 98 0 50 100 90 98 0 0 95 70 90 80 0 50 0 100 MD 6 100 0 100 0 ¦ 20 0 80 70 0 100 100 95 0 100 100 100 0 100 \ CD 7 50 0 0 0 0 50 0 50 80 0 50 50 100 0 100 PW 8 40 0 0 0 0 0 0 0 0 0 40 0 80 80 100 0 100 After it has grown up CG 9 90 70 98 100 80 70 90 90 95 80 98 40 40 90 90 100 100 70 100 95 100 Your 90 70 40 70 70 80 90 40 40 90 70 80 80 80 0 60 95 0 100 RO 11 60 0 40 0 0 ' 60 0 80 70 0 0 40 0 0 50 0 80 MD 12 80 0 0 98 50 0 60 50 90 90 100 , 70 50 100 100 80 80 0 100 90 100 CD 13 100 50 0 80 , 50 0 0 0 0 70 60 40 80 80 0 80 0 100 ^ 40 100 PW 14 70 0 60 70 50 0 0 fi 0 0 40 40 0 0 100 0 95 100 036 9 10 continuation of table 2 1 23 24 26 27 28 29 31 32 33 34> 1 36 37 38 39 40 41 42 43 44 45 46 47 , 48 * 49 50 51 52 * 53 54 * 55 * 56 57 1 2 1 90 0 100 100 90 100 90 70 90 100 100 1 95 1 98 100 100 100 Too 100 100 100 100 100 100 90 100 100 100 100 100 0 100 100 | 3 0 100 100 70 100 95 93 90 98 100 93 100 95 100 100 100 95 100 100 100 100 ' 90 100 100 100 100 100 0 95 90 1 4 0 100 100 0 100 80 0 60 100 50 60 80 80 40 100 98 100 70 98 70 80 80 0 80 98 100 98 95 0 0 70 ' 0 0 0 0 70 0 0 0 0 98 0 0 95 0 0 0 0 40 0 0 0 0 0 6 0 100 100 0 100 90 40 100 80 95 80 98 80 98 80 95 90 80 50 95 60 90 100 98 99 0 0 100 95 7 0 0 100 100 0 100 40 40 0 0 100 0 0 80 40 98 40 98 0 50 60 60 40 0 95 100 98 100 0 0 50 95 8 0 0 98 100 0 100 90 0 90 90 98 0 98 95 70 95 70 95 95 60 95 100 0 98 100 100 100 0 0 98 70 9 1 80 0 90 99 60 100 80 70 95 100 100 60 90 100 100 98 100 100 100 100 100 95 100 100 0 100 100 1 00 100 00 0 95 100 0 80 99 0 100 80 60 50 50 100 100 70 60 90 70 70 70 70 50 80 100 0 100 100 100 80 98 0 0 0 at 0 0 0 50 0 100 0 0 90 0 95 60 40 0 0 70 0 0 0 0 12 90 80 100 100 100 50 50 100 100 100 100 50 95 100 100 70 100 100 100 100 100 80 80 100 90 100 100 100 100 100 100 100 13 80 ¦0 100 98 50 100 40 0 80 70 100 50 95 100 80 80 95 100 90 95 80 8 100 95 100 100 8J 100 0 0 100 100 14 60 by ¦ 100 100 0 95 100 0 80 80 1 80 * 0 1 100 100 70 100 80 100 70 80 100 100 < 0 0 100 100 40 100 0 0 100 100 1 * - percentage of damage at the dose of 2.24 g / rn2 in the pre-and post-emergence test. ** - in pre-emergence trials, at a dose of 2.24 g / m2. '** - in post-emergence trials, at a dose of 2.24 g / m2.
Tablica 3 Numer i konfigu¬ racja badanego zwiazku 58 — cis 59 — trans Mieszanina /40:60/ Dawka g/m2 0,03 0,06 0,11 0,03 0,06 0,11 0,03 0,06 0,11 CG 100 100 100 97 98 100 100 100 100 FT 100 100 100 70 100 100 100 ) WG 80 99 100 40 80 60 90 100 RO 60 80 0 0 0 60 PB 50 80 0 0 40 60 AMG 40 70 0 0 0 0 50 GOT 50 0 0 0 0 Srednio GR 73 90 95 32 52 73 65 80 90 1 BL 27 33 67 0 0 7 | 3 23 i 4311 Zwiazki 58 /cis/ i 59 /trans/ poddaje sie próbie biologicznej ochronnego oddzialywania chwastobój¬ czego przed wzrostem. W tablicy 3 podano wyniki uzyskane przy stosowaniu dawek 0,03 g/m2, 0,06 g/m2 i 0,11 g/m2.Table 3 Number i config right subject relationship 58 - cis 59 - trans Mixture / 40: 60 / Dose g / m2 0.03 0.06 0.11 0.03 0.06 0.11 0.03 0.06 0.11 CG 100 100 100 97 98 100 100 100 100 FT 100 100 100 70 100 100 100 ) WG 80 99 100 40 80 60 90 100 RO 60 80 0 0 0 60 PB 50 80 0 0 40 60 AMG 40 70 0 0 0 0 50 GOT 50 0 0 0 0 Medium GR 73 90 95 32 52 73 65 80 90 1 BL 27 33 67 0 0 7 | 3 23 and 4311 Compounds 58 / cis / and 59 / trans / are put to the test biological protective effects of herbicides what before the growth. Table 3 shows the results obtained at doses of 0.03 g / m2, 0.06 g / m2 and 0.11 g / m2.
Obok podano wyniki uzyskane przy stosowaniu mieszaniny okolo 40% postaci cis i 60% postaci trans. Porównanie wyników swiadczy o korzyst¬ nym dzialaniu zwiazku o konfiguracji cis. W ta¬ blicy tej symbole badanych roslin CG, FT, WG i RO maja wyzej podane znaczenie, PB oznacza fa¬ sole pstrokata, AMG oznacza jednoroczny wilec pnacy /Ipomoea purpurea/ i COT oznacza Spomea trichocarpa. GR oznacza sredni wynik dla czte¬ rech pierwszych roslin, a BL oznacza sredni wy¬ nik dla trzech pozostalych roslin.The results obtained with the use are given beside a mixture of about 40% cis form and 60% form trance. Comparing the results shows that the the action of the cis-configuration compound. On this in this block the symbols of the tested plants CG, FT, WG and RO have the meaning given above, PB stands for ph variegated sole, AMG stands for one-year-old wolf pnacy / Ipomoea purpurea / and COT stands for Spomea trichocarpa. GR is the average result for four the first plants and BL is the average value a score for the three remaining plants.
Claims (4)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56328075A | 1975-03-28 | 1975-03-28 | |
| US56327975A | 1975-03-28 | 1975-03-28 | |
| US05/647,962 US4069038A (en) | 1975-03-28 | 1976-01-09 | Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their utility as herbicides |
| US05/647,963 US4110105A (en) | 1975-03-28 | 1976-01-09 | Aromatic N-substituted halo-substituted-2-pyrrolidinones and their utility as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL100036B1 true PL100036B1 (en) | 1978-08-31 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976188292A PL100036B1 (en) | 1975-03-28 | 1976-03-27 | A WORMHOUSE |
| PL1976200412A PL102693B1 (en) | 1975-03-28 | 1976-03-27 | METHOD OF PRODUCTION OF NEW DERIVATIVES OF CHLORINE-2-PYROLIDINONE |
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| Application Number | Title | Priority Date | Filing Date |
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| PL1976200412A PL102693B1 (en) | 1975-03-28 | 1976-03-27 | METHOD OF PRODUCTION OF NEW DERIVATIVES OF CHLORINE-2-PYROLIDINONE |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS6011695B2 (en) |
| AU (1) | AU502662B2 (en) |
| BE (1) | BE839977A (en) |
| BG (2) | BG29135A3 (en) |
| BR (1) | BR7601774A (en) |
| CA (1) | CA1076588A (en) |
| CH (1) | CH625394A5 (en) |
| DD (1) | DD126149A5 (en) |
| DE (2) | DE2661042C2 (en) |
| DK (1) | DK145891C (en) |
| ES (1) | ES446388A1 (en) |
| FR (1) | FR2305434A1 (en) |
| GB (1) | GB1522869A (en) |
| HU (1) | HU179058B (en) |
| IL (1) | IL49289A (en) |
| IN (1) | IN143281B (en) |
| IT (1) | IT1057396B (en) |
| MX (1) | MX3355E (en) |
| MY (1) | MY8000091A (en) |
| NL (1) | NL187313C (en) |
| NZ (1) | NZ180424A (en) |
| PH (1) | PH15176A (en) |
| PL (2) | PL100036B1 (en) |
| SU (1) | SU942590A3 (en) |
| YU (1) | YU40279B (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU527254B2 (en) * | 1979-02-26 | 1983-02-24 | Stauffer Chemical Company | Synergistic herbicides |
| DE3168705D1 (en) * | 1980-12-19 | 1985-03-14 | Ciba Geigy Ag | Fluoropyrrolidinones, process for their preparation, herbicides containing them and their use |
| DK162087C (en) * | 1983-06-16 | 1992-02-24 | Stauffer Chemical Co | PROCEDURE FOR THE PREPARATION OF N-ARYLHALOGEN PYROLIDONES |
| FI74385C (en) * | 1983-12-05 | 1988-02-08 | Stauffer Chemical Co | SYNERGISTIC HERBICIDBLANDNINGAR AV TIOKARBAMAT OCH PYRROLIDONFOERENING. |
| FR2589150B2 (en) * | 1985-10-25 | 1987-11-20 | Rhone Poulenc Spec Chim | PROCESS FOR THE PREPARATION OF N ALCENE-2 YL M.TRIFLUOROMETHYLANILINES |
| EP0205391B1 (en) * | 1985-05-22 | 1988-10-26 | Rhone-Poulenc Chimie | Process for the preparation of n-alkenyl-m-trifluoromethyl anilines |
| FR2582300B1 (en) * | 1985-05-22 | 1987-07-10 | Rhone Poulenc Spec Chim | PROCESS FOR THE PREPARATION OF N-2 ALCENE-2 YL M-TRIFLUOROMETHYLANILINES |
| FR2625197B1 (en) * | 1987-12-23 | 1990-04-27 | Rhone Poulenc Chimie | PROCESS FOR ACYLATION OF N, N-DIALLYLANILINE |
| US5210305A (en) * | 1988-07-29 | 1993-05-11 | Rhone-Poulenc Chimie | Process for preparing n-alkylanilines and n-allylanilines |
| FR2634761B1 (en) * | 1988-07-29 | 1990-11-23 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF N-ALLYL AND N-ALKYLANILINES |
| US5189220A (en) * | 1988-07-29 | 1993-02-23 | Rhone-Poulenc Chimie | Process for preparing N-alkylanilines and N-allylanilines catalyzed by iodides |
| FR2634762B1 (en) * | 1988-07-29 | 1990-11-02 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF N-ALLYL AND ALKYL-ANILINES |
| FR2643902B1 (en) * | 1989-03-03 | 1991-10-11 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF N-ALLYLMETATRIFLUOROMETHYLANILINE |
| JPH02237970A (en) * | 1989-03-13 | 1990-09-20 | Mitsui Toatsu Chem Inc | 4-ethyl-1-(3-trifluoromethylphenyl)-2-pyrrolidinone derivative and herbicide containing the derivative as active component |
| FR2663927A1 (en) * | 1989-06-05 | 1992-01-03 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF N MONOALKYL- OR ALKENYLANILINES. |
| JP2728937B2 (en) * | 1989-06-14 | 1998-03-18 | 三井東圧化学株式会社 | 1- (3-Substituted benzyl) -3-halogen-4- (1-halogenoalkyl) -2-pyrrolidinone derivatives and herbicides containing these as active ingredients |
| FR2665439B1 (en) * | 1990-08-02 | 1992-11-06 | Rhone Poulenc Chimie | N-ALLYLATION REAGENT AND METHOD FOR SYNTHESIS OF N ACYL, N ALLYLANILINE. |
| EP0470000B1 (en) * | 1990-08-02 | 1997-11-12 | Rhone-Poulenc Chimie | Allylation reagent and method of synthesis using it |
| US5538985A (en) * | 1994-01-27 | 1996-07-23 | Mitsui Toatsu Chemicals, Inc. | Pyrrolidinone derivatives |
| EP2052612A1 (en) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbicide combination |
| DE102008037629A1 (en) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides |
| CN114031536A (en) * | 2021-12-14 | 2022-02-11 | 青海省农林科学院 | Pure optical isomer compound for inhibiting weed seed germination and seedling growth and application |
| WO2023233367A1 (en) | 2022-06-03 | 2023-12-07 | Adama Agan Ltd. | Herbicidal mixtures for crop protection |
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- 1976-03-17 FR FR7607683A patent/FR2305434A1/en active Granted
- 1976-03-19 JP JP51030778A patent/JPS6011695B2/en not_active Expired
- 1976-03-23 BR BR7601774A patent/BR7601774A/en unknown
- 1976-03-23 IN IN510/CAL/1976A patent/IN143281B/en unknown
- 1976-03-23 GB GB11627/76A patent/GB1522869A/en not_active Expired
- 1976-03-24 MX MX000109U patent/MX3355E/en unknown
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- 1976-03-24 BE BE7000801A patent/BE839977A/en not_active IP Right Cessation
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- 1976-03-25 IL IL49289A patent/IL49289A/en unknown
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- 1976-03-26 AU AU12413/76A patent/AU502662B2/en not_active Expired
- 1976-03-26 IT IT48736/76A patent/IT1057396B/en active
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- 1976-03-27 PL PL1976188292A patent/PL100036B1/en unknown
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1980
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