CS244841B2

Herbicide agent and method of its production

Abstract

This record has no abstract on file.

CS244841B2, drawing sheet 1 — Sheet 1 of 4

Term

No projected expiry on record.

1 claim: 1 independent, 0 dependent

1
Accordingly, the present invention relates to a herbicidal composition, characterized in that it contains at least one cyclohexane-1H-dione derivative of the formula Z as defined above or a pyramid as an active ingredient. Předmětem předloženého vynálezu je tudíž' herbicidní prostředek, který se vyznačuje tm, že jako účinnou složku obsahuje alespoň jeden derivát cyklohexan-l^-dionu obecného vzorce Z uvedeného a definovaného shora nebo jehosůl. Sloučeniny obecného vzorce Σ se podle tohoto vynálezu připraví j tm, že se necJhdí reagovat sloučeniny obecného vzorce II The compounds of the formula (I) according to the invention are prepared by reacting the compounds of the formula (II) O in which O v němž A i R2 m!í shora uvedené významy, s hydroxyladny obecného vzorce A i R2 they have the meanings given above, with the hydroxyblades of the general formula R30 - NHj in which r3 in accordance with the foregoing, ▼ inert inert diluents at a temperature m & lt; 0 ° C boiling point го1С & 1! may be used, especially at 15 and 70 ° C. Optionally, hydroxylamine can be experienced in the form of an aqueous solution. R30 - NHj v němž r3 mí stara uvedené význawy, ▼ inertních ředidlech při teplotě m«i 0 °C teplotou varu го1С&1! směl, zejména při teplotách mesi 15 a 70 °C. Popřípadě je možno prožívat hydroxylamin ve foímě vodného roztoku. Suitable resolvents for this reaction are, for example, alcohols such as methanol, ethanol, isopropanol, cyclohexylmol, or chlorinated hydrocarbons such as hexane, cyclohexane, methylene cALorld, toluene, esters such as ethyl acetate, nitriles such as chloro-nitrile, cyclic ethers such as tetrahydrofuran. 1 Vhodnými rezpoužtědly pro tuto reakci jsou například alkoholy, jako mtlhnol, ethano!, isopropa^c^i., cykloheixmol, popřípadě chlorované uhlovodíky, jako hexan, cyklohexan, methylen cALorld, toluen, estery, jako ethy dostát, nitrily, jako lcijocitril, cyklické ethery, jako totr<hιydrefurln. 1 Reakce je ukončena po několika hodinách, přičemž. se reakční produkt mlže izolovat za· huětěníta směi, přidánm vody a extrakcí nepolárním' rozpouštědlem, jako mthylenchloridim a Oddetilcvánm rozpoiutědla za sníženého tlaku. The reaction is complete after a few hours, taking. The reaction product may be isolated by concentration in a mixture, addition of water and extraction with a non-polar solvent such as methylene chloride and removal of the solvent under reduced pressure. Soli sloučenin vzorce I s alkalickými kovy se mohou získat reakcí sloučenin vzorce I s hydroxidem sodným nebo s hydroxidem drasennýfo ve vodném roztoku v organickém rozpouUtědle, jako m Úhono lu, ethanolu, acetonu. Také alkoxidy sodné a draselné rohou sloužit jako báze. The alkali metal salts of the compounds of the formula I can be obtained by reacting the compounds of the formula I with sodium hydroxide or potassium hydroxide in aqueous solution in an organic solvent, such as carbon monoxide, ethanol, acetone. Also sodium and potassium alkoxides serve as bases. Dlií seli s kovy, tj. soli s manganem, mdí, ziiekm železem, vápníkem, hořčíkem a baryem, se mohou vyrábět ze sodných solí reakcí s odpoíeUaícltai chloridy kovů ve vodném roztoku. Antonové, sulfoniové, sulfoxoniové a fosfoniové soli se mohou vyrábět reakcí sloučenin vzorce i s hydroxidem amonným, fosfonivmhydroxidtem, sulfonumbydroxidem a sulfexorniímbydroxidem, popřípadě ve vodném roztoku. Particular metals, i.e., salts with manganese, copper, iron, calcium, magnesium and barium, can be prepared from sodium salts by reacting with metal chloride chlorides in aqueous solution. The anionic, sulfonium, sulfoxonium and phosphonium salts can be prepared by reacting compounds of the formula with ammonium hydroxide, phosphonium hydroxide, sulfonium bromide and sulfexorium bromide, optionally in aqueous solution. Compounds of formula (II) can be produced from the cyclohexun-1'-dione of formula (XII), which may also be present in the tautomers of compounds of formula (XXXa) and (IIIb). Sloučeniny vzorce II se rohou vyrábět z cyklohexun-l^-dionů obecného vzorce XII, které se mohou rovněž vyskytovat ve foirně tautomumích sloučenin vzorce XXXa a Illb O O O O OH OH OH / 11U / XXX · / / хххь / OH /11U /XXX·/ /хххь/ Mtodami known from literature / siov. Tetrahedron Mtters., 29, 2491 (1975) // Mtodami známým z literatury /siov. Tetrahedron Mtters.,· 29, 2491 · /1975// It is also possible to prepare the compounds of the formula II via the meietupeft enoleaters which are optionally formed in the reaction of the compounds of the formula III as α 1 isomers and in the presence of derivatives of irtidazole or pyridine are rearranged / cf. JP-OS 79/063052 /. Je rovněž možné vyrábět sloučeniny vzorce II přes meietupeft enoleaterú, které popřípadě vznikají při reakci sloučenin vzorce III jako аЫа1 isororů, a v příttmnoti derivátů irtidazolu nebo pyridinu se přesmfkkjí /srov. JP-OS 79/063052/. Ke sloučeninám vzorce III se dospěje postupy známými z literatury, jak vyplývá z následujícího schématu:— The compounds of formula (III) are obtained by methods known from the literature, as shown in the following scheme: CH3-C-CH3 CH3-C-CH3 A-CH-CH-C-CH 3 A-CH—CH-C-CH3 СН2 <СООН)2 pyricfin СН2<СООН)2 pyricfin -CH2CH-C-OH -CH»CH~C-0H CH2(COOCCH)2 СНзОИа CH2(COOCCH)2 СНзОИа

20 paragraphs, as filed

The present invention relates to a herbicidal composition comprising as active ingredient novel cyclohexane-1,3-dione derivatives. Furthermore, the invention relates to a process for the preparation of these novel carbocoxane-1,3-dione derivatives of carbamic acid.

It is already known to use herbicidal compositions which contain cyclohexane-1,3-dione derivatives as active ingredients for controlling undesirable grasses in dicotyledonous plant cultures. Active substances having a furyl group or a thienyl group as a substituent show a relatively weak effect (cf. DE-OS 24 39 104].

Furthermore, EP-OS 0071707 discloses cyclohexane-1,3-dione derivatives substituted with heterocyclic radicals having good herbicidal activity against plants of the grass family.

It has now been found that herbicidal compositions containing novel cyclohexane-1,3-dione derivatives with certain heterocyclic substituents at the 5-position appear to have a higher herbicidal effect against a number of grasses (wild and cultivated) than the active ingredients of prior art. These compositions exhibit excellent compatibility with both dicotyledonous crop plants and monocotyledonous crop plants which do not belong to the grass family.

In addition, some of these compounds are at the same time well tolerated by wheat as a cultural type of cereal, despite good grass activity at certain doses.

The novel cyclohexane-1,3-dione derivatives correspond to the general formula I

/ X / in which

A 'is tetrahydropyrrole-1-yl, 1,4-dioxanyl, 5,5-dimethyl-1,3-dioxan-2-yl, 2,5-dimethyl-1,4-dioxan-3-yl , 2,6-dimethyl-1,4-dioxan-3-ylmethyl, 2-methyl-1,3-dithiolim-2-yl (NH4), 2,6-dimethyl-tetrahydrothiopyran-3-yl, 2-methyl a 1,3-dimethylamino group or, optionally, an alkyl group having from 1 to 4 carbon atoms or an alkylene group having 4 or 5 carbon atoms substituted with a 1,3-dimethylamino group;

R * represents an alkyl group having 1 to 4 carbon atoms and r3 means aikyia C 1-4 alkenyl group of 3 or 4 carbon atoms; 4 C,, ch chior ch ch ch ch (C nebo ch 4 4 4 4 ch ch ch ch ch ch ch ch ch ch) C,, ch ch ch ch ch (C ch nebo 4 4 4 ch ch ch ch ch ch ch ch) C ch nebo ch ch ch ch ch ch (C ch nebo 4 4 4 4 ch ch ch) C ch ch ch ch ch ch (C ch ch 4 ch 4 4 ch ch) C ch ch 4 ch ch ch ch (C ch nebo 4 ch)

The compounds of formula Σ st can exist in several forms, all of which form a spa. - below the scope of the present invention:

The 1,3-dioxepw-5-yl groups of formula A in formula I may be substituted by straight or branched (C 1 -C 4) alkyl groups such as methyl, ethyl, isopropyl, tert. brothers left group.

In addition, 1,3-dioxtpan-5,110 may be present. groups substituted with 4 to 5 carbon-alkylene-chain, i.e., a heteroarylene group or a pentarathylene group, so that they form, for example, a spiroalkyl group.

k in formula I represents straight or branched (C1-C4) alkyl groups, i.e. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl group.

Jako zbytky R3 in formula I, come in the eyehat: propargy]pC1-4 alkyl, C3-C4 alkenyl or C3-C4 chloroalkenyl which may contain up to three chlorine atoms as suds, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl Skipina, allyl, 1-chloroprop-1-en-3-yl, 2-chloropeo] -1- (1-methyl-3-ynyl), 1'-dichloro-piperidin-1-yl, 1,2,3-chloropwhatpa 1-en-3-yl group.

The tri-cyclohexin-1,3-dione derivatives of formula I are those in which R represents an alkyl group having 2 'or 3 carbon atoms. Preferred radicals A are a tetahihydropyran-4-yl radical, a 2,6-dimethylthiomethyldrothiopyran-3-yl radical or, optionally, an alkyl group having from 1 to 4 carbon atoms or an alkylene group. 4 or 5 carbon atoms substituted. 1,3-dloxopan-5-yl radicals, in particular a 1'-dioxepan-S-yl radical or unbranched. or swirling. alkyl. (C 1 -C 4) -substituted 1,3-dioxolan-5-yl radical

Suitable salts of the compounds of the formula I are alkali metal salts, in particular potassium or sodium salts, alkaline earth metal salts, in particular calcium, magnesium or barium salts, as well as manganese salts, copper, zinc or iron salts and ammonium salts. salts and phosphonium salts, for example, alkylthimmonium salts, diacylimmonium salts, triacetone salts or tetlacylsulfonium salts, bonzyltraconium salts, trisphenoconium salts, tertiarymonium salts, or traconium salts.

32 members in 20 offices

This recordMember, by publication datePriority claim10 more offices are in the list below

Priority claims1

Priority claims
Document	Office	Kind	Date
3340265	Germany	A	1983-11-08

Members32

Family members, oldest first
Document	Office	Kind
DK529184D0	Denmark	D0	1984-11-07
GR80616B	Greece	B	1985-02-01
IE842842L	Ireland	L	1985-05-08
DK529184A	Denmark	A	1985-05-09
FI844215L	Finland	L	1985-05-09
NO844442L	Norway	L	1985-05-09
DE3340265A1	Germany	A1	1985-05-15
AU3518684A	Australia	A	1985-05-16
EP0142741A2	European Patent Office (EPO)	A2	1985-05-29
JPS60123484A	Japan	A	1985-07-02
ZA848688B	South Africa	B	1985-07-31
BR8405678A	Brazil	A	1985-09-10
DD228156A5	German Democratic Republic (until 1990)	A5	1985-10-09
HUT36984A	Hungary	A	1985-11-28
EP0142741A3	European Patent Office (EPO)	A3	1986-03-05
PH19805A	Philippines	A	1986-07-08
CS244841B2This record	Czechoslovakia (until 1993)	B2	1986-08-14
US4654073A	United States of America	A	1987-03-31
CA1230344A	Canada	A	1987-12-15
HU194017B	Hungary	B	1988-01-28
AU577327B2	Australia	B2	1988-09-22
IL73400A	Israel	A	1990-01-18
EP0142741B1	European Patent Office (EPO)	B1	1990-01-24
AT49759T	Austria	T	1990-02-15
DE3481122D1	Germany	D1	1990-03-01
FI82458B	Finland	B	1990-11-30
FI82458C	Finland	C	1991-03-11
NO169631B	Norway	B	1992-04-13
NO169631C	Norway	C	1992-07-22
MX9203414A	Mexico	A	1992-08-01
IE58200B1	Ireland	B1	1993-07-28
JPH0676398B2	Japan	B2	1994-09-28

Herbicide agent and method of its production

Abstract

Term

Priority claims1

Members32

Numbers

Titles

Classification