JPS62205079A - Sulfonylamidino-oxyazacycloalkanes - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel sulfonylamidinooxy 7-decycloalka-7s, processes for their production and novel intermediates for their production, and their use as herbicides and potatoes.

Sulfonylamidino-oxy7decycloalkanes are
Not yet known from the literature. The use of similar compounds as herbicides is also hitherto unknown.

This time, the general formula (1) [wherein R represents nine radicals consisting of a series consisting of alkyl, aralkyl, aryl and hetaryl, R2Fi water IA, halogen, hydroxyl, alkyl,
harodanoalkyl, alkoxy, halogenoalkoxy,
represents alkylthio, harodanoalkylthio, amino, alkylamino or dialkylamino, X represents nitrogen or 10H- group, Y represents nitrogen or 10R'- group, R3Fi hydrogen, halogen, cyan, alkyl, Formyl, alkyl-cal represents nyl or alkoxy-carbinyl, 2 nitrogen or -CR- group, R'ha water! , halogen, hydroxyl, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, further n represents the number of λ, M represents hydrogen, / represents an equivalent metal or group -Co-R, R
is alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl,
Represents a substituted group consisting of the series consisting of dialkylamino, aralkyl, aryl, aralkyl, aryloxy, alkylthio, aralkylthio and arylthio, where R represents a radical, R5 represents alkyl, cycloalkyl, aralkyl, aryl and arylsulfonyl series], and adducts of the compound of formula (1) with strong acids. was discovered.

When M represents hydrogen, the general formula (1) represents the individual tautomers of the formulas (IA) and (IB): [wherein n g X @ Y * Z @ R' and R2 have the above meanings] sexual forms, and their tautomers (summer A)
and (IB).

The mixing ratio depends on factors such as temperature, solvent and temperature, which determine the state of aggregation.

When M represents a group -COR, formulas (IC) and (ID)
The following isomers of the formula (I) are possible: in which n, X, Y, Z, R, R and R have the meanings given above. (,) In the formula, when M represents hydrogen, the formula (It):
[In the formula, n, X, Y, Z: lP and R2
has the above meaning] The aminonooxyazocycloalkane of the formula (■) 2R
'-8o□cl(III) [wherein R1 has the above meaning] is reacted with the sulfonic acid chloride in the presence of an acid acceptor if necessary and a diluent if necessary, or (b ) Si2 compound in which M is hydrogen, formula (■): [In the formula, X, Y, Z, R and R have the above meanings, and Rla has the same meaning as R1, but in each case and R6 represents an appropriately substituted hydrocarbon group] with an oxyazacycloalkane of the formula (V) (in which n has the above-mentioned meaning); or reacting an oxyazocycloalkane of formula (V) with a strong acid, optionally in the presence of an acid acceptor and optionally a diluent; When R represents a group C, in which R' represents an optionally substituted group selected from the series consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl and aryl, then the formula ( ■): [In the formula, X, Y, Z, R2o,! ,hiR'
has the meaning above) ] Benzodisultam of formula (V): [
where n has the above meaning] or an adduct of the oxyazocycloalkane of the formula (v) and a strong acid, optionally in the presence of an acid acceptor and optionally a diluent. or (d) when M represents a group -COR [wherein R has the above meaning], the above (a), (b): Th and (C
) A compound of formula (I) [wherein M represents hydrogen and n, X, Y, Z, R' and R2 have the above meanings] obtained by the method described in ): Q-Co-W (■) [In the formula, W represents a halogen or represents a group QCOO-, and Q has the same meaning as R, but does not represent a group -NHR]. If necessary, react in the presence of an acid acceptor and if necessary in the presence of a diluent, or (to) formula (■)
: R'NGO(■) [In the formula, R5 has the above meaning] is reacted with the isocyanate in the presence of a catalyst if necessary and a diluent if necessary, or (・) M is /
(a) above when indicating the amount of metal.

0)) and (c) ic formula obtained by the method described (
I) Compounds of the formula [in which M represents water bulk and X, Y, Z, R and R have the meanings given above] with metal hydroxides, hydrides or alkanolades or organometallic compounds as necessary or (f) in the case of preparing /di/adducts of the compound of formula (1) with strong acids, the compound of the formula (R) [wherein M represents the water volume and n
, X, Y, Z, R and R have the above meanings] with a strong acid, optionally in the presence of a diluent.

The novel sulfonylamidino-oxyazocycloalkanes of formula (1) and their adducts with strong acids are characterized by a strong herbicidal activity.

In particular, the new compound of formula (1) exhibits extremely strong herbicidal activity compared to many conventionally known compounds having the same type of activity.

R8 and R are the same or different and are hydrogen,
Halodane [e.g., especially fluorine, chlorine, bromine and /l]
or iodine], cyano, nitro or C,-C6 alkyl [which may optionally be fluorine, chlorine, bromine, cyano, xyl, C,-C4-alkylsulfonyl, C1-04-
Alkyluaminocargenyl, di(C,-C4-alkyl)aminocargenyl, hydroxyl, C,-
C4-alkoxy, formyloxy, C1-C4-furkyl-carbonyloxy, C,-C4-alkoxycargenyloxy, C,-C4-furkylaminocargenyloxy1. C, -C4-furkylthio, C,
-C4-furkylsulfinyl, C,-04-alkylsulfonyl, y -(c, -C4-alkyl)-7
Minosulfonyl, Cs-C6-cycloalkyl4L
(substituted by haphenyl), or C2
-C6-alkenyl [This is fluorine or chlorine as appropriate.

51, cyano, C, -C4-alkoxycar-nyl, car? or C2-C6-alkynyl [substituted by fluorine, chlorine, bromine, cyano, C1-C4-alco, as appropriate]; C,-04-furkoxy [which may optionally be fluorine, chlorine, bromine, cyano, cargexyl, C,
-04-alkoxy-cal? C, -C4-alkyl, c, -C4-alkoxy, c, -C-furkylthio, C, -C4-alkylsulfinyl 4 L < substituted by C, -C4-alkylsulfonyl], or C, -C
4-Alkylthio [This can be fluorine, chlorine, bromine, cyano, force/I/? xyl, C, -C4-alkylsulfonyl, C, -C4-furkylthio, c, -C4-aldf
/I/ S) k finyl 4 L < Ha c, -c4-
substituted by alkylsulfonyl] or C,-C6-alkenyloxy [which is optionally fluorine, chlorine, bromine, cyano or C,-C4-cyanoa/I/
I? or C2-C6-alkenylthio [which is optionally fluorine, chlorine, bromine, cyano,
Nitro, C1-C,-furkylthio or C1-C4
- substituted by alco-co-cycargenyl), C3
-C6-alkynyloxy or C, -C6-alkynylthio, or -5(o)-a'', where p is/or the number of ζ, and 11 G is C,
-C4-alkyl (which is optionally substituted with fluorine, chlorine, bromine, cyano or C,-C4-alkoxy-cal by nyl), C3-C6-alkenyl, C,-06
-alkynyl, c, -C4-alkoxy, c, -C4
-alkoxy-c, -C4-alkylamino, c, -
denotes C4-alkylamino or di(C,-C4-alkyl)amino, or denotes the group -NHOR, where R is C1-C12-alkyl [which may optionally be fluorine, chlorine,
cyano, c -c °-alkoxy, c, -C-furkylthio, C1-C4-alkylsulfinyl, C-C
-alkylsulfonyl, C,-04-alkyl-carbonyl, C,-C4-flukoxycar? Nil, C, -C
4-alkylaminocarbonyl or di(C1-C4
-alkyl)-amino-carbonyl] and -C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C
,-06-almonyl, C-C-cycloalkyl, C
, -C6lowcycloalkyl-C,-C2-alkylmatahaphenyl-C,-C2-alkyl [which may optionally be fluorine, chlorine, nitro, cyano, C,-C4-alkyl, C,-C4-alkoxy or C1- C4-flucoxyl? By Nil! or phenyl [which may optionally be fluorine, chlorine, nitro, cyanide, C,-C4-alkyl, trifluoromethyl, C,-04-alkoxy, C,-C2- Fluoroalkoxy, C,-04-furkylthio, and trifluoromethylthio are also L<HaC,-C4-flukoxyl?
or R8 and R further represent phenyl or phenoxy, or C1-C4 alkylcargenylamino, C,
-C4-alkoxy-carbonylamino, C, -C4-
alkylamino-carbunyl-amino or di(C,
-C4-alkyl)-aminocar/I/-nylamino, or the group -Co-R11, where R is C,
-C6-alkyl, c, -C6-alkoxy, C3-C
6-cycloalkoxy, c, -C6-flukenyloxy, C, -C4-furkylthio, C, -C4-alkylamino, C, -C4-alkoxyamino, c, -C4-
represents R'j? , t and R9 further represent C,-C4-furkyl-
Sulfonyloxy or di(C,-C4-aldP
)-aminosulfonylamino, or the group -CH
-N-R, where R is C1-C6-alkyl [this can be fluorine, chlorine, cyano, carxyl, C,-C4-alkoxy,
Carbonyl, C, -C4-alkylthio, C, -04-
Furkylsulfinylmo L < hac, -c4-alkylsulfonyl substituted], or benzyl, optionally substituted with fluorine or chlorine, or C-C-alkenyl or C-C-alkenyl or C-C-alkenyl or ，−
C6-alkynyl, which is optionally substituted by fluorine or chlorine, or phenyl, which is optionally substituted with fluorine, chlorine, bromine, C,-C4-alkyl, C,-C4-
alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio], or C,-C6-alkoxy, c, -C6
-flukenoxy, c, -C6-alkyno or benzyloxy, optionally substituted by fluorine and/or chlorine, or amino, C1-C4-alkylamino, di(C,-04-alkyl) -amino, phenylamino, C1-C4-furkyl-cal represents nyl-amino, C,-C4-furkoxycargonylamino/4L<tic, -C4-alkyl-sulfonylamino, or phenylsulfonylamino [this is substituted with fluorine, chlorine, bromine or methyl as appropriate]
or further, in formula (1) where R represents hydrogen or C,-C4-alkyl, and 114 and R are the same or different, hydrogen, fluorine, chlorine, bromine, nitro, cyano, C,-C4-alkyl [which is optionally substituted by fluorine and/or chlorine], C,-C4-alkoxy [which is optionally substituted by fluorine and/or chlorine], Cal is xyl, C, -C4-alco-dical-dicarnyl, C1
-C4-alkylsulfonyl or di(C, -C4-
alkyl)-aminosulfonyl, or compounds of formula (1) where R and R are the same or different and hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-
Compounds such as alkyl, optionally substituted by fluorine and/or chlorine, or C,-C4-alkoxy, optionally substituted by fluorine and/or chlorine.

Alternatively, in the formula (summer), R and R are the same or different, hydrogen, fluorine, #IL, bromine, nitro, cyano, C, -
C4-alkyl [which is optionally substituted by fluorine and/or chlorine] or C,-C4-alkoxy [which is optionally substituted by fluorine and/or chlorine]
or C,-C4-alkylthio, C,-C4-
alkylsulfinyl t t h c, -C4-alkylsulfonyl, which is optionally substituted by fluorine and/or chlorine; or tho(C, -C4-alkyl)-aminosulfonyl or A compound representing a cycargenyl, or further a compound in formula (1) where R and R are the same or different and hydrogen, fluorine, chlorine, bromine, Cl-C4-alkyl [this may be fluorine or / as appropriate] or C,-C4-alkoxy, which is optionally substituted by fluorine and/or chlorine; or C1-C
4-alkylthio, C1-C4-alkylsulfinyl 4t, <C1-C4-fursulfonyl, optionally substituted by fluorine and/or chlorine], or di(C,-C4-alkyl)- or further compounds of formula (I) where 8 and R are the same or different and hydrogen, fluorine, chlorine, bromine, cyano, nitro, C, -C
4-alkyl [which is optionally substituted by fluorine and/or chlorine], C,-C4-alkoxy [which is optionally substituted by fluorine and/or chlorine], C,
-C4-alkylthio, C1-04-alkylsulfinyl 4t, <ItiC4-C4-alkylsulfonyl [
These are optionally replaced by fluorine and/or chlorine].

C (c, -C4-alkyl)-amino-sulfonyl 4 L < haC,-04-alkoxycar represents nyl, and one represents oxygen, sulfur or the group: N-Z"i-, where 2 is hydrogen, C1-C4-aluminium,
(substituted by chlorine, bromine or cyano), C,
-C6-cycloalkyl, be/zyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C1-C4-alkyl, C4-C4
-FlukoxycalcenenimoL < Hashi-(c, -C
4-alkyl)-aminosulfonyl, or further in formula (1), where R represents hydrogen, C,-C5-alkyl or halogen, R25 represents hydrogen or C1-C5-alkyl, and Yl represents Compounds representing sulfur or the group N-R26, in which R represents hydrogen or C1-C5-alkyl, and also R represents hydrogen, fluorine, chlorine, bromine, C,-C4-alkyl, C-C- '/alkyl, C,-C4-alkoxy, C,-C4-halogenoalkoxy, C-C-furkylthio, C,-C4-halodanoalkylthio, amino, C1-C4-fulkylamino, dimethylamino or diethylamino , X is nitrogen or -CH
- group, Y represents nitrogen or 10R- group, where 83 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, formyl, acetyl, methoxycargonyl, Ka2 is nitrogen or -CR
- group, where R is hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C-C-alkoxy, C,-C4-alkylthio1. represents C, -C4-fulkylamino, diethylamino or diethylamino, furthermore the elbow represents the number of λ, and M represents hydrogen or/an equivalent of sodium, potassium or calcium or represents the group -COR, where R represents C,-C4-alkyl, which is optionally substituted by fluorine and/or chlorine, or C,-C2-alkyl)-amino, or benol or phenyl, which is optionally substituted by fluorine, Chlorine, bromine, cyano, nitro, c, -C4-alkyl, trifluoromethyl, c, -04-alkoxy, trifluoromethoxy, difluoromethoxy", -C4-alkylthio, C, -C4-flukoxycargenyl, C, -C4
-furkylsulfinyl, C,-C4-alkylsulfonyl, dimethylaminosulfonyl, phenylmodylated with haphenoxy], or -M radical, where B is C1-C4-alkyl, cyclohexyl,
7 syl, 7 Z nylmataha phenylsulfonyl [Here, the phenyl group is fluorine, chlorine, bromine, c, -c, -
Alkyl, c, -C2-alkoxy, trifluoromethyl, C1-02-fluoroalkoxy, C1-C2-chlorofluoroalkoxy, C1-C2-chloroalkoxy, C, -C2-alkylthio, C1-C2-alkylsulfinyl , C1-C2-alkylsulfonyl, dimethylaminosulfonyl, N-methoxy-N-methylamino-sulfonyl and/or C1-C2-alkylsulfonyl].

Furthermore, the present invention preferably provides an adduct of the compound of formula (1) with a halogenated hydroacid such as hydrogen fluoride, hydrogen chloride, hydrogen bromide or aqueous iodide, an adduct with sulfuric acid, adducts with alkanesulfonic acids having carbon atoms of It concerns adducts with acids.

In particular, the invention provides formula O) in which R8 is fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, C,-C,-alkylthio, difluoromethylthio, trifluoromethylthio, c, -c, -alkylsulfinyl, C, -C, -alkylsulfonyl, dimethylaminosulfonyl, dimethylaminosulfonyl,
N-methoxy-N-meth? Ruamino-sulfonyl, phenyl.

Phenoxy, C1-03-furkylsulfnyl, C,-
C,-alkoxyamino-sulfonyl, C,-C5-alkoxy-amino-cal represents nyl or C,-C,-fulkylamino-cargenyl, and R9 represents hydrogen, and R2 represents hydrogen, fluorine, chlorine. , bromine, methyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino.

X represents nitrogen or a -CH-' group, Y represents nitrogen or a -CR- group, R5 is hydrogen, fluorine, chlorine, bromine, methyl, formyl, acetyl, methoxycargenyl, and 2 represents nitrogen or 10R'- group, R4 is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, propoxy, isogloxy, methylthio, ethylthio, methylamine, ethylamino, dimethyl represents amino or diethylamino, n represents/or the number of co, and M represents hydrogen or 1 equivalent of sodium, potassium or calcium, or represents the group -COR, where R is methyl, ethyl, propyl , chloromethyl,
nochloromethyl, trichloromethyl, trifluoromethyl, dimethylamino or ゛benzyl, or phenyl, optionally substituted by chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, methoxy, trifluoromethoxy or difluoromethoxy or a group -NH-R, where R is C,-C3-alkyl, cyclohexyl, benzyl, phenyl 4 L<if phenylsulfonyl [wherein the phenyl group is suitably fluorine, chlorine, bromine, Methyl, methoxy,
It relates to compounds which are substituted with trifluoromethoxy, difluoromethoxy, trifluoromethyl or methoxycargel.

Furthermore, the present invention particularly provides adducts of compounds of the above formula (RI) with hydrohalic acids such as hydrogen chloride, hydrogen bromide and hydrogen iodide, adducts with sulfuric acid, having /~μ carbon atoms. and adducts with alkanesulfonic acids optionally fIt* with fluorine and/or chlorine, or benzene-substituted optionally with fluorine, chlorine, bromine or methyl.
Or it relates to an adduct with naphthalene sulfonic acid.

f'- and L, 2-fluoro-benzenesulfonyl chloride and "-(Hiro-methoxy-ot-methyl-3.6-
) diazocyclopentane-2-calgexamidine in lyazin-2-yl) -/, 2-o is used as the starting material for variant (a), the course of the reaction can be illustrated by the following equation: : For example, N'-(≠-difluoromethoxy-methyl-pyrimidin-2-yl)
Using -f-methoxy-N'-N'-bis(,2-)lifluoromethyl-benzenesulfonyl)-guanidine and isoxazolidine as starting materials for modified process>), the reaction process is shown by the following equation: The chemical reaction that proceeds according to the production method of the present invention shown in (,) above can be shown, for example, by the following formula:
) -N"-(,2-/)xycargenylpenzenesulfony") -/#-2-oxayy-,yn-2-
The force k is a modification of xyamidine and 7 cetyl chloride or methyl isocyanate (d/a) and (d〃)K
The reaction process can be expressed by the following formula: (d/C1) ↓↑ (d// ) The chemical reaction that proceeds according to the production method of the present invention shown in (・) above can be shown, for example, by the following formula: The chemical reaction that proceeds according to the production method of the invention described above in (f) can be shown, for example, by the following formula: Formula (II) can be represented by the following formula: A general definition of amidino-oxyazocycloalkanes to be used as starting materials for K is given. In formula (n), n, X, Y.

2 and R2 preferably have the same meanings as given above as preferred or particularly preferred, especially with respect to the definition of the substituents for formula (1).

Examples which may be mentioned as starting materials for formula (n) are: N'-(j, A-nomethoxypyrimidin-Hiromi-yl)
-1N'-C2,t-dimethyl-pyrimidin-hiro-yl)-1N'-(≠,6-dimethyl-pyrimidin-2-yl)-1N/(hiro-methyl-biliminon-coyl)-
1N/-(a-dityl biriminone-coyl)-1N
/ -(F-methoxy-O-methyl-pyrimidine-2-
-1m-(4L-ethoxy-6-methyl-pyrimidin-2-yl)-1N'-(gupro?xy-methyl-2-yl)-1N/ -(t,t-impropoxy-methyl-2-yl)-1N/-(t,t-impropoxy-methyl-2-yl) Lou Riminon Coil) -1N'-(
Goochlor-6-methoxy-pyrimidin-2-yl)-
1N/-(4t-chloro-6-nitoxypyrimidine-choyl)-1N/-(t,t-chloro-6-dimethylamino-pyrimidin-2-yl)-1N'-(Hiro-methyl-6 -methylthio-pyrimidin-λ-yl)+, N
'-(4t, Otsu-dimethoxypyrimidine-coil)
-, N'-(Hiro-difluoromethoxy-6-methyl-pyrimidin-λ-yl)-1N'-(Hiro-dimethylamine-ot-methyl-pyrimidin-1-yl) +, N" (
4A, A-dimethyl-8-trianon-2-yl)-1
N'-(Hiro-Metho-6-methyl-5-)riazin-yl) ~, N'-(≠-ethoxy2-methyl-triacin-2-yl)-1-(Hiro, 6- cymethoxys-triazone-λ-yl)-1■-(lIt, A
-jethoxy-3-trianon-2-yl)-1m-(
≠-Nitoxy6-MedoxyS-Driason-Coyl)-1-(≠-Methyl-1r-Methylthio-8-triazin-2-yl)-1M-(4t-Ethylthio-O-Methyl-5-) riazin-2-yl)-1N'-(4
t-methoxy-ot-methylthio-8-trianone-2-
yl)-1■-(lA-nitoxy-ot-methylthio-8
-triazin-2-yl)-1N'-(Hiro-ethylthio-ot-methoxy-1=trianon-2-yl)-1N'
-(Ethoxy-Otsu-ethylthio-s-) IJazin-2-yl)-1r-, (4t, Otsu-bis-methylthio-3-triazine-coyl)-1'-Hiro, Otsu-(bis-ethylthio -, -triazine-j -(ru)-1y-
(4L-methyl-ot-methylamino-6-triazine-
λ-yl)-, N'-(!-ethylamino-ot-methyl-5-)riazin-2-yl)-1r-(4t-dinodelamino-6-methyl-s-)riazin-2-yl)-
1N'-(Hiro-diethylamino-6-methyl-8-triazin-2-yl)-1r-(lA-methoxy-t-methylamino-8-triazin-2-yl)-1N'-(
11 to monoethylamine-6-medoxys-)riazin-2-yl)-1y-(4L-dimethylamino-ot-methoxy-1-triazin-λ-yl)-, go(≠-diethylamino-ot-methoxyS-) ) Rhiannon-Coyle) +, N/-(Hiro-Etogyushi2-methyl-amino-5-)Ryazin-λ-yl)-1y-(lA-nitoxy-O-ethylamino-3-triazine-2 −il)
-, C(≠-3-triazin-λ-yl in dimethylamino-6-eth)-1■-(μm diethylamino-
2-Ethoxy-Driazine-Coil)-1N'-
(4t-methylamino-2-methylthio-5-triazin-2-yl)-1N/ -(lA-ethylamino-ot-methylthio-8-triazin-2-yl)-1■-(
Il, -dimethylamino-6-methylthio-Hatake-triazin-2-yl) +, N'-(≠-regiethylamino-6-methylthio 8-triazin--yl) -,
N/-(Hiro-ethylthio-6-methylamino-8-triazi/-2-yl)-5"-(Hiro-dimethylamino-ot-ethylthio-5-)riazine-coyl)-1"-(
Hiro-diethylamino-Ethylthio-8-triazin-2-yl)-1N'-(J'', O-dimethyl-/1.
2 slag-triazin-3-yl)-1N/ -(!-methyl-/ , 2.lA-triazin-3-yl)- and "-(≠, O-dimethyl-pyridol-2-yl)-/, 2
-Oxyazocyclo(butan-2-cal M xyamidine and -72,2-oxyazocyclohexane-2-cal xyamidine.

The starting materials of formula (It) are new. These are the formula (■
): [In the formula, x, y, z and R have the abovementioned meaning] A cyano compound of the formula (V): [In the formula, n has the abovementioned meaning] or with an oxyazocycloalkane of the formula An adduct of (■) with a strong acid and 2
easily prepared by reaction at temperatures between θ°C and /20°C and optionally subsequent treatment of the reaction product with an acid acceptor such as sodium hydroxide or potassium hydroxide. I can do it.

Formula (X) provides the definition of the cyano compound required as an intermediate product. In this equation, x, y.

2 and R preferably have the same meanings as given above as preferred or particularly preferred, especially with regard to the definition of the substituents of formula (1).

Compounds of formula (IX) are known or can be prepared by known methods (
European Patent No. i', iri, o♂2).

Formula (V) likewise provides the definition of the oxyazocycloalkane required as starting material and its corresponding acid adduct. In this formula, n preferably has the same meaning as mentioned as preferred or particularly preferred, especially with regard to the definition of the R substituent in formula (1). Hydrogen halides, such as hydrogen chloride and hydrogen bromide, are preferably used as acid adducts.

Examples which may be mentioned of compounds of formula (V) are the following: /,
--oxyadecyclobe/thane and he-2-oxyazocyclohexane and the corresponding hydrochloride and hydrobromide compounds.

The compounds of formula (V) are known or can be prepared by methods known per se (THL(/ri♂4t), No. 3067-3070).
page].

Formula (III) further provides a general definition of the sulfonic acid chlorides to be used as starting materials for the process variant (-). In this formula R1 is preferably especially the formula (summer)
With regard to the definition of substituents fiK, preferred or particularly preferred have the same meanings as given above.

Examples which may be mentioned of starting materials of formula (III) are the following: benzenesulfonyl chloride, 2-10, 3-
Chlor-1 Hiro-Chlor-, 2,3″-Cyclol-, 2-
Fluoro-1 Hiro-Fluoro-, λ-Promo, Hiro-Fromo, Cocyano, λ-Nitro 1 Hiro-Nidro, 2
-Methyl-1hiro-methyl-12-chloromethyl-, cotrifluoromethyl-12-methoxy-1hiro-methoxy-, λ-methylthio 1λ-trifluoromethylthio, 2-nofluoromethylthio, λ-cyclopropylene Byloxycargenyl, 2-7 dinoxy, coated fluoromethoxy, coated trifluoromethoxy-12-(
2-chloroethoxy)-12-methylthiomethyl-1!
-dimethylaminosulfonyl-1λ-phenyl-12-
Methoxycargenyl, λ-ethoxycargenyl, 2
-Dimethylaminocalgeni 11? and 2-diethylaminol (2-diethylaminochloride),
Parallel to (2-10+-phenyl)-, i-cyano-phenyl)- and (2-methoxylgenylphenyl)-
methanesulfonyl chloride, and also methane-,
Chloromethane, fluoromethane, difluoromethane, trifluoromethane, ethane-12,2,2-trifluoroethane, 2. ．． 2. coated trichloroethane,
λ, 2-difluoroethane-1/-fluoro-ethane 1
．． 2-Fluoroethane-% 2-chloroethane-12-glomoethane, ethene, perfluoroethene, perfluoroethene I, 2.2-nofluoroethene, 2.2
-dichloroethene, pronoglycide, 3-chloroproprono-3-fluoroprono-, co-fluoropro/mono-, chlorofluoromethane, dichlorofluoromethane, difluorochloromethane, butane-1≠
-Chlorobutane-, perfluorobutane-1/-methylethane-, pentane-1, hegetane-.

Octane, perfluorooctane, cyclopro/4
cyclobutane, cyclopentane, cyclohexane sulfonyl chloride.

The sulfonyl chloride of formula (In) can be prepared by a known method [Journal Organic Chemistry, Vol. 33 (/6g), No. 10 Hiroshi]; Volume 25 (/P
Otsu O), No. 1♂2 Hiroshi page; German Public Notice No. 2,301,
No. 262; Yoron/9 Patent Publication No. 23. 1 Hiro O issue, 23d Hiro/issue, 23. ≠λλ No. 33, Iri 3
No., 4tt, /'Aj No. 3'/, 4'1.6,
No. titJs No. 2, No. 70.0≠1, No. ti-ti,
rot No. Oyohi No. 1 AIAI09; Rice L! i14?
Huh 2.0P! 204j, 4t, 212.2μλ;
No. ≠, 3rd issue No. 20 and No. 72.771, and Andapante Hemi +++, Volume 23 (/ri f
f/), 1st Yo/page].

Formula (IV) shows a general definition of the sulfonylguaninone derivatives to be used as starting materials for process variant (b). In this formula, the groups R,, R, #The same meanings given as preferred for R with respect to the substituent definitions apply, but in each case they must not be identical to 81 and R6 preferably represents C4-C4-alkyl or benzyl.

Particularly preferred starting materials of formula (■) are:

The radicals R, R, has the same meaning as above, and R6 represents methyl.

Examples which may be mentioned as starting materials of formula (IV) are as follows: N'-(2,6-simethoxypyriminone-≠-
yl)-, C(2-dimethyl-pyriminone-≠-yl)-1■-(!, O-nomethyl-pyrimidine-2-iA/)-, C(≠-methyl-pyriminone-2-yl) )-, C(ljt-ethyl-pyrimidine-coyl)
-1N'-(Hiro-methoxy-Otsu-methyl-pyrimidin-2-yl)+, m-(Hiro-ethoxy-6-methyl-pyrimidin-2-yl)-1N'-(Hiro-globoxy-Otsu-
Methyl-2-yl)-1"-(Hiro-isopropoxy-6
-methyl-pyrimidin-2-yl)-1y-(l/L-
Chlor-6-methoxy-pyrimidin-2-yl)-1r
-(4L-chloro-ethoxy-pyriminocy-2-yl)-1y-B-chloro-6-dimethylamino-pyrimidin-2-yl)+, m-(≠-methyl-ethoxy-pyriminone-2-yl) il)-1y-(≠, l.

-dimethoxy-pyrimidine-noyl)-1y-(≠-
difluoromethoxy-methyl-pyrimidin-2-yl)+, m-(≠-dimethylamine-6-methyl-pyrimidine-coyl)-1V-(Hiroshi, 6-dimethyl-s
-) rhianon-2-yl)-1 "-(≠-methoxy6
-methyl-triazine-λ-yl)-1r-(4-ethoxy-methyl-5-)lyazine-λ-yl'
) -, V-(l/L, Otsu-dimethoxy-5-)riazine-coyl)-1'-(previous Otsu-noethoxy-8-triazine-2-yl) +, N'-(≠-ethoxy6-
methoxy8-triazin-λ-yl)-1'-(Hiro-
methyl-6-methylthio-5-)riazin-2-yl)
-1N'-(4 is monoethylthio-methyl-triazine-coyl)-1y-(Hiro-methoxy-methyl-triazine-triazine-2-yl)-, Go(4 is mono-ethoxy-methyl-triazine-coyl)-, -triazine-coyl)-1"-(≠-ethylthio6-medoxy1-triazin-2-yl)-1N'-(4L-ethoxy-6
-ethylthios-)riazin-2-yl)-1■-(
6-(bis-ethylthio-5-)! J azin-2-yl)-, M-(≠-methyl-ot-methylamino-3-triazin-2-yl)-1'-(Hiro-ethyl-amino-ot-methyl-3-triazin-2-yl)
-1N'-(≠-dimethylamino-6-methyl-5-)
Rhianon-λ-yl)-1"-(≠-diethylamino-6-methyl-8-tri7non-2-yl)-1■-(≠
-methoxy6-methylamino-8-triazine-2-
yl)-1■-(11,-ethylamino-6-medoxys-)riazin-2-4yl>+, N/-<≠-dimethylamino-methoxyS-)riazin-1-yl)- 1r-(+-noethylamino-methoxy-3
-triazin-λ-yl)-1m-(4t-ethoxy-
6-methyl-amino-8-triazin-2-yl)-,
y-(tA-ethoxy-6-ethylamino-3-triazin-2-yl)-1y-(gage methylamino-ot-
ethoxy-S-) riazine-coyl)-1"-(≠-
Diethylamino-6-ethoxy-triazine-2-
+, m-(Hiro-methylamino-6-methylthio-triazine-coyl') +, N'-(Hiro-ethylamino-6-methylthio-triazin-2-yl)-1y-(IIt -dimethylamino-6-methylthio-triazin-λ-yl)-1■-(Hiro-diethylamino-ot-methylthio-1-triazin-d-yl) +, N'-(≠-ethylthio & -methylamino −
3-triazin-2-yl)-1"-(11t-dimethylamino-ot-ethylthio-1-triazin-2-yl)-1r-(<t-diethylamino-ot-ethylthio-
5-) riazine-coyl)-1y-B, g-dimethyl-/, 2. ≠-triazin-3-yl)+, V-(j-
Methyl-8-1≠-triazon-3-yl)- and C(!,,6-dimethyl-pyrid-λ-yl)-N“-
Methoxy-N", N"-his-(2-chlorobenzenesulfonyl)-1N", N"-bis-(2-methoxycar?nylbenzenesulfonyl)-1-N", NM-bis-(2-methyl Sulfonyl-benzenesulfonyl)-
1-N", N'-his-(2-methylthio-benzenesulfonyl)-1-N", N"-bis-C2-<2-chloroethoxy)-benzenesulfonyl]-1-N", NM
-bis-(2-trifluoromethoxy-benzenesulfonyl)-1-N", NM-bis-(2-ethoxycaryl-benzenesulfonyl)-1-N", NM-bis-
(,2-)lifluoromethyl-benzenesulfonyl)-
1-N", NM-bis-(2-isoprobylthiobenzenesulfonyl)-1-N", N'-bis-(2-N-
methoxy-N-methylaminosulfonyl-benzenesulfonyl)-1-N", NM-bis-(2-)lifluoromedelthiobenzenesulfonyl) +, -N", N
M-bis-C2J-di/lolubenzenesulfonyl)-
1-N", NM-his-(2-phenoxy-benzenesulfonyl)- and -N", NM-bis-(2-phenyl-benzenesulfonyl)-guanidine.

The sulfonylguanidine derivatives of the formula <W> to be used as starting materials are known or can be produced by known methods (Yorotsunoku Patent No. 112/, 0za 2).

Formula (v) provides a general definition of the oxyazocycloalkanes and their corresponding acid adducts to be further used as starting materials for the production process of the invention described above under (b) above.

In formula (V), n preferably has the same meaning as given above as preferred or particularly preferred, particularly with regard to the definition of the substituents for formula (1).

Examples of compounds of formula (V) and cited references have already been given in variant (a
) is the same as that shown in the explanation of the starting material.

Formula (■) gives a general definition of the benzodisultam to be used as starting material for process variant (C) according to the invention. In this formula, the radicals x, y, z and R preferably have the same meanings as preferably given above with respect to the definition of the corresponding radicals in formula (1), and R preferably represents C1''12 alkyl; Fluorine, chlorine, cyano, C, -C4-alkoxy, C, -C4 as appropriate
-alkylthio, C, -C4-alkylsulfinyl,
C-C-alkylsulfonyl, C4-C4-alkylsulfonyl, C,-04-furkoxyl? Nil,
C1-C4-alkylamino-calconylmo L<t;j
: so(C1-C4-alkyl)-7minocargenyl], or C,-C6-alkenyl [which is optionally substituted by fluorine, chlorine or not atom], C3-C6- Flukynyl, C, -C6
-cycloalkyl, C, -C6-7 chloroalkyl c,
-C2-alkyl can also be used as fluorine, chlorine, nitro, cyano, C, -
C4-alkyl, c, -C4-alkoxy or c,
-C4-alkylsulfonyl] or phenyl [which is optionally substituted with fluorine, chlorine, nitro,
cyano, C1-C4-alkyl, trifluoromethyl,
C1-C4-alkoxy, C1-02-fluoroalkoxy, C,-C4-alkylthio, trifluoromethylthio or C,-C4-alkylsulfnyl].

Particularly preferred starting materials of formula (Vl) are those in which the radicals x, y, z and R have the same meanings as given above as particularly preferred with respect to the definition of the corresponding radicals in formula (I), and 7AR is @ Preferably C,-C8-alkyl [which is optionally substituted by fluorine or chlorine], C,-C4-
alkenyl, C4-C2-alkoxyylgenylmethyl, phenyl, phenylethyl or benzyl, optionally substituted by fluorine, chlorine, nitro, cyano, methyl, methoxy or methoxy-car-nyl; Examples of starting materials for M) are given in Table 7 below: Formula (Vl
) is not known from the literature. Various types of penzodisultams are disclosed in the prior art filed and already published by the same applicant (for example, German Published Application No. 3. II 3/, q/g).

Third. 3/, No. 922 and No. J, 1It3
/, No. 929). Benzodisultam of the formula (Vl) has the formula (X): R'0 R' [wherein, X, Y, Z, R2 O! and R'ij have the same e meanings as above.] The oxyguanidine derivative of formula (M):
, cordisulfonylcyclolyte)”.

in the presence of an acid acceptor, such as pyridine, and optionally a diluent, such as methylene chloride.
Temperatures from g0°C to +700°C, particularly preferably from Kazuhiro θ°C
It is produced by reacting at a temperature of +3θ°C.

Post-processing is carried out by conventional methods.

The oxyguanidine derivatives of the formula CX') to be used as starting compounds are known or can be prepared by known methods (Yorotsu Mother Patent No. 112/, Og 2).

The benzene-to-[lambda]-zosulfonyl dichloride of formula (M) is known [Journal Oga Nick Chemistry, Vol. 37 (iq Otsu 6), pages 32gq et seq.].

Compounds of formula (■) can also be prepared by using starting materials of formula (X) and (XI) and then reacting the resulting compound of formula (Vl) with a compound of formula (V) without isolation. 1)
can be obtained in situ by generating the compound.

The oxyazocycloalkanes of the formula (V) to be further used as starting materials for process variant (C) are as already described in the description of process variant (b).

Formula (1) (where M represents hydrogen) is a modified method (d/α)
and (d/β) gives a general definition of the compounds to be used as starting materials. Formula (■) (This is a variant (d
/α) and (d/β) concerning the compound to be used as starting material for K), M represents hydrogen and n,
R, R, X, Y and 2 preferably have the same meanings as given above as preferred or particularly preferred, especially with respect to the definition of the substituents for formula (1).

The compounds of formula (1) to be used as starting materials for the modified processes (d/α) and (d/β) are the compounds described in (a) and (b) above.
and (c).

Formula (Vll) shows a general definition of the acylating agent to be further used as starting material in the process variant (d/α) according to the invention. In this formula, W is halogeno.

For example, it preferably represents fluorine, chlorine or bromine, or represents the group QCOO-. Q in this formula has the same preferred or particularly preferred meaning as the radical R.

However, Q does not represent a group -NHR.

Examples which may be mentioned as starting materials for formula (■) are: Q-Co-W (Vll), where W=fluorine, chlorine, bromine or QCOO-.

Table 2 Table 2 (Continued) The compound of formula (■) is known or can be prepared by commonly known methods.

Formula (■) shows the general definition of the incyanate to be used as starting material in the process variant (d/β)K according to the invention. In this formula (■) R5 preferably represents a group such as those already mentioned as preferred for this substituent in connection with the description of the substances of formula (1) according to the invention.

Examples which may be mentioned of compounds of formula (■) are: R5
-NC0 (■) Table 3 Table 3 (continued) The compound of formula (Vl) is a compound generally known in organic chemistry.

The formula (■), where M represents hydrogen, gives a general definition of the compounds to be used as starting materials in the variant (,). In the formula (■) (which concerns the compound to be used as starting material for the variant (,)) M represents hydrogen and R* n * X s Y *, Z and R
2 preferably has the same meaning as given above as preferred or particularly preferred, especially with respect to the definition of the substituents for formula (1).

Formula (1) to be used as starting material for variant (,)
The compounds can be formed into layers by the methods described in (a), (b) and (c).

Examples which may be mentioned of metal hydroxides, hydrides or alkanolades or organometallic compounds to be used in the variant (,) are: lithium hydroxide, sodium hydroxide, potassium hydroxide, water. Magnesium oxide and calcium hydroxide, lithium hydride.

Sodium hydride and calcium hydride, sodium methanolate and ethanolade, potassium methanolate and ethanolade, and potassium t-butanolade and butyl-lithium and inpropyl-magnesium chloride.

Formula (■) (where M represents hydrogen) gives a general definition of the compound to be used as starting material for process variant (f). In formula (■) (which concerns the compound to be used as starting material for process variant (f)) M represents hydrogen and n, X, Y, Z, R and R2 are preferably especially of the formula (
Regarding the definition of the substituents for 1), preferred or particularly preferred have the same meanings as given above.

Formula (1) to be used as starting material for variant (f)
The compounds can be prepared by the methods described in (a), (b) and (,).

Strong acids are used as starting materials in method ffi (f). These are preferably hydrohalodic acids, such as hydrogen chloride, hydrogen bromide'! 7'r ij hydrogen iodide and further sulfuric acid or alkanes having up to 4 IvA and optionally substituted by fluorine or chlorine: (
sulfonic acids, such as methanesulfonic acid, ethanesulfonic acid, chloromethanesulfonic acid, 2-chloroethanesulfonic acid and trifluoromethanesulfonic acid, trifluoroacetic acid and also benzenesulfonic acid, p-toluenesulfonic acid, naphthalene-/-sulfonic acid , naphthalene/
-2-sulfonic acid, and naphthalene-84-, -/,
,! −.

-/, , 6-, -co, 6- and -2,7-disulfonic acids.

The process according to the invention for preparing the novel compounds of formula (1) is preferably carried out using a diluent.

Possible diluents are almost all inert organic solvents, but
Preferred is an aprotic polar solvent. These may be optionally substituted with hydrocarbons such as metele/chloride, chloroform, hecodichloroethane, toluene, xylene and chlorpe/zene, nitriles such as acetonitrile and probionitrile, ethers such as octa-
- dimethoxyethane, tetrahydrofuran and dioxane as well as dimethylformamide, dimethylacetamide, trimethylsulfoxide, sulfolane, pyrine/and comeether-5-ethylpyridine.

Almost all commonly used acid binders can be used as acid acceptors in the method (,).

These include in particular alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal hydrides,
Organometallic compounds, such as butyl-lithium, and also aliphatic, aromatic or heterocyclic amines, such as trimethylamine.

Triethylamine, N,N-trimethylaniline.

N,N-dimethyl-benzylamine, diazabicyclooctane (DABCO), diazabicyclononene (DB
N), diazobicycloundecene (DBU).

Includes pyridine, -1methyl-3-ethylpyridine and hiro-dimethylamino-pyridine.

In process (a), the reaction temperature can be varied within a considerable range. Generally, one reaction is -gθ℃~+100℃
, preferably at 0°C to +5θ°C. The process according to the invention (,) is generally carried out under normal pressure.

To carry out process (,), generally /-, 1 mol, preferably 2 to 3 mol of sulfonic acid chloride of formula (III) is added to 1 amidino-oxyazocycloalkane of formula (■) 7
Use per mole.

The reaction portions are generally mixed at room temperature or with external cooling and the reaction mixture is stirred until the reaction takes place.

These new compounds are worked up and isolated by conventional methods. After distilling off volatile components as necessary.

The reaction mixture is shaken with water and a water-immiscible solvent, such as methylene chloride, chloroform or toluene, and the organic phase is washed with water, dried, filtered and concentrated. The product of formula (I) remaining in the residue is crystallized by digestion with an organic solvent such as diethyl ether, ethyl acetate, ethanol or Impro-9ol,
And if necessary, purify by recrystallization.

The production method (b) according to the invention is preferably carried out using a diluent. Possible diluents are almost all inert organic solvents, and if necessary water is mixed with these surfactants. Particularly suitable solvents are alcohols, such as methanol, ethanol, n- and l-gupronol, and
1-*8@e- and t-butanol, ketones such as acetone.

Methyl ethyl ketone and methyl isobutyl ketone, and also acetonitrile, dimethylformamide and dimethyl sulfoxide.

Optionally, process (b) according to the invention is carried out using a base. Possible bases are almost all commonly used acid binders. These are especially metal hydroxides, carbonates, hydrides and alcoholades.

Examples include sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium carbonate, sodium and calcium hydride, sodium methylate, ethylate and zolopylate, potassium methylate, ethylate and t-butylade, and aluminum isopropylate.

In process (b) according to the invention, the reaction temperature can be varied within a considerable range. The reaction generally takes place at θ℃~/30
It is carried out at a temperature of 10°C to 700°C.

The process according to the invention is generally carried out under normal pressure.

To carry out the process (b) according to the invention, generally from 7 mol to
3 moles, preferably 7 to 3 moles of oxyazocycloalkane of formula (V) or a salt thereof are used per 7 moles of sulfonyldaaninone derivative of formula (■). The reaction components are generally combined at room temperature or with external cooling, and the reaction mixture is stirred at an optionally elevated temperature until the reaction is complete.

The process (c) according to the invention for preparing the novel compounds of formula (1) is preferably carried out in water as solvent. Other possible diluents are all inert organic solvents, but preferably aprotic polar solvents. These are, for example, acetone, methyl ethyl ketone, acetonitrile, zolobionitrile.

Includes dimethyl sulfoxide, sulfolane, 2-dimethyloxyethane, dioxane, methylene chloride and chloroform.

Process (c) is preferably carried out in the presence of a base or an acid. Suitable bases that can be used are alkali radicals or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, tertiary amines such as triethylamine, N,N-dimethylaniline and N, N-dimethylbenzylamine as well as nitrogen heterocycles such as pyridine or diazobicyclooctane (DABCO). Mineral acids such as hydrochloric acid, hydrobromic acid or sulfuric acid are particularly suitable acids.

In the process according to the invention (1), the reaction temperature can be varied within a considerable range. Generally, one reaction is θ℃~17
00°C, preferably 10°C to +gθ°C.

Process (c) according to the invention is generally carried out under normal pressure.

To carry out process (C), generally 7 to 3 mol, preferably 7 to 2 mol of a compound of formula (V) or its corresponding acid adduct and optionally 7 to 3 mol, preferably 7 to 2 mol are added. mol of base is used per mol of penfudisultam of formula (■). When the compound of formula (VT) is reacted in situ, a large molar amount of the starting compound's.

and (XI) and reacting the reaction mixture with a compound of formula (V) as described above.

The reaction components are generally combined at room temperature and the reaction mixture is stirred until the reaction is complete.

Work-up can be carried out in a customary manner, for example, the mixture is acidified, for example with hydrochloric acid, concentrated to about half the volume and the product of formula (I) obtained as crystals is isolated by suction filtration.

The process (d/α) according to the invention is preferably carried out using a diluent. Possible diluents are almost all inert organic solvents, but preferably aprotic polar solvents, such as those mentioned above with respect to the description of the process according to the invention (2003).

Almost all commonly used acid binders can be prepared by the method (d/α
) can be used as an acid acceptor in These include in particular the acid binders mentioned above with regard to the description of the method according to the invention.

In process (d/α), the reaction temperature can be varied within a considerable range. The reaction is generally -, 20°C to +/20°C
"C1" is preferably carried out at a temperature in the range of 1 no.theta..degree. C. to ten/theta.theta.C.Method (d/.alpha.) II'i is generally carried out under normal pressure.

To carry out the process (d/α) according to the invention, the particular starting materials required are generally used in approximately equimolar amounts. However, it is also possible to use one of the 2m specific components in large excess. The reaction is generally carried out in the presence of an acid acceptor in a suitable diluent and the reaction mixture is stirred for several hours at the particular required temperature. Method according to the invention (
Post-processing in d/α) is carried out in the customary manner in each case.

The method (d/β) according to the invention is preferably carried out using a diluent. Possible diluents are almost all inert organic solvents, but preferably aprotic polar solvents, such as those mentioned above in connection with the description of process (a) according to the invention.

Catalysts that can be used for the reaction in process variant (d/β) are preferably tertiary amines, such as triethylamine and Hegudiazabicyclo-(2,2,23-octane), as well as organotin compounds, such as diptyl-tin thorarate. However, the addition of catalyst in this building is not essential.

In the process according to the invention (d/β), the degree of reactivity can vary within a considerable range. The reaction generally takes place at θ℃~/
It is carried out at a temperature of lI0°C, preferably θ°C to 720°C.

Generally, the method (d/β) is carried out under normal pressure.

However, it is also possible to carry out this under elevated pressure or under reduced pressure.

To carry out the process (d/β) according to the invention, the particular starting materials required are generally used in approximately equimolar amounts. However, it is also possible to use one of the two specific components in large excess. The reaction is generally carried out in the presence of a catalyst in a suitable diluent and the reaction mixture is stirred for several hours at the particular required temperature.

The work-up in the process (d/β) according to the invention is carried out in each case by customary methods.

The method according to the invention (,) preferably comprises 1. < is carried out using a diluent. Possible diluents are almost all inert organic solvents. These are in particular alcohols such as ethanol and n- and iso-pro9ols, ethers such as tetrahydrofuran, dioxane and mucodimethoxyethane.

Includes esters such as ethyl acetate and methyl acetate, and nitriles such as acetonitrile.

In the process (,) the reaction temperature can be varied within a considerable range. Reactions generally occur at temperatures between 0°C and +! It is carried out at rO<0>C, preferably in the range of θ<0>C to +30<0>C. Method(,)
is generally carried out under normal pressure.

The time required for carrying out the method according to the invention (,) is generally between 0.9 and
42 mol, preferably 0. q&~A 1 mol of metal compound is used per 7 mol of compound of formula (1).

Generally, one combines a compound of formula (1) and a diluent.

And if necessary, the metal compound dissolved in the diluent is metered in with gentle external cooling if necessary. The reaction mixture is stirred until one reaction is completed. Formula (1
) as a salt is generally obtained as crystals and can be isolated by suction filtration.

Process (f) according to the invention is preferably carried out using a diluent. Possible diluents are virtually all inert organic solvents. These are especially alcoholic.

For example methanol, ethanol and n- and isoprogol, ethers such as tetrahydrofuran, dioxane and/2,2-dimethoxyethane,
Includes esters such as methyl acetate and ethyl acetate, and ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone.

If the acid used as starting material is used as an aqueous solution, acetic anhydride can also advantageously be used as diluent.

In process (f) the reaction temperature can be varied within a considerable range. Generally the reaction is carried out at a temperature of -20°C to +50°C, preferably θ°C to +30°C. Process (f) is generally carried out under normal pressure.

To carry out the method (f) according to the invention, generally from 7 to 0
Moles, preferably 7 to 5 mols of strong acid are used per mole of compound of formula (1).

Generally, the compound of formula (1) and the diluent are combined and the strong acid is metered in, with gentle external cooling if necessary. The reaction mixture is stirred until one reaction is completed.

/:/ The adduct is generally obtained as crystals, which can be isolated by suction filtration.

The active compounds according to the invention can be used as defoliants, desiccants, eradicators of broad-leaved plants, in particular as weed killers.

Weeds should be understood in a broad sense as any plant that grows in undesirable locations. Whether the substances according to the invention act wholly or selectively as herbicides depends primarily on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants: Prunus spp., Helicoptera spp., Chickweed spp., Trifolium spp., Antimis spp., Chrysanthemum spp., Chenopodium spp., Nettles spp.

Genus Chion, Genus Hyu, Genus Superhyu, Genus Onamomi.

Conderpurus genus, Ipomoea genus, Polygonum genus, Hornwort genus, Pigweed genus, Thistle genus, Hilea thistle genus, Hachijona genus, Solanum genus, Dogweed genus, Kakushigusa genus, Crabculinus genus, Deadworm genus, Stag beetle genus, Stag beetle genus,
Emmetchus, Datura, Violet, Violet, Papaver and Cornflower.

The genus Chrysanthemum, the genus Datura, the genus Bean, the genus Trifolium, the genus Solanum, the genus Linum, and the genus Ipomoea.

Vicia faba, Nicotiana, Tomato, Peanut bean, Pillow millet, Golden poppy, Citrus and Cagocha.

sorghum, cyperus genus, foxtail genus, strawberry genus, staghorn genus, staghorn genus, staghorn genus, cyperus genus, sycamore genus, oat genus, cyperus spp. Genus Dentsuki.

genus Omodaka, genus Harii, genus Firefly, genus Spaniel,
genus Platypus, genus Sphnicrea, genus Takanopus,
The spp. Nucas, the spp. and the spp. Apella.

Triticum genus, Barley genus, Oat genus, Rye genus, Sorghum genus, Millet genus, Sugarcane genus, No9inaguru genus,
Allium spp. and Allium spp.

However, the use of the active compounds according to the invention is in no way limited to these types of plants, but can be extended to other plants as well.

Depending on the concentration, these compounds are suitable, for example, for the total eradication of weeds in industrial areas and railway tracks, roads or areas with or without vegetation. Similarly, these compounds can be used, for example, in woodlands, ornamental orchards, orchards, vineyards, citrus orchards, nut orchards, banana orchards, coffee orchards, tea orchards, coconut orchards, cocoa orchards, soft fruit orchards and hop orchards. It can be used for the selective eradication of weeds in perennial crops such as - as well as in the selective eradication of weeds in hand crops.

The compounds of formula (1) according to the invention are suitable for combating monocotyledonous and dicotyledonous weeds by one pre-emergence and post-emergence method. When used by the post-emergence method, for example in cotton, these novel active compounds exhibit a very favorable selective action against weeds such as, for example, Solanum, Cannabis, Aspergillus and Sorghum.

These active compounds can be present in the customary compositions, for example solutions, emulsions, wettable powders, suspensions, powders, dusting powders.

Pastes, soluble powders, suspension-emulsion concentrates.

It can be converted into extremely fine capsules in natural and synthetic materials, as well as in polymeric materials, impregnated with active compounds.

These m-acids can be used, for example, as bulking agents for active compounds.

That is, they are prepared in a known manner by mixing the liquid solvent and/or the solid carrier and optionally the surface-active agents, ie emulsifiers and/or emulsifiers, using dispersants and/or foam-forming agents. When using water as mt agent, it is also possible, for example, to use organic solvents as auxiliary solvents. As a liquid solvent, mainly aromatic compounds, f
cFor example, xylene and toluene are also L<d alkylnaphthalenes.

Chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons! i,
i and t chlorobenzene, chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions,
Alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as trimethylformamide and dimethyl sulfoxide, and water are suitable.

Solid carriers include, for example, ground natural minerals.

For example, kaori, clay, melk, chalk, quartz, butanolugite, montmorillonite or diatomaceous earth,
and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates are suitable. Solid carriers for granules include, for example, crushed and fractionated natural rocks, such as calcite, marble, pumice.

Suitable are sepiolite, dolomite and synthetic particles of inorganic and organic flours and particles of organic substances such as sawdust, coconut husks, corn cobs and tobacco stalks. Emulsifiers and/or foam formers include, for example, nonionic and anionic emulsifiers, such as Suitable are lyoxyethylene fatty acid esters, -lyoxyethylene fatty alcohol ethers, such as alkylarylpolyg)col ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, and also albumin hydrolysates. Suitable dispersants are, for example, lignin sulphite waste liquor and methylcellulose.

Adhesives such as cal-xymethylcellulose, natural and synthetic polymers in the form of powders, particles or latex (for example, gum arabic), polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin. and synthetic phospholipids can also be used in the composition. Other additives can be mineral and vegetable oils.

Inorganic pigments such as iron oxide, titanium oxide and Bellja blue, and colorants such as organic dyes such as alizoline dyes, azo dyes and metal phthalocyanine dyes, as well as trace nutrients such as iron, manganese, boron,
Copper, cobalt, molybdenum and zinc salts can also be used.

Generally one composition is 0. /~9S weight 4. Preferably 0
．． Contains 3-qOft% active compound.

The active compounds according to the invention can be used on their own or in their compositions for combating weeds, and can likewise be in mixtures with known herbicides, finishing compositions or tank mixtures.

Possible herbicides for the mixture are known herbicides, such as N
-(2-Benzothiazolyl) -N,N'-dimethylurea, 3-(3-chloro-gumethylphenyl)-mu/-
Dimethylurea% 3- (lIL-inzolobyrphenyl)-h no dimethylurea, lI-amino-6-(mu/-
dimethylethyl')-3-1 thio-heco, ditrianon-5-(lIH)-one, lI-amino-A-
(/,/-trimethyl-ethyl)-3-ethelthio-/,
2. 'I-triazin-5-(4H)-one, /-amino-6-ethylthio-3-(co,2-nomethylglobil) -1,3,! ;-triazineco, 1I-(la
,3H)-noone, q-amino-3-methyl-6-phenyl-7,2,dartriazin-5-(lIH)-one, 2-chloro-guethylamino-6-isozolobylamino/,J ',! ;-Triazine, (trimethylsilyl)-methyl-[Hiro-(3,S-dichloro-pyrido-
R of 2-yloxy)-phenoxy]-pyrovionate
One enantiomer, (2-pennoroxy)-ethyl λ-[Cu (3,,Si'-nochloropyrido λ-yloxy)
- R monoenantiomer of phenoxycusolobionate.

2. Kudichlorophenoxyacetic acid, 2-(,2,dartzchlorphenoxy)-zolopionic acid, gouchloroleukomethyl-phenoxyacetic acid, 2-C2-methyl-gouchlorophenoxy)-propionic acid.

3.3-Shiodo-9-hydroxybenzonitrile.

3, S-dipromoder hydroxybenzonitrile and diphenylethyl and phenylpyridazines, such as pyridate. In particular, certain mixtures also exhibit synergistic effects.

Mixtures with other known active compounds are also possible, such as stimulants, insecticides, acaricides, nematicides, bird deterrents, agents for improving plant nutrition and soil structure.

The active compounds can be used as such, as compositions thereof, or in further diluted forms.

For example, they can be used as ready-made solutions, suspensions, emulsions, powders, pastes and granules.

This is used in the usual manner, for example by irrigation, spraying, jetting or scattering.

The active compounds according to the invention can be used either before or after the emergence of the plants. Furthermore, these can be mixed into the soil before the Hanseed.

The amount of active compound used can vary within a wide range.

This depends primarily on the nature of the desired effect. Generally, the usage amount is 0.0/~10# per soil area/ha,
Preferably from 0.05 to 5 y/ha of active compound.

The following examples illustrate the preparation and use of the active compounds of the invention.

Preparation Examples Examples / (Method (a)) N'-(lIt, A-dimethyl-pyrimidi-7-coyl)-/, 2-oxyazacyccl hentan-co-lupoxyamiso/(3 and 6ico, i7 mol) in 200d methylene chloride Dissolved inside, 10! ;fi(0,'!Mok
>f) 2-Methoxycarbonyl-pe/zenesulfonyl chloride was added and the reaction mixture was cooled to -20°C. Methylene chloride 7j;
30. & 9 (0.4 t!r mol) of mortar were added dropwise at this temperature and the mixture was stirred for a further 5 hours at 20 CIIC and then for 7 nights at room temperature.

The reaction mixture was washed with dilute hydrochloric acid and then with water.

The methylene chloride phase was dried over sodium sulfate, filtered and concentrated. 2. Oily residue. It was crystallized from ether of tljLl. The coarsely cracked raw bottom material thus obtained could be purified by recrystallization from methyl isobutyl ketone.

N'-(g,6-nomethyl-pyrimidine-coyl)-N''-(comethoxycarbonyl-benzenesulfonyl')-/,2-oxyadecyclopentane-cocaru with melting point/10℃~///℃ ?Xiaminone 5Z left g (theoretical value 7f, 34) was obtained.

(Method (b)) /7.79<0.03 mol)
-N',N''-bis-(2-methoxy-carbonyl-benzenesulfonyl)-quaninont, ,!-N<0
．． 07! A mixture of mol) of inxazolidune and SOd of dimethylformamide was stirred at 30° C. for an hour. The reaction mixture was evaporated under reduced pressure and the Ka-711 residue was dissolved in methylene chloride at /θ0 #11. The methylene chloride solution was washed with 1 oz of dilute hydrochloric acid and then water, dried over sodium sulfate, filtered and concentrated. The oily residue was crystallized with ether and the crystals were filtered off with suction, washed with ether and dried in air.

λ-oxyazacyclopentane-cocarboxy to v-(tt,t,,-dimethylpyrimidine-coyl)-N"-(,2-methoxycarbonyl-benzenesulfonyl)-, melting point/10℃~///℃ 72.7 g of aminone (theoretical value 934) was obtained.

Example (Method (C)) 6.9g<0.013 mol) of benzene-muco-disulfonyl dichloride was added to 13fjc0.02! ; mol) of N'-(4-methoxy-6-methyl-pyrimidine-coyl)-N#-methoxy-guanidine; 2. g9C0
,023 mol)/, Kudiazabicyclo-[Co, Co,
Co]-octane (DABCO) and iooml methylene chloride were added with stirring to a cooled mixture to -<10<0>C. After removing the cooling bath, the reaction mixture was heated to
The mixture was stirred at ℃ to +2θ℃ for 9 hours. Inxazolidine hydrochloride of y<o, os mol) and 7,1It-diazobicyclo-(2,2,2)-octane of y<o, os mol) were added. The reaction mixture was heated at lIO°C for 7
Stirred for 3 hours, cooled with ice, stirred with ice-cold 2N hydrochloric acid for 3θ minutes, washed with water, dried over sodium sulfate, filtered and concentrated. The product remaining in the residue was crystallized by "tritylation" with ethanol.

Melting point/qO℃ to 193℃ N'-(Hiro-methoxy 6-
methyl-pyrimidin-λ-yl)-N“-(2-methoxyaminosulfonyl-benzenesulfonyl)-/, 2-
Oxyzacyclontan-cocal? I hope that xyamidine Og (theoretical value 11-g4>) is obtained.

Example 3 (Method (d/α)) Compound from Example 1! , A , 9 (0,0/ 1
mol) in 20111 methylene chloride;2.
71<o, oig mol) of 2,2-cycloacetyl chloride was added, then lI-diazobicyclo-
[ko, 2.2)-octane (DABCO), z, 1
A solution of i (0,079 mol) was added dropwise so that the reaction mixture did not heat above 30°C. The mixture was then stirred for a further 6 hours at 23-30°C.

The methylene chloride solution was washed with 7N hydrochloric acid and water. The methylene chloride phase was dried over sodium sulfate, filtered and concentrated. The oily residue was crystallized from diisopropyl ether, the crystals were filtered off with suction and dried in air.

Compound 4499 (theoretical value gts) having the above structural formula and a melting point of //θ°C to //II°C was obtained.

Example DA (Method (d/β)) The compound of Example/4 g (0.02 mol) and phenyl isocyanate, 2. A mixture of '1 l (0.02 mol), 3 drops of triethylamine and ioomt toluene was stirred at 30°C for 72 hours. The product obtained as crystals was then cooled to 70 DEG C. to 20 DEG C. and then isolated by suction filtration.

3 g (theoretical value g64) of a compound having the above structural formula with melting point/'IA° C. was obtained.

Example! (Method (f)) Example/Compound Ojt9c0.0.31. mole) is seven tons, 20I+! / dissolved in 0. ．． 96 of 33m1
A concentration of sulfuric acid was then added and the mixture was heated to 73 mL at room temperature.
It was stirred for an hour and the precipitated crystals were filtered off with suction, washed with acetate/and ether and dried in air.

Melting point/℃ (decomposition) N/-(G,6-nomethyl-pyrimidine-coyl)-N"-(methoxycarbonyl-
benzenesulfonyl')-/, 2-oxyadecyclobentane-cocal is xyamidine sulfate i, ti, g
(Theoretical value s'i,> was obtained.

Compounds of formula (1) shown in Table 9 below could be prepared by the method exemplified in the examples above: 0:0:E:I:
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Trout starting compound of formula (ff) 4 IAF fI (0,,7 mol) of cocyanoaminol, 6-dimeterubilimigne and Af, , 6 g
(0.4j mol) of inxazolidine hydrobromide and is
A mixture of omt and ethanol was then heated under reflux for 77 hours. The reaction mixture was then concentrated, the residue was dissolved in water and the undissolved material was separated off. Ffi is made alkaline by addition of sodium hydroxide solution, and 3
Extracted with 0.00 at methylene chloride. The methylene chloride phase was dried over sodium sulfate, filtered and concentrated.

N'-(4L, A-dimethyl-pyrimidine-nyyl)-7, nioxyazacyclopentane-λ-cal with a melting point of 732°C to 737°C is Kikua, and 3 g of Minon S (theoretical g, 3'6) is obtained. It was done.

For example, the following compounds were obtained in the same manner as in Example (If-/): Melting point: 97°C-7θ°C Example (II-, ?) Example (■-g) Example (ff-7 ) Melting point: 13ic/1111c0.0! i mol) of benzene-7,2-nosulfonylnochloride to ioy<o, os mol) of y
-(<z, g-dimethylbilimison-d-yl)-N"
-methoxyguanisine and /J, 9 (0, / 5 mol) of pyridine and /QQml of methylene chloride
It was added in portions to the mixture at °C. The reaction mixture was then stirred at 110 °C for 3 hours and at +20 °C for 75 °C.
Stir for hours. This was then washed with ice-cold dilute hydrochloric acid and ice water. The methylene chloride solution was dried and concentrated. The residue was tritylated with ethanol and the residue thus obtained as crystals was isolated by suction filtration.

Melting point/! A compound lA I (theoretical value sg) having the above structural formula with a temperature of 3-g°C (decomposed) was obtained.

Furthermore, when one reaction is completed, the reaction mixture is completely evaporated and the residue is dissolved in dioxane,
This dioxane mixture can be worked up by filtering and reevaporating to recrystallize the residue.

Other compounds of formula (Vl) could be prepared in the same manner as in Example (Vl-/).

Example A Pre-emergence Test/Greenhouse Solvent: 5 parts by weight of A7Tone emulsifier/2 parts by weight of alkylaryl polyglycol ether.

To prepare a suitable formulation of the active compound, 7 parts by weight of the active compound are mixed with the above amount of solvent, the above amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

The seeds of the test plants are sown in normal soil and after 2 hours are moistened with a preparation of the active compound. It is convenient to keep the amount of water per unit area constant. The concentration of active compound in the formulation is not critical, only the amount of active compound applied per unit area is decisive. After 3 weeks, the degree of eradication on the plants was compared with the expression of the untreated comparison and evaluated as eradication arc. Values indicate: 04 = no effect, same as untreated comparison) 1004 = complete eradication.

'In this test, for example, the compounds of Production Examples (1), (J5 and It showed extremely good herbicidal activity (fc e.g. 0.2 Syu/h).
When applied in the amount of a, 1 g θ to 100).

Example B Post-emergence test/greenhouse solvent = 5 parts by weight acetone emulsifier: 7 parts by weight alkylaryl,/IJ glycol ether.

In order to prepare a suitable wound of active compound, 7 parts of active compound were mixed with the above amount of solvent, the above amount of emulsifier was added and the concentrate was diluted with water to the desired concentration.

Test plants having a height of 3 to 1/3 cm were sprayed with active compound dehiscence in such a way that a specific amount of the desired active compound per unit area was applied. What is the concentration of this spray liquid?

A specific amount of the desired active compound was chosen to be applied as θ001 water/ha. After 3 weeks, the degree of eradication on plants was compared to the expression of untreated controls.

It was evaluated as the eradication range. The numerical value indicates the following: 20% =
(No effect, same as untreated comparison) 100 excellent = complete eradication.

In this test, for example, production examples (J5 and (a)
The compound is cotton (o, 2!; no damage at kg/ha)
4) showed good selective herbicidal activity against the genus Solanum, Helicoptera, Sorghum and Sorghum (for example, when applied at an amount of 0.23 kg/haO).

gθ~100%>. Compound (1) likewise showed significant activity against the same harmful plants (at 25 kg/ha/θ0min).

Claims (7)

[Claims] (1) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 is an appropriately substituted group selected from the series consisting of alkyl, aralkyl, aryl, and hetaryl. R^2 represents hydrogen, halogen, hydroxyl, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, amino, alkylamino or dialkylamino, X represents nitrogen or -CH- group, and Y represents represents nitrogen or a -CR^3- group, R^3 represents hydrogen, halogen, cyano, alkyl, formyl, alkyl-carbonyl or alkoxy-carbonyl, Z represents nitrogen or a -CR^4- group, R^ 4 represents hydrogen, halogen, hydroxyl, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, further n represents a number of 1 or 2, M represents hydrogen, 1 equivalent of a metal or a group -CO-R, R
is alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl,
represents an optionally substituted group selected from the series consisting of dialkylamino, aralkyl, aryl, aralkoxy, aryloxy, alkylthio, aralkylthio and arylthio, or R represents the group -NHR^5, R^5 is alkyl, and adducts of compounds of formula (I) with strong acids. (2) When producing the sulfonylamidino-oxyazacycloalkane of the general formula (I) described in claim 1, when M in the formula (a) represents hydrogen, the formula (II): ▲ Formula, There are chemical formulas, tables, etc. ▼ (II) [In the formula, n,
^1-SO_2Cl(III) [wherein R^1 has the above meaning] is reacted with a sulfonic acid chloride in the presence of an acid acceptor if necessary and a diluent if necessary, or (b) When M represents hydrogen, formula (IV): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IV) [In the formula, X, Y, Z, R^1 and R^2 have the above meanings. and R^1^a has the same meaning as R^1, but need not be the same as R^1 in each case, and R^6 represents an appropriately substituted hydrocarbon group]. A sulfonylguanidine derivative is an oxyazacycloalkane of the formula (V): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) [wherein n has the above meaning] or an oxyazacycloalkane of the formula (V) (c) M represents hydrogen and R^1 is a group ▲ mathematical formula, chemical formula, There are tables etc. ▼ [In the formula, R^7 is alkyl, alkenyl, alkynyl,
Indicates an appropriately substituted group selected from the series consisting of cycloalkyl, cycloalkylalkyl, aralkyl and aryl], the formula (VI): ▲A mathematical formula, a chemical formula, a table, etc.▼(VI) , X, Y, Z, R^2 and R^7 have the above meanings] Benzodisultam of formula (V): ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ (V) [In the formula, n has the above meaning] An oxyazacycloalkane of the formula (V) or an adduct of the oxyazacycloalkane of the formula (V) and a strong acid, and as necessary or (d) when M represents a group -COR [wherein R has the above meaning], the above (a) , (b) and (c) [wherein M represents hydrogen and n, X, Y, Z, R^1 and R^2 have the above meanings] (α) Formula (VII): Q-CO-W(VII) [In the formula, W represents a halogen or represents a group QCOO-, and Q has the same meaning as R, but a group- [does not exhibit NHR^5] optionally in the presence of an acid acceptor and optionally a diluent, or (β) of formula (VII
I): React with the isocyanate of R^5NCO(VIII) [wherein R^5 has the above meaning] optionally in the presence of a catalyst and optionally in the presence of a diluent, or (e) When M represents 1 equivalent of metal, the above (a), (b) and (
A compound of formula (I) [wherein M represents hydrogen and n, by reacting with oxides, hydrides or alkanolates or organometallic compounds, optionally in the presence of diluents, or (f) in the case of preparing a 1:1 adduct of a compound of formula (I) with a strong acid. , a compound of formula (I) [wherein M represents hydrogen and n, 1. A method for producing a sulfonylamidino-oxyazacycloalkane, which comprises reacting with. (3) A herbicide characterized by containing at least one sulfonylamidino-oxyazacycloalkane according to the general formula (I) according to claim 1. (4) Use of a sulfonylamidino-oxyazacycloalkane having the general formula (I) according to claim 1 for combating undesirable plant growth. (5) A method for producing a herbicide, which comprises mixing a sulfonylamidino-oxyazacycloalkane having the general formula (I) according to claim 1 with an extender and/or a surfactant. (6) General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) [In the formula, R^2 is hydrogen, halogen, hydroxyl, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio ,amino,
represents alkylamino or dialkylamino, X represents nitrogen or -CH- group, Y represents nitrogen or -CR^3- group, R^3 represents hydrogen, halogen, cyano, alkyl, formyl, alkyl-carbonyl or represents alkoxy-carbonyl, Z represents nitrogen or a -CR^4- group, R^4 represents hydrogen, halogen, hydroxyl, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, and n represents 1 or 2 Amidino-oxyazacycloalkane of [number indicated]. (7) When producing the amidino-oxyazacycloalkane of the formula (II) described in claim 6, the formula (I
X): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IX) [In the formula, X, Y, Z and R^2 are
A cyano compound of the formula (V): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) [In the formula, n has the meaning given in Claim 6] reacting with an azacycloalkane or an adduct of an oxyazacycloalkane of formula (V) with a strong acid, optionally in the presence of a diluent, and optionally treating the product with an acid acceptor. A method for producing a characterized amidino-oxyazacycloalkane.