It has been already known that certain kinds of triazines show herbicidal activity (cf.

WO 97/31904, WO 97/08156, WO 97/29095 etc.).

There have now been found novel 1,3,5-triazines of the formula (I) wherein R1 represents C1-5 alkyl, C3-7 cycloalkyl, C1-4 haloalkyl, benzyl which may be optionally halogen-substituted or C 1-4 alkyl-substituted, or phenyl which may be optionally halogen-substituted or Cri-4 alkyl-substituted, R2 represents amino, Cl 4 alkylamino, formylamino, Cl 4 alkyl-carbonylamino, C3-6 cycloalkyl-carbonylamino, Cl 1 haloalkyl-carbonylamino, benzyl- carbonylamino which may be optionally halogen-substituted or C1-4 alkyl- substituted, phenylcarbonylamino which may be optionally C alkyl- substituted, Cl4 alkoxy-substituted or halogen-substituted, Cl 4 alkyl- carbonylacetylamino, or di (C1-4 alkyl) amino-CI alkylideneamino, R3 or R4 each independently represent hydrogen atom or C1-4 alkyl,

Rs represents halogen, Cl. alkyl, Cl 1 haloalkyl, C14 alkoxy, C14 haloalkoxy, C1-4haloalkylthio,C1-4alkylsulfinyl,C1-4alkylsulfonyl,phenyl C1-4alkylthio, which may be optionally halogen-substituted or C1-4 alkyl-substituted, phenoxy which may be optionally halogen-substituted or C14 alkyl- substituted, nitro or cyano, m represents an integer of 1-4, and the R3 substituents may be identical or different, in case m represents an integer of 2 or more, n represents an integer of 0-5, and the R5 substituents may be identical or different, in case n represents an integer of 2 or more.

The compounds of the formula (I), according to the invention, can be obtained by a process in which a) in case R represents amino: compounds by the formula (II) wherein

R3, R4, R5, m and n have the same definitions as aforementioned, and X represents halogen, preferably chlorine or bromine, are reacted with compounds of the formula (III) RICO2R6 (III) wherein R'has the same definition as aforementioned, and R6 represents Ci-4 alkyl, preferably methyl or ethyl, in the presence of an inert solvent, and if appropriate, in the presence of an acid binding agent, or b) in case R2 represents formylamino, Cl4 alkyl-carbonylamino, C3_6 cycloalkyl- carbonylamino, C1-4 haloalkyl-carbonylamino, benzylcarbonylamino which may be optionally halogen-substituted or Cl4 alkyl-substituted, or phenylcarbonylamino which may be optionally Cl4 alkyl-substituted, C14 alkoxy-substituted or halogen-substituted: compounds of the formula (Ia)

wherein R', R3, R4, R5, m and n have the same definitions as aforementioned, are reacted with compounds of the formula (IV) R'CO2R6 (IV) wherein R6 has the same definition as aforementioned, hydrogenatom,C1-4alkyl,C3-6cycloalkyl,C1-4haloalkyl,benzylR7 represents which may be optionally halogen-substituted or Cl4 alkyl-substituted, or phenyl which may be optionally CI-4 alkyl-substituted, Cri-4 alkoxy- substituted or halogen-substituted, in the presence of an inert solvent, and if appropriate, in the presence of an acid binding agent, or c) in case R2 represents C1-4 alkyl-carbonylacetylamino:

the compounds of the formula (Ia) are reacted with compounds of the formula (V) wherein R8 represents C14 alkyl, preferably C13 alkyl, in the presence of an inert solvent, or d) in case R2 represents di (C1-4 alkyl)-C1-4 alkylideneamino: the compounds of the formula (Ia) are reacted with compounds of the formula (VI) wherein R6 has the same definition as aforementioned, R9 represents C1-4 alkyl, preferably C13 alkyl, and Rl° represents a hydrogen atom or Cl3 alkyl, preferably hydrogen atom, methyl or ethyl,

in the presence of an inert solvent, and if appropriate, in the presence of an acid catalyst, or e) in case R2 represents C14 alkylamino: compounds of the formula (VII) wherein R', R3, R4, R5, m and n have the same definitions as aforementioned, and Rl l represents Cl 4 alkylidene, preferably Cl 3 alkylidene, are reduced in the presence of an inert solvent, and in the presence of catalyst.

The triazines of the formula (I), according to the present invention show stronger herbicidal action compared with the compounds described in the aforementioned prior art literature.

In the formulae: "Halogen"represents fluorine, chlorine, bromine or iodine, and preferably represents fluorine, chlorine or bromine.

"Alkyl"can be straight chain or branched chain and can represent, for example, CI-4 alkyl, and there can be mentioned specifically methyl, ethyl, n-or iso-propyl, n-, iso-, sec-or tert-butyl.

As"cycloalkyl"there can be mentioned, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

"Haloalkyl"is halogen-substituted straight chain or branched chain alkyl and there can be mentioned, for example, C14 alkyl substituted with 1-9 fluorine, chlorine and/or bromine atoms, specifically fluoromethyl, fluorochloromethyl, fluoro- bromomethyl, fluorodichloromethyl, fluorodibromomethyl, difluoromethyl, difluoro- chloromethyl, difluorobromomethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, perfluoroethyl, 1-chloroethyl, 1,2-dichloroethyl, 1-bromo- ethyl, perfluoropropyl, 1-fluoro-1-methylethyl, 1-chloro-1-methylethyl, 1-bromo-1- methylethyl, 1- (trifluoromethyl)-2,2,2-trifluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 3- fluoropropyl, 3-chloropropyl, 2,2,3,3,3-pentafluoropropyl, 1,2,2,3,3,3-hexafluoro- propyl or perfluorobutyl.

"Alkoxy"is alkyl-O-, of which the alkyl part has the above-mentioned meaning, and can represent, for example, Ci4 alkoxy. There can be mentioned specifically methoxy, ethoxy, n-or iso-propoxy, n-, iso-, sec-or tert-butoxy.

"Alkylthio"is alkyl-S-, of which the alkyl part has the above-mentioned meaning, and can represent, for example, C14 alkylthio. There can be mentioned specifically methylthio, ethylthio, n-or iso-propylthio, n-, iso-, sec-or tert-butylthio.

"Alkylsulfinyl"is alkyl-SO-, of which the alkyl part has the above-mentioned meaning, and can represent, for example, C14 alkylsulfinyl. There can be mentioned

specifically methylsulfinyl, ethylsulfinyl, n-or iso-propylsulfinyl, n-, iso-, sec-or tert-butylsulfinyl.

"Alkylsulfonyl"is alkyl-SOz-, of which the alkyl part has the above-mentioned meaning, and can represent, for example, Clx alkylsulfonyl. There can be mentioned specifically methylsulfonyl, ethylsulfonyl, n-or iso-propylsulfonyl, n-, iso-, sec-or tert-butylsulfonyl.

"Alkylamino"is alkyl-NH-, of which the alkyl part has the above-mentioned meaning, and can represent, for example, C14 alkylamino. There can be mentioned specifically methylamino, ethylamino, n-or iso-propylamino, n-, iso-, sec-or tert- butylamino.

"Alkyl-carbonylamino"is alkyl-CONH-, of which the alkyl part has the above- mentioned meaning, and can represent, for example, C2-5 alkyl-carbonylamino in total. There can be mentioned specifically methylcarbonylamino, ethylcarbonyl- amino, n-or iso-propylcarbonylamino, n-, iso-, sec-or tert-butylcarbonylamino.

"Cycloalkyl-carbonylamino"is cycloalkyl-CONH-, of which the cycloalkyl part has the above-mentioned meaning, and can represent, for example, ¬4-7 cycloalkyl- carbonylamino. There can be mentioned specifically cyclopropylcarbonylamino or cyclobutylcarbonylamino, cyclopentylcarbonylamino, cyclohexylcarbonylamino.

"Haloalkyl-carbonylamino"is haloalkyl-CONH-, of which the haloalkyl part has the above-mentioned meaning, and can represent, for example, C25 haloalkyl-carbonyl- amino. There can be mentioned specifically fluoromethylcarbonylamino, difluoro- methyl-carbonylamino, difluorochloromethylcarbonylamino, difluorobromo-methyl- carbonylamino, trifluoromethylcarbonylamino, 1-fluoroethylcarbonylamino, 2- fluoromethylcarbonylamino, 2,2,2-trifluoroethylcarbonylamino, 1,2,2,2-tetrafluoro- ethylcarbonylamino, perfluoroethylcarbonylamino or perfluoropropylcarbonylamino, perfluorobutylcarbonylamino.

In"benzyl which may be optionally halogen-substituted or alkyl-substituted"and "benzylcarbonylamino which may be optionally halogen-substituted or alkyl- substituted"the halogen atoms are the same as mentioned above for"halogen"and the alkyl part has the same meaning as the above-mentioned"alkyl". As specific examples of"benzyl which may be optionally halogen-substituted or alkyl- substituted"there can be mentioned benzyl, 2- (3- and 4-) fluorobenzyl or 2- (3- and 4-) chlorobenzyl, 2- (3- and 4-) methylbenzyl, 2,5-, 2,6-, 3,4-, 3,5-)- difluorobenzyl and as specific examples of"benzyl carbonylamino which may be optionally halogen-substituted or alkyl-substituted"there can be mentioned benzyl- carbonylamino, 2-, 3-or 4-fluorobenzylcarbonylamino, 2-, 3-or 4-chlorobenzyl- carbonylamino, 2-, 3-or 4-methylbenzylcarbonylamino, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-difluorobenzylcarbonylamino.

In"phenyl which may be optionally halogen-substituted or alkyl-substituted"the halogen atoms are the same as mentioned above for"halogen"and the alkyl part has the same meaning as the above-mentioned"alkyl". As specific examples of"phenyl which may be optionally halogen-substituted or alkyl-substituted"there can be mentioned phenyl, 2-, 3-or 4-fluorophenyl, 2-, 3-or 4-chlorophenyl, 2-, 3-or 4- methylphenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-difluorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-dichlorophenyl or 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-dimethylphenyl.

In"phenylcarbonylamino which may be optionally alkyl-substituted, alkoxy- substituted or halogen-substituted"the alkyl part has the same meaning as the above- mentioned"alkyl", the alkoxy part has the same meaning as the above-mentioned "alkoxy"and the halogen atoms are the same as mentioned above for"halogen". As specific examples of"phenylcarbonylamino which may be optionally alkyl substi- tuted alkoxy-substituted or halogen-substituted"there can be mentioned phenyl- carbonylamino, 2-, 3-or 4-fluorophenylcarbonylamino, 2-, 3-or 4-chlorophenyl- carbonylamino, 2-, 3-or 4-methylphenylcarbonylamino, 2-, 3- or 4-methoxyphen. yl- carbonylamino, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-difluoro phenylcarbonylamino, 2, 3-,

2,4-, 2,5-, 2,6-, 3,4-, or 3,5-dichlorophenylcarbonylamino or 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-dimethylphenylcarbonylamino.

In"alkylcarbonylacetylamino"the alkyl part has the same meaning as the above- mentioned"alkyl"and as specific examples of"alkylcarbonylacetylamino"there can be mentioned acetoacetylamino, propionylacetylamino, butyrylacetylamino, iso- butyrylacetylamino, valerylacetylamino, isovalerylacetylamino or pivaloylacetyl- amino.

In"dialkylaminoalkylideneamino"the alkyl part has the same meaning as the above- mentioned"alkyl"and the above-mentioned alkylidene part can be straight chain or branched chain and can represent, for example, Cl alkylidene. As examples of "dialkylaminoalkylidene-amino"there can be mentioned dimethylaminomethylidene- amino, 1- (dimethylamino) ethylideneamino, 1- (dimethylamino) (n-propylidene) amino, 1-(dimethylamino) (n-butylidene)(dimethylamino) (n-butylidene) amino, 1- (dimethylamino) (iso-butylidene) amino, diethylaminomethylideneamino, di (n-propyl) aminomethylideneamino, di (n-butyl)- aminomethylideneamino, (N-methyl-N-ethylamino) methylideneamino or (N-methyl- N- (n-propyl) amino) methylideneamino.

As a preferable group of compounds of the present invention there can be mentioned compounds which in the formula (I) Rl represents C14 alkyl, C35 cycloalkyl, C13 haloalkyl, benzyl which may be optionally fluoro-substituted, chloro-substituted or CI-3 alkyl-substituted, or phenyl which may be optionally fluoro-substituted, chloro-substituted or CI-3 alkyl-substituted, RZ represents amino, C1-3 alkylamino, formylamino, Cl3 alkyl-carbonylamino, C35 cycloalkyl-carbonylamino, C13 haloalkyl-carbonylamino, benzyl- carbonylamino which may be optionally fluoro-substituted, chloro-substituted or CI_3 alkyl-substituted, phenylcarbonylamino which may be optionally C13

alkyl-substituted, Cl 3 alkoxy-substituted, fluoro-substituted or chloro- substituted, ordi(C1-3alkyl)amino-C1-3alkyl-carbonylacetylamino, alkylideneamino, R3 or R4 each independently represent hydrogen atom or Cl 3 alkyl, R5 represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, tert- butyl, C1-3 haloalkyl, C1-3 alkoxy, C)-3 haloalkoxy, C)-3 alkylthio, C)-3 haloalkylthio, C1-3 alkylsulfinyl, Cri-3 alkylsulfonyl, phenyl which may be optionally fluoro-substituted, chloro-substituted or Cl 3 alkyl-substituted, phenoxy which may be optionally fluoro-substituted, chloro-substituted or C 3 alkyl-substituted, nitro or cyano, m represents an integer of 2-4, and the R3 substituents may be identical or different, n represents an integer of 0-4, and the R5 substituents may be identical or different, in case n represents an integer of 2 or more.

And as a more preferable group of compounds there can be mentioned compounds which in the compounds of the aforementioned formula (I) R'represents methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclo- butyl, fluoromethyl, fluorochloromethyl, fluorobromomethyl, fluorodi- chloromethyl, fluorodibromomethyl, difluoromethyl, difluorochloromethyl, difluorobromomethyl, trifluoromethyl, chloromethyl, trichloromethyl, bromo- methyl, 1-fluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, perfluoro- ethyl, 1-chloroethyl, 1,2-dichloroethyl, 1-bromoethyl, perfluoropropyl, 1-

fluoro-1-methylethyl, 1-chloro-1-methylethyl, 1-bromo-1-methylethyl, 1- (trifluoromethyl)-2,2,2-trifluoroethyl, benzyl which may be optionally fluoro- substituted or methyl-substituted, or phenyl which may be optionally fluoro- substituted, chloro-substituted or methyl-substituted, R2 represents amino, methylamino, ethylamino, formylamino, acetylamino, ethylcarbonylamino, cyclopropylcarbonylamino, fluoromethylcarbonylamino, trifluoromethylcarbonylamino, 1-fluoroethylcarbonylamino, perfluoroethyl- carbonylamino, benzylcarbonylamino which may be optionally chloro- substituted or methyl-substituted, phenylcarbonylamino which may be optionally fluoro-substituted, chloro-substituted, methyl-substituted or methoxy-substituted, acetoacetylamino, or dimethylaminomethylideneamino, R3 or R4 each independently represent hydrogen atom, methyl or ethyl, R5 represents fluoro, chloro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfinyl, methyl- sulfonyl, phenyl which may be optionally fluoro-substituted or methyl- substituted, phenoxy which may be optionally fluoro-substituted or methyl- substituted, nitro or cyano, m represents an integer of 3 or 4, and the R3 substituents may be identical or different, n represents an integer of 0-3, and the R5 substituents may be identical or different, in case n represents an integer of 2 or 3.

The aforementioned preparation process (a), in case, for example, 2-benzylcyclo- pentylbiguanide hydrochloride and methyl a-fluoro-a-methylpropionate are used as the starting materials, can be illustrated by the following reaction scheme.

,, NH NH lCCH N N t N t NH HCI + CH3 C02CH , CH2 H H F WJ CH3 I base CH3 NON - | I N vN CIH N N NH , 4, CH2 H The aforementioned preparation process (b), in case, for example, 2-amino-4- (2'- benzylcyclopentylamino)-6- ( (x-fluoroisopropyl)-1, 3,5-triazine and ethyl acetate are used as the starting materials, can be illustrated by the following reaction scheme: CH3 F CH3 l CH NIIN +'' w>, CH2 H I 1- : CH3 F CH3 N4N ° > gFr N N N CH3 N H CH3 H The aforementioned preparation process (c), in case, for example, 2-amino-4- (2'- benzylcyclopentylamino)-6- (a-fluoroisopropyl)-1,3,5-triazine and acetyl-Meldrum's acid are used as the starting materials, can be illustrated by the following reaction scheme:

0 0 CH3 Il F-CH, O CHcH, ' N Ji N 1 NH CH3 gCH2 H F+HC3H3N N ° ONllN N H CH3 CHEZH c3 F CH3 /F CH3 N N O O > CH2 H C H 2 H H CH2 H c The aforementioned preparation process (d), in case, for example, 2-amino-4- (2'- (2- fluorobenzyl) cyclopentylamino)-6- (a-fluoroethyl)-1,3,5-triazine and N, N-dimethyl- formamide dimethylacetal are used as the starting materials, can be illustrated by the following reaction scheme: The aforementioned preparation process (e), in case, for example, 2-ethyideneamino- 4-(2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl)-1,(2'-be nzylcyclopentylamino)-6-(a-fluoroisopropyl)-1, 3,5-triazine is used as the starting material, can be illustrated by the following reaction scheme:

C CHg CH3 CH3 J reducing J agent NI N CH-CH---- CHH. J/C2Hs N N N= CHCH3 N N N H I I The compounds of the formula (II), the starting materials in the above-mentioned preparation process (a) are novel compounds which were not described in the literature and can be prepared according to the process described in, for example, Japanese Laid-open Patent Application Nos. 246279/1989,264465/1988, 222166/1988, No. 146876/1988, No. 51379/1988 by reacting, for example, a compound of the formula (VIII) wherein R3, R4, R5, m and n have the same definitions as aforementioned and X represents halogen, with cyanoguanidine in an appropriate diluent, for example, n-decane. The compounds of the above-mentioned formula (VIII) can be prepared by reacting compounds of the formula (IX),

wherein R3, R4, R5, m and n have the same definitions as aforementioned, with an appropriate hydrogen halide acid, such as hydrochloric acid.

The compounds of the above-mentioned formula (IX), a part of which is novel and not described in the literature, can be prepared according to the process, (Leuckart's reaction) described in, for example, Organic Reaction, Vol. 5, p. 301 (1962), John Wiley & Sons, INC., by reacting compounds of the formula (X) wherein R3, R4, R5, m and n have the same definitions as aforementioned, with formamide and formic acid.

The compounds of the above-mentioned formula (X), a part of which is novel and not described in the literature, can be easily prepared by reacting, for example, in the commonly well known decarboxylation of B-ketoesters, namely, compounds represented of the formula (XI)

wherein R3, R4, R5, m and n have the same definitions as aforementioned, and R6 represents Cri-4 alkyl, with an appropriate mineral acid, for example, hydrobromic acid.

The compounds of the above-mentioned formula (XI), a part of which is novel and not described in the literature, can be easily obtained by, for example, the process described in"SEIMITSU YUKI GOSEI" (Precise organic syntheses), Nankodo, p. 160,1983, namely, by reacting compounds of the formula (XII) wherein

R3 and m have the same definitions as aforementioned, and R6 represents C14 alkyl, with compounds of the formula wherein R4, R5 and n have the same definitions as aforementioned, and Xl represents halogen, using an appropriate acid binding agent, for example, an aqueous solution of sodium hydroxide in an appropriate diluent, for example, dichloromethane in the presence of a phase transfer catalyst, for example, tetrabutylammonium hydrogen sulfate.

The compounds of the above-mentioned formula (XII), a part of which is novel and not described in the literature, can be easily prepared according to the process described in, for example, Organic Reaction, Vol. 15, p. 1 (1967), John Wiley & Sons, INC.

The compounds of the above-mentioned formula (XIII) are known compounds and can be easily prepared according to the process described in, for example,"SHIN JIKKEN KAGAKU KOZA" (New experimental chemistry lectures), edited by the Chemical Society of Japan, Vol. 14 (I), p. 331,1962, published by Maruzen.

As compounds of the formula (II) used as the starting materials in the above- mentioned preparation process (a) there can be mentioned the following:

2-benzylcyclopentylbiguanide hydrochloride, 2- (2'-fluorobenzyl) cyclopentylbiguanide hydrochloride, 2- (3'-fluorobenzyl) cyclopentylbiguanide hydrochloride, 2- (3'-methylbenzyl) cyclopentylbiguanide hydrochloride, 2-benzylcyclohexylbiguanide hydrochloride, 2- (2'-fluorobenzyl) cyclohexylbiguanide hydrochloride, 2- (3'-fluorobenzyl) cyclohexylbiguanide hydrochloride and 2- (3'-methylbenzyl) cyclohexylbiguanide hydrochloride.

The compounds of the formula (III) are known compounds and can be commercially obtained. They can also be easily prepared according to the process described in EP-A-850911.

As compounds of the formula (III) used as the starting materials in the above- mentioned preparation process (a) there can be mentioned the following: ethyl fluoroacetate, ethyl fluorochloroacetate, ethyl fluorobromoacetate, ethyl difluorochloroacetate, ethyl dibromofluoroacetate, ethyl trifluoroacetate, methyl pentafluoropropionate, ethyl a-fluoropropionate, ethyl a-fluoro-a-methylpropionate, ethyl acetate, ethyl propionate, ethyl n-butyrate, ethyl isobutyrate, ethyl cyclopropanecarboxylate, ethyl cyclopentanecarboxylate and ethyl cyclohexanecarboxylate.

The compounds of the formula (Ia) used as the starting materials in the above- mentioned preparation processes (b)- (d) are a part of the compounds of the formula (I) of the present invention and can be easily prepared by the above-mentioned preparation process (a).

In formula (IV) according to the above-mentioned preparation process (b) R7 preferably represents a hydrogen atom, C13 alkyl, C35 cycloalkyl, C13 haloalkyl, benzyl which may be fluoro-substituted, chloro-substituted or Cl3 alkyl-substituted, or phenyl which may be Cri-3 alkyl-substituted, Cri_3 alkoxy-substituted, fluoro- substituted or chloro-substituted.

The compounds of the formula (IV) are known compounds and can be obtained as commercially available. Or they can be easily synthesized according to the process described in, for example, EP-A-850911.

As compounds of the formula (Ia) used as the starting materials in the above- mentioned preparation processes (b)- (d) which are included in the formula (I), there can be mentioned the following: 2-amino-4-(2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl)- 1,(2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl)-1, 3,5-triazine, 2-amino-4-(2'-benzylcyclopentylamino)-6-(a-fluoroethyl)-1,(2 '-benzylcyclopentylamino)-6-(a-fluoroethyl)-1, 3,5-triazine, <BR> <BR> <BR> 2-amino-4- (2'- (2-fluorobenzyl) cyclopentylamino)-6- (a-fluoroisopropyl)-1,3,5-triazine, 2-amino-4-(2'-(2-fluorobenzyl) cyclopentylamino)-6-(a-fluoroethyl)-1,(2'-(2-fluorobenzyl) cyclopentylamino)-6-(a-fluoroethyl)-1, 3,5-triazine, <BR> <BR> <BR> 2-amino-4- (2'- (2-fluorobenzyl) cyclopentylamino)-6- (trifluoromethyl)-1,3,5-triazine, 2-amino-4- (2'- (3-fluorobenzyl) cyclopentylamino)-6- (a-fluoroisopropyl)-1, 3,5-triazine, <BR> <BR> <BR> 2-amino-4- (2'- (3-fluorobenzyl) cyclopentylamino)-6- (a-fluoroethyl)-1,3,5-triazine,<BR> <BR> <BR> <BR> 2-amino-4- (2'- (3-fluorobenzyl) cyclopentylamino)-6- (trifluoromethyl)-1,3,5-triazine, 2-amino-4- (2'- (3-methylbenzyl) cyclopentylamino)-6- (a-fluoroisopropyl)-1,3,5-triazine, 2-amino-4- (2'- (3-methylbenzyl) cyclopentylamino)-6- (a-fluoroethyl)-1,3,5-triazine, <BR> <BR> <BR> 2-amino4-(2'-(3-methylbenzyl) cyclopentylamino)-6-(a-fluoroisopropyl)-1, 3, 5-triazine,- 2-amino-4-(2'-benzylcyclohexylamino)-6-(a-fluoroisopropyl)-1 ,(2'-benzylcyclohexylamino)-6-(a-fluoroisopropyl)-1, 3,5-triazine,

2-amino-4-(2'-benzylcyclohexylamino)-6-(a-fluoroethyl)-1,(2' -benzylcyclohexylamino)-6-(a-fluoroethyl)-1, 3,5-triazine, <BR> <BR> <BR> <BR> 2-amino-4- (2'- (3-fluorobenzyl) cyclohexylamino)-6- (a-fluoroisopropyl)-1, 3,5-triazine,<BR> <BR> <BR> <BR> <BR> <BR> 2-amino-4- (2'- (3-fluorobenzyl) cyclohexylamino)-6- (a-fluoroethyl)-1,3,5-triazine,<BR> <BR> <BR> <BR> <BR> <BR> 2-amino-4- (2'- (3-methylbenzyl) cyclohexylamino)-6-isopropyl-1,3,5-triazine and<BR> <BR> <BR> <BR> <BR> 2-amino-4- (2'- (3-methylbenzyl) cyclohexylamino)-6-ethyl-1,3,5-triazine.

As compounds of the formula (IV) used as starting materials in the above-mentioned preparation process (b) there can be mentioned the following: as follows: ethyl acetate, ethyl propionate, ethyl n-butyrate, ethyl isobutyrate, ethyl pivalate, ethyl cyclopropanecarboxylate, ethyl cyclopentanecarboxylate, ethyl cyclohexanecarboxylate ethyl phenylacetate, ethyl benzoate, ethyl 3-methylbenzoate, ethyl 2-chlorobenzoate and ethyl trifluoroacetate.

The compounds of formula (V), used as the starting materials in the above-mentioned preparation process (c) are known compounds and can be easily prepared according to the process described in, for example, Chem. Pharm. Bull. (1987), 35 (5), 1860- 1870.

As compounds of the formula (V) used as starting materials in the above-mentioned preparation process (c) there can be mentioned the following: 6-dione,

5-propionyl-2, 2-dimethyl-1,3-dioxan-4,6-dione, 6-dione, 5-isobutyryl-2,2-dimethyl-1,3-dioxan-4,6-dione, 6-dione, 5-cyclohexylcarbonyl-2,2-dimethyl-1,3-dioxan-4,6-dione and 5- (2-fluorobenzoyl)-2, 2-dimethyl-1,3-dioxan-4,6-dione.

As compounds of formula (VI), used as the starting materials in the above-mentioned preparation process (d), are known compounds and can be easily prepared according to the process described in, for example, Japanese Laid-open Patent Application No.

277251/1996.

The compounds of the formula (VI) used as the starting materials in the above- mentioned preparation process (d) there can be mentioned the following: N, N-dimethylformamide dimethylacetal, N, N-diethylformamide dimethylacetal, N, N-dipropylformamide dimethylacetal, N-methyl-N-ethylformamide dimethylacetal, N-methyl-N-propylformamide dimethylacetal, N, N-dimethylformamide diethylacetal, N, N-diethylformamide diethylacetal, N, N-dimethylacetamide dimethylacetal and N, N-diethylacetamide dimethylacetal.

The compounds of the formula (VII) used as the starting materials in the above- mentioned preparation process (e) are novel and not described in the literature and can be prepared according to the process described in, for example, Japanese Laid- open Patent Application No. 51379/1988, for example, by reacting the compounds of the aforementioned formula (Ia) with aliphatic aldehydes or aliphatic ketones with in total 1 to 4 carbon atoms in the aliphatic groups of the formula (XIV)

O=R11 (XIV) wherein Rl l means the remaining aliphatic group forcing the aliphatic aldehydes/ketones.

The compounds of the formula (XIV) are known compounds and can be commer- cially obtained.

As compounds of the formula (VII) used as starting materials in the above-mentioned preparation process (e) there can be mentioned the following: <BR> <BR> <BR> 2-methylideneamino-4-(2'-benzylcyclopentylamino)-6-(a-fluoro isopropyl)-1, 3, 5-triazine, 2-ethylideneamino-4-(2'-benzylcyclopentylamino)-6-(a-fluoroi sopropyl)-1,(2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl )-1, 3,5-triazine, 2-propylideneamino-4-(2'-benzylcyclopentylamino)-6-(a-fluoro isopropyl)-1,(2'-benzylcyclopentylamino)-6-(a-fluoroisopropy l)-1, 3,5-triazine, 2-isopropylideneamino4-(2'-benzylcyclopentylamino)-6-(a-fluo roisopropyl)-1,(2'-benzylcyclopentylamino)-6-(a-fluoroisopro pyl)-1, 3,5-triazine, <BR> <BR> <BR> <BR> 2-methylideneamino-4-(2'-benzylcyclopentylamino)-6-(a-fluoro ethyl)-1, 3, 5-triazine, 2-ethylideneamino-4-(2'-benzylcyclopentylamino)-6-(a-fluoroe thyl)-1,(2'-benzylcyclopentylamino)-6-(a-fluoroethyl)-1, 3,5-triazine, <BR> <BR> <BR> <BR> 2-propylideneamino-4- (2'-benzylcyclopentylamino)-6- (a-fluoroethyl)-1,3,5-triazine,<BR> <BR> <BR> <BR> <BR> 2-methylideneamino-4-(2'-benzylcyclohexylamino)-6-(α-fluoro isopropyl)-1,3,5-triazine,<BR> <BR> <BR> <BR> <BR> 2-ethylideneamino-4-(2'-benzylcyclohexylamino)-6-(α-fluoroe thyl)-1,3,5-triazine,<BR> <BR> <BR> <BR> <BR> 2-ethylideneamino-4- (2'- (3-fluorobenzyl) cyclopentylamino)-6- (a-fluoroisopropyl)- 1,3,5-triazine, <BR> <BR> <BR> <BR> 2-ethylideneamino-4- (2'- (3-methylbenzyl) cyclopentylamino)-6- (a-fluoroethyl)-l, 3,5- triazine and 2-ethylideneamino-4- (2'-benzylcyclohexylamino)-6-isopropyl-1,3,5-triazine.

As another alternative to the preparation according to process (e) compounds of formula (I) can also be prepared according to process (b), if, instead of compounds of the formula (IV) compounds of the formula (XV) R12_xl (XV)

wherein Rl2 represents ClX alkyl, and X'represents halogen, are used.

The reaction of the above-mentioned preparation process (a) can be conducted in an appropriate diluent. As examples of such diluents used in that case there can be mentioned ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) or diethylene glycol dimethyl ether (DGM); alcohols, for example, methanol, ethanol, isopropoanol, butanol or ethylene glycol; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone or hexamethylphosphoric triamide (HMPA); sulfones and sulfoxides, for example, dimethyl sulfoxide (DMSO) or sulfolane; bases, for example, pyridin.

The preparation process (a) can be conducted in the presence of an acid binding agent. As an acid binding agent usable in that case there can be mentioned, as inorganic bases, hydrides, hydroxides, carbonates or bicarbonates of alkali metals and alkaline earth metals, for example, sodium hydride, lithium hydride, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide; inorganic alkali metal amides, for example, lithium amide, sodium amide or potassium amide; and as organic bases, alcoholates, tertiary amines, dialkyl- aminoanilines and pyridines, for example, sodium methoxide, sodium ethoxide, potassium tert-butoxide, triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N-dimethylaniline, N, N-diethylaniline, pyridine, 4-dimethylamino- pyridine (DMAP), 1,4-diazabicyclo [2,2,2] octane (DABCO) or 1,8-diazabicyclo- [5,4,0] undec-7-ene (DBU).

The preparation process (a) can be conducted at various of temperatures. Suitable temperatures are in the range of generally about 0-about 100°C, preferably about 20 to about 80°C. Said reaction may be conducted desirably under normal pressure. Optionally, however, it is possible to conduct it under elevated pressure or under reduced pressure.

In conducting the preparation process (a) the objective compound of the formula (I) can be obtained, for example, by reacting 1 mole of a compound of the formula (II) with 0.8-2.2 moles of a compound of the formula (III) in a diluent, for example, methanol, in the presence of 2-3 moles of sodium methoxide.

Further, in the preparation process (a) the reaction to produce the compound of the formula (II) from a compound of the formula (IX) through the intermediate compound of the formula (VIII) can be also conducted continuously.

The reaction of the above-mentioned preparation process (b) can be conducted in an appropriate diluent. As examples of such diluents used in that case there can be mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene etc.; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) or diethylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone or methyl isobutyl ketone (MIBK); nitriles, for example, acetonitrile, propionitrile or acrylonitrile; alcohols, for example, methanol, ethanol, isopropanol, butanol or ethylene glycol; esters, for example, ethyl acetate or amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone or hexamethyl- phosphoric triamide (HMPA); sulfones and sulfoxides, for example, dimethyl sulfoxide (DMSO) or sulfolane; bases, for example, pyridine.

The preparation process (b) can be conducted in the presence of an acid binding agent. As an acid binding agent usable in that case there can be mentioned, as inorganic bases, hydrides, hydroxides, carbonates or bicarbonates of alkali metals and alkaline earth metals, for example, sodium hydride, lithium hydride, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide; inorganic alkali metal amides, for example, lithium amide, sodium amide or potassium amide; and as organic bases, alcoholates, tertiary amines, dialkylaminoanilines and pyridines, for example, triethylamine, 1,1,4,4-tetramethyl- ethylenediamine (TMEDA), N, N-dimethylaniline, N, N-diethylaniline, pyridine, 4- dimethylaminopyridine (DMAP), 1,4-diazabicyclo [2,2,2] octane (DABCO) or 1,8- diazabicyclo [5,4,0] undec-7-ene (DBU); organolithium compounds, for example, methyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, phenyl lithium, dimethyl copper lithium, lithium diisopropylamide, lithium cyclohexylisopropyl- amide, lithium dicyclohexylamide, n-butyl lithium-DABCO, n-butyllithium-DBU or n-butyl lithium-TMEDA.

The preparation process (b) can be conducted at various temperatures. Suitable temperatures are in the range of generally about 0-about 150°C, preferably about 40 -about 80°C. Said reaction may be conducted desirably under normal pressure.

Optionally, however, it is possible to conduct it under elevated pressure or under reduced pressure.

In conducting the preparation process (b) the objective compound of the formula (I) can be obtained, for example, by reacting 1 mole of a compound of the formula (Ia) with 2-20 moles of a compound of the formula (IV) in the presence of 1-2 moles of sodium methoxide.

The reaction of the above-mentioned preparation process (c) can be conducted in an appropriate diluent. As examples of such diluents used in that case there can be

mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene or dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) or diethylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone or methyl isobutyl ketone (MIBK); nitriles, for example, acetonitrile, propionitrile or acrylonitrile; alcohols, for example, methanol, ethanol, isopropanol, butanol or ethylene glycol etc.; esters, for example, ethyl acetate or amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethyl- acetamide (DMA), N-methyl-pyrrolidone, 1,3-dimethyl-2-imidazolidinone or hexa- methylphosphoric triamide (HMPA); sulfones and sulfoxides, for example, dimethyl sulfoxide (DMSO) or sulfolane; bases, for example, pyridine.

The preparation process (c) can be conducted at various temperatures. Suitable temperatures are in the range of generally about 20-about 180°C, preferably about 60-about 120°C. Said reaction may be conducted desirably under normal pressure. Optionally, however, it is possible to conduct it under elevated pressure or under reduced pressure.

In conducting the preparation process (c) the objective compound of the formula (I) can be obtained, for example, by reacting 1 mole of a compound of the formula (Ia) with 1-2 moles of a compound of the formula (V) in a diluent, for example, benzene.

The reaction of the above-mentioned preparation process (d) can be conducted in an appropriate diluent. As examples of such diluents used in that case there can be mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene or dichlorobenzene; ethers, for

example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) or diethylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone or methyl isobutyl ketone (MIBK); nitriles, for example, acetonitrile, propionitrile or acrylonitrile; alcohols, for example, methanol, ethanol, isopropanol or butanol, ethylene glycol; esters, for example, ethyl acetate or amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methyl-pyrrolidone, 1,3-dimethyl-2-imidazolidinone or hexamethyl- phosphoric triamide (HMPA); sulfones and sulfoxides, for example, dimethyl sulfoxide (DMSO) or sulfolane; bases, for example, pyridine.

The preparation process (d) can be conducted in the presence of an acid catalyst. As examples of such acid catalysts usable in that case there can be mentioned mineral acids, for example, hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid or sodium hydrogen sulfite; organic acids, for example, formic acid, acetic acid, trifluoroacetic acid, propionic acid, methanesulfonic acid, benzenesulfonic acid, p- toluenesulfonic acid; organic amine hydrochlorides, for example, pyridine hydro- chloride or triethylamine hydrochloride; amine sulfonates, for example, pyridine p- toluenesulfonate or triethylamine p-toluenesulfonate.

The preparation process (d) can be conducted at various temperatures. Suitable temperatures are in the range of generally about 20-about 180°C preferably about 60-about 120°C Said reaction may be conducted desirably under normal pressure. Optionally, however, it is possible to conduct it under elevated pressure or under reduced pressure.

In conducting the preparation process (d) the objective compound of the formula (I) can be obtained, for example, by reacting 1 mole of a compound of the formula (Ia) with 2-4 moles of a compound of the formula (VI) in a diluent, for example, benzene in the presence of a catalytic amount of p-toluenesulfonic acid.

The reaction of the above-mentioned preparation process (e) can be conducted in an appropriate diluent. As examples of such diluents used in that case there can be mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene or dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) or diethylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone or methyl isobutyl ketone (MIBK); nitriles, for example, acetonitrile, propionitrile or acrylonitrile; alcohols, for example, methanol, ethanol, isopropanol, butanol or ethylene glycol; esters, for example, ethyl acetate or amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methyl-pyrrolidone, 1,3-dimethyl-2-imidazolidinone or hexamethyl- phosphoric triamide (HMPA); sulfones and sulfoxides, for example, dimethyl sulfoxide (DMSO) or sulfolane; bases, for example, pyridine.

The preparation process (e) can be conducted in the presence of a catalyst. As examples of such catalysts usable in that case there can be mentioned 10% palladium-carbon.

The preparation process (e) can be conducted at various temperatures. Suitable temperatures are in the range of generally about 0-about 120°C, preferably about 25 -about 80°C. Said reaction may be conducted desirably under normal pressure.

Optionally, however, it is possible to conduct it under elevated pressure or under reduced pressure.

In conducting the preparation process (e) the objective compound of the formula (I) can be obtained, for example, by reacting 1 mole of a compound of the formula (VII) with 1-2 moles of hydrogen gas in a diluent, for example, methanol in the presence of a catalytic amount of 10% palladium-carbon.

The active compounds of the formula (I), according to the present invention can be used as herbicides. In the present specification weeds mean, in the broadest sense, all plants which grow in locations where they are undesired. The compounds of the present invention act as total or selective herbicides depending upon the applied concentration. The active compounds of the formula (I) of the present invention can be used, for example, for the following weeds and cultures.

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Ipomoea, Polygonum, Ambrosia, Cirsium, Sonchus, Solanum, Rorippa, Lamium, Veronica, Datura, Viola, Galeopsis, Papaver, Centaurea, Galinsoga, Rotala, Lindernia etc.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita etc.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Agrostis, Alopecurus, Cynodon etc.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium etc.

The use of the compounds, according to the present invention, is not restricted to the above-mentioned plants, but may be applied to other plants in the same manner.

According to the invention all plants and plant parts can be treated. The term plants includes all plants and plant populations, such as desired or undesired wild plants and cultivated plants (including naturally occurring cultivated varieties). Cultivated

plants can be plant varieties that were obtained by conventional breeding and optimizing processes or by biotechnological and genetic engineering methods or a combination of such processes and methods, including transgenic plants and including plant varieties that cannot or can be protected by plant patents or plant variety rights. Plant parts are all parts and organis of plants occurring above or below the surface of the soil, e. g. shoots, leaves, needles, stalks and stems, trunks, flowers, fruits and seeds as well as roots, tubers, bulbs and rhizomes. The term plant parts also includes harvested crops and propagation material, e. g. cuttings, tubers, bulbs, rhizomes, shoots and seeds.

According to the invention the plants and plant parts are treated using the usual methods by applying the active ingredients or compostions containing them directly to the plants or plant parts or to this surroundings (including the soil) or storeroom, e. g. by dipping, spraying, dusting, fogging, spreading and in the case of propagation material also by coating using one or multiple layer.

The active compounds of the present invention can, depending upon the applied concentration, non-selectively control weeds and may be used, for example, on industrial terrain, rail tracks, paths, places with or without tree plantings.

Moreover, the active compounds, according to the present invention, can be used for controlling weeds in perennial cultures and applied in, for example, afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings, hopfields etc. and can be applied also for the selective controlling of weeds in annual cultures.

The active compounds of the formula (I), according to the present invention, can be made into the customary formulations in case of using. As such formulations there can be mentioned, for example, liquids (emulsifiable concentrates etc.), wettable powders, emulsions, suspension concentrates, powders, water-dispersible granules,

tablets, granules, suspension-emulsion concentrates, microcapsules in polymeric substances or jumbo formulations.

The formulations can be prepared according to known methods, for example, by mixing the active compounds with extenders, namely liquid and/or solid diluents or carriers, and optionally with surface-active agents, namely emulsifiers and/or dispersants and/or foam-forming agents.

As liquid diluents or carriers there can be mentioned, for example, aromatic hydrocarbons (for example, xylene, toluene or alkylnaphthalene), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chlorides or methylene chloride), aliphatic hydrocarbons [for example, cyclohexane or paraffins (for example, mineral oil fractions)], alcohols (for example, butanol or glycol) and their ethers, esters etc., ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (for example, dimethylformamide or dimethyl sulphoxide) or water. In case of using water as extender, for example, organic solvents can be used as auxiliary solvents.

As solid diluents or carriers there can be mentioned, for example, ground natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth), ground synthetic minerals (for example, highly dispersed silicic acid, alumina or silicates) etc. As solid carriers for granules there can be mentioned, crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite or dolomite) or synthetic granules of inorganic and organic meals or particles of organic materials (for example, sawdust, coconut shells, maize cobs and tobacco stalks).

As emulsifiers and/or foam-forming agents there can be mentioned, for example, nonionic and anionic emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (for example, alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates or arylsulphonates)] or albumin hydrolysis products.

As dispersants there are included, for example, ligninsulphite waste liquor or methyl cellulose etc.

Tackifiers may also be used in formulations (powders, granules, jumbo formulations, emulsions). As said tackifiers there can be mentioned, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum arabic, polyvinyl alcohol or polyvinyl acetate).

Colorants may also be used. As said colorants there can be mentioned inorganic pigments (for example, iron oxide, titanium oxide and Prussian Blue) and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and further trace nutrients such as salts of metals such as iron, manganese, boron, copper, cobalt or molybdenum or zinc.

Said formulations can contain in a range of generally 0.1-95 % by weight, preferably 0.5-90 % by weight of the aforementioned active components.

The active compounds of the formula (I) of the present invention can be used as such or in form of formulations for controlling weeds. They can be used also as a mixed agent with known herbicides. Such a mixed agent can be previously prepared in a final formulation form or can be prepared by tank-mixing on the occasion of the application. As a mixing partner for a possible combination there can be mentioned, for example, sulfonylurea type herbicides for paddy field use.

Furthermore, the active compounds of the formula (I) of the present invention can be also mixed with a safener and their application as a selective herbicide may be broadened by such a mixing. As an example of the safener for that purpose l- (a, a- dimethylbenzyl)-3-p-tolylurea can be mentioned.

Surprisingly, some of the mixing partners of the compounds of the present invention show synergistic effects.

In case of using the active compounds of the formula (I) of the present invention they can be directly employed as such or in the aforementioned forms of formulation or applied in the application forms prepared by further dilution. They can be applied by means of, for example, watering, spraying, atomizing, dusting or granule application.

The active compounds of the formula (I) of the present invention can be applied at any stages before and after germination of plants. They may also be taken into the soil before sowing.

The application rate of the active compounds of the present invention is not strictly restricted but may be varied in a wide range according to the desired effect, kind of objective plant, location and period of application. In case of herbicidal use, as the application rate there can be mentioned, for example, ranges of about 0.001 to about 5 kg, preferably about 0.05 to about 2 kg of the active compounds per hectare.

Then the preparations and applications of the compounds of the present invention will be described more specifically by the following examples. However, the present invention should not be restricted to them in any way."Parts"are"parts by weight", unless specified.

Svnthesis Example 1

2-Benzylcyclopentylamine (3 g) was slowly added drop by drop to concentrated hydrochloric acid (3.6 ml) under ice cooling. After stirring of the mixture for 30 minutes, water was distilled off under reduced pressure to obtain 2-benzylcyclo- pentylamine hydrochloride (3.1 g).

The above-mentioned 2-benzylcyclopentylamine hydrochloride (3.1 g) and cyano- guanidine (1.23 g) were suspende in n-decane (30 ml) and heated at 130°C for 4.5 hours. After cooling, the deposited crystals were filtered, washed with n-hexane and dried under reduced pressure to obtain 2-benzylcyclopentylbiguanide hydrochloride After adding sodium (0.31 g) in 12 ml of dry methanol and stirring for 5 minutes, the above-mentioned 2-benzylcyclopentylbiguanide hydrochloride (2 g) was added and the mixture stirred at room temperature for 30 minutes. Then methyl a-fluoro-a- methylpropionate (1.62 g) was added to the mixture, which was stirred at room temperature for 10 hours. Thereafter 50 ml of water were added and the reaction product was extracted with ethyl acetate. After drying with anhydrous sodium sulfate, the ethyl acetate was distilled off under reduced pressure and the residue was treated by silica gel column chromatography (eluent: hexane: ethyl acetate = 1: 1) to obtain 2-amino-4- (2'-benzylcyclo-pentylamino)-6-(a-fluoroisopropyl)-1, 3,5-triazine (1.65 g). mp 50-55°C.

Synthesis Example 2

After adding sodium (0.1 g) in dry methanol (5 ml) and stirring for 5 minutes, 2- amino-4-(2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl)-1, (2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl)-1, 3,5-triazine (1 g) was added and the mixture was stirred at 50°C for 1 hour. After cooling, methanol was distilled off under reduced pressure. Then ethyl acetate (10 ml) was added and the mixture was stirred at 50°C for 1 hour. After cooling, water (30 ml) was added and the reaction product was extracted with ethyl acetate. After drying with anhydrous sodium sulfate, the ethyl acetate was distilled off under reduced pressure and the residue was treated by silica gel column chromatography (eluent: hexane: ethyl acetate = 3: 2) to obtain 2-acetylamino-4- (2'-benzylcyclopentylamino)-6- (a-fluoroiso- propyl)-1,3,5-triazine (0.57 g). n°2o 1.5512.

Synthesis Example 3

2-Amino-4-(2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl)- 1,(2'-benzylcyclopentylamino)-6-(a-fluoroisopropyl)-1, 3,5-triazine (0.5 g) and acetyl-Meldrum's acid (0.28 g) were dissolved in benzene (20 ml) and refluxed for 1 hour upon heating. After cooling, the solvent was distilled off under reduced pressure and the residue was treated by silica gel column chromatography (eluent: hexane: ethyl acetate = 3: 2) to obtain 2-acetoacetylamino-4- (2'-benzylcyclopentyl- amino)-6- (a-fluoroisopropyl)-1,3,5-triazine (0.55 g). n°2o 1.5433.

Synthesis Example 4 2-Amino-4- (2'- (2-fluorobenzyl) cyclopentylamino)-6- (1-fluoroethyl)-1,3,5-triazine (0.3 g), N, N-dimethylformamide dimethylacetal (0.32 g) and a catalytic amount of p- toluenesulfonic acid monohydrate were dissolved in benzene (20 ml) and refluxed for 1.5 hours upon heating. After cooling, the solvent was distilled off under reduced pressure and the residue was treated by silica gel column chromatography (eluent: dichloromethane: methanol = 90: 5) to obtain 2-N', N'-dimethylmethyleneimino-4- (2'- (2-fluorobenzyl) cyclopentylamino)-6- (l-fluoroethyl)-1,3,5-triazine (0.34 g). n°zo 1.5776.

The compounds, which can be obtained in the same manner as the above-mentioned Synthesis Examples 1 to 4, are shown in the following Table 1, together with the compounds synthesized according to the Synthesis Examples 1 to 4.

Table 1 Com- pound No. Rl R2 R4 (R5) n mp or nD20 1. CH3 NH2 H H 2. C2H5 NH2 H H 3. C3H7-nNHHH 4. C3H7-iso NH2 H H 5. C4H9-n NH2 H H 6. C4H9-sec NH2 H H 7. C4H9-isoNH2HH 8. C4H9-tert NH2 H H 9. CHn-nNH2HH 10. NH2 H H 11. < NH2 H H 12. NH2 H H 13. NH2 H H 14. NH2 H H 15. CH2F NH2 H H 16. CH2CI NH2 H H Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 17. CH2Br NH2 H H 18. HHNH2 19. HHNH2 20. HHNH2 21. HHNH2 22. HHNH2 23. NH2HHCl 24. HHNH2 25. CF3 NH2 H H 26. CC13 NH2 H H 27. CH3CHF NH2 H H 1.5557 28. CH3CHF NH2 H 2-F 1.5525 29. CH3CHF N=CH(CH3)2 H 2-F 1.5776 30. CH3CHF NH2 H 3F 1.5485 31. H4FNH2 32. CH3CHF NH2 H 3-CH3 1.5420 33. HHNH2 34. HHNH2 35. CH3CHBr NH2 H H 36. HH50-55°CNH2 37. (CH3)2CF NH2 H 2-F 1.5469 38. (CH3)2CF NH2 H 3-F 1.5239 39. H4-FNH2 40. (CH3) 2CF NH2 H 2-Cl Table 1 (continued) Com- pound No. R'R2 R4 mp or nD20 41. H3-ClNH2 42. H4-ClNH2 43. H3-BrNH2 44. 4-BrH 45. H2-CH3NH2 46. (CH3)2CF NH2 H 3-CH3 1.5359 47. H4-CH3NH2 48. H3-C2H5NH2 49. H4-C2H5NH2 50. (CH3) 2CF NH2-H 4-C3H7-n 51. (CH3) 2CF NH2 H 4-C3H7-iso 52. (CH3) 2CF NH2 H 4-C4H9-tert 53. H2-CF3NH2 54. (CH3) 2CF NH2 H 3-CF3 55. H4-CF3NH2 56. H2-OCH3NH2 57. H3-OCH3NH2 58. H4-OCH3NH2 59. (CH3) 2CF NH2 H 3-OC2H5 60. H4-OC2H5NH2 61. H4-OC3H7-isoNH2 62. (CH3) 2CF NH2 H 3-OCF3 63. H4-OCF3NH2 64. (CH3) 2CF NH2 H 4-OCHF2 65. H4-OCH2CF3NH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 66. (CH3)2CF NH2 H 3-SCH3 67. (CH3)2CF NH2 H 4-SCH3 68. (CH3)2CF NH2 H 4-SC2H5 69. (CH3) 2CF NH2 H 3-S (O) CH3 70. (CH3) 2CF NH2 H 4-S (O) CH3 71. (CH3) 2CF NH2 H 3-SO2CH3 72. (CH3) 2CF NH2 H 4-SO2CH3 73. (CH3)2CF NH2 H 3-SCF3 74. (CH3)2CF NH2 H 4-SCF3 75. (CH3) 2CF NH2 H 3-SCH2CF3 76. (CH3) zCF NHZ H s/\ 77. (CH3) 2CF NH2 H 78. (CH3) ZCF NH2 H s/\ 79. (CH3) 2CF NH2 H 3 CH3 80. (CH3) 2CF NH2 H 3-0 81. (CH3) zCF NHZ H 3-0 82. (CH3) 2CF NH2 H 4-Ot 83. (CH3) 2CF NH2 H 4-0 o CH3 84. H4-NO2NH2 85. H4-CNNH2 86. (CH3) 2CF NH2 H 2, 4-F2 87. (CH3) 2CF NH2 H 3, 4-F2 88. (CH3) 2CF NH2 H 3, 5-F2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 89. (CH3) 2CF NH2 H 2, 4-C12 90. (CH3) 2CF NH2 H 3, 4-C12 91. H3,5-Cl2NH2 92. (CH3) 2CF NH2 H 2,4-(CH3) 2 93. (CH3) 2CF NH2 H 3,4-(CH3) 2 94. (CH3) 2CF NH2 H 3,5-(CH3) 2 95. H3,5-(CF3)2NH2 96. H3,4-(OCH3)2NH2 97. (CH3) 2CF NH2 H 2, 3,4-Cl3 98. (CH3) 2CF NH2 H 2, 4,6- (CH3) 3 99. HHNHCHO 100. (CH3)2CF NHCOCH3 H H 1.5512 101. (CH3) 2CF NHCOC2H5 H H 102. (CH3) 2CF NHCOC3H7-n H H 103. (CH3) 2CF NHCOC3H7-iso H H 104. (CH3) 2CF NHCOC4H9-tert H H 105. (CH3) 2CF NHCO H H 106. (CH3) 2C NHCO < H H u 107. (CH3) 2CF NHCO < H H u 108. HHNHCOCH2F Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 109. (CH3)2CF NHCOCF3 H H 110. (CH3) 2CF NHCOCHFCH3 H H 111. (CH3) 2CF NHCOCF2CF3 H H 112. (CH3) 2CF NHCOCH2 H H CH3 113. (CH3) 2CF NHCOCH2 H H ci 114. (CH3) 2CF NHCOCH2 t H H 115. (CH3) 2CF NHCO H H F 116. (CH3) 2CF NHCO H H Cl 117. (CH3) 2CF NHCO 4 H H 118. (CH3) 2CF NHCH H H F 119. (CH3) 2CF NHCO < F H H Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 CH3 120. (CH3) 2CF NHCO H H CH3 121. (CH3) 2CF NHCOCH2COCH3 H H 1.5433 122. (CH3) 2CF N=CHN (CH3) 2 H H 123. (CH3) 2CCI NH2 H H 124. (CH3) 2CBr NH2 H H 125. CICH2C1CH2 NH2 H H 126. CH2CF3 NH2 H H 127. CHFCF3 NH2 H H 128. CH2CF3 NH2 H H 129. CF2CF2CF3 NH2 H H 130. (CF3) 2CH NH2 H H 131. CF2CF2CF2CF3 NH2 H H 132. CHZ2 H H F 133. CH2-3 NH2 H H CH3 CHg 134. NH2 H H CH.-J Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 - 135. NH2 H H F bd 136. \=/12 H H ci 137. NH2 H H 138. H H Cl 139. NH2 H H ci H3C 140. CH3 NH2 H H 141. CF3 NH2 CH3 H 142. CF3 NH2 CH3 3-F 143. CF3 NH2 CH3 3-CH3 144. CF3 NH2 CH3 3,5-F2 145. CF3 NH2 CH3 3, 5- (CH3) Z 146. CH3CHF NH2 CH3 H Table 1 (continued) Com- pound No. 4(R5)nmpornD20R2 147. CH33-FNH2 148. CH33-CH3NH2 149. CH3CHFNH2CH3, 5-F2 150. CH3CHFNH2CH33, 5- (CH3) 2 151. (CH3) 2CF NH2 CH3 H 152. CH33-FNH2 153. CH33-CH3NH2 154. (CH3) 2CFNH2CH33, 5-F2 155. CH33,5-(CH3)2NH2 156. CF3 NH2 C2H5 H 157. CF3 NH2 C2H5 3-F 158. CF3NH2C2H53-CH3 159. C2H5HNH2 160. C2H53-FNH2 161. CH3CHFNH2CHs3-CH3 162. (CHjCFNH2C;H 163. C2H53-FNH2 164. C2H53-CH3NH2 165. C3H7-nHNH2 166. CH3CHF NH2 C3H7-n H 167. C3H7-nHNH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 168. CF3 NH2 H H 169. H2-FNH2 170. CF3 NH2 H 3-F 171. H4-FNH2 172. CF3NH2H2-C1 173. CF3 NH2 H 3-Cl 174. H4-ClNH2 175. H3-BrNH2 176. H3-CF3NH2 177. CF3 NH2 H 2-CH3 178. H3-CH3NH2 179. H4-CH3NH2 180. H2-OCH3NH2 181. CF3 NH2 H 3-OCH3 182. H4-OCH3NH2 183. CF3 NH2 H 3-SCH3 184. HHNH2 185. H2-FNH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 186. H3-FNH2 187. H4-FNH2 188. CH3CHF NH2 H 2-Cl 189. CH3CHF NH2 H 3-Cl 190. CH3CHF NH2 H 4-Cl 191. H3-BrNH2 192. H3-CF3NH2 193. H2-CH3NH2 194. CH3CHF NH2 H 3-CH3 195. H4-CH3NH2 196. CH3CHF NH2 H 2-OCH3 197. H3-OCH3NH2 198. H4-OCH3NH2 199. H3-SCH3NH2 200. H3,5-F2NH2 201. CH3CHFNH2H3, 5- (CH3) 2 202. HHNH2 203. H2-FNH2 204. H3-FNH2 205. H4-FNH2 206. (CH3) 2CF NH2 H 2-Cl 207. H3-ClNH2 208. H4-ClNH2 209. H3-BrNH2 210. H3-CF3NH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 211. H2-CH3NH2 212 (CH3) 2CF NH2 H 3-CH3 213. H4-CH3NH2 214. H2-OCH3NH2 215. H3-OCH3NH2 216. H4-OCH3NH2 217. (CH3) 2CF NH2 H 3-SCH3 218. H3,5-F2NH2 219. (CH3) 2CF NH2 H 3, 5-(CH3) 2 220. CH3HNH2 221. CH33-FNH2 222. CH3HNH2 223. CH3CHFNH2CH33-F 224. CH3HNH2 225. CH33-FNH2 226. CF3 NH2 C2H5 H 227. CHCHFNHCHH 228. (CH3) 2CF NH2 C2H5 H 229. C3H7-nHNH2 230. CH3CHF NH2 C3H7-n H 231. C3H7-nHNH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 NH2HH232.CF3 233. CF3 NH2 H 3-F 234. CF3 NH2 H 3-CH3 235. H3,5-F2NH2 236. CF3NH2H3, 5- (CH3) 2 237. CH3CHF NH2 H H 238. H3-FNH2 239. 3-CH3NH2 240. 3,5-F2NH2 241. CH3CHF NH2 H 3, 5- (CH3) 2 242. HHNH2 243. H3-FNH2 244. H3-CH3NH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 245. (CH3) 2CF NH2 H 3,5-F2 246. (CH3) 2CF NH2 H 3,5- (CH3) 2 247. CF3 NH2 CH3 H 248. CF3 NH2 C2H5 H 249. CH3CHF NH2 CH3 H 250. CH3CHF NH2 C2H5 H 251. (CH3) 2CF NH2 CH3 H 252. (CH3) 2CF NH2 C2H5 H Table 1 (continued) Com- pound No. R'R2 R 4 mp or nD20 253. CH3 NH2 H H 254. C2H5 NHW H H 255. C3H7-n NH2 H H 256. C3H7-iso NH2 H H 257. C4H9-n NH2 H H 258. C4H9-sec NH2 H H 259. C4H9-iso NH2 H H 260. C4H9-tert NH2 H H 261. C3H7-n NH2 H H 262.--a NH2 H H 263.4 NH2 H H Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 264. < NH2 H H 265. {@ NH2 H H 266.-/hNH2HH 267. CH2F NH2 H H 268. CH2CI NH2 H H 269. CH2Br NH2 H H 270. CHFCI NH2 H H 271. CHFBr NH2 H H 272. CFC12 NH2 H H 273. CFBr2 NH2 H H 274. CHF2 NH2 H H 275. CF2CI NH2 H H 276. CF2Br NH2 H H 277. CF3 NH2 H H 278. CC13 NH2 H H 279. CH3CHF NH2 H H 280. CH3CHF NH2 H 2-F 281. CH3CHF NH2 H 3-F 60-66°C 282. CH3CHF NH2 H 4-F 283. CH3CHF NH2 H 3-CH3 284. CH2CH2F NH2 H H Table 1 (continued) Com- pound No. R4(R5)ompornD20R2 285. CH3CHCI NH2 H H 286. CH3CHBr NH2 H H 287. (CH3)2CF NH2 H H 1.5332 288. (CH3) 2CF NH2 H 2-F 289. H3-F72-80°CNH2 290. H4-FNH2 291. H2-ClNH2 292. H3-ClNH2 293. H4-ClNH2 294. H3-BrNH2 295. H4-BrNH2 296. H2-CH3NH2 297. H3-CH3NH2 298. H4-CH3NH2 299. (CH3) 2CF NH2 H 3-C2H5 300. H4-C2H5NH2 301. (CH3) 2CF NH2 H 4-C3H7-n 302. (CH3) 2CF NH2 H 4-C3H7-iso 303. (CH3) 2CFNH2H4-C4H9-tert 304. H2-CF3NH2 305. H2-CF3NH2 306. H4-CF3NH2 307. (CH3) 2CF NH2 H 2-OCH3 308. (CH3) 2CF NH2 H 3-OCH3 309. H4-OCH3NH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 310. N3-OC2H5NH2 311. (CH3) 2CF NH2 H 4-OC2H5 312. H4-C3H7-isoNH2 313. H3-OCF3NH2 314. H4-OCF3NH2 315. H4-OCHF2NH2 316. H4-OCH2CF3NH2 317. H3-SCH3NH2 318. H4-SCH3NH2 319. H4-SC2H5NH2 320. (CH3) 2CF NH2 H 3-S (O) CH3 321. (CH3) 2CF NH2 H 4-S (O) CH3 322. H3-SO2CH3NH2 323. (CH3) 2CF NH2 H 4-SO2CH3 324. H3-SCF3NH2 325. H4-SCF3NH2 326. (CH3) 2CF NH2 H 4-SCH2CF3 327. (CH3) 2CF NH2 H 3 3 328. (CH3) 2CF NH2 H 4 < 3-WF 329. (CH3) 2CF NH2 H \==/ Table 1 (continued) Com- pound R2R4(R5)nmpornD20No.R1 330. (CHhCFNH2Hs--CHg 331. (CH3) 2CF NH2 H 3-0 332. (CH3) 2CF NH2 H 4-O t 333. (CH3) 2CF NH2 H 4-NO2 334. H4-CNNH2 335. H2,4-F2NH2 336. (CH3) 2CF NH2 H 3, 4-F2 337. H3,5-F2NH2 338. (CH3) 2CF NH2 H 2, 4-C12 339. H3,4-Cl2NH2 340. H3,5-Cl2NH2 341. (CH3) 2CF NH2 H 2, 4-(CH3) 2 342. H3,4-(CH3)2NH2 343. H3,5-(CH3)2NH2 344. H3,5-(CF3)2NH2 345. (CH3) 2CF NH2 H 3,4-(OCH3) 2 346. H2,3,4-Cl3NH2 347. (CH3) 2CF NH2 H 2, 4,6- (CH3) 3 348. (CH3) 2CF NHCHO H H 349. (CHhCFNHCOCH3HH 350. HHNHCOC2H5 351. (CH3) 2CF NHCOC3H7-n H H Table 1 (continued) Com- pound No. R4(RT)nmpornD20R2 352. (CH3) 2CF NHCOC3H7-iso H H 353. (CH3) 2CF NHCOC4H9-tert H H 354. (CH3) 2CF NHCO H H NHCO H 355. (CH3) 2CF NHCO H H 356. (CH3) 2CF NHCO {@ H H u 357. (CH3) 2CF NHCOCH2F H H 358. (CH3) 2CF NHCOCF3 H H 359. (CH3) 2CF NHCOCHFCH3 H H 360. (CH3) 2CF NHCOCF2CF3 H H 361. (CH3) 2CF NHCOCF H H ci 362. (CH3) 2CF NHCOCH2 H H 363. (CH NHCO H H F 364. (CH3) 2CF NHCO H H Cl 365. (CH3) 2CF NHCO 4 H H Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 366. (CH3) 2CF NHCO H H F 367. (CH3) 2CF NHCO H CH3 368. (CH3) 2CF NHCO < H H CH3 369. HHNHCOCH2COCH3 370. (CH3) 2CF N=CHN (CH3) 2 H H 371. HHNH2 372. HH 373. CH2CICH2CI NH2 H H 374. HHNH2 375. HHNH2 376. CF2CF3 NH2 H H 377. HHNH2 378. (CF3) 2CH NH2 H H 379. CH3HNH2 380. CH33-FNH2 381. CH33-CH3NH2 382. CF3NH2CH33, 5-F2 383. CF3NH2CH33, 5- (CH3) 2 384. CH3HNH2 385. CH33-FNH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 386. CH33-CH3NH2 387. CH33,5-F2NH2 388. CH33,5-(CH3)2NH2 389. CH3HNH2 390. (CH3) 2CF NH2 CH3 3-F 391. CH33-CH3NH2 392. CH33,5-F2NH2 393. (CH3)2CF 3,5-(CH3)2CH3 394. C2H5HNH2 395. C2H53-FNH2 NH2C2H53-CH3396.CF3 397. CH3CHF NH2 C2H5 H 398. CH3CHF NH2 C2H5 3-F 399. CH3CHF NH2 C2H5 3-CH3 400. C2H5HNH2 401. (CH3) 2CF NH2 C2H5 3-F 402. (CH3) 2CF NH2 C2H5 3-CH3 403. CF3 NH2 C3H7-n H 404. CH3CHF NH2 C3H7-n H 405. (CH3) 2CF NH2 C3H7-n H Table 1 (continued) com- pound No. R4(R5)nmpornD20R2 406. CF3 NH2 H H 407. CF3 NH2 H 2-F 408. CF3 NH2 H 3-F 409. H4-FNH2 410. 2-ClH 411. CF3 NH2 H 3-Cl 412. CF3NH2H4-C1 413. H3-BrNH2 414. H3-CF3NH2 415. H2-CH3NH2 416. H3-CH3NH2 417. H4-CH3NH2 418. H2-OCH3NH2 419. CF3 NH2 H 3-OCH3 420. CF3 NH2 H 4-OCH3 421. H3-SCH3NH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 NH2HH422.CH3CHF 423. H2-FNH2 424. H3-FNH2 425. CH3CHF NH2 H 4-F 426. CH3CHF NH2 H 2-Cl 427. CH3CHF NH2 H 3-Cl 428. CH3CHF NH2 H 4-Cl 429. H3-BrNH2 430. H3-CF3NH2 431. H2-CH3NH2 432. H3-CH3NH2 433. H4-CH3NH2 434. CH3CHF NH2 H 2-OCH3 435. CH3CHF NH2 H 3-OCH3 436. H4-OCH3NH2 437. H3-SCH3NH2 438. H3,5-F2NH2 439. CH3CHF NH2 H 3, 5-(CH3) 2 440. (CH3) 2CF NH2 H H 441. H2-FNH2 442. H3-FNH2 443. H4-FNH2 444. H2-ClNH2 445. H3-ClNH2 446. (CH3) 2CF NH2 H 4-Cl Table 1 (continued) Com- pound No. R4(R5)NmpornD20R2 447. H3-BrNH2 448. H3-CF3NH2 449. (CH3) 2CF NH2 H 2-CH3 450. (CH3) 2CF NH2 H 3-CH3 451. H4-CH3NH2 452. H2-OCH3NH2 453. H3-OCH3NH2 454. H4-OCH3NH2 455. H2-SCH3NH2 456. H3,5-F2NH2 457. (CH3) 2CF NH2 H 3, 5- (CH3) 2 458. CH3HNH2 459. CF3 NH2 C2H5 H 460. CH3CHF NH2 CH3 H 461. CH3CHF NH2 C2H5 H 462. CH3HNH2 466. C2H5HNH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 464. CF3 NH2 H H 465. CF3 NH2 H 2-F 466. CF3 NH2 H 3-F 467. CF3 NH2 H 4-F 468. CF3 NH2 H 2-C1 469. H3-ClNH2 470. H4-ClNH2 471. H3-BrNH2 472. H3-CF3NH2 473. CF3 NH2 H 2-CH3 474. H3-CH3NH2 475. H4-CH3NH2 476. CF3 NH2 H 2-OCH3 477. CF3 NH2 H 3-OCH3 478. H4-OCH3NH2 479. H3-SCH3NH2 480. CH3CHF NH2 H H 481. H2-FNH2 Table 1 (continued) Com- pound No. R4(R5)nmpornD20R2 482. H3-FNH2 483. H4-FNH2 484. CH3CHF NH2 H 2-Cl 485. CH3CHF NH2 H 3-Cl 486. CH3CHF NH2 H 4-Cl 487. CH3CHF NH2 H 3-Br 488. H3-CF3NH2 489. CH3CHF NH2 H 2-CH3 490. H3-CH3NH2 491. H4-CH3NH2 492. CH3CHF NH2 H 2-OCH3 493. H3-OCH3NH2 494. H4-OCH3NH2 495. H3-SCH3NH2 496. H3,5-F2NH2 497. CH3CHFNH2H3, 5- (CH3) 2 498. HHNH2 499. H2-FNH2 500. H3-FNH2 501. H4-FNH2 502. (CH3) 2CF NH2 H 2-Cl 503. (CH3) 2CF NH2 H 3-Cl 504. H4-ClNH2 505. H3-BrNH2 506. H3-CF3NH2 Table 1 (continued) Com- pound No. RI R2 R4 mporn°2o 507. (CH3) 2CF NH2 H 2-CH3 508. (CH3) 2CF NH2 H 3-CH3 509. (CH302CF NH2 H 4-CH3 510. (CH3) 2CF NH2 H 2-OCH3 511. (CH3)2CF NH2 H 3-OCH3 512. (CH3)2CF NH2 H 4-OCH3 513. (CH3)2CF NH2 H 3-SCH3 514. (CH3)2CF NH2 H 3,5-F2 515. (CH3) 2CF NH2 H 3, 5-(CH3) 2 516. CF3 NE2 CH3 H 517. CF3 NE2 C2H5 H 518. CH3CHF NH2 CH3 H 519. CH3CHF NH2 C2H5 H 520. (CH3) 2CF NH2 CH3 H 521. (CH3) 2CF NH2 C2H5 H Table 1 (continued) Com- pound R2R4(R5)nmpornD20No.R1 522. HHNH2 523. H3-FNH2 524. H3-CH3NH2 525. H3,5-F2NH2 526. CF3 NH2 H 3, 5-(CH3) 2 527. CH3CHF NH2 H H 528. H3-FNH2 529. CH3CHF NH2 H 3-CH3 530. H3,5-F2NH2 531. CH3CHF NH2 H 3, 5-(CH3) 2 532. HHNH2 533. H3-FNH2 534. H3-CH3NH2 535. H3,5-F2NH2 536. (CH3) 2CF NH2 H 3, 5-(CH3) 2 537. CF3 NH2 CH3 H 538. CF3 NH2 C2H5 H 539. CH3HNH2 540. C2H5HNH2 Table 1 (continued) Com- pound No. Rl R2 R4 (R5)n mp or nD20 541. (CH3) 2CF NH2 CH3 H 542. (CH3) 2CF NH2 C2H5 H The compounds, obtained by using methyl iodide, ethyl iodide or propyl iodide, instead of the compounds of the formula (IV) in the aforementioned preparation process (b), are shown in the following Tables 2 and 3.

Table 2 Com- pound No. R4(R5)nmpornD20R2 543. (CH3) 2CF NHCH3 H H 544. (CH3)2CF NHC2H5 H H 545. (CH3)2CF NHC3H7-n H H Table 3

Com- pound No. Rl 2 R4 (R5)n mp or nD20 546. (CH3) 2CF NHCH3 H H 547. (CH3)2CF NHC2H5 H H 548. (CH3) 2CF NHC3H7-n H H Svnthesis Example 5 A mixture of 2-benzylcyclopentanone (11.51 g) and formamide (44.41 ml) was heated at 140-150°C. Then formic acid (9.13 g) was slowly added to the mixture drop by drop at the given temperature. After finishing the addition, the mixture was heated at 150°C for further 2 hours. After cooling, water was added to the mixture and the reaction product was extracted with methylene chloride. The methylene chloride layer was washed with water and dried with anhydrous sodium sulfate.

After the methylene chloride was distilled off under reduced pressure, concentrated

hydrochloric acid (36.85 ml) was added to the residue and refluxed for 2 hours by heating. After cooling, water was added, alkalized with sodium hydroxide and the product was extracted with methylene chloride. The methylene chloride layer was washed with water and dried with anhydrous potassium carbonate. After the methylene chloride was distilled off under reduced pressure, the residue was purified by distillation to obtain 2-benzylcyclopentylamine (5.18 g). n 20 = 1.5371.

Svnthesis Example 6 48% hydrobromic acid (50 ml) was added to 2-benzyl-2-ethoxycarbonylcyclo- pentane (23.17 g) and refluxed at 120°C for 4 hours by heating. After cooling, ice (100 g) was added to the mixture and the reaction product was extracted with diethyl ether. After washing the diethyl ether layer with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, it was dried with anhydrous sodium sulfate. After the diethyl ether was distilled off under reduced pressure, the residue was purified by distillation to obtain 2-benzyl- cyclopentanone (11.51 g). n°zo = 1.5288.

Svnthesis Example 7

To a solution of 2-ethoxycarbonylcyclopentanone (13.37 g) in methylene chloride (143 ml), tetrabutylammonium hydrogen sulfate (29.1 g), benzyl iodide (37.37 g) was added and then a solution of sodium hydroxide (6.86 g) in water (143 ml) was added. After the mixture was stirred at room temperature for 4 hours, the methylene chloride layer was separated and the water layer was extracted with methylene chloride (200 ml, 3 times). The methylene chloride layers were put together, washed with water, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After the methylene chloride was distilled off under reduced pressure, the residue was treated by silica gel column chromatography (eluent: hexane: ethyl acetate = 9: 1) to obtain 2-benzyl-2-ethoxycarbonylcyclopentanone (16.8 g). nid20= 1.5156.

Test Example 1: Test for herbicidal effect against paddy field weeds Preparation of a formulation of the active compound Carrier: Acetone 5 parts by weight Emulsifier: Benzyloxypolyglycolether 1 part by weight A formulation of the active substance is obtained as emulsion by mixing 1 part by weight of the active compound with the above-mentioned amount of carrier and emulsifier. A prescribed amount of said solution of active ingredients is diluted with water and used for the test.

Test method In a greenhouse 3 seedlings of paddy rice (cultivar: Nihonbare) of 2.5 leafstage (15 cm tall) were transplanted in a 500 cm2 pot filled with paddy field soil. Then seeds of barnyard grass, smallflower, bulrush, monochoria and broad-leaved weeds (common false pimpernel, Indian toothcup, long stemmed watenvort, Ammannia

multiflora Roxb., Dopatrium junceum Hammilt etc.) were sown and water was poured to a depth of about 2-3 cm.

5 days after the paddy rice transplantation a solution of each active compound prepared according to the aforementioned preparation method was applied to the surface of the water. The herbicidal effect was examined on the day after 3 weeks from the treatment during which period the water depth of 3 cm was maintained.

The herbicidal effect was rated as 100% in the case of complete death and as 0% in the case of no herbicidal effect.

As a result, the compounds of the present invention No. 27,30,32 and 36 showed at the application rate of 0.25 kg/ha of active compound a sufficient herbicidal effect against paddy field weeds and showed safety to the transplanted paddy rice.

Formulation Example 1 (Granule) To a mixture of the compound No. 36 of the present invention (10 parts), bentonite (montmorillonite) (30 parts), talc (58 parts) and ligninsulphonate salt (2 parts), water (25 parts) is added. The mixture is well kneaded, made in granules of 10-40 mesh by extrusion granulator and dried at 40-50°C to obtain a granule.

Formulation Example 2 (Granule) Clay mineral particles having particle size distribution of 0.2-2 mm (95 parts) are put in a rotary mixer. While rotating it, the compound No. 27 of the present invention (5 parts) is sprayed together with a liquid diluent into the mixer wetted uniformly and dried at 40-50°C to obtain a granule.

Formulation Example 3 (Emulsifiable concentrate) The compound No. 32 of the present invention (30 parts), xylene (5 parts), poly- oxyethylenealkyl phenyl ether (8 parts) and calcium alkylbenzenesulfonate (7 parts) are mixed and stirred to obtain an emulsion.

Formulation Example 4 (Wettable powder) The compound No. 30 of the present invention (15 parts), a mixture of white carbon (hydrous amorphous silicon oxide fine powders) and powder clay (1: 5) (80 parts), sodium alkylbenzenesulfonate (2 parts) and sodium alkylnaphthalenesulfonate- formalin-polymer (3 parts) are mixed in powder form and made into a wettable powder.

Formulation Example 5 (Water-dispersible granule) The compound No. 36 of the present invention (20 parts), sodium ligninsulfonate (30 parts), bentonite (15 parts) and calcined diatomaceous earth powder (35 parts) are well mixed, added with water, extruded using a 0.3 mm screen and dried to obtain a water-dispersible granules.