Triazine derivatives, and herbicides containing the derivatives as the effective component

A triazine derivative represented by the general formula: ##STR1## or the general formula: ##STR2## (wherein X.sup.1 represents a hydrogen atom, a halogen atom an alkyl group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms, Z represents an oxygen atom or a sulfur atom, R.sup.1 represents an alkyl group having 1 to 4 carbon atom, and R.sup.2 represents a halogen atom, an alkylthio group having 1 to 4 carbon atoms, or an alkoxyl group having 1 to 4 carbon atoms). This invention also provides a process for efficiently preparing said triazine derivative and a herbicide containing said triazine derivative as a herbicidally effective component.

FIELD OF THE INVENTION 
The present invention relates to novel triazine derivatives, a process for 
preparing the triazine derivatives, and herbicides containing the 
derivatives as the herbicidally effective component. 
BACKGROUND OF THE INVENTION 
Various triazine-based herbicides have heretofore been known. For example, 
2-methylthio-4,6-bis(alkylamino)-s-triazine derivatives are known to be 
effective herbicides having a high weed control activity. However, the 
effect of 2-methylthio-4,6-bis(ethylamino)-s-triazine, for example, 
greatly varies with conditions such as the type of soil and temperature. 
In more detail, when used in a mild district, it causes phytotoxicity 
(injury) even in the commonly used amount, and in a cold district, its 
effect is exhibited only insufficiently. Thus 
2-methylthio-4,6-bis(ethylamino)-s-triazine has a disadvantage in that it 
can be applied as a herbicide only in a limited district. 
The present invention is intended to overcome the above problems and an 
object of the present invention is to provide a process for preparing a 
novel herbicide which can exhibit its herbicidal activity nearly equal 
under various soil and temperature conditions, and also can exhibit its 
herbicidal activity against various annual weeds and perennial weeds while 
causing no injury against paddy rice plants and furthermore causing no 
injury against upland field crops such as corn, oats, wheat, barley and 
grain sorghum. 
As a result of extensive investigations, it has been found that the above 
objects can be attained by using specified triazine derivatives having a 
benzofuranyl or thianaphthenyl group, or a dihydrobenzofuranyl or 
dihydrothianaphthenyl group. 
SUMMARY OF THE INVENTION 
The present invention relates to a triazine derivative represented by the 
general formula (I): 
##STR3## 
or the general formula (II): 
##STR4## 
(wherein X.sup.1 represents a hydrogen atom, a halogen atom, an alkyl 
group having 1 to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon 
atoms, Z represents an oxygen atom or a sulfur atom, R.sup.1 represents an 
alkyl group having 1 to 4 carbon atoms, and R.sup.2 represents a halogen 
atom, an alkylthio group having 1 to 4 carbon atoms or an alkoxyl group 
having 1 to 4 carbon atoms). The present invention also relates to a 
process for preparing the triazine derivative represented by the general 
formula (I) or (II). These triazine derivatives can be prepared by the 
following six methods of the present invention. 
Method 1 
1-Benzofuranylalkylamino or 1-thianaphthenylalkylamine represented by the 
following general formula (III): 
##STR5## 
(wherein X.sup.1, Z and R.sup.1 are the same as defined above) is reacted 
with dihalogenated aminotriazine represented by the general formula (IV): 
##STR6## 
(wherein X.sup.2 and X.sup.3 each represent a halogen atom) to prepare a 
triazine derivative (halogen-containing triazine derivative) represented 
by the general formula (I'): 
##STR7## 
(wherein X.sup.1, X.sub.2, Z and R.sup.1 are the same as defined above). 
Method 2 
1-Dihydrobenzofuranylalkylamine or 1-dihydrothianaphthenylalkylamine 
represented by the general formula (III'): 
##STR8## 
(wherein X.sup.1, Z and R.sup.1 are the same as defined above) is reacted 
with dihalogenated aminotriazine represented by the above general formula 
(IV) to prepare a triazine derivative (halogen-containing triazine 
derivative) represented by the general formula (II'): 
##STR9## 
(wherein X.sup.1, X.sup.2, Z and R.sup.1 are the same as defined above). 
Method 3 
A halogen-containing triazine derivative represented by the general formula 
(I') is reacted with alkylmercaptan represented by the general formula 
(V): 
EQU R.sup.3 SH 
(wherein R.sup.3 represents an alkyl group having 1 to 4 carbon atoms), or 
alkylmercaptide represented by the general formula (VI): 
EQU (R.sup.3 S).sub.n M 
(wherein M represents an alkali metal or an alkaline earth metal, n 
represents the valence of M, and R.sup.3 is the same as defined above) to 
prepare a triazine derivative (sulfur-containing triazine derivative) 
represented by the general formula (I"): 
##STR10## 
(wherein X.sup.1, Z, R.sup.1 and R.sup.3 are the same as defined above). 
Method 4 
A halogen-containing triazine derivative represented by the general formula 
(II') is reacted with alkylmercaptan represented by the general formula 
(V) or alkylmercaptide represented by the general formula (VI) to prepare 
a triazine derivative (sulfur-containing triazine derivative) represented 
by the general formula (II"): 
##STR11## 
(wherein X.sup.1, Z, R.sup.1 and R.sup.3 are the same as defined above). 
Method 5 
A halogen-containing triazine derivative represented by the general formula 
(I') is reacted with alcohol represented by the general formula (VII): 
EQU R.sup.3 OH 
or alkoxide represented by the general formula (VIII): 
EQU (R.sup.3 O).sub.n M 
(wherein R.sup.3, M and n are the same as defined above) to prepare a 
triazine derivative (oxygen-containing triazine derivative) represented by 
the general formula (I"'): 
##STR12## 
(wherein X.sup.1, Z, R.sup.1 and R.sup.3 are the same as defined above). 
Method 6 
A halogen-containing triazine derivarive represented by the general formula 
(II') is reacted with alcohol represented by the general formula (VII) or 
alkoxide represented by the general formula (VIII) to prepare a triazine 
derivative (oxygen-containing triazine derivative) represented by the 
general formula (II"'): 
##STR13## 
(wherein X.sup.1, Z, R.sup.1 and R.sup.3 are the same as defined above). 
The present invention further relates to a herbicide comprising (i) a 
herbicidal carrier, and (ii) an effective amount of a triazine derivative 
represented by the general formula (I) or (II). 
DETAILED DESCRIPTION OF THE INVENTION 
The symbols used in the general formula (I) are described below in detail. 
X.sup.1 represents a hydrogen atom a halogen atom, an alkyl group having 1 
to 4 carbon atoms or an alkoxyl group having 1 to 4 carbon atoms. 
Typical examples of the halogen atom are a chlorine atom, a bromine atom 
and an iodine atom. Typical examples of the alkyl group are a methyl 
group, an ethyl group, a propyl group, and a butyl group. Typical examples 
of the alkoxyl group are a methoxy group, an ethoxy group, a propoxy group 
and a butoxy group. 
Z represents an oxygen atom or a sulfur atom. 
R.sup.1 represents an alkyl group having 1 to 4 carbon atoms, such as a 
methyl group, an ethyl group, a n-propyl group, an isopropyl group, a 
n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl 
group. 
R.sup.2 represents a halogen atom, an alkylthio group having 1 to 4 carbon 
atoms, or an alkoxyl group having 1 to 4 carbon atoms. Typical examples of 
the halogen atom are a chlorine atom, a bromine atom and an iodine atom. 
Typical examples of the alkylthio group are a methylthio group, an 
ethylthio group, a propylthio group, and a butylthio group. Typical 
examples of the alkoxyl group are a methoxy group, an ethoxy group, a 
propoxy group and a butoxy group. 
The triazine derivatives represented by the general formula (I) can be 
divided into the four groups shown below depending on the type of Z and 
the linking position of the aminoalkyl group 
##STR14## 
to the benzofuranyl or thianaphthenyl group. 
Z=oxygen atom 
Triazine derivatives (triazine derivatives containing a 2-benzofuranyl 
group) represented by the general formula (I-1): 
##STR15## 
Triazine derivatives (triazine derivatives containing a 3-benzofuranyl 
group) represented by the general formula (I-2): 
##STR16## 
Z=sulfur atom 
Triazine derivatives (triazine derivatives containing a 2-benzothiafuranyl 
group (2-benzothiophenyl group or 2-thianaphthenyl group)) represented by 
the general formula (I-3): 
##STR17## 
Triazine derivatives (triazine derivatives containing a 3-benzothiafuranyl 
group (3-benzothiophenyl group or 3-thianaphthenyl group)) represented by 
the general formula (I-4): 
##STR18## 
The compounds represented by the general formula (II) are also triazine 
derivatives (triazine derivatives containing a dihydrobenzofuranyl or 
dihydrobenzothiafuranyl group). The single difference between the triazine 
derivatives of the general formula (I) and the triazine derivatives of the 
general formula (II) is if or not the carbon-carbon double bond in the 2 
and 3-positions of the benzofuranyl or benzothiafuranyl group is 
saturated. Thus, the representative examples of X.sup.1, Z, R.sup.1 and 
R.sup.3 in the general formula (II)are the same as listed in the general 
formula (I). 
The triazine derivatives represented by the general formula (II) can also 
be divided into the four groups shown below depending on the type of Z and 
the linking position of the aminoalkyl group 
##STR19## 
to the benzofuranyl or thianaphthenyl group as in the general formula (I). 
Z=oxygen atom 
Triazine derivatives (triazine derivatives containing a 
2-dihydrobenzofuranyl group) represented by the general formula (II-1): 
##STR20## 
Triazine derivatives (triazine derivatives containing a 
3-dihydrobenzofuranyl group, represented by the general formula (II-2): 
##STR21## 
Z=sulfur atom 
Triazine derivatives (triazine derivatives containing a 
2-dihydrobenzothiafuranyl group (2-dihydrobenzothiophenyl group or 
2-dihydrothianaphthenyl group)) represented by the general formula (II-3): 
##STR22## 
Triazine derivatives (triazine derivatives containing a 
3-dihydrobenzothiafuranyl group (3-dihydrobenzothiophenyl group or 
3-dihydrothianaphthenyl group)) represented by the general formula (II-4): 
##STR23## 
Representative examples of the triazine derivatives represented by the 
general formulae (I-1) to (I-4) and (II-1) to (II-4) according to the 
present invention are 
2-chloro-4-amino-6-[1'-(2'-benzofuranyl)ethylamino)]-s-triazine; 
2-bromo-4-amino-6-[1'-(2'-benzofuranyl)ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-benzofuranyl)-propylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-benzofuranyl)butylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-benzofuranyl)ethylamino]-s-triazine; 
2-ethylthio-4-amino-6-[1'-(2'-benzofuranyl)ethylamino]-s-triazine; 
2-propylthio-4-amino-6-[1'-(2'-benzofuranyl)-ethylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-benzofuranyl)propylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-benzofuranyl)butylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(5'-chlorobenzofuranyl))ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(3'-thianaphthenyl)ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-thianaphthenyl)ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(2',3'-dihydrobenzofuranyl)ethylamino]-s-triazi 
ne; 
2-methylthio-4-amino-6-[1'-(2'-(5'-chlorobenzofuranyl))ethylamin]-s-triazi 
ne; 2-methylthio-4-amino-6-[1'-(3'-thianaphthenyl)ethylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-thianaphthenyl)ethylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-(2',3'-dihydrobenzofuranyl))ethylamino]-s-t 
riazine; 
2-ethylthio-4-amino-6-[1'-(2'-thianaphthenyl)ethylamino]-s-triazine; 
2-methoxy-4-amino-6-[1'-(2'-benzofuranyl)ethylamino]-s-triazine; 
2-methoxy-4-amino- 6-[1'-(2'-benzofuranyl)propylamino]-s-triazine; 
2-methoxy-4-amino-6-[1'-(2'-thianaphthenyl)ethylamino]-s-triazine; 
2-ethoxy-4-amino-6-[1'-(2'-benzofuranyl)ethylamino]-s-triazine; 
2-ethoxy-4-amino-6-[1'-(2'-thianaphthenyl)ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-thianaphthenyl)propylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-thianaphthenyl)butylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(5'-fluorobenzofuranyl)ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(5'-chlorothianaphthenyl))ethylamino]-s-triazin 
e; 
2-chloro-4-amino-6-[1'-(2'-(7'-chlorobenzofuranyl))ethylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-trianaphthenyl)propylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-thianaphthenyl)butylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-(5'-chlorothianaphthenyl))ethylamino]-s-tri 
azine; 
2-methylthio-4-amino-6-[1'-(2'-(5'-fluorobenzofuranyl))ethylamino]-s-triaz 
ine; 
2-methylthio-4-amino-6-[1'-(2'-(7'-chlorobenzofuranyl))ethylamino]-s-triaz 
ine; 
2-ethylthio-4-amino-6-[1'-(2'-(thianaphthenyl))propylamino]-s-triazine; 2- 
ethylthio-4-amino-6-[1'-(2'-(thianaphthenyl))butylamino]-s-triazine; 
2-ethylthio-4-amino-6-[1'-(2'-(5'-chlorothianaphthenyl))ethylamino]-s-tria 
zine; 
2-ethylthio-4-amino-6-[1'-(2'-(5'-fluorobenzofuranyl))ethylamino]-s-triazi 
ne; 2-ethylthio-4-amino-6-[1' 
-(2'-(7'-chlorobenzofuranyl))ethylamino]-s-triazine; 
2-methoxy-4-amino-6-[1'-(2'-thianaphthenyl)propylamino]-s-triazine; 
2-methoxy-4-amino-6-[1'-(2'-thianaphthenyl)butylamino]-s-triazine; 
2-methoxy-4-amino-6-[1'-(2'-(5'-chlorothianaphthenyl))ethylamino]-s-triazi 
ne; 
2-methoxy-4-amino-6-[1'-(2'-(5'-fluorobenzofuranyl))ethylamino]-s-triazine 
; 2-methoxy-4-amino-6-[1'-(2'-(7'-chlorobenzofuranyl))ethylamino]-s-triazin 
e; 2-ethoxy-4-amino-6-[1'-(2'-thianaphthenyl)propylamino]-s-triazine; 
2-ethoxy-4-amino-6-[1'-(2'-thianaphthenyl)butylamino]-s-triazine; 
2-ethoxy-4-amino-6-[1'-(2'-(5'-chlorothianaphthenyl))ethylamino]-s-triazin 
e; 
2-ethoxy-4-amino-6-[1'-(2'-(5'-fluorobenzofuranyl))ethylamino]-s-triazine; 
2-ethoxy-4-amino-6-[1'(2'-(7'-chlorobenzofuranyl))ethylamino]-s-triazine; 
2-methylthio-4-amino-6-[1'-(2'-(5'-methylbenzofuranyl))ethylamino]-s-triaz 
ine; 
2-methylthio-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))ethylamino]-s-triaz 
ine; 
2-methylthio-4-amino-6-[1'-(2'-7'-methylbenzofuranyl))ethylamino]-s-triazi 
ne; 
2-methylthio-4-amino-6-[1'-(2'-(5'-methoxybenzofuranyl))ethylamino]-s-tria 
zine; 
2-methylthio-4-amino-6-[1'-(2'-(6'-methoxybenzofuranyl))ethylamino]-s-tria 
zine; 
2-methylthio-4-amino-6-[1'-(2'-(7'-methoxybenzofuranyl))ethylamino]-s-tria 
zine; 
2-methylthio-4-amino-6-[1'-(2'-(6'-ethylbenzofuranyl))ethylamino]-s-triazi 
ne; 
2-methylthio-4-amino-6-[1'-(2'-(6'-isopropylbenzofuranyl))ethylamino]-s-tr 
iazine; 
2-methylthio-4-amino-6-[1'-(2'-(6'-tert-butylbenzofuranyl))ethylamino]-s-t 
riazine; 
2-methylthio-4-amino-6-[1'-(2'(6'-ethoxybenzofuranyl))ethylamino]-s-triazi 
ne; 
2-methylthio-4-amino-6-[1'-(2'-(6'-isopropoxybenzofuranyl))ethylamino]-s-t 
riazine; 
2-methylthio-4-amino-6-[1'-(2'-(6'-tert-butoxybenzofuranyl))ethylamino]-s- 
triazine; 
2-methylthio-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))propylamino]-s-tria 
zine; 
2-methylthio-4-amino-6-[1'-(2'-(6'-isopropylbenzofuranyl))propylamino]-s-t 
riazine; 
2-ethylthio-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))ethylamino]-s-triazi 
ne; 
2-methoxy-4-amino-6-[1'-(2'-(5'-methylbenzofuranyl))ethylamino]-s-triazine 
; 2-methoxy-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))ethylamino]-s-triazin 
e; 
2-methoxy-4-amino-6-[1'-(2'-7'-methylbenzofuranyl))ethylamino]-s-triazine; 
2-methoxy-4-amino-6-[1'-(2'-(5'-methoxybenzofuranyl))ethylamino]-s-triazin 
e; 
2-methoxy-4-amino-6-[1'-(2'-(6'-methoxybenzofuranyl))ethylamino]-s-triazin 
e; 
2-methoxy-4-amino-6-[1'-(2'-(7'-methoxybenzofuranyl))ethylamino]-s-triazin 
e; 
2-methoxy-4-amino-6-[1'-(2'-(6'-ethylbenzofuranyl))ethylamino]-s-triazine; 
2-methoxy-4-amino-6-[1'-(2'-(6'-isopropylbenzofuranyl))ethylamino]-s-triaz 
ine; 
2-methoxy-4-amino-6-[1'-(2'-(6'-tert-butylbenzofuranyl))ethylamino-s-triaz 
ine; 
2-methoxy-4-amino-6-[1'-(2'-(6'-ethoxybenzofuranyl))ethylamino]-s-triazine 
; 2-methoxy-4-amino-6-[1'-(2'-(6'-isopropoxybenzofuranyl))ethylamino]-s-tri 
azine; 
2-methoxy-4-amino-6-[1'-(2'-(6'-tert-butoxybenzofuranyl))ethylamino]-s-tri 
azine; 
2-methoxy-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))propylamino]-s-triazin 
e; 
2-methoxy-4-amino-6-[1'-(2'-(6'-isopropylbenzofuranyl))propylamino]-s-tria 
zine; 
2-ethoxy-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(5'-methylbenzofuranyl))ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(7'-methylbenzofuranyl))ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(5'-methoxybenzofuranyl))ethylamino]-s-triazine 
; 2-chloro-4-amino-6-[1'-(2'-(6'-methoxybenzofuranyl))ethylamino]-s-triazin 
e; 
2-chloro-4-amino-6-[1'-(2'-(7'-methoxybenzofuranyl))ethylamino]-s-triazine 
; 2-chloro-4-amino-6-[1'-(2'-(6'-ethylbenzofuranyl))ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(6'-isopropylbenzofuranyl))ethylamino]-s-triazi 
ne; 
2-chloro-4-amino-6-[1'-(2'-(6'-tert-butylbenzofuranyl))ethylamino]-s-triaz 
ine; 
2-chloro-4-amino-6-[1'-(2'-(6'-ethoxybenzofuranyl))ethylamino]-s-triazine; 
2-chloro-4-amino-6-[1'-(2'-(6'-isopropoxybenzofuranyl))ethylamino]-s-triaz 
ine; 
2-chloro-4-amino-6-[1'-(2'-(6'-tert-butoxybenzofuranyl))ethylamino]-s-tria 
zine; 
2-chloro-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))propylamino]-s-triazine 
; 2-chloro-4-amino-6-[1'-(2'-(6'-isopropylbenzofuranyl))propylamino]-s-tria 
zine; 
2-bromo-4-amino-6-[1'-(2'-(6'-methylbenzofuranyl))ethylamino]-s-triazine. 
Triazine derivatives represented by the general formula (I) can be prepared 
by various methods. In particular, Methods 1, 3 and 5 of the present 
invention as described above permit efficient preparation of the triazine 
derivatives. 
The triazine derivatives represented by the general formula (I) of the 
present invention can be divided into the triazine derivatives 
(halogen-containing triazine derivatives) represented by the general 
formula (I'), the triazine derivatives (sulfur-containing triazine 
derivatives) represented by the general formula (I"), and triazine 
derivatives (oxygen-containing triazine derivatives) represented by the 
general formula (I"') depending on the substituent linked to the triazine 
ring. 
The halogen-containing triazine derivatives represented by the general 
formula (I') can be efficiently prepared by Method 1 of the present 
invention. In accordance with Method 1, 1-benzofuranylalkylamine or 
1-thianaphthenylalkylamine represented by the general formula (III) is 
reacted with dihalogenated aminotriazine represented by the general 
formula (IV) to form the desired halogen-containing triazine derivative of 
the general formula (I'). 
Representative examples of the 1-benzofuranylalkylamine or 
1-thianaphthenylalkylamine represented by the general formula (III) are 
1-(2'-benzofuranyl)ethylamine, 1-(2'-benzofuranyl)propylamine, 
1-(2'-benzofuranyl)butylamine, 1-(2'-(5'-chlorobenzofuranyl))ethylamine, 
1-(2'-(5'-fluorobenzofuranyl))ethylamine, 
1-(2'-7'-chlorobenzofuranyl))ethylamine, 1-(2'-thianaphthenyl)ethylamine, 
1-(2'-thianaphthenyl)propylamine, 1(2'-thianaphthenyl)butylamine, 
1-(3'-thianaphthenyl)ethylamine, 1-(3'-thianaphthenyl)propylamine, 
1-(3'-thianaphthenyl)butylamine, 
1-[2'-(5'-chlorothianaphthenyl)]ethylamine, 
1-]2'-(5'-chlorothianaphthenyl)]propylamine, 
1-[2'-(5'-chlorothianaphthenyl)]butylamine, 
1-[2'-(5'-methylbenzofuranyl)]ethylamine; 
1-[2'-(6'-methylbenzofuranyl)]ethylamine; 
1-[2'-(7'-methylbenzofuranyl)]ethylamine; 
1[2'-(5'-methoxybenzofuranyl)]ethylamine; 
1-[2'-(6'-methoxybenzofuranyl)]ethylamine; 
1-[2'-(7'-methoxybenzofuranyl)]ethylamine; 
1-[2'-(6'-ethylbenzofuranyl)]ethylamine; 
1-[2'-(6'-isopropylbenzofuranyl)]ethylamine; 
1-[2'-(6'-tert-butylbenzofuranyl)]ethylamine; 
1-[2'-(6'-ethoxybenzofuranyl)]ethylamine; 
1-[2'-(6'-isopropoxybenzofuranyl)]ethylamine; 
1-[2'-(6'-tert-butoxybenzofuranyl)]ethylamine; 
1-[2'-(6'-methylbenzofuranyl)]propylamine; 
1-[2'-(6'-isopropylbenzofuranyl)]propylamine. This 
1-benzofuranylalkylamine or 1-thianaphthenylalkylamine can be prepared by 
various methods. In accordance with one of the methods, it can be prepared 
as follows. 
Benzofuranylalkylketone or thianaphthenylalkylketone (e.g., 
2-benzofuranylmethylketone and 2-thianaphthenylmethylketone) represented 
by the general formula (IX): 
##STR24## 
(wherein X.sup.1, Z and R.sup.1 are the same as defined above) is reacted 
with hydroxylamine, for example, to form benzofuranylalkylketoneoxime or 
thianaphthenylalkylketoneoxime (e.g., 2-benzofuranylmethylketoneoxime and 
2-thianaphthenylmethylketoneoxime) represented by the general formula (X): 
##STR25## 
(wherein X.sup.1, Z and R.sup.1 are the same as defined above), and the 
benzofuranylalkylketoneoxime or thianaphthenylalkylketoneoxime thus formed 
is reduced with a reducing agent or is subjected to catalytic reduction to 
form the 1-benzofuranylalkylamine or 1-thianaphthenylalkylamine 
represented by the general formula (III). 
Also, by replacing hydroxylamine with ammonium formate in the above 
reaction to form the corresponding formamine derivative and hydrolyzing 
the formamide derivative with concentrated hydrochloric acid or caustic 
alkali, the 1-benzofuranylalkylamine or 1-thianaphthenylalkylamine can be 
obtained. 
The dihalogenated aminotriazine represented by the general formula (IV), 
that is, 2,6-dihalogeno-4-amino-s-triazine includes 
2,6-dichloro-4-amino-s-triazine. This dihalogenated aminotriazine can be 
obtained by reacting cyanuric halide, such as cyanuric chloride, with 
ammonia. 
In accordance with Method 1 of the present invention, as described above, 
the 1-benzofuranylalkylamine or 1-thianaphthenylalkylamine represented by 
the general formula (III) is reacted with the dihalogenated aminotriazine 
represented by the general formula (IV). In this reaction, the compounds 
are used in an equimolar amount, and a solvent is not always needed. 
Solvents which can be used include ketones such as acetone, methyl ethyl 
ketone, and cyclohexanone, aliphatic hydrocarbons such as n-hexane, and 
n-heptane, cyclic hydrocarbons such as benzene, decalin and 
alkylnaphthalene, chlorinated hydrocarbons such as carbon tetrachloride 
and ethylene tetrachloride, and ethers such as tetrahydrofuran and 
dioxane. It is effective to add a deacidification agent 
(dehydrohalogenation agent) such as sodium hydrogencarbonate and 
triethylamine to the reaction system. The reaction temperature is not 
critical; the reaction proceeds satisfactorily at various temperatures 
from high temperatures to low temperatures, more specifically 10.degree. 
to 100.degree. C. 
In accordance with Method 1 of the present invention, the 
halogen-containing triazine derivative represented by the general formula 
(I') is prepared in high purity and high yield. 
In accordance with Method 3 of the present invention, the 
halogen-containing triazine derivative represented by the general formula 
(I') is first prepared by Method 1 of the present invention, and then the 
above triazine derivative is reacted with alkylmercaptan represented by 
the general formula (V) or alkylmercaptide represented by the general 
formula (VI) to form the desired sulfur-containing triazine derivative 
represented by the general formula (I"). 
Examples of the alkylmercaptan are methylmercaptan, ethylmercaptan and 
propylmercaptan. Examples of the alkylmercaptide are sodium 
methylmercaptide (CH.sub.3 SNa), potassium methylmercaptide (CH.sub.3 SK), 
magnesium methylmercaptide ((CH.sub.3 S).sub.2 Mg), sodium ethylmercaptide 
(C.sub.2 H.sub.5 SNa), potassium ethylmercaptide (C.sub.2 H.sub.5 SK) and 
magnesium ethylmercaptide ((C.sub.2 H.sub.5 S).sub.2 Mg). In a case where 
alkylmercaptan is used in Method 3, it is preferred that the reaction be 
carried out in the presence of caustic alkali, such as sodium hydroxide 
and potassium hydroxide. 
In Method 3 of the present invention, the mixing ratio of the 
halogen-containing triazine derivative represented by the general formula 
(I') and the alkylmercaptan or alkylmercaptide is not critical; usually 
they are used in such an amount that the molar ratio of the 
halogen-containing triazine derivative of the general formula (I') and the 
alkylmercaptan or alkylmercaptide is nearly equal. This reaction can be 
carried out in the absence or the presence of a solvent, such as isopropyl 
alcohol, dimethylformamide, toluene, xylene, acetone and benzene. The 
reaction temperature is not critical; the reaction proceeds satisfactorily 
at various temperatures from high temperatures to low temperatures, more 
specifically 10.degree. to 150.degree. C. 
After the reaction is completed, the reaction mixture is cooled, and the 
solid material thus obtained is washed and further purified by 
chromatography using a silica gel column, whereupon the sulfur-containing 
triazine derivative represented by the general formula (I") is obtained in 
high purity and high yield. 
In accordance with Method 5 of the present invention, the 
halogen-containing triazine derivative represented by the general formula 
(I') is first prepared by Method 1 of the present invention, and then the 
halogen-containing triazine derivative thus obtained is reacted with the 
alcohol represented by the general formula (VII) or alkoxide represented 
by the general formula (VIII) to form the desired oxygen-containing 
triazine derivative represented by the general formula (I"'). 
Examples of the alcohol are methyl alcohol, ethyl alcohol and propyl 
alcohol. Examples of the alkoxide are sodium methoxide (CH.sub.3 ONa), 
potassium methoxide (CH.sub.3 OK), calcium methoxide ((CH.sub.3 O).sub.2 
Ca), sodium ethoxide (C.sub.2 H.sub.5 ONa), potassium ethoxide (C.sub.2 
H.sub.5 OK), and calcium ethoxide ((C.sub.2 H.sub.5 O).sub.2 Ca). In a 
case where alcohol is used in Method 5, it is preferred that the reaction 
be carried out in the presence of alkali metal, such as metallic sodium 
and metallic potassium. 
In Method 5 of the present invention, the mixing ratio of the 
halogen-containing triazine derivative of the general formula (I') and the 
alcohol or alkoxide is not critical; usually they are used in such an 
amount that the molar ratio of the halogen-containing triazine derivative 
of the general formula (I') to the alcohol or alkoxide is nearly equal. 
The reaction can be carried out in the absence or the presence of a 
solvent. Preferred examples of solvents which can be used are alcohols 
such as methyl alcohol, ethyl alcohol and isopropyl alcohol. The reaction 
temperature is not critical; the reaction proceeds satisfactorily at 
various temperatures from high temperatures to low temperatures, more 
specifically 10.degree. to 110.degree. C. 
After the reaction is completed, the reaction mixture is cooled, and the 
solid material thus obtained is washed, purified by chromatography using a 
silica gel column, and dried, whereupon the oxygen-containing triazine 
derivative represented by the general formula (I") can be obtained in high 
purity and high yield. 
The triazine derivative (triazine derivative containing a 
dihydrobenzofuranyl or dihydrobenzothiafuranyl group) represented by the 
general formula (II) can also be prepared by various methods as in the 
preparation of the triazine derivative of the general formula (I). In 
particular, Methods 2, 4 and 6 of the present invention as described above 
permit efficient preparation of the triazine derivatives. 
The triazine derivatives represented by the general formula (II) of the 
present invention can be divided into the triazine derivative 
(halogen-containing triazine derivative) represented by the general 
formula (II'), the triazine derivative (sulfur-containing triazine 
derivative) represented by the general formula (II") and the triazine 
derivative (oxygen-containing triazine derivative) represented by the 
general formula (II"') depending on the type of the substituent linked to 
the triazine ring. 
The halogen-containing triazine derivative represented by the general 
formula (II') can be prepared efficiently by Method 2 of the present 
invention. In accordance with Method 2 of the present invention, the 
1-dihydrobenzofuranylalkylamine or 1-dihydrothianaphthenylalkylamine 
represented by the general formula (III') is reacted with the 
dihalogenated aminotriazine represented by the general formula (IV) to 
form the desired halogen-containing triazine derivative represented by the 
general formula (II'). 
Examples of the 1-dihydrobenzofuranylalkylamine or 
1-dihydrothianaphthenylalkylamine represented by the general formula 
(III') are 1-[2'-(2',3'-dihydrobenzofuranyl)]ethylamine, 
1-[2'-(2',3'-dihydrobenzofuranyl)]propylamine, 
1-[2'-(2',3'-dihydrobenzofuranyl)]butylamine, 
1-[2'-(2',3'-dihydrothianaphthenyl)]ethylamine, 
1-[2'-(2',3'-dihydrothianaphthenyl)]propylamine, 
1-[2'-(2',3'-dihydrothianaphthenyl)]butylamine, 
1-[3'-(2',3'-dihydrothianaphthenyl)]ethylamine, 
1-[3'-(2',3'-dihydrothianaphthenyl)]propylamine, 
1-[3'-(2',3'-dihydrothianaphthenyl)]butylamine, 
1-[2'-(5'-chloro-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(5'-fluoro-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(7'-chloro-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(5'-methyl-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-methyl-(2',3' -dihydrobenzofuranyl))]ethylamine, 
1-[2'-(7'-methyl-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(5'-methoxy-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-methoxy-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(7'-methoxy-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-ethyl-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-isopropyl-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-tert-butyl-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-ethoxy-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-tert-butoxy-(2',3'-dihydrobenzofuranyl))]ethylamine, 
1-[2'-(6'-methyl-(2',3'-dihydrobenzofuranyl))]propylamine, 
1-[2'-(6'-isopropyl-(2',3'-dihydrobenzofuranyl))]propylamine. 
In preparing the above 1-dihydrobenzofuranylalkylamine or 
1-dihydrothianaphthenylalkylamine, various methods may be employed. An 
example of these methods is a method of catalytically reducing the 
1-benzofuranylalkylamine or 1-thianaphthenylalkylamine represented by the 
general formula (III) as described above. 
Method 2 of the present invention can be carried out in the same manner as 
in Method 1 as described above except that the 
1-dihydrobenzofuranylalkylamine or 1-dihydrothianaphthenylalkylamine of 
the general formula (III') is used in place of the 
1-benzofuranylalkylamine or 1-thianaphthenylalkylamine of the general 
formula (III). 
In accordance with Method 2, the halogen-containing triazine derivative 
represented by the general formula (II') can be obtained in high purity 
and high yield. 
In accordance with Method 4 of the present invention, the 
halogen-containing triazine derivatives represented by the general formula 
(II') is prepared according to Method 2 of the present invention as 
described above, and thereafter the triazine derivative of the general 
formula (II') is reacted with the alkylmercaptan represented by the 
general formula (V) or the alkylmercaptide represented by the general 
formula (VI) to form the desired sulfur-containing triazine derivative 
represented by the general formula (III'). 
Method 4 can be carried out in the same manner as in Method 3 as described 
above. 
In accordance with Method 6 of the present invention, the 
halogen-containing triazine derivative represented by the general formula 
(II') is prepared according to Method 2 of the present invention as 
described above and, thereafter, the triazine derivative of the general 
formula (II') is reacted with the alcohol represented by the general 
formula (VII) or the alkoxide represented by the general formula (VIII) to 
form the desired oxygen-containing triazine derivative represented by the 
general formula (II"'). 
Method 6 can be carried out in the same manner as in Method 5 as described 
above. 
The halogen-containing triazine derivative represented by the general 
formula (I') which is prepared by Method 1 of the present invention, the 
sulfur-containing triazine derivative represented by the general formula 
(I") which is prepared by Method 3 of the present invention, and the 
oxygen-containing triazine derivative represented by the general formula 
(I"') which is prepared by Method 5 of the present invention are all 
included in the triazine derivative represented by the general formula (I) 
of the present invention and are all novel compounds. 
The halogen-containing triazine represented by the general formula (II') 
which is prepared by Method 2 of the present invention, the 
sulfur-containing triazine deirvative represented by the general formula 
(II") which is prepared by Method 4 of the present invention, and the 
oxygen-containing triazine derivative represented by the general formula 
(I"') which is prepared by Method 6 of the present invention are all 
included in the triazine derivative represented by the general formula 
(II) of the present invention and are all novel compounds. 
The triazine derivative represented by the general formula (I) or (II) 
inhibits the germinating and growth of weeds and further exhibits high 
selectivity and, therefore, is suitable for use as a herbicide. Moreover 
the triazine derivatives are excellent herbicidal activity against annual 
broadleaf weeds such as Rotala indica(Willd.)Koehne var. 
uligirosa(Miq.)Koehne, Lindernia pyxidaria L. and Monochoria vaginalis 
Presl var. plantaginea(Roxb.)Solms-Laub., species of Cyperaceae such as 
Cyperus difformis L., and Graminceae such as Echinochloa crus-galli L., as 
well as perennial weeds such as Scirpus juncoides Roxb. var. Hotarui Ohwi, 
Cyperus serotinus Rottb. and Sagittaria pygmaea Miq. which are now 
considered to be difficult to control, without causing phytotoxicity to 
paddy rice plants. 
The triazine derivative represented by the general formula (I) or (II) 
exhibits an excellent herbicidal activity against troublesome weeds such 
as sicklepod (Cassia obtusifolia L), tallmorning glory (Ipomea purpurea 
(L) Roth) and velvet leaf (Abutilon theophrasti Medik) without injuring 
corns, grain sorghums, wheat, barley and oats. 
Herbicides of the present invention comprises (i) a herbicidal carrier, and 
(ii) an effective amount of the triazine derivative of the general formula 
(I) or (II). 
The herbicides of the present invention can be applied in the form of 
compositions such as a wettable powder, an emulsifiable concentrate, dust, 
granule and the like. Such compositions are prepared by mixing the 
triazine derivative of the general formula (I) or (II) as the effective 
component with a liquid carrier such as an organic solvent and the like or 
a solid carrier such as a mineral powder and the like. Addition of a 
surfactant is preferred to impart the properties of ready emulsifying, 
dispersing, spreading and the like to the preparations. 
When the herbicides of this invention are applied in the form of wettable 
powder, the herbicides usually comprise 10-55 parts by weight of the 
triazine derivative as the effective component, 40-88 parts by weight of a 
solid carrier and 2-5 parts by weight of a surfactant. When the herbicides 
are applied in the form of emulsifiable concentrate, the herbicides 
usually comprise 20-50 parts by weight of the triazine derivative as the 
effective component, 35-75 parts by weight of a solvent and 5-15 parts by 
weight of a surfactant. 
When the herbicides are applied in the form of dust, the herbicides usually 
comprise 1-15 parts by weight of the triazine derivative as the effective 
component, 80-97 parts by weight of a solid carrier and 2-5 parts by 
weight of a surfactant. When the herbicides are applied in the form of 
granule, the herbicides usually comprise 0.2-15 parts by weight of the 
triazine derivative as the effective component, 80-97.8 parts by weight of 
a solid carrier and 2-5 parts by weight of a surfactant. 
A mineral powder can be used as the solid carrier described above. The 
mineral powder includes oxide such as diatomaceous earth and slaked lime, 
phosphate such as apatite, sulfate such as gypsum, and silicate such as 
talc, pyrophyllite, clay, kaolin, bentonite, acid clay, white carbon, 
quartz powder and silica powder. 
An organic solvent can be used as the solvent described above. The organic 
solvent includes an aromatic hydrocarbon such as xylene, toluene and 
benzene, a chlorinated hydrocarbon such as o-chlorotoluene, 
trichloromethane and trichloroethylene, an alcohol such as cyclohexanol, 
amylalcohol and ethylene glycol, a ketone such as isophorone, 
cyclohexanone and cyclohexenylcyclohexanone, an ether such as 
butylcellosolve, dimethylether and methylethylether, an ester such as 
isopropyl acetate, benzyl acetate and methyl phthalate, an amide such as 
dimethylformamide, and a mixture thereof. The above surfactant includes 
various kinds of surfactant, that is anion type, cation type, nonion type 
and amphoteric ion type (e.g. amino acid and betaine). 
The novel triazine derivatives of the general formula (I) or (II) of the 
present invention, which are a novel compound, is high weed control 
activity against annual weeds as well as perennial weeds and exhibits high 
selectivity and thus is useful as a herbicide not causing any injury 
against paddy rice plants. Furthermore, when the triazine derivative of 
the general formula (I) or (II) is used as a foliage-applied herbicide for 
upland field crops such as corn, wheat, barley, oats and grain sorghum, it 
is more effective than the conventional foliage-applied herbicide for 
upland field crops. 
In the herbicide of the present invention, as the effective component, 
other herbicidal materials can be used in combination with the triazine 
derivative of the general formula (I) or (II). These other herbicidal 
materials include conventionally used herbicides. Examples of such 
conventionally used herbicides are a pheoxy-based herbicide, a diphenyl 
ether-based herbicide, a triazine-based herbicide, a urea-based herbicide, 
a carbamate-based herbicide, a thiol carbamate-based herbicide, an acid 
anilide-based herbicide, a pyrazole-based herbicide, phosphoric acid-based 
herbicide, a sulfonylurea-based herbicide, and an oxadiazone-based 
herbicide. 
If desired, the herbicide of the present invention can be used in admixture 
with an insecticide, a germicide, a plant growth-regulator, a fertilizer 
and so forth. 
As described above, the triazine derivative of the present invention is a 
novel compound and can be used effectively as a herbicide. In accordance 
with Methods 1 to 6 of the present invention, the triazine derivative of 
the general formula (I) or (II) can be prepared in high purity and high 
yield. The herbicide of the present invention, containing the triazine 
derivative of the general formula (I) or (II) as an effective component is 
more effective and less damages plants than the conventional herbicides 
for rice plants and furthermore has a feature that the herbicidal spectral 
width is broad. In more detail, the herbicide of the present invention is 
excellent herbicidal activity against Echinochloa crus-galli L. and annual 
broadleaf weeds, as well as in killing perennial weeds such as Sagittaria 
pygmaea Miq., Scirpus juncoides Roxb. var. Hotarui Ohwi and Cyperus 
serotinus Rottb. 
Furthermore, even when the herbicide of the present invention is used as a 
herbicide for upland crops, it is more effective against weeds and more 
selective against crops than the conventional farm herbicides. More 
specifically the herbicide of the present invention can be used safely in 
cultivation of corn and grain sorghum, and further is greatly effective 
against troublesome weeds such as sicklepod, tallmorning glory and 
velvetleaf.