Herbicidal 4-cyanophenylimino heterocycles of the formula ##STR1## in which R.sup.1 represents hydrogen or halogen, PA1 R.sup.2 represents halogen, cyano, hydroxyl, amini, X--R.sup.3, --N(R.sup.4)--CO--R.sup.5 or --N(R.sup.4)--SO.sub.2 R.sup.5, PA1 X represents oxygen, sulphur or a single bond, PA1 A represents alkanediyl or alkenediyl each of which is optionally substituted, PA1 E represents nitrogen or carbon, and PA1 G represents nitrogen or represents carbon which is bonded to hydrogen or alkyl via an exo single bond or to oxygen or sulphur via an exo double bond, with some exceptions.

Preperations examples: 
EXAMPLE 1 
##STR1341## 
26 ml (0.05 mol) of a 20% solution of phosgene in toluene are added 
dropwise, at 20.degree. C., to a solution of 9.7 g (0.03 mol) of 
1-N-(4-cyano-2-fluoro-5-i-propoxyphenyl)!-tetrahydro-(2H)-pyridazine-thio 
carboxamide in 150 ml of dichloromethane. The reaction mixture is stirred 
at 20.degree. C. for 3 hours and then added to about the same quantity of 
ice water. The organic phase is separated off, dried with magnesium 
sulphate and filtered. The filtrate is concentrated in a water suction 
vacuum and the residue is purified by column chromatography (silica gel, 
dichloromethane). 
1.4 g (13% of theory) of 
9-(4-cyano-2-fluoro-5-isopropoxy-phenyl-imino)-8-thia-1,6-diazabiazabicycl 
o4.3.0!-nonan-7-one are obtained with a melting point of 108.degree. C. 
EXAMPLE 2 
##STR1342## 
A solution of 3.2 g (0.08 mol) of sodium hydroxide in 10 ml of water is 
added, at 0.degree. C., to a mixture of 10.8 g (0.08 mol) of 
2-iminopiperidine hydrochloride and 100 ml of dichloromethane. The mixture 
is then stirred for one hour, after which a solution of 15.7 g (0.08 mol) 
of 4-cyano-2,5-difluorophenyl isothiocyanate in 150 ml of dichloromethane 
is added dropwise at from 0.degree. C. to 5.degree. C. The mixture is then 
stirred at room temperature for three hours. Subsequently, the reaction 
mixture is cooled down to -20.degree. C. and 12.8 g (0.08 mol) of bromine 
in 40 ml of dichloromethane are added to it. This mixture is then stirred 
for three hours, after which the solid is filtered off and the filtrate is 
washed successively with sodium hydrogencarbonate solution and water. The 
organic phase is dried over magnesium sulphate and freed of solvent in 
vacuo. The remaining solid is recrystallized from a little acetonitrile. 
3.1 g (13% of theory) of 
9-(4-cyano-2,5-difluoro-phenylimino)-8-thia-1,7-diazabicyclo4.3.0!non-6-e 
ne are obtained with a melting point of 137.degree. C. 
The compounds of the formula (I) listed in Table 2 below, for example, can 
also be prepared in analogy with Examples 1 and 2 and in correspondence 
with the general description of the preparation processes according to the 
invention. 
TABLE 2 
__________________________________________________________________________ 
Examples of compounds of the formula (I) 
Melting 
Ex. point 
No. 
R.sup.1 
R.sup.2 
A E G (.degree.C.) 
__________________________________________________________________________ 
3 F NHSO.sub.2 CH.sub.3 
(CH.sub.2).sub.4 
C N 
4 F OCH(CH.sub.3).sub.2 
(CH.sub.2).sub.4 
C N 
5 F NHSO.sub.2 C.sub.2 H.sub.5 
(CH.sub.2).sub.4 
C N 
6 F OCH(CH.sub.3).sub.2 
CH.sub.2(CH.sub.3).sub.2CH.sub.2 
C N 
7 F F CH.sub.2CH.sub.2CHCH 
N 
##STR1343## 
85 
8 F NHSO.sub.2 C.sub.3 H.sub.7 
(CH.sub.2).sub.4 
C N 140 
9 F F (CH.sub.2).sub.4 
C N 200 
10 F OC.sub.2 H.sub.5 
(CH.sub.2).sub.4 
C N 194 
11 F OC.sub.2 H.sub.5 
CH.sub.2CH.sub.2CHCH 
N 
##STR1344## 
135 
12 F 
##STR1345## 
CH.sub.2CH.sub.2CHCH 
N 
##STR1346## 
(amorph) 
13 F NHSO.sub.2 C.sub.2 H.sub.5 
(CH.sub.2).sub.4 
N 
##STR1347## 
174 
14 F NHSO.sub.2 CH.sub.3 
(CH.sub.2).sub.4 
N 
##STR1348## 
215 
15 F NHSO.sub.2 C.sub.3 H.sub.7 
(CH.sub.2).sub.4 
N 
##STR1349## 
176 
16 F OCH(CH.sub.3).sub.2 
(CH.sub.2).sub.4 
N 
##STR1350## 
106 
__________________________________________________________________________ 
Starting Compounds of the Formula (III) 
EXAMPLE (III-1) 
##STR1351## 
8.0 g (34 mmol) of 4-cyano-2-fluoro-5-isopropoxy-phenyl isothiocyanate are 
added, at 20.degree. C. and while stirring, to a solution of 2.9 g (34 
mmol) of hexahydropyridazine in 40 ml of toluene. The reaction mixture is 
stirred at 20.degree. C. for 16 hours and subsequently concentrated in a 
water suction vacuum. 
10.3 g (94% of theory) of 
1-N-(4-cyano-2-fluoro-5-isopropoxy-phenyl)!-tetrahydro-(2H)-pyridazine-th 
io-carboxamide are obtained as an oily residue which gradually solidifies 
in crystalline form. 
Melting point: 42.degree. C. 
TABLE 3 
__________________________________________________________________________ 
Example of compounds of the formula (III) 
Ex. No. 
R.sup.1 
R.sup.1 A Melting point (.degree.C.) 
__________________________________________________________________________ 
III-2 
F F --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.dbd. 
126 
III-3 
F OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 
--CH.sub.2 --CH.sub.2 --CH.dbd.CH-- 
58 
III-4 
F NHSO.sub.2 CH.sub.3 
--(CH.sub.2).sub.4 -- 
III-5 
F OCH(CH.sub.3).sub.2 
--CH.sub.2 --CH.sub.2 --CH.dbd.CH-- 
147 
__________________________________________________________________________ 
Starting Compounds of the Formula (VIII) 
EXAMPLE (VIII-1) 
##STR1352## 
7.8 g (0.04 mol) of 4-cyano-2-fluoro-5-isopropoxy-aniline in 25 ml of 
dichloromethane are added, at about 30.degree. C. and while stirring, to a 
mixture consisting of 6 g (0.06 mol) of calcium carbonate, 30 ml of water, 
6.9 g (0.06 mol) of thiophosgene and 30 ml of dichloromethane. The 
reaction mixture is stirred at 30.degree. C. to 35.degree. C. for about 18 
hours. After filtration, the organic phase is then separated off, dried 
with magnesium sulphate and filtered. The solvent is carefully distilled 
off from the filtrate in a water suction vacuum. 
8.4 g (89% of theory) of 4-cyano-2-fluoro-5-isopropoxyphenyl isothiocyanate 
are obtained as an oily residue which gradually solidifies in crystalline 
form. 
Melting point: 73.degree. C. 
TABLE 4 
______________________________________ 
Examples of the compounds of the formula (VIII) 
Melting 
Example No. 
R.sup.1 R.sup.2 point (.degree.C.) 
______________________________________ 
(VIII-2) F F 37 
(VIII-3) F NHSO.sub.2 CH.sub.3 
166 
______________________________________ 
Starting Compounds of the Formula (X): 
EXAMPLE X-1 
##STR1353## 
A mixture consisting of 92.4 g (0.6 mol) of 4-cyano-2,5difluoro-aniline, 60 
g (0.60 mol) of methanesulphonamide, 166 g of potassium carbonate and 80 
ml of N-methylpyrrolidone is heated at 180.degree. C. for 10 hours. After 
having been cooled down, the mixture is stirred into 5 litres of water and 
the resulting solution is washed twice with 400 ml of ethyl acetate on 
each occasion. The aqueous phase is then overlaid with 300 ml of ethyl 
acetate and acidified with 10% hydrochloric acid. The product, which 
arises in crystalline form, is then isolated by filtering off with 
suction. 
70 g (51% of theory) of 
N-(5-amino-2-cyano-4-fluorophenyl)-methanesulphonamide are obtained with a 
melting point of 238.degree. C. 
TABLE 5 
______________________________________ 
Examples of the compounds of the formula (X) 
Example No. 
R.sup.1 
R.sup.2 Melting point (.degree.C.) 
______________________________________ 
X-2 F NHSO.sub.2 C.sub.2 H.sub.5 
X-3 H NHSO.sub.2 CH.sub.3 
X-4 F NHSO.sub.2 C.sub.3 H.sub.7 -n 
X-5 F NHSO.sub.2 C.sub.3 H.sub.7 -iso 
X-6 F 
##STR1354## 
X-7 F 
##STR1355## 
X-8 H NHSO.sub.2 C.sub.2 H.sub.5 
X-9 Cl NHSO.sub.2 CH.sub.3 
X-10 Cl NHSO.sub.2 C.sub.2 H.sub.5 
______________________________________ 
Application Examples 
EXAMPLE A 
Post-emergence test 
Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of 
alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent, the stated 
amount of emulsifier is added and the concentrate is diluted with water to 
the desired concentration. 
Test plants which have a height of 5-15 cm are sprayed with the preparation 
of the active compound in such a way as to apply the particular amounts of 
active compound desired per unit area. After three weeks, the degree of 
damage to the plants is rated in % damage in comparison to the development 
of the untreated control. 
The figures denote: 
0%=no action (like untreated control) 
100%=total destruction 
When used in a quantity of 15 g/ha, the compound in accordance with 
Preparation Example 1, for example, exhibits a strong effect in this test 
against weeds such as Abutilon (100%), Amaranthus (80%), Chenopodium 
(95%), Ipomoea (100%) and Veronica (85%), while being very well tolerated 
by cultivated plants, such as, for example, barley (0%). 
EXAMPLE B 
Pre-emergence test 
Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of 
alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent, the stated 
amount of emulsifier is added and the concentrate is diluted with water to 
the desired concentration. 
Seeds of the test plants are sown in normal soil and, after 24 hours, 
watered with the preparation of the active compound. It is expedient to 
keep constant the amount of water per unit area. The concentration of the 
active compound in the preparation is of no importance, only the amount of 
active compound applied per unit area being decisive. 
After three weeks, the degree of damage to the plants is rated in % damage 
in comparison to the development of the untreated control. 
The figures denote: 
0%=no action (like untreated control) 
100%=total destruction 
When used in a quantity of 60 g/ha, the compound in accordance with 
Preparation Example 1, for example, exhibits a strong effect in this test 
against weeds such as Aeopecurus (90%), Digiteria (95%), Abutilon 100%), 
Chenopodium 100%), Matricaria (100%) and Dinapis (80%), while being very 
well tolerated by cultivated plants, such as, for example, barley (0%). 
It will be understood that the specification and examples are illustrative 
but not limitative of the present invention and that other embodiments 
within the spirit and scope of the invention will suggest themselves to 
those skilled in the art.