Note: Descriptions are shown in the official language in which they were submitted.
s~ :
The present invention ~elates to new 4-benzofuranyl
esters, the preparation of these compounds, their use as herbicides,
and herbicides containing these compounds as active ingredients.
It is known (German Laid-Open Application DOS 1,926,139)
to use 2,3-dihydro-3,3-dime-thyl-2-ethoxybenzofuran-5-yl
methanesulfonate as a herbicide; however, its action is poor.
We have now found that benzofuran-5-yl esters of the
formula
\ " 3
0
oR3
where Rl denotes hydrogen, unsubstituted or chloro- or loweralkoxy-
substituted loweralkyl, loweralkenyl or loweralkynyl, R denotes
loweralkyl, loweralkenyl, loweralkynyl, a metal atom, loweralkyl-
sulfonyl or acyl of the formula
-C-R4
11 ,
O
R4 denoting unsubstituted or chloro-, loweralkoxy- or loweralkyl-
thio-substituted loweralkyl, loweralkenyl or loweralkynyl, .
loweralkylamino, di-loweralkylamino, or unsubstituted or chloro-
substituted loweralkoxy, and R3 denotes hydrogen, unsubstituted
or chloro- or loweralkoxy-substituted loweralkyl, loweralkenyl or
loweralkynyl, or acyl of the formula
O
R5 denoting unsubstituted or chloro-, loweralkoxy, or loweralkyl-
. 30 thio-substituted loweralkyl, loweralkenyl or loweralkynyl, ~.
loweralkylamino, di-loweralkylamino, or unsubstituted or chloro-
.` substituted loweralkoxy, have a herbicidal action which is superior .
to that of prior art herbicides. Furthermore, the new compounds
- 1 - ' .`,'.' '
, ~. .
9'~39
have better selectivity in crop.s such as Gossypium hirsutum, Zea
mays and seta spp. than 2,3-dihydro-3,3-dimethyl-2-ethoxybenzo-
furan-5-yl methanesulfonate.
t
The compounds of the invention may be prepared for
instance by the following methods:
a) Acylation of benzofuran-5-yl aminosulfonates in
accordance with the foLIow~ng eq~ation:
" "
'~:
., . ~
, ~.
,, ' ,' ~ ~"
., . ~ .
::'
.,
.
.... ..
~., i
~. ' -
;' . :
i, ..
,: '
,~ - 2 -
A
~04g53g
OOZ. 30,334
R1 O R~ O
\~ Nso ~ 0CH3 + XCu ~ R~ CV' o ~ H3 ,
R1, R3 and R4 having thef above meanings and X denot;ng for
instance halogen (chloro, bromo) or the radical
-OCR
Tha banzofuran-5-yl aminosulfonates used as starting materials
are known.
b) Acylation of 2-hydroxybenzofuran-5-Yl aminosulfonates in
accordance with tha following equation: ;
R2 0 ~ ~ CH3 + XCR5 ~ 2/ O ~ 13
OH OCR
O
R1, R2 and R5 having the abova meanings and X denoting for
instance halogen (chloro, bromo) or the radical
.~ -oCR5 . ,.
.,~, o .
The benzofuran derivatives used as starting materials may
~-, 10 be preparad as follows:
+ / C~CH-N 3
O
:, ~
- 3 ~
.. .
, , :
1~49539
O.Z. 30,334
HO H C O H O H C
2) ~ Cl; ~ ClS~NHR _ ~ / " ~ C~3
N~
:.','`
3) / N-SO ~ l~ R1 0 ~ H~
.. .. .
4) / N-SO ~ l~ R30H/H ~ \ N-SO ~ 3
OH OR3
Reaction 1) is known from Dutch PUblish~d Application
6,512,311; ~. Prakt. Chem., 4th series, 32, 144, 1966; and
U.S. 3,184,457.
Reactions 2), 3) and 4) are illustrated by the following
l~ experiments.
1 ~xperiment A
! 2,3-dihydro-3,3-dimethyl-2-morpholinobenzofuran-5-yl
meth~laminosulfonate _ _ _
At Oc to 5~C and while stirring, 36 parts (by weight) of
methylaminosulfonyl chloride was added to a solution of 48.8
i parts of 2,3-dihydro-3,3-dimethyl-2-morpholino-5-hydroxybenzo-
furan and 27.3 parts of triethylamine in 130 parts of tetra-
1 hydrofuran. The reaction mixture was stirred for 1 hour at
¦ room temparature and then filtered. The filtrate was concen-
~ ~ 4 ~
, . . . .
!
.. ~
, ~ .
. ~, . .. . . .. ... .. . . . . . .... .. .
1~4'~539 o. z . 30,334
trated in vacuo and the r~sidue di solvad in 250 parts of
methanol. Aftex addition of 100 parts of water and treatment
of tha solution with activated carbon, crystallization was
initiated by cooling. Tha mush Or crystals was suction filtered,
washed with 50 wt~ aqueous methanol and driad in vacuo. The
crude product melted at 125 to 128C. Pure 293-dihydro-3,3-
dimethyl-2-morpholinob~nzofuran-~-yl methylaminosulfonate was
obtainad by recrystallizing a sample from ~0% m2thanol.
Melting point: 129 to 131C.
Experiment 8
- 2,3-dihydro-3,3-dimethyl-Z-hydroxybenzofuran-5-yl methyl-
aminosulfonate
~ At ~0C ar.d while stirring, 6~ parts of 2,3-dihydro-3,3-
; dim~thyl-2-morpholinobenzofuran-5-yl methylaminosulfonata was
added all at onca to a mixture of 133 parts of water and
~ parts of concentratad hydrochloric acid~ The resultant
mixtura was haat2d rapidly to 90 to 95C and kept at this
temperature for 2 minutes, aftar which it was imm~diately cooled
by the addition o~ ic?. Tha ~olution was ex~racted with ether,
~, .
and the ather solution was washed twice with ~ater, dried ~lith
magnesium sulfata and concentrated in vacuo.
,. . . .
The YiSCoUS residue was dis~olved in 100 parts of ether.
60 parts of n-haxana was addad, and 2,3-dihydro-3,3-dimethyl-
2-hydroxybenzofuran-5-yl methylaminosulfonata was obtained in
tha form of crystals upon cooling. Melting point: 111 to 112C.
Tha compou-nd has the followlr.g structural formula:
~ H~CNH-S-0 ~ H~
;.` '~ ~; , ` . :,
, - , .: :
, ~
': ' , . ' .:
~49539 o~zO 30,334
Experiment C
:
2,3-dihydro-3,3-dimethyl~2-methoxybenzofuran-5-yl ~ethylamino-
sulfonate
4 drops of concentrated su~furic acid was added to a
solution of 22.5 parts of 2,3-dihydro-3,3-dimethyl-2-hydroxy- -
benzofuran-5-yl methylaminosulfonate in 200 parts of methano~.
; The mixtura was subsequantly boiled for 30 minutes under ~;
reflux, and then coolad. The mixture was neutralized with `
triethylamine and concentrated to dryness in vacuo. Treatment
of the viscous residue with a mixture of ether and n-hexane
gave cystals of 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-
5-yl methylaminosulfonate; melting point: ~9 to 91C.
The compound has the following structural formula:
H C-N-S-O ~ -3HH3
OCH3
If, in methods a) and b), R4 is alkylamino, the acylating
~-l agent is an isocyanake - the following equation exempli~ies
this for methyl isocyanate:
,
- NS ~ R \ C ~ CH3
O-CNHCH
`i OH o
c) Reaction of benzofuran-5-yl aminosulfonates with an alkyl-
~, sulfonyl or aminosulfonyl halide - the following equation
I demonstrates this for methylsulfonyl chloride:
- 6 -
. ' " .
:`, -.
.
1049S3~
O.Z. 30,334
R1 0 H C O R1 0
/ NSO ~ CH ~ CH3SCl ~ ~ NSO CH3
H ~ O ~ H C O=S=O O ~ H3
oR3 3 OR
~) Action of metal hydroxides, preferably alkali metal and
alkaline earth metal hydroxides, o~ benzofuran-5-yl amino-
sulfonates, as is illustrated by the following equation which
uses sodium hydroxide by way of example:
:,
NSO ~ CcH NSO ~ ~
I H O ~ 3 + NaOH ~ Na O R3
I OR
R1 and R3 having the mea~ings given above.
e) Alkylation of benzofuran-5-yl aminosulfonates with alkenyl
or alkynyl halides. There are used as reactants for instance
the salts prepared under d), as is demonstrated in the
following equation ~or alkyl bromide:
I R1 ~ NO',O H3CCH R1
`i` Na O ~ 33 + BrCH2-CH=CH~ ~ H2C=CH-CH2 Q
R1 and R3 having the meanings given above.
The following examples illustrate the preparation of the
! new compounds.
EXAMPLE 1
~t 15 to 20C and while stirring, 9 parts by weight of
acetyl chloride was added to a solution of 30.1 parts by weight
` - 7 -
,' .
' . ' ::': ,:
.~
.` ''
~049539
o.Z. 3,334
. of 2,3-dihydro-3,3-dimethyl-2-ethoxybanzo~ran-5-yl methyl-
aminosulfonate and 12 parts by weight of triethylamine in 90
. parts by weight of ether. After 1 hour the reaction mixture
was extracted 3 times with water~ The ethereal solution was
~ dried with magnesium sulfate, and left, upon concentration in
~ vacuo, an oily residue of the compound 2,3-dihydro-3,3-d;methyl-
2-ethoxybenzofuran-5-yl-N-methylcarbonyl methylaminosulfonate ~;
; which did not crystallize even after standing for a fairly long
period of time.
10 n25: 1.5402
Analysis and infrared and nmr spectra agree well with the
. following structural formula: ;
~ j ~
!~ H3C H3C
I - N-S0 ~ ~.
" 0~ OC 2H5
~i The following compounds were prepared analogously:
'f',~ 2~3-dihydro-3~3-dim~thyl-2-metho~ybenzofuran-5-yl-N-metpy~
``I carbonyl methylaminosulfonate, n25: 1.50~5 ~;
~ 2,3-dihydro-3,3-dimathyl-2-methoxybenzofuran-5-yl-N-methyl-
::'. carbonyl ethylaminosulfonate ~-
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-ethyl-
I carbonyl methylaminosulfonate
`i~ 20 ?, 3-dihydro-3~3-dimethyl-2-athoxybenzofuran-5-yl-N-ethyl-
carb~nyl methylaminosulfonate
~;I 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-chloro- -
m~thylcarbonyl methylaminosulfonate, n25: 1.5195
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-chloro-
methylcarbonyl methylamino~ulfonate, n25: 1.5140
.. . .
;~ . .
;. :
, . ,
~ .
~049539 o. z . 30,334
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofura~. 5-yl-N-dichloro-
methylcarbonyl methylaminosulfonate, n25: 1.5165
2,3-dihydro-3,3-dimethyl-2 methoxybenzofuran-5-yl-N-chloro-
methylcarbonyl ethylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-methoxy-
carbonyl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2 methoxybenzofuran-5-yl-N-ethoxy-
carbonyl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-iso-
10 propoxycarbonyl methylaminosulfonate --
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methoxy-
carbonyl mathylaminosulfonate, n25: 1.5000
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethoxy-
carbonyl methylaminosulfonate, nD5: 1.4945 --
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-isopropoxy-
carbonyl methylaminosulfonate, n25: 1.4880.
~,
EXAMPLE 2 -
At -~C to -12C and while stirring, 10.3 parts by weight ~-
of acetyl chloride was added to a solution of 28.7 part~ by
wei~ht of 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yl
dimethylaminosulfonate and 14.1 part~ by weight of triethyl-
amine in 110 parts by weight of ether. The mixture was worked ~
up as in Example l,the compound 2,3-d;hydro-3,3-dimethyl-2- ;
. . .
methylcarbonyloxybenzofuran-5-yl dimethylaminosulfonate being
obtained in the form of crystals; melting point: 67 to 68C. ~;~
The compound has the following struc~ural formula:
:: .
H3C ~ H3C
NS0 ~ H3
9 o , .
` 1~495.~9 O.Z. 30,334
The following compounds were prepared analogously:
2,3-dihydro-3,3-dimethyl-2-ethylcarbonyloxybenzofuran-5-yl
dimathylaminosulfonate, m.p. 53 to 54C
2,3-dihydro-3,3-dimethyl-2-chloromethylcarbonyloxybenzofuran-
5-yl dimethylaminosulfonate, m.p. 87 to 88C
2,3-dihydro-3,3-dimethyl-2-chloromethylcarbonyloxybenzofuran-
5-yl diethylaminosulfonate, n25: 1.5078 - `
2,3-dihydro-3,3-dimethyl-2-dichloromethylcarbonyloxybenzo-
furan-5-yl dimethylaminosulfonate
: 10 2,3-dihydro-3,3-dimethyl-2-dichloromethylcarbonyloxybenzofuran-
5-yl diethylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl
dimethylaminosulfonate, m.p. 101 to 102C
2,3-dihydro-3,3-dimethyl-2-ethoxycarbonyloxybenzofuran-5-yl
dimethylaminosulfonate, m.p. 84 to 85C
2,3-dihydro-3,3-dimethyl-2-isopropoxycarbonyloxybenzofuran-5-
yl dimethylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl ~ `
di~thylaminosulfonate, m.p. 95 to 96C.
2,3-dihydro-3,3-dimethyl-2-ethoxycarbonyloxybenzofuran-5-yl
diethylaminosulfonate
2~3-dihYdro-3~3-dimethyl-2-isopropoxycarbonyloxybenzofuran
s-yl die~hylaminosulfonate,
EXAMPLE 3
After the addition of 1 part by weight of triethylamine,
6.9 parts by waight of methyl isocyanate was added at room
t~mperature (20C) to a solution of 28.7 parts by weight of
2,3-dihydro-3 9 3-dimethyl-2-hydroxybenzofuran-5-yl dimethyl-
aminosulfonate in 90 parts by weight of tetrahydrofuran. The
- 10 -
.... . . . ....
~4~S39
O.Z. 30,334
t~mp0rature rose slightly,after which the mixture was left for
24 hours. The solvent was then ramoved in vacuo and the residue
recrystallized from ether; melting point: 101 to 103C.
The compound, 2,3-dihydro-3,3-dimethyl-2-methylamino~
carbonyloxybenzofuran-5-yl dimethylaminosulfonate, has the
following structural formula:
,..... .
H C -
" ~ 3
0-CNHCH3
The following compounds were prepared analogously~
2,3-dihydro-3,3-dimethyl-2-ethylaminocarbonyloxybanzofuran- ;~
5-yl dimathylaminosulfonate, m.p. 112 to 113C
2,3-dihydro-3,3-dimethyl-2-propylaminocarbonyloxybenzofuran-
5-yl dimethylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-isopropylaminocarbonyloxybenzo-
furan-5-yl dimethylaminosulfonate, m.p. 107 to 109C
2,3-dihydro-3,3-dimethyl-2-methylaminocarbony~oxybenzofuran-
5-yl diethylaminosulfonate, m.p. 122 to 123C
2,3-dihydro-3,3-dimethyl-2-ethylaminocarbonyloxybenzofuran-
5-yl diethylaminosulfonate, m.p. 124 to 125C
2,3-dihydro-3,3-dimethyl-2-methylaminocarbonyloxybenzofuran-
5-yl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-ethylaminocarbonyloxybenzofuran-
5-yl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-propylaminocarbonyloxybenzofuran-
5-yl methylaminosulfonate
-- 11 -- ,
~049539 O.Z. 30,334
2,3-dihydro-3,3-dimethyl-2-isopropylarninocarbonyloxybenzo-
furan-5-yl methylaminosulfonate.
EXAMPLE 4
~ t 10C and while stirring, 56 parts by weight of acetic
anhydride was added to a solution o~ 6~ parts by weight of
2,3-dihydro-3,3-dimathyl-2-hydroxybenzofuran-5-yl methylamino-
8ulfonate and 55.5 parts by weight of triethylamine.
After standing overnight, the precipitated reaction pro-
duct was suction filtered, washed With cold ether and Water,
and dried in vacuo at 60Cj melting point: 103 to 104C.
The compound, 2,3-dihydro-3,3-dimethyl-2-methylcarbonyloxy-
benzofuran-5-yl-N-methylcarbonyl methylaminosulfonate, has the
following structural formula:
H3C 0 H C
3 " ~ H3
0 ,c,cH3
O
The following compounds wers prepared analogo~sly:
2,3-dihydro-3,3-dimethyl-2-chloromethylcarbonyloxybenzofuran-
5-yl-N-chloromethylcarbonyl methylamino9ulfonate
2,3-dihydro-3,3-dimethyl-2-ethylcarbonyloxybenzofuran-5-yl-N-
ethylcarbonyl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-mathylcarbonyloxybenzofuran-5-yl-
N-methylcarbonyl ethylaminosulfonate.
EXAMPLE 5
At -~ to ~12C, a solution of 130~ parts by weight of
methylsulfonyl chloride in 30 parts by weight of dichloro-
- 12 -
.. .. . ~
~ 49539 oO z . 30,3~4
methane was added to a solution of 2~.7 parts by weighk of
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl methylamino-
sulfonate and 13 3 parts by weight of triethylamine in 130
parts by weight of dichloromethanaO 30 minutes after the
raaction was over the mixture was extracted three times with
water. The organic phase was dried with magnesium sulfate and
fraed from solvent in vacuo. The sirupy residue (n25: 1.5150)
did not crystallize even upon standing ~or a fairly long period ~ ;~
of time.
~, ,, ~ ~, .v . , ,
Infrared and nmr spectra and ultimata analysis of the
residue agree well with the compound 2,3-dihydro-3,3-dimethyl-
2-methoxybenzofuran-5-yl-N-methylsulfonyl methylaminosulfonate
having the following structural ~ormula: ~;
H C
3 \ ,0, H C
CS/ ~ ~ 3 .
C 3
The following compounds were prepared analogously:
2,3-dihydro-3,3 dimethyl-2-ethoxybenzofuran-5-yl-N-methyl-
sulfonyl mathylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-ethyl-
sulfonyl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-et~oxyhenzofuran-5-yl ethylsulfonyl
methylamino~ul~onate.
EXAMPLE 6 -
After the addition of 0.5 part by weight of triethyl-
amine, 5.15 parts by weight of msthyl isocyanate was added to -~
- 13 -
10~9~3~ o o z 30,334
a solution of 20.5 parts by weight of 2,3-dihydro-3,3-dimethyl-
2-ethoxybenzofuran-5-yl methylamino~ulfonate in 70 parts by
weight of tetrahydro~uran. Subsequently, the mixkure was left
for 48 hours. The solution was then concentrated in vacuo and
the residue taken up in ether and treated three times with
water. The organic phase was dried with magnesium sulfate 9 and
concentrated in vacuo after having been treated with activated
carbon.
n25: 1.5085
Infrared and nmr spectra and ultimate analysis of the
sirupy residue agree well with the compound 2,3-dihydro-3,3-
dimethyl-2-ethoxybenzofuran-5-yl-N-methylaminocarbonyl methyl-
aminosulfonate having the following structural formula:
H3C \ 0 H C
o ~ .
- OC2H5
The following compounds were pr2pared analo~ously:
2~3-dihydro-3~3-dimethyl-2-m~thoxybenzofuran-5-yl-N-meth
aminocarbonyl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethylamino-
carbonyl methylaminosulfonate
2~3-dihydro-3,3 dimethyl-2-methoxybanzofuran-5-yl-N-ethyl-
aminocarbonyl methylaminosulfonate.
EXAMPLE 7
A solution of 4 parts by weight of sodium hydroxide in
20 parts by weight of water was added to a suspension of 30.1
parts by weight of 253-dihydro-3,3-dimethyl-2-ethoxybenzofuran-
- 14 -
- 1049539 o . z 30,~34 .
5~yl methylaminosulfonate in 55 parts by weight of water. From
the solution which formed it was possible to obtain the salt
by evaporating the water in va¢uo.
Infrared and nmr ~pectra and ultimate an~al~is of the salt
agree wall with the compound 2,3-dihydro-3,3-dimethyl-2-ethoxy- .. -
benzofuran-5-yl methylaminosulfonate, sodium salt~ having the :
followi.ng str.uctural formula:
H3C~ ~0, H3C
" ~ 3 :
0 ~ H ; .
2 5 .:
The lithium and potassium salts of the following compounds
were prepared analogously:
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl methylamino- .: .
~ulfonate ~ .
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl methylamino- ;.
sulfonate
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-~-yl ethylamino-
sulfonate
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl ethylamino-
sulfonate.
EXAMPLE
At 20 to 23C and while stirring, a solution of 8.5 parts
by weight of propargyl bromid~ in 20 part~ by weight of acetone
was added to 46 parts by weight of a 50 wt% ~queous solution
of the ~odium salt of 2,3-dihydro-3,3-dimethyl~2-ethoxybenzo-
furan-5-yl methylaminosulfonate (prepared as in Example 7).
- 15 ~
1~9539 o. z . 30,33~
The temperature rose slightly to 29C~ To complete the
reaction the mixture was stirred for a further 6 hours at 35C.
Ethyl acetate wa~ then added and extraction was carried out
three times with water. ~he organic ph~e was dried with
magne~ium sulfate and subsequently concentrated to dryness in
vacuo.
n2255: 1.5085 .
Infrared and nmr spectra and ult~mate analysis of the -~
sirupy residue agree well with the compound 2,3-dihydro-3,3-
dimethyl-2-ethoxybenzofuran-5-yl-N-propargylmethylaminosulfonate
having the following structural formula:
\ " H C
HC_ C CH
rH
OC 2H5
The followin~ compounds were prepared analogously~
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-allyl
methylaminosulfonate, b.p. (0.01 mm) 137 to 146C,
n25: 1.5065
2,3-dihydro-3~3-dimethyl-2-ethoxybenzofuran-5-yl propargyl-
aminosulfonate
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl allylamino-
sulfonate
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl propargyl-
aminosùlfonate
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl~allylamino-
sulfonate
- 16 -
~: . . . . . . .
~0~953~ :
0.Z, 30,334
2,3-dihydro-3,3-dimethyl-2-ethoxybenzo~uran~5-yl diallylamino-
sulfonate.
The new active ingredients have a strong herbicidal
action and may therefore be used as weedkillers or for con-
trolling the growth of un~anted plants, Whether they are used
as total or selective agents depends in essence on the amount
of ingredient used per unit area.
By weeds and unwanted plant growth are meant all mono-
cotyledonous and dicotyledonous plants which grow in loci where
theY are not desiredO
The agents according to the invention may therefore be
used for controlling for instance ~ :
Gramineae, such as
Cynodon spp. Dactylis spp.
Digitaria 3pp. Avena spp.
Echinochloa spp. Bromus spp.
Setaria spp. Uniola spp.
Panicum spp. Poa spp. -
Alopecurus spp. Leptochloa spp. -~
Lolium 8pp . Brachiaria spp.
Sorghum spp. Eleusine spp.
Agropyron spp. Cenchrus spp.
Phalaris spp. Eragrostis spp.
Apera spp. Phragmites communis
etc.;
Cyperaceae, such as
Carex spp. Eleocharis spp~
Cyperus spp. Scirpus spp.
etc.; - 17 - ~ .
, ,. . " ,.,,~, , .. . . ~ ,. . .
~049~i39 O.Z. 3,33~ -
dicot~ledenous w~eds, such as .
Malvaceaa, e.g.,
Abutilon theoprasti Hibiscus spp.
Sida spp. Malva spp.
~tc.;
Compositae, such as .
Ambrosia spp. Centaurea spp.
Lactuca spp. Tussilago spp.
Senecio spp. Lapsana communis
Sonchus spp. Tagetes spp.
Xanthium spp. Erigeron spp.
Iva spp. Anthamis spp.
Galinsoga spp. Matricaria spp,
Tara~acum spp. Artemisia spp.
Chrysanthamum spp. Bid2ns spp.
Cirsium spp. etc.;
Convolvulacea~, such as
Convolvulus spp. Cu8 cuta spp.
Ipomea spp. Jaquemontia tamnifolia
etc.;
Cruci~erae, such as
Barbarea vulgaris Arabidopsis thaliana
Brassica spp. Descurainia spp.
Capsella spp. Draba spp.
Sisymbrium spp. Coronopus didymus
Thlaspi spp. Lapidium spp.
Sinapis arvansis Raphanus spp.
etc.;
~ ~ .
1~49539 o z 30,334
Geraniaceae, such as
Erodium spp. Geranium spp.
etc.;
Portulacaceae, such as -
Portulaca spp. etc.;
Primulaceae, such as
Anagallis arvensis Lysimachia spp.
etc.
Rubiaceae, such as
Richardia spp. Diodia spp.
Galium spp. etc.,
Scr ~hulariaceaa, such as
Linaria spp. Digitalis spp.
Veronica spp. etc.;
Solanaceae, such as
Physali~ spp. Nicandra spp.
Solanum spp. Datura spp. ~
etc.; ~ ~ `
Urticacea~, such as
Urtica spp.
Violaceae, such as
Viola spp. etc.;
Zygophyllacea~, such as
Tribulus terrestris etc.;
Euphorbiaceae, such as
Mercurialis annua Euphorbia spp.
Umbelliferae, such as
Daucus carota Ammi majus
- 19 -
.
4~539
o.z. 30,33
Aethusa cynapium etc.;
CDmmelinaceae, such as
Commelina spp. etc.;
Labiatae, such as
Lamium spp. Galeopsis spp.
etc.;
Leguminosae, such as
Madicago spp. Sesbania exaltata
Trifolium spp. Cassia spp.
Vicia spp. Lathyrus spp.
etc.;
Plantaginaceae, uch as
Plantago spp. etc.;
Polygonaceae, such as `~
Polygonum spp. Fagopyrum spp.
Rumex spp. etc.;
Aizoaceaey such as
Mollugo verticillata ~tc.;
Amaranthaceae, such as
Amaranthus spp. etc.,
80raginacea~, such as
Amsinckia spp. Anchu~a spp.
Myostis spp. Lithospermum spp.
etc.j
Caryophyllaceae, such as
Stellaria spp. Silane spp.
Spergula spp. Cerastium spp.
Saponaria spp. Agrostemma githago
Scleranthus annuus etc.;
- 20 -
" 1~49539
O.Z. 30,334
ChPnopodiaceae, such as
Chenopodium spp. Atriplex spp.
.. ... .
Kochia 8pp. Monolepsis nuttalliana
Salsola Kali etc.;
Lythraceae, such as
Cuphea spp. etc.j -
Oxalidaceae, such as
Oxalis spp.
Ranunculaceae, such as
Ranunculus 8pp. Adonis spp.
Delphinium spp. etc.;
Papaveraceae, ~uch as
Papaver 8pp. Fumaria officinalis~ `
etc.;
Onagraceae, such as
Jussiaea spp. etc.; ~ -
Rosaceaa, such as
Alchemillia spp. Potentilla spp.
~tc.;
Potamogetonaceae, such as
Potamogeton spp. etc.; ' :
Na j adaceae, such as
Najas spp. etc.;
Eq~isetaceae
Equisbtum spp. etc.;
Marsileaceae, such as ;
Marsilea quadrifolia etc.;
Polypodiaceae,
Pteridium quilinum
- 21 -
~049S3~ -z~ 30~334
Alismataceae, such as
Alisma 8pp. Sagittaria sagittifolia
etc.
The amount used of the agents according ~o the invention
may vary and depends in essence on the type of effec~ ~o~be
achieved; it is generally from O.1 to 15 (and more), prefer-
ably from 0.2 to 6, kg per hectare of active ingredient.
The herbicides according to the invention may he used in
cereals such as
Avena spp. Sorghum
Triticum spp Zea mays
Hordeum spp. Panicum miliaceum
Secale spp- Oryza 5pp. "
Saccharum officinarum ;
and in dicotyledon crops such as
Cruciferae, e.g.
Bras~ica spp. Raphanus spp.
Sinapis spp. Lepidium spp. ~ -
Compositae, e.g.
Lactuca spp. Carthamus spp.
Helianthus spp. Scorzonera spp.
Malvaceae, e.~.
Gossypium hirsutum
Leguminosae, e.g.
Medicago spp. Phaseolus spp.
Tri~oliu~ spp. Arachis spp.
Pisum spp. Glycine max.
- 22 -
'. ;'.:' , :
': ,
104~S39 o . z . 30, 334 - :
Chenopodiaceae, e.g.
Beta vulgaris
Spinacia spp.
Solanaceae, e.g.
Solanum Bpp. Capsicum annuum
Nicotiania spp. ~ -
Linaceae, e.~g.
Linum spp.
Umbelliferae, e.g.
Petroselinum spp. Apium graveolens
Daucus carota
Rosaceae, e.g. Fragaria -
Cucurbitaceae, e.g.
Cucumis spp. Cucurbita spp. -~
Liliaceae, e.g. ~;
Allium 8pp. ~ .
Vi~aceae, e.g.
Vitis vinifera
Bromeliaceae, e.g.
Ananas sati~us.
Applications may be effected for instance in the form o~
directly sprayable solution~, powders, suspen8ion~, di~per-
sions~ emulsions, oil dispersions, pastes, dusts, broadcast-
ing agents, or granules by spraying, atomizing, dusting, bPQad-
casting or wataring. The forms of application depend entirely
on the purpose for which tha agents are being used; in ~ny
case they should ensure a fine distribution of the active
ingredient.
- 23 -
1049539
O.Z. 30,334
For the preparakion of solutions, emu'sions, pastes and
oil dispersions to be sprayed direct, mineral oil fractions of
medium to high boiling point, such as kerosene or diesel oil,
further coal-tar oils, etc. and oilR of veg~table or animal
origin, aliphatic, cyclic and aroma~ic hydrocarbons such as
benzene, toluene, xylene, paraffin, tetrahydronaphtalene,
alkyl~ted naphthalenes and their derivatives such as methanol,
ethanol, propanol, butanol, chloroform~ carbon tetrachloride,
cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc.
and strongly polar solvents such as dimethylformamide, dimethyl
sulfoxide, N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion ~on~
centrates, paste~, oil dispersions or wettable powders by
adding water. To prepare emulsions, pastes and oil Idispersions
the ingredients as such or dissolved in an oil or solvent may
be homogeni7ed in water by mean~ of wetting or dispersing
agents, adherents or emulsifiers. Concantrates which are suit-
able for dilution with water may be prepared from active
ingredient, wetting agant, adherent, emul~ifying or dispersing
agent and possibly solvent or oil.
Examples of surfactants are; alkali metal, alkaline earth
metal and ammonium salts of ligninsulfonic acid, naphthalene-
sulfonic acids, phenolsulfonic acids, alkylaryl sulf~nates,
alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline
earth metal salts of dibutylnaphthalenesulfonic acid, lauryl
ether sulfate, fatty a~ohol sulfates, alkali metal and
alkaline earth metal salts of fatty acids, salts of sulfated
hexadecanols, heptadecanols, and octadecanols, salts of
sulfated fatty alcohol glycol ethar, condensation products of
- 24 -
~ 0 ~9 539 O.Z. 30,334
sulfonat~d naphthalene and naphthalene derivatives with
formaldehyde, condensation products of naphthalene or naphtha-
lenesulfonic acids with phenol and formaldehyde, polyox~et~ylene
octylphenol ethars, ethoxylated isooctylphenol, ethoxylated
octylphenol and ethoxylated nonylphenol, alkylphenol~olyglycol
ethers, tributylphenyl poly~lycol ethers, alkylaryl polyether
alc~hols, isotridecyl alcohol, fatty alcohol ethylene oxide :
condensates, e~hoxylated castor oil 9 polyoxyethylene alkyl
ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol
ether acetal~ sorbitol esters, lignin, sulfite waste llquors
and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared ~y .
mixing or ~rinding the active ingredients with a solid carrier.
Granules, a.g., coated, impregnated or homogeneous gra-
nules, n;ay be prepared by bonding the active ingredients to
solid carriers. ~xample~ of solid carriers are mineral earths
such as silica gel, silicic acid, silica gels, silicates,
talc, kaolin, limestone, lime, chal]c, bole, loess, clay,
dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,
magnesium oxide, ground plastics, fertilizers such as ammonium
sulfate, ammonium phosphate, ammonium nitrate,. and ureas, and
ve~etable products such as grain flours, bark meal, wood meal,
and nutshell meal, cellulosic powders, etc. ~.
The formulations contain from 0.1 to 95, and preferably
0.5 to gO~0 by weight of active ingredient.
There may be added to the compositions or individual
activ~ ingredierlt~ (if desired, immediately before use (tank- :
mix) ) oils of various types, herbicides, fungicides, nernato-
cidas, insecticides, bactericides, trace element~, fertilizer3,
25 - .
,
~,
,.. .
. , ; , . ... : ~ , ~ ,
. .
10~953~
O.Z. 30,334
antifoams (e.g., silicones), growth regulators, antidotes and
othar herb~cidally effective compounds such as
substituted anilines
substitutad aryloxycarboxylic acids and salts, esters and
amides thereof,
substituted ethers
substituted arsonic acids and their salts, esters and amides
substituted benzimidazoles
substituted benzisothiazoles ;
substitu~ed benzothiadiazinone dioxides
substituted benzoxazines
substibuted benzoxadinones
æubstituted benzothiadiazoleæ
substituted biurets
substituted quinolines
substituted carbamates ;:
substituted aliphatic carboxylic acids and their salts, esters
and amides
substit~ted aromatic carboxylic acids and their salts, esters
and amides
su~stituted carbamoyla~kylthlol- or dit~iophosphates : ~
substituted quinazolines ;. .
~ubstituted cycloalkylamidocarbothiolic acids and their saltæ,
esters and amides
substituted cycloalkylcarbonamidothiazoles
substituted dicarboxylic acids and their salts, esters and ~- :
amides
substituted dihydrobenzofuranyl sulfonates
- 2~ - ` ~-.
-
,'
,
1~49539
O.Z. 30,33substituted disul~ides
substituted dipyridylium salts
substituted dithiocarbamates
substituted dithiophosphoric acids and their salts, esters
and amides
substituted ureas
substituted hexahydro~ carbothioates
substituted hydantoins
substituted hydrazi~as .
substituted hydrazonium salts
substituted isoxazol~ pyrimidones
substituted imidazoles
substituted isothiazole pyrimidones
substituted ketones
substi~uted naphthoquinones
substituted aliphatic nitriles
substituted aromatic nitriles
substituted oxadiazoles
substituted oxad~iazinones. .
substituted oxadiazolidone diones
substituted oxadiazine diones
substituted phenols and their salts and esters
substituted phosphonic acids and their salts, esters and
amides
substituted phosphonium chlorides
substituted phosphonalkyl glycines :
substituted phosphites
substituted phosphoric acids and their salts, esters and
amides - 27 -
. . . .
. . : , . - , . ~: . . ~ ,
~49S39 o.z, 30,334
substituted piperidines
substituted pyrazoles
substituted pyrazole alkylcarboxylic acids and their salts,
esters and amides
substituted pyrazolium salks
substituted pyrazolium alkyl sulfates
substituted pyridazines
subskituted pyridazones
substituted pyridine carboxylic acids and their salts, es~ers
and amides
substituted pyridinas
subStituted pyridine carboxylates
substituted pyridinones
substituted pyrimidines
substituted pyrimidones
substituted pyrrolidone carboxylic acid and its salts, esters ~ :
and amidas
substituted pyrro~idine~
substituted pyrrolidones : .
substitiuted arylsulfonic acids and their salts, esters and
amides ~:
subskituted styrenas
substituted tetrahydrooxadiazine diones :
substituted tetrahydroxadiazole diones
substituked tetrahydromethanoindenes
substituted tetrahydroxadiazole thiones
substituted ~ietrahydrothiadiazine ~hiones ~:
substituted tetrahydrothiadiazole diones
. - 2
.... - . . , .. : : .
~4~53~ o . z . ~0,S34
substituted aromatic thiocarbonylamides
substituted thiocarboxylic ac~ds and their salts, esters and
amides
substituted thiol carbamates
substituted thioureas
substituted thiophosphoric acids and their salts, esters and
amides
substituted triazines
substituted triazoles
substituted uracils, and
substituted uretidine diones.
The last-mentioned herbicidal compounds may also be ap-
-- lied before or after the activa ingredient~ or compositions
thereof according to the invention.
These agents may be added to the herbicides according to
the invention in a ratio by weight of from 1:10 to 10:1. The
same applies to oils, fungicides, nematocides, insecticides,
bactericides, antidotes and growth regulators.
The herbicide according to the invention may ba used one
or more times before or after planting, be~ore sowing, pre-
emergence, po~temergence or during emergence of tha crop or
unwanted plants.
EXAMPLE 9
In the greenhouse, loamy sandy soil was filled into pots
and sown with the seeds of various plants. The soil was im-
mediately treatad with 2 kg per hectare of each of the
following active ingredients, each being dispersed, emulsi~ied
i, .
or dissolvèd`in 500 liters of watar per hectare;
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl methylamino-
sulfate, ~odium salt ~I) -
- 29 -
... . . . . .
- ~.
-.
; . . .
~04~39 o. z . 30,334
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methyl-
carbonyl methylaminosulfonate (II)
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-chloro-
methylcarbonyl methylaminosulfonate (III)
2,3-dihydro-3,3-dim~thyl-2-methoxyb2nzofuran-5-yl-N-methyl-
carbonyl methylaminosulfonake (IV)
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-chloro-
methylcarbonyl methylaminosulfonate (V)
2,3-dihydro-3,3-dimethyl-2-methylcarbonyloxybenzofuran-5-yl-N-
10 methylcarbonyl methylaminosulfonate (VI) :~
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methoxy- : :
carbonyl methylaminosulfonate (VII)
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethoxy-
carbonyl methylaminosulfonate (VIII)
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-isopropoxy-
carbonyl methylaminosulfonate (IX)
2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl
dimethylaminosulfonate (X) ~ ~:
2,3-dihydro-3,3-dimethyl-2-ethoxycarbonyloxybenzo~uran-5-yl ;
dime~hylaminosulfQnate (XI)
2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl
diethylaminosulfonate (XII)
and, for comparison,
2-ethoxy-2,.3 dihydro-3,3-dimethyl-5-benzofuranyl methane-
sulfonate (XIII)
2~3-dihydro-3,3-dimethyl-2-isopropoxybenzofuran-5-yl ethyl- :
aminosulfonate (XIV).
- 30 -
109~9~39
O.Z. 30,334
After 4 to 5 weeks it was ascertained-that active
ingredients I to XII had a better herbicidal action than com-
pounds XIII and XIV, combined with the same crop plant
compatibility.
The results are given below:
. - 31 -
: , , `' . , ,: ' : - ~ ' '
104953g 0 . Z . 30, 334
~H ~U O O O O Ll~ C~
O O o o L~ o L~ ir\ o o ' ~' '' '.
H ~ a~ O cr~ 0~o ~C)
X
X ~ O o o o o o o o o
O O O O O ~ ',
X :,
H ~J O O O O O O 1~ L~ IS~O
~ 3 :
H O O O O 15~ L~ L~
H a~ 0~C~ J
~? . '',, ~
H ~`J O O O O lS~ O L~ O O O
P ' a~ o ~ o o
H (~J O O O O O O O O O O . . ~
~ c~ 3 : :
. ' ' ~ ' .',~', .
p t\l O O O O Lr\ g Lr~ O g O
H ~ O O OO lr~ O `~D O O O
~ O C~ O O
H
H (~l O O OO ~ O 15~ O ~ Ll~
1_1 C~ O ~ O C~Lr~ ,
-"''':.
H ~1 O 15~ O O O OL~ O O 15~
H O O O~ O O~D :
': :
H ~\1 O O OO O O O O O O .:
~ O O 0 ~0 ~0~ Co ,"~,, ~
' g '~'''''
rl '
Ul rl
r~
r
rl U~ h I :J
a~ ~ 0~~3 o r
rl CO ~0 ~ ~ O ~!j r-l C'~ ~0
:1 r~ S ~ O ~ S~
a~ ~ 0 E~ rl
~a ~ H ~ U H
bO ~ ~ m ~ ~ ~ o r~
~ ~ 1 ~ ::tr~
rl ~d p, ~ ~ cd ~ O O
~1 p, Or~ O ~ ~S O ,C~ O
a~ ~ ~ rl O~ ~ C> O ~ 5:`, rl
~d u~ l S ~
P ~ rl ~ ~ rl rl
O ~ ~d ~ r l ~ ~ O ~ O O
o bD ~1 ~ ~ : -r-l O:~1 0rl O
~: ~ c~ m m P~ x P ~
- 32 - .
~'"' '''
., ,, , , , ~ , - , , - - - - , .
~049~3~ -z., 30,334
;
'
~ O O O O O O O O U~ O . ':
X : . .
H ~U O Lr~ O OL~ O O If~ O
X ~1 .1 ~a~ ) N
~.'
~ '
W ." ~ :
~I h
rl
oq o
~: h ~ h ~1 ~ . .-
~d ~ Gq 0~:~ O
5:: ~ O h
h t~~> ~1
~: ~ ~ ~
rl t~ ~ ~ ~ ~ h,s~ 5 o O
~1p~C) r I ~a) ~
G~ Qu~ O ~ ~ C~ O ~ 5: rl
~ Oqa) ~d
rl S ~ ~ rla1 S~
O ~ ~ ~ a) o ~ ~ o o
c~ bD ha) h S a)~: ~ O O ~1 O
¢ ~: ~ m a~ ¢ ¢ ~ ~
' ' '
'''' '''" '"
; .
- 33 - ~
. .
" '' ,
- . , -: . :: .
-1~4953~ ~:
O.Z. 30,334 : :
EXAMPLE 10 -
In the greenhousa, various plants were treated at a growth -
height of from 2 to 15 cm with 2 kg per hectare of each of - .
active ingrediants I to XIV (as defined in Example 9), aach
being emul~ified, dispersed or dissolved in 500 litars of water
per hectare. ~: :
After 2 to 3 weaks it was ascartained that active :~
ingradients I ~o XII had a better herbicidal action than com- -
pounds XIII and XIV, combined with the same crop plant compati~ :
bility.
Tha results ara given below~
. , ,
.
- 34 - ~:
104~539 " ~ Z . 30, 3311
H r~l O-Ir~ IS`\ O O 1~
~C x) a\ o~
.'-,,
H N OO 0 15~ O
X o~ a~ o~ o
~ ,,
X ~ OO Lr~ O O O
~ ra~ O -
X N OO O Lr~ O L~
H O~ O~ ~
H ~ '.
H N OO ~D ~0 ~ ~ .
P O~ 0~
H ~U O O L~
P O~ O~
: ' -
H N OO O Lr~ O 1~
O~ X~ O~
. r~
P N OO L
O~ ~ C~ ' ''
~ N O O L~
H ~ r J~
H O L~ O O
H N OO C~
' ''
H N OO O ~ In
H O~ O~
H N OO O O O I
o a~ o CJ~ '
g
~ ,;
H ~ h
~ r~ ~ "
5~ ~
~rl ~ ~ h O bO a
c~ ~ Cd
a) .. p, ~d
~q ~ ~
b~ ~ 5: R ~ O ~Q ~ Q.
S~ ~ . ~ ~1
~ ~d ~ ~ -d ~ O O
H ~C) Q) ~ r~
07rl ~ O ,~, C)
a ~ ~ i~(d ~ 11 11
~rl rC ~ ~ S~
O ~ ~ ~:~V ,5~ l O O O ' .,
C) bl~ ~ID S~ ~ ~ C) O vl O
~: ~ t~ ~ m ~ ~
- 3~ -
,. . - . , ~ ~ . i
~L~4953~ o . z . 30, 334
o o o ~ o
H ~I o~ ~ x) x~
X ,' ' '
' .:- ~
~ ,'
O O L~ O O o
H ~I
' 5: '' .
O '.': '
o
t~
~0 0 ~-
J~ I h ~ ..
5:: ' ~ '' :,:
u~
~rl 0 J~ h O ~o a~ -
~ ~ ~> ~ ~ ~ .
~d ~ ~
~o .~~: ~ ::f o
s:: s::~ ~ ~ ~ o o ''
~ ~ o 9) ~ o ~ ~ ~ o
a~ Q ~q rl ~ O
, 5 ~ u~ ~ ~ ~ ~ a) " ,.
,1 .C t2 ~ d
O ~ ~ a) 5:: ~d O O O
o ~0 h ~ h ~ :~ o O ~ O
~: ~ ~m ~q ~
..
'. ".. . ....
,
.':
" ' ' '
~.
-- 36 --
~ ~ ~9 53 9 O.Z. 30,334
The action of the following compounds-corre~ponds to that
of the compounds according ko the invention in tha foregoing
examples:
2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-methyl-
sulfonyl methylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl
diathylaminosulfonate
2,3-dihydro-3,3-dimethyl-2-mathoxycarbonyloxybenzofuran-5-yl
dimethylaminosulfonata
2,3-dihydro-3,3-dimethyl-2-ethoxycarbonylbanzofuran-5-yl
dimethylaminosulfonate
EXAMPLE 11
In the greenhouse, loamy sandy ~oil was ~illed into pots
and sown with the saeds of various plants. The soiI was then
immediately treated with 3 kg per hectare of each of the
following active ingredients, each baing dispersed or emulsified
in 500 liters of water per hectare~
2,3-dihydro-3,3-dimethyl-2-ethoxybsnzofuran-5-yl-N-methyl-
carbonyl methylaminosulfonate (II)
~,3-dihydro 3,3-dimethyl-2-athoxybanzofuran-5-yl-N-chloromethyl-
carbonyl methylaminosulfonate (III)2,3-dihydro-3,3-dimethyl-2-sthoxybenzofuran-5-yl-N-methoxy-
carbonyl ~,ethylaminosulfonate (VII)
2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethoxy-
carbonyl methylaminosulfonate (VIII)
and, for comparison,
2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methane-
sulfona~a (XIII).
- 37 -
1049539 o z 30,33~
During the experimant the plants were watered well.
After 3 to 4 week6 it was ascertained that active
ingredients II, III, VII and VIII had better crop plant com-
patibility than compound XIII, combined with the same herbididal ~
action. :
Tha results are given below~
Activ ingredient II III VII VIII XIII
kg/ha 3 3 3 3 3 .
~.. . .
Cro~ ~lants:
'
Gossypium hirsutum 5 0 5 10 40
Zea mays 20 5 10 15 60 ~
Beta spp. 10 0 5 5 3 .
Unwanted plants: ~
.
-~chinochloa crus-galli100100100 100 100 : -
Setaria faberii 100100100 100 100 :~
Alopecurus myosuroide~ 100 100 100 100 100
Avena fatua 100100100 100 100
Galium aparine 100100100 100 100
,; . . .
0 - no damaga
100 ~ complete de~truction .
' ~
, .:-
- 38 ~
