Note: Descriptions are shown in the official language in which they were submitted.
The present inve-ntion relates to new carbamoyl eulpho-
xide derivatives having the general formula
0 0 R
11 / 1 ,i
R - S - C - N (I)
Rz
wherein R i9 a phenyl or benzyl group ~hich may be substituted
with an alkyl containin~ 1 to 4 carbon atom~ an alkoxy con-
taining 1 to 4 carbon atom~ or a halogen atom, or R represents
an alkyl radical containing 1 to 4 carbon atom~ and which msy
b~ ~ubstituted with a halogen atom9 ~ and R2 are the same or
di~ferent snd each represents a hydrogen, an alkyl containing
1 to 4 carbon atomq or a cycloalkyl containing 4 to 7 carbon
atoms or Rl and ~2~ when ~aken together~ re~resent an alk~lene
containing 4 to 7 carbon atoms.
The carbamoyl sulphoxides belonging to the cla0s of
formula (I) are new compound~, not previously described in the
literature~ which can be u~efully employed a~ ef~ective pe~ticide~
and in particular for killing infesting plant~.
We have found that the new compounds of formula (I)
are unexpectedly stable and can be ea~ily prepared by oxidizing
thlolic sulphur to ~ulphoxidic sulphur according tv the follo~ :
ing equation:
R S - C - N + OX ~R - S - _ N
\ R2 \` :R.
wherein R, R1 and R2 hsve the meaning specified ~bove and OX i8
an oxidizer such a~, for instance, perbenzolc acid or methachloro
perbenzoic acid.
The reaction i8 conducted at atmospherlc pre~sure and
at a temperature ranging ~rom ~50~ to +50C, depending on the
oxydi~ing agent employed and on the nature of the ~tarting
thiolcarbamate.
Generally the products obtained are ea~ily cryatalliz-
able colids and, in 90me casea, oils.
On infrared-ray ~pectrographic analysia~ the compound~
of thi~ invention reveal a band comprised between 9.2 and 9 r 6
micron which ia characteristic o~ the ~S - O ~roup and a band
comprised between 5.8 and 6.1 micro~ which i~ typical o~ the
~ C = O --- ............. _ . ............................ ,j,~
~ -1a- .
group; such bands, along with the elementary analysis, prove L
the carbamoyl sulphoxidic structure of said compounds.
The following examples are given to illustrate -the
invention and are not intended to be limiting.
EXAMPLE 1
O / C4EIg s c Cl
l / C4Hg sec. Cl ~ ~O
\ C4Hg sec- \ OH t
~ solution of 2.9 g of (technical) methachloroper-
benzoic acid in CH2C12 (60 ml) is admixed, drop by drop, to a
solution of N,N-disec.-butyl-S-benzyl-thiolcarbamate in CH2C12
- (15 ml) cooled down to 0C; when such addition has ended, the
reaction mixture temperature is kept at 0C for about further E~
30 minutes, then it is allowed to rise up to room temperature.
Traces of methachlorobenzoic acid in the solid state, if any,
are filtered. The chloromethylene solution is washed with a
saturated aqueous solution of NaHCO3 (2 portions of 70 ml
each) and then with H2O ~2 portions of 70 ml each). The
chloromethylene phase is separated and then anhydrified with ?
Na2SO4O It is evaporated to dryness. 2 g of N,N-disec.butyl-
carbamoyl-benzyl~sulphoxide (melting point at 63-64C) are
thus obtained.
Analysis:
Calculated values: N 4.7% S 10.8%
Found values: N 4.7% S 10.7%
EXAMPLE 2 - 31
.
- ~ -
- .
-The following Table I illustrates a series of new
carbamoyl sulphoxides prepared according to Example 1, the
only difference being in the starting thiocarbamate. F
3 -
~ 3 ra ra F
I O r-l O r-l ~r l ~ ) ~rl 11~ ra O ~rl U
~1 ~ ~rl r-l ~1 r-l o r-l~ ~1 ~D ~ r-l o
r-l O r-l O r~ O O ~1O ~1 r-l ~ ~ Zl) ra L
a) ~ ~ u~~ O ~D ~ U~
~ ~ U~ ~ ~ ~ U~ U ~ l ~
-,1 ~ U ~ ~ ~ I ~ I O a~ O c
~ h -r~ ~ U ~) UOrl R.~r-l .,~ ~o $ Q ~ .,~ Q~ ~ ~1
rC rC U I tn U~~ ~C r~¦ rC ~ rl ~1 ~ r~ ~ ~
U ~rl ~ ~1 r~ r~3 E~ r-l 3 E~ 0 ~ ~C ~ ~) 3 ~ 1~ O
r~ r-l ~ 3 X 1~ ~1 ¦ t)
O L~ ~ Lt~
r-J O ~ ~ ~ ~ r-l~ ~ ~ (~l Ll r~
~ ~ ~ ~P r~l
ra ~ r-l ra r-l ~1 ra ~ ~ ra ~ r-l ra r-l r-l ra ~1 ~ r~l
C r~ ~ 1: ~ c~ ~ r-l 1: ~ r~l r~
o\o :~ ::1 ~ ~:i ~ ~
_ O O r-l O O O r-l O r-l
-r~ 14Z u~ 14 U Z u~ ~I Zu~ 1:4 Z u~ ¢I V Z u~ 14 V Z ~n
U~ ~D O ~ . ~r ~ o ~
~ 1~~ ~ ~ a~ln ~ ~ ~ ~ ~ ~ r
r-l ~ ~N 11~ r~ O ~I ~ ~ ~r Lf~ ~1 ~ ~ r-l
~d ~r O ~ r-l r~l . ~ ~ Ltl r~ . r-l r-l ~ r~i r~l
C O r--l O~ ~ ~ r~l O O
r--lr~l r-lr~l r-¦ r-l
1~(~ r-l li~(d t;~ r-l 11~ r-l
~ v z u~ v u z u~ c.) z tq v z u~ o U ~ V V Z u~ i.~ o ~ ~ ~ o ~
t
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EXAMPLE 32
2 g of N,N-disec.butyl~S-benzyl-thiolcarbamate are
reacted at 40C with 240 ml of peracetic acid (200 ml of
glacial acetic + 40 ml of perhydrol). After 45 minutes,
400 ml of 15% Na2SO2 and 280 ml of NaOH 10N are added. Sub-
sequently, 1000 ml of CHC13 are admixed under intense stirring t
for 5 minutes. The chloroformic phase is separated and con-
centrated to 10 ml.
The solution contains 1 g of unreacted N,N-disec.butyl-
S-benzyl-thiolcarbamate and 1 g of N,N-disec.butyl-carbamoyl-
ben~yl-sulphoxide. The latter is separa-ted fro~ the N,N-disec.
butyl-thiolcarbamate by chromatography on a thin layer, thus
obtaining 0.90 g of N,N-disec.butyl-carbamoyl-benzyl-sulphoxide
in the form of whitish solid. After crystallization by means
of n-hexane, a white crystalline solid (melting point between
64 and 68C) is obtained, which, on analysis, gives the
following data:
calculated values N 4.7% S 10.8%
found values N 4.7% S 10.2%
and the infrared spectrum of which exhibits a band at 5.92-6
micron, characteristic of ~,C = O and a band at 9.55 micron
characteristic of ~ S - O.
EXAMPLE 33
The compounds of this invention exhibit a considerable L
weeding activity in pre-emergence. Some data concerning the ~ `
week-killing activity in pre-emergence exerted by some com- F
pounds of the inven-tion on some types of infesting and useful
plants are repor-ted hereinafter.
Two sets of little square section tanks of 11 cm side,
filled with field earth admixed with 50% of sand, were sown at
a depth of 0.5-1 cm with the following grass species: Echi-
nocloa crus-galli, Setaria glauca, Avena fatua, Panicum
- 10 -
dicothomiflorum, Digitaria sanguinalis, Vicia sativa, and
Convolvulus sepium and Amaranthus retroflexus.
After sowlng, the ground surface was uniformly sprayed
with 2.4 ml/tank of a hydroacetone solution containing com-
pounds of the invention in quantities equivalent to -treatment
doses of 0; 0.5; 1; 2; 4-kg of a.p./ha. All the tanks were
kept in an air conditioned chamber, having a daily variation
in temperature comprised between -~10 and +25C and a 14-hour
photoperiod, and were watered every dav. 25 days after the
treatment the final results were gathered, attributiny the L
following scale of values to each treatment: ~
0 = regular emergence and growth; ~ `
1 = slight differences with respect to the check;
2 = activity of a certain degree, with partial damages,
which, however, do not jeopardize the life of the
plant;
3 = considerable activity causing a damaye which defini-
tively jeopardizes the further growth of most of the
plants; an activity degree of practical utility;
~ = thorough prevention of emergnece or stopping of growth
at 0.5 cm and successive death of the plants.
In the case of-an intermediate activity between two
values, both are reported, the value to which the relative
- activity is closer being indicated first.
Table II shows the relative data.
The reference number of the compounds relates to the
numbers of the preceding examples.
~i -- 11 --
,~ i;.; .
,.
g
Rice Isubmerged _
culture)~r ~r ~r I o o I ~r ~r ~r ~r ~r I ~r ~r
.
Alfa AlfaI I 1. l l l l l l l l l l l l
_
~ ~ ~ ~ ~ I ~7
Pisus Sativum I ~ ~ _ I ~ I I ~ ~ N N
BeanI o o I o o I o o I ~ ~ N
Cottonr I o o _~ ~ I
~ ~r ~ ~ ~ ~
Soya-Bean I ~ ~ l l l I ~ ~ o I ~ O
~ _
Sugar-Beet l ~ ~ l ~ ~ l ~ ~ l ~ ~ l ~ ~
, o
Corn ~r ~r ~r l l I I ~ ~ ~ r I ~r ~r
_
Mais I o o I I~ I ~ ~ I o o
Stellaria ~ _ I N ~ O N =
Album ~r ~ ~ l l l ~r ~r ~r ~r ~r ~r I
_ _ _
H Capsella~ ~r ~r l l l ~;r ~r .~r ~ ~r ~r ~r ~r ~r
H Bursapastoris .
~ Convolvolus.~r ~ ~ r ~ ~ ~ ~ ~ o ~ ~ ~ ~,`
) 1 Sepium ~ N O __ ~r ~
m Vicia Sativa ~ ~ ~ ~ ~ ~ ~ ~ o
Amaranthus ~r
Retroflexus _ _ _ _ r ~ ~ r ~r ~r r ~r ~r
Rumex Crispus I ~ ~ ~ ~ ~, I ~ ~r r ~r ~ ¦
Panicum ~r ~r ~r I ~ r~) ~r ~r ~ ~r ~r ~r ~r ~r ~r
Dicotomiflorum
Alopecurus ~ ~r ~r l l l ~ ~r ~ ~r ~r ~r ~r ~r ~r .'
Myosuroides ~
Poa ~r ~ ~r l l l ~r ~r ~r ~ ~r ~r ~r ~r ~r
Pratensis
. . . __ l l
Digitaria ~r ~ ~r I ~ ~ I ~ ~ ~r ~r ~ ~r ~ ~ t
Sanguinalis ~ ~
l I
Setaria Glauca ~r ~r ~r ~ ~ ~ ~r ~ ~ ~ ~r ~ ~r ~r ~r
. .. ., _ I
Echinochloa r ~r ~r ~ ~r ~ r ~ ~ ~ ~r ~r ~ ~r ~ ¦
Avena Fatua r ~ I ~ ~ ~ ~r
_ . ... . _
KG / HA ~D ~r ~ ~ ~r ~ ~ ~r ~ ~D ~r ~ ~ r
. :1
Compound No. . _ _ _ _ ~ ~r
_ _ __~
continue~
.,
~ - 12 -
5~9
Rice (submerged _
culture) ~ ~ ~ ~ ~ ~ I ~ ~ I ~ o
. . _ .... . .
Alfa Alfa l l l l l l ,~ l l l ,~ ~r
_ .
Pisus Sativum . ,~ ~ ~ ,~,~ ~ l l l o
.___ . _
Bean I ~ ~ I o o,~ I ~ I ~ o
... _
Cotton ~ ~ I ~ ~ I ~ ~ I l l l ~ ~ ~
__ _ t
o . ~ ~ ~ ~,,
Soya-Bean l ~ ~ l ~ ~ l ~ ~ l l l ~
_ ~ ~ ~ ~ ~ F
Sugar-Beet ~ ~ ~ ~ ~ ~ I ~ ~ I ,~ o ~ ~ ~
......... ___ _ .
Corn
...._
Mais I o o I o o I o o I ,_~ ~ I o o
_
Stellaria ~ ~ ~ .
Media ~ ~ ~ ~ ~ ~ ~ ~ l ~ ,~
Chenopodium
Album
H Capsella
H Bursapastoris
Convolvolus . ,~ s
Sepium ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ o o ~ N
~ . .... _ _ l
m . ~ ~ ~ ~ ~ ,~ ~ ,
Vicia Sativa _ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ,
Amaran-thus ~ ~ ~ d' ~ ~ ~ ~' ~ ~ ~ ~ ~ ~ . F
Retroflexus .
_ .__ .
Rumex Crispus ~ ~ ~ ~ ~ ~ I ~ ~ l l l l l l . '.
. _ . . ,
Panicum ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ r
Dicotom~.:Elorum
_ t
Alopecurus ~ d' ~ ~ ~ ~ ~ ~ ~ ~ d'
Myosuroides . .
Poa ~ ~ ~
Pratensis . ~ ~ ~ ~ ~ ~ ~ - ~ ~ ~1 1
Digitaria f
Sanguinalis~ d' ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
__. _ - ................. ____
Setaria Glauca d' ~ d' ~ d' d' ~ ~ d' - ~' d' d' d' ~ ~
_ _
Echinochloa
Crus Gali
__ ,'
Avena Fatua ~ ~ ~ ~ ~ ~ ~ d' ~ I ~ ~ ~ ~ ~ !.
~ ___ P
A S ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ¦~
_ __ . _ _ . ~_
Compound No. . , ~1 _
continued
- 13 -
~ .~.. .
-
1 1 ~ 3
Rice (submerged
culture)
I L
Alfa Alfa I N ~ _ _ ~:
Pisus Sativum l l l l l l l l l l l l
_ l
Bean I o o o I o o
~ .
Cotton I ~ ~ l l l l l l l l l l l l F
l E
Soya-Bean I ~ ~ l l l l l l l l l I I I ~
I
Sugar-Beet~ ~ ~ I ~ ~ I ~ ~ I ~ ~ l l l
_ . _.
Corn~ ~ ~ l l l l l l l l l l I ~
_
MaisI o o I o o I ~ o I o o l l l
o L
S-tellaria
Media ~ ~ I ~ c
Chenopodium
Album _
H Capsella . _
Convolvolus ~ ~ ~ ~ o ~ ~ ~ ~ ~ ~ ~ I I .
r~ Sepium ~ ~ _
m Vicia Sativa ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ I I E
~ , _ t
Amaranthus
Retroflexus _
Rumex Crispus _ __
Panicum
Dicotomlflorum
_
Alopecurus
Myosuroides
Poa ~ ~ ~ I i I
Pratensis _ _ _ .
Digitaria
Sanguinalis
.
Setaria Glauca ~ ~ ~ ~ ~1 ~ ~ ~ ~ ~ ~ ~ . .
Echinochloa
Crus Gali
_. ~ .. _
Avena Fatua ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ o
A. S. . _
KG / HA
..... ..... _ . _~
Compound No.
_ ~ ~ ~ ~ ~I
. .. .
con inue~
- 14 -
- 1~3~9
Rice (submerged _
culture) l l ~ l l l l l l l l l l I ~ ~ .
... ._ . _ _ .
Alfa Alfa I ~ ~ l l l l l l I I l l l l l l f
....
Pisus Sa-tivum
. . ~
Bean I o o I o o I o o I ~ ~ ~ ~ I ~ o
_ ___ _ .... __ _ _ ._.__ L
Cot-ton I ~ l l l l l l l l l l l l l l l i~
_
Soya-Bean ~ ~ ~ l l l l l l l l l l l l l l l
. ~
Sugar-Beet
_ , . ._ ... ... _
Corn
.~ . _ . . _
Mais N I O O I O OI ~ t~l I ~I rI I o O
Stellaria _ . _ ~ __
Media ~ ~ ~ ~ ~ ~ I ~ ~ I ~ ~ ~ ~ ~ I ~
Chenopodium _ _ _
Capsella _ _ _ _
H Bursapastoris .
Convolvolus .
Sepium ~ ~ ~ ~ o o ~ ~ o ~ ~ ~ ~ ~ ~ ~ ~ ,_~
~ _ _ , .. .__
m Vicia Sativa ~ ~ ~ ~ ~ ~ r~
~1
. . _ . __
Amaranthus
Retroflexus ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ t
_ __ __ ____ _ _ __ _ _ n. _____
Rumex Crispus l l l l l l l l l l l l l l l l l l L . .___ .. _ _ .. .
Panicum
Dicotomifloxum _
~lopecurus
Myosuroides .
Poa _ _ _ _
Pratensis ____ .
Digitaria ~ L
Sanguinalis ~ ~ ~ ~ ~ ~ I N
- -- . ..~ . ,.,
Seteria Glauca
~chinochloa .
Crus Gali
....... _ ......
Avena Fatua
. A. S.
KG / HA .
Compound No. r~ ~ o _ ~ ;
` - 15 -
; 8 J
,. . _
Rice (submerged ~ _
culture) I I I . l l l l l l I N O I i l O O O b
. - ._ _ .___ ~ ._
Alfa Alfa l l l I 1.
_ . ._ ._ . .. _ . . _ .
Pisus Sa-tivum l l l l l l l l l l l l l l l l
. .
Bean I o o I o o I o o ~ ~ o
Cotton
. _ ... . __ ~
Soya-Bean
~ ~ ~ . _ . _ ___
Sugar-Beet
I ~ o l I I I ~ ~ I ~ ~1 I ~ o ~ ~ o
O .. _ . o,_ _._ _ ~ ._ ~ .
Corn l l l l l l l l l l l l ~ I I l l l
p:; . ._ __ _. ._ . i '
Mais I ~ o l l l I o o I o o I o o ~ ~
~; . ._ _ _ _ ......... _~
Stellaria
~ Media l l l l l l l l l l l l ~ ~r N I 1- 0
Fl:l _
~ Chenopodium
O Album
-- . _ . .
Capsella
o Bursapastoris :. __ _ _ ~ _ _
~ Convolvolus~ ~ ~ ~ ~ ~ ~
o Sepium~ ~ ~ ~ I 1 ~ ~ ~ ~ ~1 ~ ~ ~ ~ ~ ~ ~ E
~: . . _ .
Vicia Sativa ~ ~ o ~ I I ~ ~ ~ ~ ~ ~ ~ ~ ~ l l l
E~ _ .. _ .. ___ . __ . . . . . . . . ___ . . _._ _ r
o Amaran-thus~ ~ ~ ~ I I ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ o o
Retroflexus~ ~ ~ o P
w ._ .. .... .
Z Rumex Crispus
E~ . . .__ .. .. _
Panicum l l l l l l ~ ~ ~ I ~ ~ ~ ~ ~ ~ ~ ~ ~:
Dicotomiflorum ~ ~
_ _ _ _
Alopecurus
~ Myosuroldes ~r
C~ ................... ... . . _
~H Pratensis _ _ _ ~ __
Digitaria
~C Sanguinalis _
Setaria Glauca
~ .__ ~ , _ ~ ~
Echinochloa
Crus Gali
.. ..... . .
. Avena Fatua
A. S.
KG / HA ~ ~ ~ ~ ~ ~ . ~ ~ ~ ~ ~ ~ w ~ ~
. Trade Mark Suta~ Til1am Ve.rnam Okdram Eptam Orepamor
- 16 -
EXAMPLE 34
TABLE III
p,
Weeding activity determined in an air conditioned
chamber with treatment in pre-emergence with N,N di-sec.butyl-
carbamoyl-sulfoxide (compound No. 1)
kg/ha of active product r
GRASS SPE~IES 4 2 1 0.5
Echinochloa 4 4 3 2
crusgalli
Setaria glauca 4 4 3 2/3
Avena fatua _ 3/4 2 1
Panicum _ 3/4 3 3
dicothomiflorum
Digitaria - 4 3 2
sanguinalis
Vicia sativa 2 2 1
Convolvulus - _ 1/2 1/2 1
sepium
Amaranthus _ 3 1 0
retroflexus _ ~
~.
EXAMPLE 35
TESTS IN_GREENHOUSES: for pre-emergency activities.
Eternit vats of 1000 sq.cm. and with a depth of
40 cm were filled with field soil. The product, diluted in a
hydroacetonic solution corresponding to 2000 lt/ha, was !~
incorporated into the first 5 cm overlying soil.
In the case of infesting herbs Iweeds) the seeds
were carefully admixed -to the above indicated 5 cm layer after
the latter had been suitably -treated, while the useful plants
were sown or transplanted le.g.: tomatoes and tobacco)
immediately after the treatment.
Each vat, in which three infesting plan-ts or three
useful plants had been planted, was sprinkled daily.
- 17 -
,
The tests were conducted in greenhouses during -the
months of July - August and at an .interval of 28 days, and at
the end of the test the ~inal results of the treatment were
ascertained. The observations made, besides the re-confirma-
tion of the excellent herbicide activity on a wide variety of
infesting plants, brought into evidence a pronounced selec- F
tivity on mais, peanuts, potatoes and beans.
~ .
r
~ .
- 18 -
TABLE IV
_ Vlcla Sativa ~ N _ _
_
Portulaca .
oleracea
.. __ ........... _ '.~ ~
Amaranthus o ~ o ~ ~ ~ ~ F
Retroflexus
.
Chenopodium r,
album ~ ~ ~ ~ ~ ~
. ~. . . . . .
Solanum
Nigrum ~ .
_ . _ ..
Sorghum ~ ~ ~ ~ ~ ~
. __ ._
Echinochloacrus .
Galli
. .... _ . 1 ~ .
Setaria
Glauca
. . _ _ ._ _, _ ~ _
. Lolium ~ ~ ~ ~ ~ ~ 7
. _ .. . __ ¦ r
Avena Fatua ~ ~ ~ ~ ~ ~
. . _ _ _ . -I
Digi-taria .
Sanguinalis ~ ~ ~ ~ ~ ~ L
.. .... .. _ . .. .
Poa Pratensis ~ ~ ~ ~ ~ ~
_ , ,_ _ . _
Kg/Ha ~ ~ ~ ~ ~ ~
Compound No. _ _ _ ~ ~ ~ ~ I - t
. ~ 1-l~_~ N O O ~J O O
~xi -- 19 --
..i
;.
'3
Potato o o o o o o L
Bean ~ o ,~ o o o
Tobacco
l l
. Tomato ~ ~ ,~ ~ ~ ~
l l
Carrot ~ ~ ~ ~ o . ~
_ _ I ~'
Alfa Alfa ~~ _ ~ o
Pisus
Sativum ~_ _ _ ~
Peanut o o o o O O r'
. __ _
. Soya-Bean ,~ ~ ~ ~ ~ ~
.. r
Cotton ~ ~ ~ ~ ~ ~ r
_ t:~
Mais o o o o ,~
_ __ .~
Vigna
Beet
_ _ _~
S.A. -
Kg/Ha ~ w ~ .
- - r r ~ ~ r~
Compound No. ,~ ,~ ,~ ~ ~ o o ~ o o
~ \ e_
2 0 -- i
EXAMPLE 36
L
The compounds of the invention also show a high
degree of activity when used in post-emergence treatment.
Table V shows the results.
-
'~ ~ 21 - ;
TABLE V
o ~ _ D ~ ~ _
Z ~ O t-l F:l U~ ~ ~ H
i~ ~ C~)-¢ 1~ ~ ~ ~1
O l O t~) H ~ O O ~ ~¢
1:4 . H tl~ 1~ P:; ~ ~ H H
~ t/~ :C ~ ,~ I¢ E~ ~; ~
O . ~ E~ ~ . ~1 O ~:1 H
C_) ~ 1:~C) ~1 ~; C)U~ ~
6 4 4 4 ~ 4
1 4 4 4 4/3 4 3/4 ~'.
2 3/4 3 2/3 3/2 3/~
_ . _
6 4 4 4 3 2
2 4 2 2 2 O O
2 O O 1 O O
_
l 10 1 2 3 ~ 3 2 ~ 2 ~ O
. .
6 4 4 4 3 4/3
14 4 4 4 4 2 2/3
2 4/3 3/4 2 2 2
~ . ~ _ ~: '
6 4 4 4 4 2
16 ~ 4 4 ~: 2 1
2 3 3/4 3 1 O
' _ I. I,
6 4 4 4 3/4 O
17 4 4 4/3 4 3 O
2 3 ~ 3 3 O
continued
22 -
L
O ~' ~ U~ U~ . ~
Z ~ O H 1~ U~ ~ ~ H
W ~ ~ ~ X 1~ E~
n ~ ~ ~ x ~ o
Z t~ ~ ~ E~ ~ ~ u~
~ l O ~ H Z ~4 ~
o z ~; ~ o O ~ ~ C
P~ . H U~ ~ p~ p:; ~ H H ¦~
~ U) ~ E~ ~ E~ æ ~ o
O . C,~ 1~ 1:~ ~ ~LI O l L1 H
O l¢ ~1 C) U~ f~ ; O U~
.~
. 6 4 4 4 3/4 3
18 4 4 4 4/3 3 3
2 4/3 3 2/3 2 0
_ . . .
6 4 4 4 3 2/3
19 4 4 4 4 3 2
2 3 3 2 2 1 .
_
6 3/4 4 3 3 3
4 3/4 3/4 3 2 3
2 3 3 2 2 0
. _
6 4 4 4 3/4 3/2 .
21 4 4 4 4 3 2
2 3 3 4 3 1
_~
6 4 4 4 3 4/3
22 4 4 4 4 3 3
2 3 3 2 3 2 I:
. .... ___ .
6 4 4 4 4 3
23 4 4 4 3 3 2
... _ 2 2 2 2 1 0
con-tir .ued
- 2 3 -
o ~ ~ ¢ ~ ~.
Z ~ O H ~~ ~C H
Cl ;~; O ~ ~ E-l ~1 ~0 1¢
O O ~ H ~ O r.l H
~,) l¢ ~Ll O U~ ~ ~ ~ ~
_ .
24 6 4/3 _ 4 _ 3
:~ 3 3/4 4 2 3
25 6 -3 4 4 1 O
2 _ _ _ _ _
6 4 4 4 3 2
- 26 2 4/3 4 33 3 1
: . ~ _ 1. .
27 6 3/4 4 4 2 2 '';
2 3 3/4 4 2- 2 1,~
28 6 _ 3/4 _ 2 2
2 3 3 4 2 2 I j:
29 4 _ 4 _ 4 _
2 3 4/3 3 3 3
- continued
- 24 -
,. . .
$ ~
;'
r
_
O ~: U ~ U X ~:1 D ~
O . H U~ H ~ ~ H H
U~ C ) ~ ~ ~ 1 0 1:'1 H
O F~ ~ O U~ . fI~ ~ O U~ ~
. _
6 4 4 4 3 3
. 30 4 4 4 4 3 3 F
2 3 3 2 2 2 . ~
_ t
6 4 4 3/4 3 3
31 4 4 ~ 3/4 2 3/2
2 3 - 3 2 1/2 2
.... ~, ,
SUTAN 6 2 2 2 1 0
(CONTROL ) 4 _ _ _ _ _
. 2 _ _ _ _ _ t
. . _
TILLAM 6 2 3 3 2 0
( CONTROL ) 4 _ _ _ _
2 _ _ _ _ _
__ . ~fVERNAM 6 4 4 4 3 0
( CONTROL ) 4 . _ _ _ _ _
2 3 3 2 2 0
: _
EP TAM G 3 j 4 4 3 3 / 4 0
_ . _ . .
( CRoNPAMROoL ~ 6 > 2 / 3 2 1/ 2 O
.. -- .~
-- 25 --
