CA1156669A - Carbamoyl sulphoxide compounds having pesticial activity - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE:

Compounds of the class of carbamoyl sulphoxides, having the general formula:

Description

The present inve-ntion relates to new carbamoyl eulpho-xide derivatives having the general formula 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.

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%

.

- ~ -- .

-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 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 ,~ r~ ~ r I~ ~_~ I~ ~ ~
_ ... I
. . a~ .
. ~ ~ O * ~:* r~
O ~ O a) O r-l ~ r--l ~ ~ X ~ O
ra ~ ) u~ u~ r-l ~ r~l ~ V V
r~ u~ ~n ~ 5 ~ t~) ~ V V \ /
~ ~ 1:~ ~ X ~ ~5 X ~O \ / Z
O X ~ ~r ~ U U U V Z l .~: ~ ~ V O \ / \ / l O=V
~ V V\ / Z' Z O=V l r~l \ ~ Z I I I O~U~ r ~ O = UZ O=V O=y O= lVO<~ 1~
l l O~U~ O~U~ ~I 5~
r O~u~ O~tq l I Pd U
o ,J\ ~ m~ m~

U U U U U U O ¦
~t~
r-l O _ GO
S ~ ~ ~ ,_ ~ r~ .~ oo '~ ~h a ~D ,~ ,~ ,_ ~0 ~ .
a) a) o ~, O ~` O ,~ ~ o`
... ___ . .. _ r~
~ . .
O O ~ * ~ ~ ~ . .
a) a)a) a) r~, r-l r~) m ~
u~ u~ ~ r~l ~ r-l tr) ~ ~ U
m m ~ ~ m ~ ~ u x ~ m m ~D ~ ~ ~D u\ u ~` /
~ u\ /v~ u~\ v~ u\ v u\ y o-v o-u h I O=V O-~V I
t~ O = V O=V l I u~
r l ~ u~ u~ 1~ m~
r~ ~i 1 m m v v E~ ~ ~C~ ~ ~ ~ ~ ~

. . . .
æ _ . . *' _ ~ _ ~a) ~ ~ ~ 00 c~ '~ ~ .
o ~ a) ~ ~ oP ~ ~ ~ ~,~ ~ ~
~ ~ ~ ~ ~rl ~ ~ 3 0 ~ ~, ~ ~ t)O U~ O .,, ~ ~ a~ ." ~ ~ ~ I ~ O ~ S
0 ~ r~ ~ ~ U~ O ~ ~i~l O ~ ~'~ ~~ ~ ~~ ~ ~ . 3 ~ rd tQ ~ o~1 ~ ~' i .C,!: ~ S~ ~ ~ ~ ~rJ a) O ~
~ t) rl C) . ~r ~ ~ O
F~ I O
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n ~. ~ N a~ 0~ r I Ll-) ~r o In ~ ~ m m ~
O ~I ~ ~ ~
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O Ux\ /~ O~ ~ZU ( ) o._Z

U~ l l Z 0 O--U , 0~ 1 O=U
~ O ~U~ ~ l ~q ~, i~ I /1 .C~ ~ ~ o~

~5 _ O . . o - _ . ~:
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O=C~ Ul~ ' lZ/

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h Ql ~ ~-) O . o O O r~ L
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,~ ~ ~r ~ I ~ I ~ I O ~-1 o .,~ ~
~ I ~ I r-l ~D r~ r~ a~ ,~ ~ ~J -'o ~r' ~0 ~ o Ln ~ O o O r ~, In ,, ~ GO ~I rn r~ r~t~ o~ ~D ~D r o ~
~l- Ln l- ~ D~ l~ N O C~ r _ ~~ ~r o ~ ~r o n ~~r o ~r ~
o\ _l,~ ~1 r~ ~1r-i 1--I~1 u~ O Z U~ C.) Z tJ~ Z V~Z V~ z r~q ~ Ln ~ ~I Lr) ~ (~ ~ r~~) ~1 ~r ~
rl ~ D 1~ ~ ~O N ~ ~ N C~ F
~ ~ ~ O r~l ~ O Ln ~~r ~ Ln rl r~; r~ rl ~-1 rlr l r l ~'t ~_'t Z t,~_ O Z U~ , Z U~_ Z t~ Z U~
C
t~ _ r~ Ln ,~
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N N N N
t'~) t~ t~ C t N
'X ' I ~1 ~1 ~_X~ ~t ;~ O=C) O=C,t O=c.) ~_~ lZ t ~ o~ ~ o ~n o ~u, z o =~ t ,~ N ~ N O y O~-U~
O O C,) C~ O ~ U~ N

t.~ Xt ~1 CO rxt rxt . ~ t,- ~D ~ ~ rl ~0 . _ ' ._...r~ <~ 1 t~
t.~ N N N
. N
r~ I ~ ~
$ ~1 ~1~ I C~ C~ r~
Z Zlt, 5~_~., r~
t~O = U O--1~ O--t;~ Z _ r~ N ~1 ~n ~ o=y rt X C ) :C J~ U~
~ f~ ~ ~ _~_ ~
_. .__ -I
O N ~) ~ Lr) iSt rl rl r~ rl rl _ ~, -- 6 .~t. . ~

-- - - -- - -r~ r~ r~
l o rl o ~ ~: r~ l ,~ ~ ~ ~ ~ ~ ~ ~ L
~ ~ ~ U7 ~ IU~ U~ I
O t.) U)3: rl ~ 3 r~ 3 0 ~ O 3 QIr rl (~ ~)O ~ O O ~ O tn O ~ O u~ ~ ri .
u~ h r~,~ ,a t~ ,~ ,~ ~ o rl r->1 11~ ~r~ O U~ r-l O r-l 1~ U~ 13 r-l r-l t~l O r-~
u~ a) ~ " a) ~ a) s~ ~ o Q~ 1 ~ ~1 ~> ~ ~H >1 0 ~ O ~ ~ ~1 0 ~ ) . _ _ . ~ ~ 1- ~ a~ ~ ~-~~ ~ ~ ~01:) r l r-l OD t~ u7 _ ~ ~ ~ >
O~o ~ ~Lr~ ~r o u~ ~ ~ Lf) u~ ~o r~ ' r~ r~ r~
r ~ z u~ ~ ~ ~
~ r ,~ ~ ,~ ~r Lr o ~ o~ ~ a~ ~
~D I~ ~ O ~ r~ ~ r~ ~D
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O ~D In ~r o ~D ~ ~r o r~ r~ r~ r~ r~ r~
z u~ z u~ z u~ z u~ z u~ l~
l l l ~) o Lr) ~ ~ r~ o ~ o o $ ~ ~ _ ~ I j a) ~ ~ ~ ~
~X ~;~ ~ X~ ~Z/ ~q~

,~ ~1 o~ z o=~,) ~:1 ~ Z 0~ ~ O--~ O~n o=o ~ o=~ l l ~ o~v~
~ o~l ~ o~ ~ ~
R U U U I ~ X
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h ~ ~ ~ o ~ ! .
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a)-- ~ O O o Lt~
r~ O ~ O .
_ ,. r~ r~ _ ~ - ~ -~ -~ ul 'c:l ~z/ c~l Q ~ 1 -C,) - = ~ --C) h Z I o=o (`l ul ,01 0-0 ~ ~r ~ ~`
E~ ~ ~ t)l [~ ~:1 . , . ~
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--- - -l ~ ~a ~
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1~ ~ ~ O O O o ~-~1 ~ rl O O I Lq ~) u~ O u~ ~1 3 rl -~1 ~ I a~ o , u~ I Ql~ ~ O .1~ o .~ !' ~n h I ~J t) .~ . ~ rl I 1~ ~1 td ~1 ~
I ~ 1 E~ Q. I ~ r O ~1 ~1 O ~1~1 ~ P
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oP ~ ~ ~ U~ ~D U~ ~\3~D ~ ~ ~r _ ~ ~1 ~1 ~1 ~ r . zu~ æ u~ z u~ zu~ z ~ t ~ ~r ~ o ~ ~D ~ OD ~ ~ ~ I
~ N1~ O 1` ~D ~ ~)~D ~ ~D
~ O ~t~~o ~ 11~ ~ ~9 ~r ~1 ~1 ~1 ~1 r-l Zu~Z u~ Z u~ Z u~ Z u~
I _ l I
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iV N
X X N Nin ~ N
O C~ _ ~ N U ~
Ql u~l X ~U ~1 u Z U~ Ul \ / ~:1 o=u ~1 z æ ~z o~ l ~z o=u O_y O=y ~o J\ o=y o~ 'o~v~ O~n ~ r~ I O~u~ I~ r~ t~
R ~ tc~ ~1 ml ~C

O Cl h rl I~ in ~-1 N tJ~r~ ID i-- ~
OR~NCJ~ .~ l ~ i IJ h r ~ " r~, ~~ _~1 O ~

N
N N ~ N

~ O-u Ul Ul U~ ~U~I ~
O Cl~ l O=U O=U O--U
5~: ~ O-U 11 Il~ _~~ ~ , U N m~ I u I
_ .
O N ~ ~r In ~D
Z N N _ ~ ~ N

,:

_ ~ 3, o ~ Ql o IL
Ul r-l . ~ ~ ~ ~ ~
~ ~ .,~ ~ U~ o ~ o .,, u u m 3 ~ i ~ oo 3 ,~
o O O ~1 In O ~ ~ I
u~ ~ ~ U. ~ I ~ (d ~ ~ ~
~n O ~D ~ O ~'O O r u~~ ,~ ~ ~ u~ ~ a) ~ rl ~ ~
U rl :~ O ~ ~ :~ ~ O
a~ ~ ~r ~ oo o I ~ c~ In ~ ~ I~ ~ ~ U~ O 00 ,~ ~
O~o~ ul ~ ~' ~ ~ n ~ a~ .
,1 X ~ Z U~ Z V~ Z U~ Zi ~1 ~ ~ , ~ ~ o ~ ~ ~ .
S: . U~ ~1 ~ O Ul ~ ~D ~) ~r ~
~I .~ ~1 ~1 Z U~ Z U~ Z U~ Z U~ Z U~ .

. _ O O _ O U) b .~Q ~~D ~ ~ ~ ~ .
. I_ ~- ~-~:~ X

X ~ N Z ~ X Z
~ '\<Z/ 0~1~ ~ ~ O=U t ; 1 O--: ~ ~ O ~ A ~ ~

O~ _ ~ Z _ ~:: N ~ ~ ~ I~ ~

~ " ~ o~~ ~ `I

C',~ ~ r~ ~ _"

~ ~ 5~ o=Z ~ w~ _ u 0=~) . ~ O=oO~ u~

W~ 5r~ m~

Z . _ O _ ~ 9 ~ ' G '~

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.

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 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 ~ .~.. .

-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~

- 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 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 _ ~
~.

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.

, 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 ~ .

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 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/~
_ . _ _ l 10 1 2 3 ~ 3 2 ~ 2 ~ O
. .

~ . ~ _ ~: ' 16 ~ 4 4 ~: 2 1 ' _ I. I, 2 3 ~ 3 3 O

continued 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 _ . . .

2 3 3 2 2 1 .
_

4 3/4 3/4 3 2 3 . _ 6 4 4 4 3/4 3/2 .

_~

2 3 3 2 3 2 I:
. .... ___ .

... _ 2 2 2 2 1 0 con-tir .ued 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 2 _ _ _ _ _ : . ~ _ 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 _ - continued ,. . .

$ ~

;' 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~ ~
. _ . 30 4 4 4 4 3 3 F
2 3 3 2 2 2 . ~
_ t 31 4 4 ~ 3/4 2 3/2 .... ~, , (CONTROL ) 4 _ _ _ _ _ . 2 _ _ _ _ _ t . . _ ( CONTROL ) 4 _ _ _ _ 2 _ _ _ _ _ __ . ~fVERNAM 6 4 4 4 3 0 ( CONTROL ) 4 . _ _ _ _ _ : _ EP TAM G 3 j 4 4 3 3 / 4 0 _ . _ . .
( CRoNPAMROoL ~ 6 > 2 / 3 2 1/ 2 O
.. -- .~

Claims (2)

The embodiments of the invention in which an exclusive property or p.rivilege is claimed are defined as follows:

1. The compound having the formula:

2. A method of controlling undesirable vegetation comprising applying to the locus where control is desired an effective amount of a compound having the formula: