1-DIMETHYLCARBAMYL-3-BRANCHED ALKYL-1,2,4-TRIAZOL-5-YL-(N-SUBSTITUTED) SULFONAMIDES AND USE AS INSECTICIDES

SULFONAMIDES DE DIMETHYL-1 CARBAMYL-3 ALCOYLE RAMIFIE TRIAZOL-1,2,4 YL-5 (SUBSTITUES EN N)

English Abstract

Abstract of the Disclosure
Triazolylsulfonamides of a limited class are
substantially non-phytotoxic and are useful as insecti-
cides. For example 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-dimethylsulfonamide is effective
in aphid control, both by foliar application and
systemically.

Claims

The embodiments of the invention in which an exclusive property
or privilege is claimed are defined as follows:
1. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-
N,N-dimethylsulfonamide.
2. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-
N,N-(3-oxapentamethylene)sulfonamide.
3. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-
N,N-diethylsulfonamide.
4. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-
sulfonamide.
5. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N-
methylsulfonamide.
-16-

6. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N-
methylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-
N,N-diethylsulfonamide.
7. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N,N-
pentamethylenesulfonamide.
8. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethyl-3-propyl-1,2,4-triazol-5-yl-N,N-dimethyl-
sulfonamide.
9. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N-
butyl-N-methylsulfonamide.
10. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-isopropyl-1,2,4-triazol-5-yl-N,N-
diethylsulfonamide.
-17-

11. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N,N-
(1,4-dimethyltetramethylene)sulfonamide.
12. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N-
propylsulfonamide.
13. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N,N-
(1-oxa-4,4-dimethyltetramethylene)sulfonamide.
14. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N-
phenylsulfonamide.
15. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-cyclopropyl-1,2,4-triazol-5-yl-
N,N-dimethylsulfonamide.
-18-

16. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-cyclopropyl-1,2,4-triazol-5-yl-
N-ethylsulfonamide.
17. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-cyclopropyl-1,2,4-triazol-5-yl-
sulfonylazide.
18. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-N-
benzyl-N-isopropylsulfonamide.
19. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of 1-N,N-
dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-5-yl-
sulfonyl azide.
20. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-dimethylsulfonamide.
21. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-(3-oxapentamethylene)sulfonamide.
22. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-diethysulfonamide.
-19-

23. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-sulfonamide.
24. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-methylsulfonamide.
25. 1-N-methylcarbamyl-3-tert.butyl-1,2,4-
triazol-5-yl-N,N-diethylsulfonamide.
26. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-pentamethylenesulfonamide.
27. 1-N,N-dimethyl-3-propyl-1,2,4-triazol-
5-yl-N,N-dimethylsulfonamide.
28. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-butyl-N-methylsulfonamide.
29. 1-N,N-dimethylcarbamyl-3-isopropyl-
1,2,4-triazol-5-yl-N,N-diethylsulfonamide.
30. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-(1,4-dimethyltetramethylene)
sulfonamide.
31. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-propylsulfonamide.
32. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-(1-oxa-4,4-dimethyltetramethylene)
sulfonamide.
33. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-phenylsulfonamide.
-20-

34. 1-N,N-dimethylcarbamyl-3-cyclopropyl-
1,2,4-triazol-5-yl-N,N-dimethylsulfonamide.
35. 1-N,N-dimethylcarbamyl-3-cyclopropyl-
1,2,4-triazol-5-yl-N-ethylsulfonamide.
36. 1-N,N-dimethylcarbamyl-3-cyclopropyl-
1,2,4-triazol-5-yl-sulfonylazide.
37. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-benzyl-N-isopropylsulfonamide.
38. 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-sulfonyl azide.
-21-

39. The method of killing aphids on plants
comprising applying to the plants a substantially non-
phytotoxic but aphicidally effective amount of a
compound having the generic structural formula
<IMG> I
in which R1 is C3 to C4 secondary or tertiary alkyl or
cycloalkyl, R2 is hydrogen or methyl, R3 is methyl, R4
is hydrogen, methyl or ethyl, R5 is methyl or ethyl or
R4 and R5 together may be azo, with the added provision
that when R1 is tert.butyl, R4 may also be C3 or C4
alkyl or cycloalkyl, R5 may also be C3 or C4 alkyl or
cycloalkyl or phenyl or R4 and R5 together may also re-
present the remainder of a 3- to 6- membered ring structure,
selected from one of the following:
<IMG> , <IMG> , <IMG> ,
<IMG>
-22-

40. A compound having the generic structural
formula
<IMG> I
in which R1 is C3 to C4 secondary or tertiary alkyl or
cycloalkyl, R2 is hydrogen or methyl, R3 is methyl, R4
is hydrogen, methyl or ethyl, R5 is methyl or ethyl or
R4 and R5 together may be azo, with the added provision
that when R1 is tert.butyl, R4 may also be C3 or C4
alkyl or cycloalkyl, R5 may also be C3 or C4 alkyl or
cycloalkyo or phenyl or R4 and R5 together may also re-
present the remainder of a 3- to 6- membered ring structure,
selected from one of the following:
<IMG> , <IMG> , <IMG> ,
<IMG>
23

Description

:
~ DESCRIPTION OF THE INVENTION
'
It is known that some carbamyltriazolylsulfon-
amides are useful as herbicides. However, we have dis-
. covered that substantially non-phytotoxic compounds
- which are extraordinarily effective as both systemic and
.
;.: contact insecticides are members of the class having the
. generic structural formula .
`''' . `'' '
:
',:', '
~ 2
,............................................. / .: ~
. R4 O=C-N
\ N~ R3 ~ :
; R5
~,
'` ~. . :::
. ':;. ,~
,: ~ ` '.: '
,
.. .. .
. :
. ` ,
.. , ~
.. " `,.-: .
: -2- ~ :
- :
. ' .
, . - , , ~ .

104~0~
in which R is C3 to C4 secondary or tertiary alkyl or
cycloalkyl, R is hydrogen or methyl, R3 is methyl, R4
is hydrogen, methyl or ethyl, R5 is methyl or ethyl or
;: R4 and R5 together may be a20, with the added provision
;~,k 5 that when Rl is tert.butyl, R4 may also be C3 or C4
alkyl or cycloalkyl, R may also be C3 or C4 alkyl or
; cycloalkyl or phenyl or R and R5 together may also re-
, present the remainder of a 3- to 6- membered ring structure,
as for example, one of the following:
.
/CH2-CH2 lCH3 / CH2CH2
-' lS) ~ CH-fH2 ~CH2
. CH2-CH2 , ~CH-CH ~C C/
."A. CH3
.~ .
'''' '
: ~ ` f
~C~CH2
CH3 CH3
The nature of the substituent group Rl appears to
be particularly critical with respect to absence of phyto-
toxicity and efficacy as insecticides. The nature of the
substituents, R and R5 also has an observable effect on
insecticidal characteristics, both on contact and
. . .
systemically.
Preferred compounds are those which are effective
: both systemically and by contact, as they are more versatile
and more economical to use to combat chewing or sucking
. .
.
_3_ S-553
.' , .
. .
.

` 104109~
insects such as aphids. Particularly preferred compounds
are those in which Rl is te~ t . bu~yl. A laboratory method
-~ of preparation of these compounds from cor~ercially avail-
js
` able intermediates is as follows: -
Preparation of 3-tert . butyl-4H-
- 1,2,4-triazolin-5-thione
';
To a suspension of 50 g (0.55 mol) of thiosemi-
carbazide and 43 g (0.05 mol) of pyridine in 300 ml of
dioxane was added 42.6 g (0.6 mol) of pivalyl chloride,
with cooling. The reaction was stirred at room tempera-
ture for 72 hours, then poured into water. The resulting ~
solid was collected, washed with water and dried. The ~-
unpurified pivalyl thiosemicarbazide was heated at reflux
temperature in 300 ml of 10~ sodium hydroxide solution for
3 hours. After cooling, the pH was adjusted to 4 with
hydrochloric acid and the product collected, washed with
:- -
water and dried to give 43.8 gr m.p. 200-203. Recrystalli-
zation from methanol chloroform gave a sample, m.p. 203-205.
Using a similar procedure, 3-isopropyl-4H~1,2,4-
triazolin-5-thione, m.p. 194-5, was prepared.
The structural formula may be written in either
the thiol or thione form, as shown in the outline of
synthesis reactions below.
.~;.. ; . . ,
-: ,
.:
',
,; - ~ .
;: , , .. '~v
.- :
~ -4- S-553
,''' .'~
,:; :
, .
.. : . ', '
.

'" la4l0~6
Synthesis o~ 3-tert.butyl-4H-1,2,4-
triazol-5-yl N,N-dimethylsulfonamide
.~ This synthesis may be conveniently accomplished
. ~ , . .
~ by means of two steps which are outlined as follows:
., .
1.)HS ~ ~Cl ~ ClSO2 ~ N
~ H C(CH3)3 E li c (CH3~3
. ,~' . .
., ,
, . ' .
2.) ClSO2 ~ +(CH3)2NH ~(CH3 ) 2N-S~ 11
H-N C(CH3)3 H-~- ( 3)3
Reaction 1.)
" ' ' ' '
; Chlorine gas is introduced through a fritted glass
delivery tube beneath the surface of a stirred slurry of 50 g
(0.32 mol) of 3-tert.butyl-4H-1,2,4-triazolin-5-thione in
. 450 ml water. The temperature of the reaction mixture is
maintainea at 0 to -10 by means of an ice-salt bath. When
absorption of the chlorine is complete (about 76 g C12) the
slurry is filtered and the solid washed with water. When dry,
the solid 3-tert.butyl-4H-1,2,4~triazol-5-yl sulfonyl chloride
melts at 166-168. The solid is used while still slightly
damp for the next step in the reaction sequence.
:.
-5- S-553
. ' ' ' ' ~

`;` 104~
.:.. : : .
;~ Reaction 2.)
,, ~ .
, ;~ .
:'" The entire product from reaction 1.) is added
~,~, in small portions to 72 g (0.64 mol) of 40~i aqueous di- ~
' methylamine wi~h stirring and cooling. The slurry is ~-
stirred one hour, then the solid is filtered and washed
with water to give 46.0 g (62% yield) of 3-tert.butyl-
,~ 4H-1,2,4-triazol-5-yl N,N-dimethylsulfonamide,
. .
m.p. 204-207.
, By using similar procedures and various commer-
cially available amines in Reaction 2.) a great variety
. . .
;'~ of compounds ha~ing structure II may be prepared.
; ~.. . .
::':'.~,'
. :-, .
. "i . ': ~ ' '
N-SO2 ~1 ~N II
.' R H-N ll Rl
Specific examples of such compounds are listed below:
R R -~- - R5 m p. (C)
rJ 15 (CH312CH- CH3 CH3 162-4
;~1 (CH3)3C- C2H5 C2H5 158-60 ;~
(CH3)3c- C2H5 H 194-6
~";,, (CH3)3C- CH3 H 205-7
' '' (CH ) C H H 166-172
(CH3)3c- -CH2-CH2-0-CH2-CH2- 229-231
: - ,. , .:
.:
.
:,
, -6- S-553
' , : .
' , . ' ., .

~ 1(341096
. .
Synthesis o~ l-N,N-dirnethylcarbamyl-3-
tert.butyl-1,2,4-triazol-5-yl-N,N-
dimethylsulfona~lide (Compound No. l)_
~"~
.
~` - o=f -N(CEI3)2
(CH3)2NS2 ~cl-~-N(cH3)3 --~ (CH3)2NSO ~ N ~N
H- C(CH3)3 N ~ C(CH3)3
~. ~
Dimethylcarbamyl chloride (3.4 g, 0.032 mol) is added
510wly to a solution of 4.2 g (0.018 mol) of 3-tert.butyl-4H-
- 1,2,4-triazol-5-yl N,N-dimethyl sulfonamide in 20 ml of benzene
and 20 ml of ~yridine. After refluxing overnight, the mixture
is evaporated and the residue is partitioned between water and
.
10 chloroform. The chloroform solution is evaporated and the
. .
residue parti;ioned between water and ether. Evaporation of
the ether solution and recrystallization of the residue from
hexane gives l-N,N-dimethylcarbamyl-3-tert.butyl-1,2,4-triazol-
..-. !
5-yl-N,N-dimethylsulfonamide (compound No. 1) m.p. 108-110.
~, . .
Synthesis of l-N-methylcarbamyl-
. 3-tert.butyl-1,2,4-triazol-5-yl-
N,N-dimethylsulfonamide
''.
' ,:.:~
0=IC-NHCH3
(CH3)2NSO ~ ~ ~CH3-NCO ~(CH3)2NSO ~
- H-N C(CH3)3 ( 3)3
-:.
~ .
A solution of 8.0 g (0.034 mols) of 3-tert.butyl-
~ 4H-1,2,4-triazol-5-yl-N,N-dimethylsulfonamide and 3.4 g
-7- S-553
~. . ~ . : ;; -
. , .

` lV~1096
(0.06 mol) of methyl isocyanate in 20 ml of triethylamine
is stirred overnight at room ternperature. The solvent is
; evaporated under vacuum and the residue is slurried in
water. The resultant solid is collected by filtration and
recrystallized from ethanol to give l-N-methylcarbamyl-3-
tert.butyl-1,2,4-triazol-5-yl-N,N-dimethylsulfonamide,
m.p. 193-194.5.
Using procedures of the type exemplified above,
the following compounds represented by structural formula I
,;' ,. '
/ R
R \ ~ N \ \ R3
N 1I Rl
'. ' :
,. . . .
were prepared, as listed below.
..,;
.' ' :
' ~ '
. .
-8- S-553
- -
.'
.. . ~ ,. . .
. : . .

''''' 104~0~
COMPOUND MELTING POINT (Dey. C.)
l-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-dimethyl- 93-95
sulfonamide
1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-(3-oxapenta-
methylene~sulfonamide dec. 183-185
l-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-diethylsulfon- 90-92
- l-N,N-dimethylcarbam~1-3-tert.butyl-
1,2,4-triazol-5-yl-sulfonamidesemi-solid
~ l-N,N-dimethylcarbamyl-3-tert.butyl-
; 1,2,4-triazol-5-yl-N-methylsulfon-162-165
amide
l-N-methylcarbamyl-3-tert.butyl-1,2,4-
triazol-5-yl-N,N-diethylsulfonamide 56-60
l-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-pentamethylene- 106-108
sulfonamide
.
l-N,N-dimethyl-3-propyl-1,2,4-triazol-
5-yl-N,N-dimethylsulfonamide semi-solid
l-N,N-dimethylcarbamyl-3-tert.butyl-
: ~ 1,2,4-triazol-5-yl-N-butyl-N-methyl-semi-solid
-~ 25 sulfonamide
: l-N,N-dimethylcarbamyl-3-isopropyl-
.. : 1,2,4-triazol-5-yl-N,N-die-thyl- oil
sulfonamide
- l-N,N-dimethylcarbamyl-3-tert.butyl-
. 30 1,2,4-triazol-5-yl-N,N-(1,4-~imethyl- oil
; tetramethylene)sulfonamide
l-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-propylsulfonamide oil
l-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-(l-oxa-4,4-
dimethyltetramethylene)sulfonamide oil
l-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-phenylsulfonamide oil
'' ',
.
- 9 S-553

-
; 104~Q9~i
.
~ COMPOUND MELTING POINT (Deg. c.)
.::
l-N,N-dimethylcarbamyl-3-cyclo-
propyl-1,2,4-triazol-5-yl-N,N- 92-95
dimethylsulfonamide
1-N,N-dimethylcarbamyl-3-cyclo-
propyl-1,2,4-triazol-5-yl- oil
N-ethylsulfonamide
l-N,N-dimethylcarbamyl-3-cyclo-
propyl-1,2,4-triazol-5-yl-
sulfonylazide 63-67
.
.,? l-N,N-dimethylcarbamyl-3-teYt.butyl-
- 1,2,4-triazol-5-yl-N-benzyl-N-iso-
propylsulfonamide 126-127
l-N,N-dimethylcarbamyl-3-tert.butyl-
. ~ 15 1,2,4-triazol-5-yl-sulfonyl azide oil
:.'. .
':
,.'~.~ ' ' `~
.~ -:
. , ~ ~ . .: .: . :
, , :
. .
', ,
'
' "
.
: .
. : .
.
-10- 5--553
. . , : ' ' , " ' . .; '
.' .~ '; , ' :
- :
: ,.

104~0~
The structure illustra~ed by st~uctural formula I
above corresponds to the chemical names assigned to the
compounds listed above and is considered most li~ely
correct for these compounds. The presence of two other
` 5 possible isomeric structures represented by structural
formulas III and IV cannot, however, be excluded.
". -'.
~4 N
\NSO2 ~ N R \ N \ ~ R2
R~ ll 1 R~ ~N/------ i Rl R
R~ O l
.;:.,
III IV
.......
~,i INSECTICIDAL USE
:,, -----
The insecticides listed above were employed in the
-~; 10 killing of insects according to the following procedure, so
as to obtain comparative data:
Two 5 oz. Dixie cups containing Henderson Dwarf
lima bean plants and one 5 oz. Dixie cup containing Orange
Gem nasturtiums, all growing in vermiculite, are placed on
the turntable, and sprayed to thorough wetness with 25 ml
of an aqueous dispersion of the candidate chemical at con-
centrations of 500, 250, 125, 62, 31 and 15 ppm. Nasturtiums
were already infested with 50-100 bean aphids. The effects
on aphids were judged by examination of the nasturtium plants
24 hours later and were rated according to the following
schedule:
'
~ S-553
: , .

:
41096
.
0 = none dead
1 = 1-25 percent dead
, ..
; ; 2 = 26-50 percent dead
- .:
` 3 = 51-75 percent dead
4 = 76-99~ percent dead
.;. ~ . ~
5 = 100 percent dead
,: . , ,
~: ~ All of the compounds listed above gave a rating
of 5 at concentrations of 500, 250 and 125 parts per
; million. All but seven also gave a rating of 5 at 62 parts
lX;;~
;~ 10 per million concentration. All but si~ of the compounds on
, the list gave a rating of at least 4 at only 15 parts per
;~ million, indicating that they were capable of giving satis-
.
`~; factory control with repeated spraying at this concentration
~' level. The following compounds gave a rating of 5 (total kill),
even at the lowest concentration ~15 ppm) and are preferred
aphicides on the basis of contact efficacy.
,' ' . ' '
l-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-dimethyl- -
sulfonamide. ~ -
1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N,N-diethylsulfon-
amide.
: l-N,M-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-sulfonamide. -
- 25 1-N,N-dimethylcarbamyl-3-tert.butyl-
1,2,4-triazol-5-yl-N-methylsulfon-
amide.
l-N-methylcarbamyl-3-tert.butyl-1,2,4-
- triazol-5-yl-N,N-diethylsulfonamide.
' :
: . .
:,~. . . .
-12- S-553

~)410~
... , . i
. ` .
l-N,N-dimethylcarbamyl-3-te~t.butyl-
~- 1,2,4-triazol-5-yl-N,N-pentamethylene-
sulfonamide.
:.
1-N,N-dimethylcarbamyl-3-tert.butyl-
~ 1,2,4-triazol-5-yl-N~butyl-N-methyl-
;; sulfonamide.
:, .J
l-N,N-dimethylcarbamyl-3-tert.butyl-
- 1,2,4-triazol-5-yl-N-propylsulfonamide.
~" ,,
When 20 ml of aqueous dispersions of l-N,N-
- i
dimethylcarbamyl-3-ter~.butyl-1,2,4-triazol-5-yl-N,N-
~`l dimethylsulfonamide was applied at various concentrations
to the soil in which plants were growing instead of the
. . . .
; foliage, systemic aphicidal activity was demonstrated.
.~,.......................................................... . .
~`' This is shown in the table below, in which the same
` 15 scoring system was used and Meta Systox R was included
-~!
` in the same experiment as a standard for comparison
, ........................................................... . .
:
Score of Test Score of
Concentration (p~m) Compound Meta Systox R
1 4 5
....
The aqueous dispersions employed in the above
, ~ illustrative examples were prepared by dissolving 25 mg.
of aphicidal compound in 5 ml. of acetone and then
diluting to the desired concentration with water contain-
ing 1.2 ml. of a commercial octylphenoxy polyethoxyethanol
non-ionic surfactant (Triton X-100) per liter. By keeping
surfactant concentration constant during dilution, dis-
.
persion is quick and the resulting homogeneous liquid has
: 3C the appearance and behavior of a true solution. By
- spraying at a variety of concentrations, the efficacy
* Trade Mark
-13- S-553
.'',- ,~ ..' ' ~' .
-, ", .

~;
:
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of the aphicides is demonstrated and a standard is provided
, -~ by means of which the skilled worker in the art can adjust
the concentration to suit his needs. Water-dispersible
solutions of the aphicides are readily prepared by conven-
,x;~ 5 tional methods, employing non-phytotoxic commercially ~ -~
available emulsifiers, dispersing agents and auxiliary
~i .. . .
~, solvents. Other additives may be employed in formulations
to reduce spray drift and aerosol formation, regulate
., .
, viscosity and for other purposes, according to known practices.
In commercial use the aphicides are conveniently
stored and shipped in the form of water-dispersible solutions
i
~i or wettable powders and are diluted with water just prior to
spraying. Because of the rather high efficacy of the compounds
it is impractical to apply them uniformly to plants without
~,..................................................................... . . .
~ 15 some sort of carrier or diluent. Water is the preferred ~'
, .
carrier or diluent but either or both solid and liquid diluents
~' may be employed with the aphicides of this invention. The
- aphicides may be conveniently formulated as liquid emulsifia~le
concentrates or as emulsifiable powders according to repre-
: . :
~ 20 sentative procedures given below. All parts are parts by -~
;` weight unless otherwise indicated.
:: -
" Wettable Powder
Aphicide , 10 parts
~' Barden clay 8 parts
, 25 Sodium dialkylnaphthalene 1 part
sulfonate (75~ active;
;~ *Sellogen HR)
- Sodium-based lignin sulfon- 1 part ate dispersing agent
: 30 *(Polyfon H)
,
, * Trade Marks
:
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-14- S-553
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; :
:; ~
1~4109f~
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;~ The resulting dry powder was easily dispersed
, in water to make up liquids for spray application.
' Water Dispersible Concentrate
, In a solvent mixture containing 257 parts of
...
:', 5 isophorone and 257 parts of mesityl oxide there was
. .:;,
, dissolved 40 parts of aphicidal compound, 30 parts of
i#i lipophilic emulsifier blend of anionic and nonionic
surfactants (T-Mulz 0) and 30 parts of a hydrophilic
emulsifier blend of anionic and nonionic surfactants
(T-Mulz W). The resulting liquid was a 6.5 percent
active water-emulsifiable concentrate which was useful
f~)r rep~ring Aqueotl~ ~sprav mixtllres.
. . .
The aphicides of this invention may also be
formulated according to conventional methods as oil
, 15 sprays, microencapsulated powders, dusts and thickened
; aqueous sprays. The aphicides of the present invention
need not be applied directly to the body of each insect,
but only to the locus of the insects, that is, the place
inhabited by the aphids, generally stPms and foliage.
~ 20 Whether the aphids contact the aphicide during or after
,,- spraying is immaterial. Toxicity of the compounds to other
types of insects, in general is relatively low, so that
. .~ .
populations of predatory and competing species will remain
established, even though plants are sprayed to obtain a
substantially complete kill of aphids.
~ .,
* Trade Marks
i: . '.
'"' '
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-15- S-553
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' S~s ~'
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