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Патент USA US2127879

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I Patented
2,127,879
23, ‘1938 ‘Y 1
UNITED‘ STATES PATENT OFFICER
1 2.12am
on. m m ms'rrnoor'md ;
msnwuann Us]:
>
-
um Martin, Basel, Switserland, alalgnor' to
the?nn o! I. IL'Geigy 8. A" Basel,‘ Swltlcr
No' Drawing. ‘Application mm." 2a, 1031. so
its?‘ No. 123.061. In Germany, February 7L
i 11 cums, (01. 161-31)
Instead of CH; other alkyl or aralkyl and aryl
tain the live or six'sided atomic ring group
groups such as ethyl, butyl, amyl, benzyl, phenyl,
It has been found that compounds which con- '
' ethyl,- phenyl, p-chlorophenyl may be present.
00
(4) Benzotet'ronlc-acid-s-carboxylic acid-ben
,
“ \o?-co-n
zylester
\ 2*‘)
,
0
00
in the molecule are valuable insect combatting
agents. .
\
In the above formula:
.
- group.
(5) Benzotetronic acid-m-carboxylic acid-amide
and can at the same time be a. member of
'
co
R represents —0-alkyl. --O-aralkyl, '--NH:,
—NH-alkyl, —NH-aryl, NH-- and N=cyclo
guanyl radicals, other nitrogen-containing
I
a
(6) Benzotetronic acid-a-carboxylic acid-pi
’
peridide
‘Such compounds are for example:
'(1) Tetronic-a-csrboxylic acid ester
-
'
-
,
co
'
/
Y
cur-om '
' )cn-co-né
0/ O
CH1
on, >
CHr-CBI/
The nitrogen atom may bear other divalent cyclo
alkyl radicals, nicotine or anabasine being em '30
ployed in the place of piperidine.
0
, wherein alkyl vis represented by the groups CH1.‘
vCiHs, C3111; C4110, 651111. In the place of
[(7) Benzotetronic ‘acid-u-carbonylic ‘acid-‘ure
ide
at.
3.5'
.\
.
I
co
acn-cofnn-‘co-Nm
'
in the ‘above formula there can be they grouping ’
0/
cam-0n
(8) Benzotetronic
guanidide
l (2) Dehydracetic
V l acid
_
acid - a - carboxylic
'
'
_
\
40
.
aCH-CO-NH-f-(f-NE
o
CH:—
acid
,
co
CH/C0\aCH-CO-CH:,
45
o
or the custom‘, CaH-z, CsHo, CsHu amide thereof
radicals or ring‘ systems, or simple or substi;
'40
'H
0/
stituted tertiaryv amino groups, ureido- and
tuted alkyl-, ar'alkyl- or aryl groups.
\
_ \uCH—CO-—N<H
alkyl or corresponding single or mixed sub- _
20
10
from OH: to CsHu may also replace the benzyi
rated or unsaturated,‘ unsubstituted or sub
stituted carbon bridge which closes the ring
further ring systems, and
,
'I‘he'chlorobenzyl, phenylethyl or alkyl radicals
x represents a single‘ or double membered, satu
‘
\
wn-co-o-cm-O
o/to
.
I
H
s
0/
(9)‘ Benzotetronic acid-a-carboxylicacld-anilide
O
o
The two methyl groups can 8also be replaced by
.one or two phenyl groups.
-
'
(3) a-Aceto-benzotetronic acid ‘
CO
.
-,
:OILCO-CH:
0/o
Instead of the phemrlradlcal there may be men
tioned tolyl, unsubstituted or substituted amino
phenyl, mono- or dichloro-phenyl, ¢_-/p-naphtbyl,
.
,
,
2
2,127,a're
cyclohexyl, methyl-cyclohexyl, diethylaminoeth
ylene and similar radicals.
(10) Benzotetronic
methylanllide
acid-a-carboxylic
CO
acid
skin (according to Anschiitz, Annalen der Chemie.
1909, 887, page 201, halogen cumarines produce
blisters on the skin and strong itching) ; in addi
tion they are quite colourless, which is an ad
vantage over the yellow coloured thiocumarine;
the latter feature is particularly important as
regards the use of these insect combatting agents
CH:
aCH-C O—N
0/0
on textiles.
10
I
The above mentioned insect combatting agents
The alkyl group may vary from CH: to CsHn;
instead of the phenyl radical there may be at the
same place the groups mentioned below of
15 Formula 9.
(11) Benzotetronic acid-a-carboxylic acid
phenyl-hydrazide.
10
can be employed by. the usual processes. Solu
tions in water or in cheap organic solvents can
be used for spreading, sprinkling or dipping the
materials and textiles to be protected; they can
also be atomized without harmful effects being 15
noticed on warm-blooded beings. Pelts, feathers
The phenylradical may also be substituted by
or wool treated with such solutions can be pro
tected in a lasting manner against moths. Pre
cipitation of the effective substance from alkaline
solution on to the article to be protected by 20
means of acid leads to the same result. If plant
parasites are sprayed it will be found, for example
one or more halogen atoms.
on ?ies or walking-sticks that the poisoning ef
20
0/. °
v25
-.
.\
fective and in\\par't more bearable to the human
(12) ‘2.3 - naphthotetronic acid - a - carboxylic
acid-ester
v
'
-
The following examples illustrate the invention,
the parts being by weight:
o/0
30
feet by contact is very good.
Furthermore, solutions or emulsions in oils, 25
creams, fats may be used or the compounds may
be added to powders or they may be used in any
form usual for combatting insects.
'
The alkyl group may vary from CH: to CsHn.' -
30
Example I
The atom grouping
2 parts of dehydracetic acid are dissolved in 98
parts. of alcohol; pelts, feathers or wool are
3'5
treated for example by dipping, then centrifuged
and dried. The goods so treated are moth proof. 86
Quite dilute solutions sumce to obtain a satis
0
is an essential part of all these compounds, X
40 being a single or two membered carbon bridge.
Through the substitution by three CO groups,
factory protection against moths.
If instead of the above mentioned dehydracetic
acid, use be made of derivatives of tetronic acids,
as dichlorbenzo- or benzotetronic acid
the hydrogen atom of the a-carbon atom becomes such
carboxylic acid ester, for example the methyl-,
very reactive, wherefore compounds of this kind ‘ethyl-, propyl-, amyl- and other esters, or other
have a strongly acid character. They therefore
dissolve easily in alkalies and can be precipitated mentioned a-ketosubstituted tetronic acid deriva
tives such as ketones, carboxylic acid-amides,
again by the addition of strong acids. By suitable -anilides
or -diethylethylenediamides, an equiva
substitution in the groups linked to the above lent effect is obtained.
typical atom grouping the solubility in water or or
ganic solvents can be altered and the physiologi
50 cal effectiveness in?uenced. In particular amino
or halogen substituents in the aromatic and ali
phatic side groups have notable in?uence.
Substituted condensation products of un
saturated aromatic hydroxy-acids have already .
been proposed as insect destroying agents.
Under these fall halogen substitution products of
cumarine or the homologues thereof or the de
rivatives thereof, all substances containing a
substituted pyrone ring. Fluo-, bromo-, chloro-,
00 alkyl, aryl-
and thio-cumarines are named.
The type of compound used in the present process
can be termed an a-keto-y-lakton, in which how
ever to obtain remarkable effectiveness an addi
tional -CO-group must be bound to the a-posi
tion carbon atom. Chemical consideration of the
structure of these curamine derivatives in com
parison with the present a-ketotetronic acids
40
Certain parasites such as walking-sticks are
killed by spraying with the above mentioned alco
holic solutions. The said compounds are. also’
good when used as contact agents against ?ies.
Example II
A concentrated aqueous solution of the com
pounds mentioned in Example I, is made with
the aid of alkalies, the material to be treated
dipped therein and then acidi?ed, whereby a sat
isfactory protection against insects is again ob
’ tained.
What I claim is:
1. A devitalizing composition of matter for 60
combatting pests of the insect class, containing
as its essential active ingredient a compound
represented by the formula
/
65
(a-carbonyltetronic acids) immediately shows
the fundamental difference between them. De
hydracetic acid which is outstandingly effective,
behaves chemically entirely differently from a‘
cumarine. The same applies to the a-kEtOSllb
stituted tetronic acids.
'
'
Compared with the cumarine derivatives men
75 tioned above, they are in part notably more ef
X being a ring closing grouping selected from
the groups
70
-cm-, >CH-lower alkyl, -—CH=(|J—- , —CH=C—-,
CH|
cHl
phe'nylene, 'naphthylene, and R. being a mem
75
3
2,127,879
ber of the group consisting of —0.lower alkyl, . as its essential active ingredient a compound
--O.arallryl, —-N'Hz, —NH.lower alkyl, -NI-I.aryl, represented by the formula
aryllllower alkyl, -NH— and —N=cycloalwl.
00
acH-c0-c.ni.+1
lower alkyl, aralkyl and phenyl.
2. A devitalizing composition of matter for
0 .
combatting. pests of the insect class, containing
0/
as its essential active ingredient a compound
represented by the formula
10
00
n being a number from 1 to 5.
a 6. A devitalizing composition of matter for
combatting pests of the insect class, containing 10
°
\wnJL-R
as its essential active ingredient a compound
represented by the formula
0
00
0/
- “on-coo c.H,.+1
15 B being a member of the group consisting of
alkyl, —-NH.aryl, aryllTlZlower alkyl, —N'H—- and
-—N=cycloalky1, lower alkyl, aralkyl and phenyl.
20
3. A devitalizing composition of matter for
combatting pests of the insect class, containing
as its essential active ingredient a compound
15
o
—O.lower alkyl, —0.aralkyl, —NH:, -NH.lower
0/
n being a number from 1 to 5.
_
-
7. A devitalizing composition of matter for
combatting pests of the insect class, containing‘as 20
its essential active‘ ingredient a compound repre
sented by the formula
represented by the formula
00
25
0
Emma-on
GR
0,
0/
' B being a member of the group consisting of zero
R being a member of the group consisting of and CH3.
,
30 lower alkyl and aralkyl.
4. A devitalizing composition of matter for
8. A devitalizins composition of matter for 30
combatting pests of the insect class, containing
combatting pests of the insect class, containing
as its essential active ingredient ¢-aceto—benao
as its essential active ingredient a compound
tetronic acid.
represented ‘by the formula
,
9. A devitalizing composition of matter for
_ combatting pests of the insect class, containing
as its essential active ingredient u-carbanilido
benzctetronic acid.
0
.
X:
0/
wherein X1 is a member of the group consisting
of H, lower alkyl, aryl of the benzene and naph
thalene series, monovalent cycloalkyl radicals,
and X: is a member of the group consisting of
H, lower alkyl, aryl of the benzene series, X1 and
x: being together a divalent cycloalkyl radical.
5. A devitalizlng composition of matter for
combatting pests of the insect class. containing
25
10. A devitalizing composition of matter for
combatting pests of the insect class, containing.
as its essential active ingredient benzotetronic
acid ethyl ester.
11. A method of protecting materials against
pests of the insect class, comprising treating the
materials first‘ with a strong alkaline aqueous
solution of a compound named in claim 1 and
thereupon with an acid agent.
HENRY MARTIN.
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