Cyclic guanidine derivatives and their use as pesticides

Details Cyclic guanidine derivatives and their use as pesticides Cyclic guanidine derivatives and their use as pesticides

2001-08-17

2004-01-27

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Abscission agent, defoliant, or desiccant

C514S183000, C514S222500, C514S223800, C514S229200, C544S005000, C544S007000, C544S009000, C544S066000, C544S067000, C544S179000, C544S212000, C544S245000

Reexamination Certificate

active

06683028

ABSTRACT:

The present invention relates to novel guanidine derivatives, to a process for their preparation and to their use for controlling animal pests.
It is already known that certain heterocyclic compounds have insecticidal properties (cf., for example, EP-A 0 386 565, EP-A 0 428 941, EP-A 0 483 055, EP-A 0 580 553, U.S. Pat. Nos. 5,032,589 and 5,034,524).
However, the activity and activity spectrum of these compounds is, in particular at low application rates and concentrations, not always entirely satisfactory in all areas of use.
This invention provides novel guanidine derivatives of the formula (I)
in which
R
1
represents a five- or six-membered heterocycle which contains 1, 2, 3 or 4 nitrogen atoms and/or one or two oxygen or sulfur atoms as heteroatom ring members—where the number of heteroatoms is 1, 2, 3 or 4—and which is optionally substituted by halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkinyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkinyloxy, alkylthio, halogenoalkylthio, alkenylthio, halogenoalkenylthio, alkinylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, amino, alkylamino, dialkylamino, aryl, arylthio, arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and/or alkoxycarbonyl,
R
2
represents hydrogen or alkyl,
R
3
represents a radical from the group consisting of —OR
4
, —OCOR
5
, —OCOOR
6
, —OCONR
7
R
8
, —OSO
2
R
9
and —S(O)
n
R
10
, where
R
4
, R
5
, R
6
and R
10
independently of one another represent a radical from the group consisting of alkyl, alkoxyalkyl, halogenoalkyl, alkenyl, alkinyl, alkylaminoalkyl, dialkylaminoalkyl, optionally substituted cycloalkyl and in each case optionally substituted phenyl and benzyl,
n represents 0, 1 or 2,
R
7
and R
8
independently of one another represent a radical from the group consisting of hydrogen, alkyl, alkenyl and in each case optionally substituted phenyl and benzyl and
R
9
represents alkyl or optionally substituted phenyl,
A represents oxygen, sulfur or represents NR
11
, where
R
11
represents a radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, optionally substituted cycloalkyl or optionally substituted aralkyl and
Z represents cyano or nitro.
Furthermore, it has been found that the compounds of the formula (I) are obtained when compounds of the formula (II)
in which
R
1
, A and Z are as defined above, are reacted with halogen compounds of the formula (III)
 in which
R
2
and R
3
are as defined above and
X represents halogen (in particular chlorine or bromine),
in the presence of a base and, if appropriate, in the presence of a diluent.
Finally, it has been found that the novel compounds of the formula (I) have pronounced biological properties and are suitable especially for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forests, in the protection of stored goods and materials, and also in the hygiene sector.
The formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned above and below are illustrated below.
R
1
preferably represents a five- or six-membered heterocycle from the group consisting of pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl and pyrimidinyl which is optionally substituted by one or two, preferably one, substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, C
1
-C
2
-alkyl (which is optionally substituted by fluorine and/or chlorine), C
1
-C
2
-alkoxy (which is optionally substituted by fluorine and/or chlorine), C
1
-C
2
-alkylthio (which is optionally substituted by fluorine and/or chlorine), or C
1
-C
2
-alkylsulfonyl (which is optionally substituted by fluorine and/or chlorine).
R
2
preferably represents hydrogen or C
1
-C
6
-alkyl.
R
3
preferably represents a radical from the group consisting of —OR
4
, —OCOR
5
, —OCOOR
6
, —OCONR
7
R
8
, —OSO
2
R
9
and —S(O)
n
R
10
.
R
4
, R
5
, R
6
and R
10
independently of one another preferably represent a radical from the group consisting of C
1
-C
12
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms; C
2
-C
4
-alkenyl, C
2
-C
4
-alkinyl, C
1
-C
4
-alkylamino-C
1
-C
4
-alkyl, di(C
1
-C
4
)-alkylamino-C
1
-C
4
-alkyl, represent C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents, preferred substituents being halogen, C
1
-C
4
-alkyl and C
1
-C
4
-halogenoalkyl having 1 to 5 identical or different halogen atoms, such as F, Cl and Br atoms, or represents phenyl or benzyl, each of which is optionally mono- to trisubstituted by identical or different substituents, preferred substituents on the phenyl ring being in each case halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different substituents from the group consisting of halogen atoms, such as fluorine, chlorine and bromine atoms, and nitro.
n preferably represents 0, 1 or 2.
R
7
and R
8
independently of one another preferably represent a radical from the group consisting of hydrogen, C
1
-C
6
-alkyl, C
2
-C
4
-alkenyl and represent phenyl or benzyl, each of which is optionally mono- to trisubstituted by identical or different substituents, preferred substituents on the phenyl ring being in each case halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms.
R
9
preferably represents C
1
-C
4
-alkyl or represents phenyl which is optionally mono- to trisubstituted by identical or different substituents, possible substituents being halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms.
A preferably represents oxygen, sulfur or represents —NR
11
.
R
11
preferably represents C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkinyl, C
1
-C
4
-alkoxy, represents C
5
-C
6
-cycloalkyl, which is optionally mono- to trisubstituted by identical or different substituents, preferred substituents being halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, or represents phenyl-C
1
-C
4
-alkyl, which is mono- to trisubstituted by identical or different substituents, preferred substituents being halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms.
Z preferably represents cyano or nitro.
R
1
particularly preferably represents 6-chloro-3-pyridyl(6-chloro-pyridin-3-yl) or represents 2-chloro-5-thiazolyl(2-chloro-thiazol-5-yl).
R
2
particularly preferably represents hydrogen or C
1
-C
5
-alkyl.
R
3
particularly preferably represents a radical from the group consisting of —OR
4
, —OCOR
5
, —OCOOR
6
, —OCONR
7
R
8
, —OSO
2
R
9
and —S(O)
n
R
10
.
R
4
, R
5
, R
6
and R
10
independently of one another particularly preferably represent C
1
-C
8
-alkyl, C
1
-C
2
-alkoxy-C
1
-C
2
-alkyl, C
1
-C
2
-halogenoalkyl having 1 or 2 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms; allyl, propargyl, C
1
-C
2
-alkylamino-C
1
-C
2
-alkyl, di(C
1
-C
2
)-alkylamino-C
1
-C
2
-alkyl, cyclopropyl, cyclopentyl, cyclohexyl or represent phenyl or benzyl, each of which is optionally mono- or disubstituted by identical or different substituents, possible substituents on the phenyl ring being in each case fluorine, chlorine, bromine, methyl, metho

Affiliated with

Also associated with

Rating

Cyclic guanidine derivatives and their use as pesticides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Cyclic guanidine derivatives and their use as pesticides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cyclic guanidine derivatives and their use as pesticides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3245083