Title of Invention

INDANYL-AND TETRAHYDRONAPHTYL-AMINO-THIOUREA COMPOUNDS FOR COMBATING ANIMAL PESTS

Abstract Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds for combating animal pests The present invention relates to Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula I wherein the variables R1 to R4 are as in the description. The invention relates also to methods of combating or controlling insects, arachnids or nematodes, to methods for protecting growing plants from attack or infestation by insects, arachnids or nematodes, to methods for the protection of seeds from soil insects and of the seedlings' roots and shoots from soil and foliar insects and to methods for treating, controlling, preventing or protecting animals against infestation or infection.
Full Text Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds for combating animal pests
The present invention relates to Indanyl- and Tetrahydronaphtyl-amino-thiourea com-
pounds for combating animal pests.
Animal pests and in particular insects, arachnids and nematodes destroy growing and
harvested crops and attack wooden dwelling and commercial structures, causing large
economic loss to the food supply and to property. While a large number of pesticidal
agents are known, due to the ability of target pests to develop resistance to said
agents, there is an ongoing need for new agents for combating animal pests. In par-
ticular, animal pests such as insects, arachnids and nematodes are difficult to be effec-
tively controlled.
Therefore, it was an object of the present invention to provide compounds having a
good pesticidal activity and show a broad activity spectrum against a large number of
different anmimal pests, especially against difficult to control insects, arachnids and
nematodes.
However, no Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds have been
described so far for combatting animal pests.
Conventional art describes in US 3953506, US 3953606, US 4005140 and US
4062856 ureidotetralin compounds and their use as herbicidal agents and/or animal
growth regulators.
It has been found that Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of
the formula I

m is 1,2,3 or 4, wherein when m is greater than 1, the radicals R1 may have
the same or different meanings

R1 is selected from hydrogen, halogen, OH, SH, NH2, SO3H, COOH, cyano,
azido, nitro, formyl, CONH2, CSNH2, CH=N-OH, CH=N-O-(C1-C6)-alkyl,
C(=O)R1c, C(=S)R1c, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-
cycloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-
alkylthio, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkenylamino, C2-C6-
alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, C2-C6-
alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl,
C2-C6-alkynylsulfonyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl,
(C2-C6-alkynyloxy)-carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-
)carbonyl-oxy or (C2-C6-alkynyl)carbonyloxy, (C2-C6-alkenyl)carbonyl-amino,
wherein the carbon atoms in the aliphatic radicals of the aforementioned
groups may carry any combination of 1, 2 or 3 radicals, independently of
one another selected from the group consisting of halogen, cyano, nitro,
hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
C(O)NR1aR1b, (SO2)NR1aR1b, and wherein
R1a and R1b are each independently hydrogen, OH, NH2, C1-C6-alkyl, C1-
C6-haloalkyl, C2-C6-alkenyl or C2-C6-alkynyl, and
R1c is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-
C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino,
hydrazino, (C1-C6-alkyl)hydrazino, di(C1-C6-alkyl)hydrazino, phenyl
and heteroaryl, which can be a mono- or bicyclic 5 to 10 membered
heteroaromatic ring, which contains 1,2,3 or 4 heteroatoms selected
from O,S and N;
a radical Y-Ar or a radical Y-Cy, wherein
Y is a single bond, oxygen, sulfur, nitrogen, C1-C6-alkandiyl or C1-C6-
alkandiyloxy;
Ar is phenyl, naphthyl or a mono- or bicyclic 5- to 10-membered heteroaro-
matic ring, which contains 1, 2, 3 or 4 heteroatoms selected from 2
oxygen, 2 sulfur and 3 nitrogen atoms as ring members, wherein Ar is
unsubstituted or may carry any combination of 1 to 5 radicals, inde-
pendently of one another selected from the group consisting of halo-
gen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-
C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy and C1-C6-alkylthio;
Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5
radicals, independently of one another selected from the group con-
sisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkenyloxy, C1-C6-
alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
and wherein the radical R1 that are bound to adjacent carbon atoms of the
phenyl rings may form, together with said carbon atoms, a fused benzene

ring, a fused saturated or partially unsaturated 5-, 6-, or 7-membered car-
bocycle or a fused 5-, 6- or 7-membered heterocycle, which contains 1, 2, 3
or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as
ring members, and wherein the fused ring is unsubstituted or may carry 1,
2, 3 or 4 radicals, independently of one another selected from the group
consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, d-
C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy and C1-C6-alkylthio;
R2 is selected from hydrogen, C(=O)R2d, C(=S)R2d, C1-C6-alkyl, C1-C6 -
alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkenyl, C2-C6-alkenylamino, C2-C6-
alkynyl, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkylsulfonyl, C2-
C6-alkenylsulfonyl, C2-C6-alkynylsulfonyl C1-C6-alkylsulfinyl, C2-C6-
alkenylsulfinyl, C2-C6-alkynylsulfinyl, C3-C12-cycloalkyl, P(=O)R2aR2b,
P(=S)R2aR2b, NR2aR2b, SiR2aR2bR2c, N=CR2aR2b, CR2a=NR2b;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem
which may contain 1 to 4 heteroatoms selected from oxygen, sulfur and ni-
trogen and which are unsubstituted or substituted with any combination of 1
to 5 groups selected from halogen, cyano, nitro, hydroxy, mercapto, amino,
carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-
C6-haloalkoxy, or C1-C6-alkylthio; and wherein
R2a, R2b and R2c are selected each independently from hydrogen, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-alkylthio, and wherein the carbon atoms in these groups
may be substituted by 1 to 3 of a substituent selected by halogen, cyano,
nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-
alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy,
or C1-C6-alkylthio; and
R2d is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-
C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkynylamino, di(C2-C6-
alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
alkylthio, and wherein the carbon atoms in these groups may be substituted
by 1 to 3 of a substituent selected by halogen, cyano, nitro, hydroxy, mer-
capto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-
alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-
alkylthio; phenyl or a mono- or bicyclic 5- to 10-membered aromatic ring-
system which may contain 1 to 4 heteroatoms selected from oxygen, sulfur
and nitrogen and which are unsubstituted or substituted with any combina-
tion of 1 to 5 groups selected from halogen, cyano, nitro, hydroxy, mer-
capto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;

R3,R4 are selected from hydrogen, cyano, nitro, formyl, C(=O)R3c/or4c, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy , (C1-C6-
alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl or C1-C6-
alkylsulfonyl wherein the carbon atoms in the aliphatic radicals of the
aforementioned groups may carry any combination of 1, 2 or 3 radicals, in-
dependently of one another selected from the group consisting of halogen,
cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy,
C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio, or
C(O)NR3a/°r4aR3b/or4b, (SO2)NR3a/or4aR3b/°r4b, phenyl, phenyloxy or benzyl,
each of the last three mentioned radicals may be unsubstituted or substi-
tuted with 1 to 5 radicals, independently of one another selected from the
group consisting of halogen, C1-C6-alkyl, Cc-C6-haloalkyI, C1-C6-alkylthio,
C1-C6-haloalkylthio, C1-C6-alkoxy and C1-C6-haloalkoxy; and wherein
R3a/or4a abd R3b/or4b are each independently hydrogen, C1-C6-alkyl, C1-C6-
haloalkyl, C2-C6-alkenyl, or C2-C6-alkynyl; and R3c/or4c are selected
from hydrogen, C1-C6-alkyI, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-
cycloalkyl, C1-C6-alkylthio, C1-C6-alkoxy, (C1-C6-alkyl)amino, di(C1-C6-
alkyl)amino, phenyl and heteroaryl, which can be a mono- or bicyclic
5 to 10 membered heteroaromatic ring, which contains 1,2,3 or 4
heteroatoms selected from O,S and N;
with the proviso that at least one of R3 and R4 is hydrogen;
or the enatiomers and the agriculturally or veterinary acceptable salt thereof,
exhibit a high pesticidal activity and are active against a broad spectrum of animal
pests, in particular against insects, arachnids and nematodes.
The invention relates to Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of
the formula "

and/or to the agriculturally or veterinary acceptable salt thereof, wherein the variables
have the meanings defined above with respect to formula I, with the proviso that for-
mula I is not representing a 3-(1,2,3,4-tetrahydro-1-naphtyl)-thio-urea derivative,
wherein (R1)m,R3 and R4 are hydrogens and R2 is hydrogen or R2 is CH3.
The present invention relates also to the use of the compounds of formula I and of the
salts thereof for combating animal pests and also to a method of combating animal

pests which comprises contacting the animal pests, their habit, breeding ground, food
supply, plant, seed, soil, area, material or environment in which the animal pests are
growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be
protected from animal attack or infestation with a pesticidally effective amount of at
least one Indanyl- and Tetrahydronaphtyl-amino-thiourea compound of the formula
and/or at least one agriculturally acceptable salt thereof.
Furthermore, the present invention provides a method for protecting crops from attack
or infestation by animal pests, particularly insects, arachnids or nematodes, which
comprises contacting a crop with a pesticidally effective amount of at least one Indanyl-
and Tetrahydronaphtyl-amino-thiourea compound of the formula I and/or at least one
salt thereof.
Furthermore, the invention relates to agricultural compositions, preferably in the form of
directly sprayable solutions, emulsions, pastes, oil dispersions, powders, materials for
scattering, dusts or in the form of granules, which comprise at least one 1-(1,2-
diphenyl-ethyl)-3-(2-hydroxyethyl)-thiourea compound of the formula I as defined
above and/or at least one salt thereof, admixed with one or more agronomically ac-
ceptable inert, solid or liquid carrier(s) and, if desired, at least one surfactant.
And another object of the present invention is to provide new methods to control para-
sites in and on animals, providing safer pesticides for animals that may be used in
lower doses than existing pesticides and which permit a long residual control of the
parasites.
The compounds of the formula I may have one or more centers of chirality, in which
case they are present as mixtures of stereoisomers, such as enantiomers or di-
astereomers. The present invention provides both the pure stereoisomers, e.g. the
pure enantiomes or diastereomers, and mixtures thereof. The compounds of the for-
mula I may also exist in the form of different tautomers. The invention comprises the
single tautomers, if seperable, as well as the tautomer mixtures.
Salts of the compounds of the formula I which are suitable for the use according to the
invention are especially agriculturally acceptable salts. They can be formed in a cus-
tomary method, e.g. by reacting the compound with an acid of the anion in question if
the compound of formula I has a basic functionality or by reacting an acidic compound
of formula I with a suitable base.
Suitable agriculturally useful salts are especially the salts of those cations or the acid
addition salts of those acids whose cations and anions, respectively, do not have any
adverse effect on the action of the compounds according to the present invention.
Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium

and potassium, of the alkaline earth metals, preferably calcium, magnesium and bar-
ium, and of the transition metals, preferably manganese, copper, zinc and iron, and
also ammonium (NH4+) and substituted ammonium in which one to four of the hydro-
gen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-
C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl and/or benzyl. Examples of sub-
stituded ammonium ions comprise methylammonium, isopropylammonium, dimethyl-
ammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetra-
ethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-
hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammo-
nium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions,
preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-
alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen
sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen
carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and
the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and bu-
tyrate. They can be formed by reacting a compound of formulae I with an acid of the
corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid,
phosphoric acid or nitric acid.
The organic moieties mentioned in the above definitions of the variables are - like the
term halogen - collective terms for individual listings of the individual group members.
The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the
group.
The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particu-
lar fluorine, chlorine or bromine.
Examples of other meanings are :
The term "C1-C6-alkyl" as used herein and in the alkyl moieties of C1-C6-alkoxy, C1-C6-
alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylthio, C1-C6-alkylsulfonyl, C1-C6-
alkylsulfoxyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthiocarbonyl, and
C1-C6-alkylcarbonyloxy refer to a saturated straight-chain or branched hydrocarbon
group having 1 to 6 carbon atoms, especially 1 to 4 carbon groups, for example
methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-
dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,
1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-
methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-
dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-
ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-

2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. C1-C4-
alkyl means for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-
methylpropyl or 1,1-dimethylethyl.
The term "C1-C6-haloalkyl" as used herein refers to a straight-chain or branched satu-
rated alkyl group having 1 to 6 carbon atoms (as mentioned above), where some or all
of the hydrogen atoms in these groups may be replaced by halogen atoms as men-
tioned above, for example C1-C4-haloalkyl, such as chloromethyl, bromomethyl, di-
chloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloro-
fluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,
1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,
2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoro-
ethyl and the like.
The term, "C1-C6-alkoxy" as used herein refers to a straight-chain or branched satu-
rated alkyl group having 1 to 6 carbon atoms (as mentioned above) which is attached
via an oxygen atom. Examples include C1-C6-alkoxy such as methoxy, ethoxy, OCH2-
C2H5, OCH(CH3)2) n-butoxy, OCH(CH3)-C2H5l OCH2- CH(CH3)2, OC(CH3)3, n-pentoxy,
1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,
1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy,
1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,
1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,
2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,
1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1 -ethyl-2-
methylpropoxy and the like.
The term "C1-C6-haloalkoxy" as used herein refers to a C1-C6-alkoxy group as men-
tioned above wherein the hydrogen atoms are partially or fully substituted by fluorine,
chlorine, bromine and/or iodine, i.e., for example, C1-C6-haloalkoxy such as chloro-
methoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy,
trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,
2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,
2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-
2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-
fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-
chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-
trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropro-
poxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-
(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, nona-
fluorobutoxy, 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-
pentoxy, 5,5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-
hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluoro-

hexoxy, in particular chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,
2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy.
The term "C1-C6-alkoxy-C1-C6-alkyl" as used herein refers to C1-C6-alkyl wherein 1 car-
bon atom carries a C1-C6-alkoxy radical as mentioned above. Examples are CH2-
OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (1-
methylpropoxy)methyl, (2-methylpropoxy)methyl, CH2- OC(CH3)3, 2-(methoxy)ethyl, 2-
(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-
methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-
(methoxyjpropyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-
(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-
dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-
methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-
methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,
2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-
methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-
(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-
butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-
dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-
methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-
methylpropoxy)butyl, 4-(1,1-dimethylethoxy)butyl and the like.
The term "(C1-C6-alkyl)carbonyl" as used herein refers to a straight-chain or branched
saturated alkyl group having 1 to 6 carbon atoms (as mentioned above) bonded via the
carbon atom of the carbonyl group at any bond in the alkyl group. Examples include
C1-C6-alkylcarbonyl such CO-CH3, CO-C2H5, n-propylcarbonyl, 1-methylethylcarbonyl,
n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-
dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl,
3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-
dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-
methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-
methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-
dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-
dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-
trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl
or 1-ethyl-2-methylpropylcarbonyl and the like.
The term "(C1-C6-alkoxy)carbonyl" as used herein refers to a straight-chain or
branched alkoxy group (as mentioned above) having 1 to 6 carbon atoms attached via
the carbon atom of the carbonyl group, for example CO-OCH3, CO-OC2H5, COO-CH2-
C2H5, CO-OCH(CH3)2, n-butoxycarbonyl, CO-OCH(CH3)-C2H5, CO-OCH2-CH(CH3)2,
CO-OC(CH3)3, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-

methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-
hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-
methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-
methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-
dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-
dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-
trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-
methylpropoxycarbonyl or 1 -ethyl-2-methylpropoxycarbonyl.
The term "(C1-C6-alkyl)carbonyloxy" as used herein refers to a straight-chain or
branched saturated alkyl group having 1 to 6 carbon atoms (as mentioned above)
bonded via the carbon atom of the carbonyloxy group at any bond in the alkyl group,
for example O-CO-CH3, O-CO-C2H5> n-propylcarbonyloxy, 1-methylethylcarbonyloxy,
n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-
dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-
methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy or
1,2-dimethylpropylcarbonyloxy.
The term "C1-C6-alkylthio (C1-C6-alkylsulfanyl: C1-C6-alkyl-S-)" as used herein refers to
a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms (as
mentioned above) which is attached via a sulfur atom, for example C1-C4-alkylthio such
as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-
methylpropylthio, 1,1-dimethylethylthio, n-pentylthiocarbonyl, 1-methylbutylthio, 2-
methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-
hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-
methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-
dimethylbutylthio, 1,3-dimethylbutythio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
3,3-dimethylbutylthio, 1-ethylbutlthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-
trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.
The term "C1-C6-alkylthiocarbonyl" as used herein refers to a straight-chain or
branched alkthio group (as mentioned above) having 1 to 6 carbon atoms attached via
the carbon atom of the carbonyl group. Examples include CO-SCH3, CO-SC2H5,
CO-SCH2-C2H5, CO-SCH(CH3)2, n-butylthiocarbonyl, CO-SCH(CH3)-C2H5, CO-SCH2-
CH(CH3)2, CO-SC(CH3)3, n-pentylthiocarbonyl, 1-methylbutylthiocarbonyl, 2-
methylbutylthiocarbonyl, 3-methylbutylthiocarbonyl, 2,2-dimethylpropylthiocarbonyl, 1-
ethylpropylthiocarbonyl, n-hexylthiocarbonyl, 1,1-dimethylpropylthiocarbonyl, 1,2-
dimethylpropylthiocarbonyl, 1-methylpentylthiocarbonyl, 2-methylpentylthiocarbonyl, 3-
methylpentylthiocarbonyl, 4-methylpentylthiocarbonyl, 1,1-dimethylbutylthiocarbonyl,
1,2-dimethylbutylthiocarbonyl, 1,3-dimethylbutythiocarbonyl, 2,2-
dimethylbutylthiocarbonyl, 2,3-dimethylbutylthiocarbonyl, 3,3-dimethylbutylthiocarbonyl,
1-ethylbutlthioycarbonyl, 2-ethylbutylthiocarbonyl, 1,1,2-trimethylpropylthiocarbonyl,

1,2,2-trimethylpropylthiocarbonyl, 1-ethyl-1-methylpropylthiocarbonyl or 1 -ethyls-
methyl propylth iocarbonyl.
The term "C1-C6-alkylsulfinyl" (C1-C6-alkylsulfoxyl: C1-C6-alkyl-S(=O)-), as used herein
refers to a straight-chain or branched saturated hydrocarbon group (as mentioned
above) having 1 to 6 carbon atoms bonded through the sulfur atom of the sulfinyl group
at any bond in the alkyl group, for example SO-CH3, SO-C2H5, n-propylsulfinyl, 1-
methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-
dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-
methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-
dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-
methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-
dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-
dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-
ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-
trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.
The term "C1-C6-alkylamino" refers to a secondary amino group carrying one alkyl
group as defined above, e.g. methylamino, ethylamino, propylamino, 1-
methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-
dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-
methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-
dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-
methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-
dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-
dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-
ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-
trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino.
The term "di(C1-C6-alkyl)amino" refers to a tertiary amino group carrying two alkyl radi-
cals as defined above, e.g. dimethylamino, diethylamino, di-n-propylamino, diisopro-
pylamino, N-ethyl-N-methylamino, N-(n-propyl)-N-methylamino, N-(isopropyl)-N-
methylamino, N-(n-butyl)-N-methylamino, N-(n-pentyl)-N-methylamino, N-(2-butyl)-N-
methylamino, N-(isobutyl)-N-methylamino, N-(n-pentyl)-N-methylamino, N-(n-propyl)-
N-ethylamino, N-(isopropyl)-N-ethylamino, N-(n-butyl)-N-ethylamino, N-(n-pentyl)-N-
ethylamino, N-(2-butyl)-N-ethylamino, N-(isobutyl)-N-ethylamino or N-(n-pentyl)-N-
ethylamino.
The term "C1-C6-alkylsulfonyl" (C1-C6-alkyl-S(=O)2-) as used herein refers to a straight-
chain or branched saturated alkyl group having 1 to 6 carbon atoms (as mentioned
above) which is bonded via the sulfur atom of the sulfonyl group at any bond in the
alkyl group, for example SO2-CH3, SO2-C2H5, n-propylsulfonyl, SO2-CH(CH3)2, n-

butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, SO2-C(CH3)3l n-
pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-
dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-
ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-
methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-
dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-
dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-
ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1
methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.
The term "C2-C6-alkenyl" as used herein and in the alkenyl moieties of C2-C6-
alkenyloxy, C2-C6-alkenylamino, C2-C6-alkenylthio, C2-C6-alkenylsulfonyl, (C2-C6-
alkenyl)carbonyl, (C2-C6-alkenyloxy)carbonyl and (C2-C6-alkenyl)carbonyloxy refers to
a straight-chain or branched unsaturated hydrocarbon group having 2 to 6 carbon at-
oms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-
methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-
propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl; 1-pentenyl, 2-pentenyl, 3-
pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-
methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-
methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-
propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2
hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3
methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-
methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-
methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-
methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-buteny
1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-
butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-
dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-
butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,
2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2,-trimethyl^-propenyl, 1-
ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1 -ethyl-2-methyl-2-
propenyl.
The term, "C2-C6-alkenyloxy" as used herein refers to a straight-chain or branched
saturated alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is
attached via an oxygen atom, such as vinyloxy, allyloxy (propen-3-yloxy), methallyloxy
buten-4-yloxy and the like.
The term "C2-C6-alkenylthio" as used herein refers to a straight-chain or branched
saturated alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is

attached via a sulfur atom, for example vinylsulfanyl, allylsulfanyl (propen-3-ylthio),
methallylsufanyl, buten-4-ylsulfanyl and the like.
The term "C2-C6-alkenylamino" as used herein refers to a straight-chain or branched
saturated alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is
attached via a sulfur atom, for example vinylamino, allylamino (propen-3-ylamino),
methallylamino, buten-4-ylamino and the like.
The term "C2-C6-alkenylsulfonyl" as used herein refers to a straight-chain or branched
saturated alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is
attached via a sulfonyl (SO2) group, for example vinylsulfonyl, allylsulfonyl (propen-3-
ylsulfonyl), methallylsufonyl, buten-4-ylsulfonyl and the like.
The term "C2-C6-alkynyl" as used herein and in the alkynyl moieties of C2-C6-
alkynyloxy, C2-C6-alkynylamino, C2-C6-alkynylthio, C2-C6-alkynylsulfonyl, C2-C6-
alkynylcarbonyl, C2-C6-alkynyloxycarbonyl and C1-C6-alkynylcarbonyloxy refers to a
straight-chain or branched unsaturated hydrocarbon group having 2 to 10 carbon at-
oms and containing at least one triple bond, such as ethynyl, prop-1-yn-1-yl, prop-2-yn-
1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl,
n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl,
n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-
1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-
yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-
methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-
yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl and
the like.
The term, "C2-C6-alkynyloxy" as used herein refers to a straight-chain or branched
saturated alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is
attached via an oxygen atom, such as propargyloxy (propin-3-yloxy), butin-3-yloxy and
butin-4-yloxy.
The term "C2-C6-alkynylthio" as used herein refers to a straight-chain or branched satu-
rated alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is at-
tached via a sulfur atom, such as propargylsulfanyl (propin-3-ylthio), butin-3-ylsufanyl
and butin-4-ylsulfanyl.
The term "C2-C6-alkynylamino" as used herein refers to a straight-chain or branched
saturated alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is
attached via a sulfur atom, such as propargylamino (propin-3-ylamino), butin-3-amino,
and butin-4-ylamino.

The term "C2-C6-alkynylsulfonyl" as used herein refers to a straight-chain or branched
saturated alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is
attached via a sulfonyl (SO2) group, such as propargylsulfonyl (propin-3-yltsulfonyl),
butin-3-ylsufonyl and butin-4-ylsulfonyl.
The term "C3-C12-cycloalkyl" as used herein refers to a mono- or bi- or polycyclic hy-
drocarbon radical having 3 to 12 carbon atoms, in particular 3 to 6 carbon atoms. Ex-
amples of monocyclic radicals comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclo-
hexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl. Examples of bicyclic radicals
comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicy-
clo[3.2.1]nonyl. Examples of tricylcic radicals are adamantyl and homoadamantyl.
The term "mono- or bicylcic heteroaromatic ring" as used herein refers to a monocyclic
heteroaromatic radical which has 5 or 6 ring members, wich may comprise a fused 5, 6
or 7 membered ring thus having a total number of ring members from 8 to 10, wherein
in each case 1, 2, 3 or 4 of these ring members are heteroatoms selected, independ-
ently from each other, from the group consisting of oxygen, nitrogen and sulfur. The
heterocyclic radical may be attached to the remainder of the molecule via a carbon ring
member or via a nitrogen ring member. The fused ring comprises C5-C7 ycycloalkyl, C5-
C7-cycloalkenyI, or 5 to 7 membered heterocyclyl and phenyl.
Examples for monocyclic 5- to 6-membered heteroaromatic rings include triazinyl,
pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl,
triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl and isoxa-
zolyl.
Examples for 5- to 6-membered heteroaromatic rings carrying a fused phenyl ring are
quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl,
benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzoxazolyl, and benzimidazolyl. Ex-
amples for 5- to 6-membered heteroaromatic rings carrying a fused cycloalkenyl ring
are dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydrochinolinyl, dihydroiso-
chinolinyl, chromenyl, chromanyl and the like.
The term "5 to 7 membered heterocyclyl" comprises monocyclic heteroaromatic rings
as defined above and nonaromatic saturated or partially unsaturated heterocyclic rings
having 5, 6 or 7 ring members. Examples for non-aromatic rings include pyrrolidinyl,
pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydro-
furanyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothienyl, oxazolidinyl, isoxazolidinyl,
oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl,
oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, diox-
anyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and
the like.

As regards the pesticidal activity of the compounds of formula I, preference is given to
those compounds of formula I, in which the variables - independently of one another or
in combination with any of the other variables - have the following meanings:
Indanyl-amino-thiourea compounds of the formula I, wherein n is 1.
Tetrahydronaphtyl-amino-thiourea compounds of the formula I, wherein n is 2.
Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula I, wherein m is
1,2 or 3.
Preferably Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula I,
wherein m is 1 or 2.
More preferably Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula
I, wherein m is 1.
Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula I, wherein R1 is
selected from cyano, azido, halogen, OH, SH, NH2, CONH2, SO3H, COOH, C(=O)R1c,
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-
alkyl)amino, di(C1-C6-alkyl)amino, wherein the carbon atoms in the aliphatic radicals of
the aforementioned groups may carry any combination of 1, 2 or 3 radicals, independ-
ently of one another selected from the group consisting of halogen, cyano, nitro, hy-
droxy, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy,
C1-C6-haloalkoxy, and wherein R1c is selected from hydrogen, C1-C6-alkyl, C2-C6-
alkenyl, C2-C6-alkinyl, Cs-Ce-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)amino, di(C1-C6-
alkyl)amino, phenyl and heteroaryl, which can be a mono- or bicyclic 5 to 10 mem-
bered heteroaromatic ring, which contains 1,2,3 or 4 heteroatoms selected from O,S
and N.
Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of the formula I, wherein
R2 is selected from C(=O)R2d, C(=S)R2d, C1-C6-alkyl, phenyl or a mono- or bicyclic 5- to
10-membered aromatic ringsystem which may contain 1 to 4 heteroatoms selected
from oxygen, sulfur and nitrogen and which are unsubstituted or substituted with any
combination of 1 to 5 groups selected from halogen, cyano, nitro, hydroxy, mercapto,
amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy, or C1-C6-alkylthio; and wherein R2d is selected from hydrogen, C1-C6-alkyl,
C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-
alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-alkylthio, and wherein the carbon atoms in these groups may be
substituted by 1 to 3 of a substituent selected by halogen, cyano, nitro, hydroxy, mer-
capto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;

phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem which may con-
tain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and which are un-
substituted or substituted with any combination of 1 to 5 groups selected from halogen,
cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio.
More perferably Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of the
formula I, wherein R2 is selected from C(=O)R2dphenyl or a mono- or bicyclic 5- to 10-
membered aromatic ringsystem which may contain 1 to 4 heteroatoms selected from
oxygen, sulfur and nitrogen and which are unsubstituted or substituted with any combi-
nation of 1 to 5 groups selected from halogen, cyano, nitro, hydroxy, mercapto, amino,
carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy, or C1-C6-alkylthio; and wherein R2d is selected from C1-C6-alkyl, C2-C6-
alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkynylamino,
di(C2-C6-alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
alkylthio, and wherein the carbon atoms in these groups may be substituted by 1 to 3
of a substituent selected by halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem which may con-
tain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and which are un-
substituted or substituted with any combination of 1 to 5 groups selected from halogen,
cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio.
Most preferred are Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of the
formula I, wherein R2 is selected from C(=O)R2dphenyl or a mono- or bicyclic 5- to 10-
membered aromatic ringsystem which may contain 1 to 4 heteroatoms selected from
oxygen, sulfur and nitrogen and which are unsubstituted or substituted with any combi-
nation of 1 to 5 groups selected from halogen, cyano, nitro, hydroxy, mercapto, amino,
carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy, or C1-C6-alkylthio; and wherein R2d is selected from C1-C6-alkyI, C2-C6-
alkenyl, C2-C6-alkynyl, phenyl or a mono- or bicyclic 5- to 10-membered aromatic ring-
system which may contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitro-
gen and which are unsubstituted or substituted with any combination of 1 to 5 groups
selected from halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl,
C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio.
Preferred are Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula I,
wherein R3 and R4 are selected from hydrogen, cyano, C(=O)R3c/or4c, C1-C6-alkyl, C2-
Ce-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy , (C1-C6-alkoxy)methylen, d-

Ce-alkylsulfinyl, C1-C6-alkylsulfenyl or C1-C6-alkylsulfonyl; and wherein R3c/or4c are eacn
independently selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-
cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyOamino, dKC1-C6-alkyOamino, phenyl and het-
eroaryl, which can be a mono- or bicyclic 5 to 10 membered heteroaromatic ring, which
contains 1,2,3 or 4 heteroatoms selected from O,S and N; and
with the proviso that at least one of R3 and R4 is hydrogen.
More preferred are Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of for-
mula I, wherein R3 and R4 are selected from hydrogen, cyano, C(=O)R3c/or4c, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkinyl; (C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-
alkylsulfenyl or C1-C6-alkylsulfonyl; and wherein R3c/or4c areselected from C1-C6-alkyl
C1-C6-alkoxy, phenyl and heteroaryl, which can be a mono- or bicyclic 5 to 10 mem-
bered heteroaromatic ring, which contains 1,2,3 or 4 heteroatoms selected from O,S
and N; and
with the proviso that at least one of R3 and R4 is hydrogen.
Most preferred are Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of for-
mula I, wherein R3 and R4 are selected from hydrogen, cyano, C(=O)R3c/or4c, (C1-C6-
alkoxy)methylen, and wherein R3c/°r4c are selected from C1-C6-alkyl or C1-C6-alkoxy.
with the proviso that at least one of R3 and R4 is hydrogen.
Especially preferred are Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of
formula I, wherein R3 and R4 are both hydrogen.
The compound of the present invention can be e.g. prepared from the corresponding
amines II by the synthetic route outlined in the following scheme:


According to the method outlined in the scheme, an amine II (or its salt) is converted to
the corresponding isothiocyanate IV by conventional means, e.g. by reacting II with
thiophosgene (see e.g. Houben-Weyl, E4, "Methoden der Organischen Chemie", chap-
ter lle, pp. 837-842, Georg Thieme Verlag 1983. The isothiocyanate IV is then reacted
with an aminoethanol V, thereby obtaining the thiourea 1Mb.
The reaction of the aminoethanol with isothiocyanate IV can be performed in accor-
dance with standard methods of organic chemistry, see e.g. Biosci. Biotech. Biochem.
56(7), 1062-65(1992).
Compounds of the formula Ilia and 1Mb can be further converted into new compounds
of the general formula III by modification of R2. In particular if R2 is hydrogen these
compounds Illc can e.g. converted by esterification reactions e.g. with carboxylic acids
or carboxylic acid chlorides or e.g. by electrophilic substitution by reaction with an elec-
trophile, e.g. with an alkylating agent by methods familiar to an organic chemist and
well known in the art, as outlined in the following scheme and described below.


Due to their excellent activity, the compounds of the formula I may be used for control-
ling animal pests, selected harmful insects, arachnids and nematodes. Accordingly, the
invention further provides agriculturally composition for combating such animal pests,
which comprises such an amount of at least one compound of the general formula I or
at least an agriculturally useful salt of I and at least one inert liquid and/or solid
agronomically acceptable carrier that it has a pesticidal action and, if desired, at least
one surfactant.
Such a composition may contain a single active compound of the formula I or a mixture
of several active compounds I according to the present invention. The composition
according to the present invention may comprise an individual isomer or mixtures of
isomers as well as individual tautomers or mixtures of tautomers.
Pests
The compounds of the formula I and the pestidicidal compositions comprising them are
effective agents for controlling animal pests, selected from insects, arachnids and
nematodes. Animal pests controlled by the compounds of formula I include for exam-
ple:
insects from the order of the lepidopterans {Lepidoptera), for example Agrotisypsilon,
Agrotis segetum, Alabama argillacea, Ant/cars/a gemmatalis, Argyresthia conjugella,
Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheima-
tobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis
unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandi-
osella, Ear/as insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bou-
liana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha mo-
lesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia
defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lamb-
dina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocol-
letis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria
monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseu-
dotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma

saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris bras-
sicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frus-
trana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera
frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix
viridana, Trichoplusia /7/and Zeiraphera canadensis;
beetles (Co/eoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscu-
rus, Amphimallus solstitialis, Anisandrus d/'spar, Anthonomus grandis, Anthonomus
pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufi-
manus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cero-
toma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus nap/, Chaetocnema tibi-
alis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-
punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus
brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus,
Lema bilineata, Lema melanopus, Leptinotarsa decem/ineata, Limonius californicus,
Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hip-
pocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhyn-
chus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyl-
lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona
lineatus and Sitophilus granariar,
dipterans {Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens,
Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya homi-
nivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga,
Culex pip/ens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicu-
laris, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis
equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii,
Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetio/a destruc-
tor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hyso-
cyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi,
Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa,
thrips (Thysanoptera), e.g. Dichromothripscorbetti, Frankliniella fusca, Frankliniella
occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips pafmi and Thrips
tabaci,
hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta
texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, So-
lenopsis geminata and Solenopsis invicta,
heteropterans (Heteroptera), e.g. Acrosternum hi/are, Blissus leucopterus, Cyrtopeltis
notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps,

Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis,
Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor,
homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula
nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae,
Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum
solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachy-
caudus persicae, Brachycaudus prunicoia, Brevicoryne brassicae, Capitophorus horni,
Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordman-
nianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis
plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactu-
cae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura
viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus as-
calonicus, Myzus cerasi, Myzus persicae, Myzus varians, Nasonovia ribis-nigri, Nila-
parvata lugens, Pemphigus bursarius, Perkinsiella saccharic/da, Phorodon humuti,
Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosi-
phum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis
graminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furcifera Trialeurodes
vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii;
termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes
flavipes, Reticulitermes lucifugus und Termes natafensis,
orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis, Blattellagermanica,
Forficula auricularia, Gryllotalpa gryflota/pa, Locusta migratoria, Melanoplus bivittatus,
Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melano-
plus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca ameri-
cana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus,
Arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and
Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persi-
cus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor
silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus mou-
bata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendi-
culatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. suchasAcu-
lus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp.
such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp.
such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus,
Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telariusand Tetranychus
urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis,
Siphonatera, e.g. Xenopsylla cheopsis, Ceratophyllus spp

The compositions and compounds of formula I are useful for the control of nematodes,
especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla,
Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species;
cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Hete-
rodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and
other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar
nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus
and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and
other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella
species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes,
Ditylenchus destructor, Ditylenchus dipsaciand other Ditylenchus species; Awl nema-
todes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and
other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora
species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes,
Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nemato-
des, Longidorus elongatus and other Longidorus species; Pin nematodes, Paratylen-
chus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans,
Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Bur-
rowing nematodes, Radopholus similis and other Radopholus species; Reniform nema-
todes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species;
Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratri-
chodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus
dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species;
Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.
In a preferred embodiment of the invention the compounds of formula I are used for
controlling insects or arachnids, in particular insects of the orders Lepidoptera, Coleop-
tera and Homoptera and arachnids of the order Acarina. The compounds of the for-
mula I according to the present invention are particularly useful for controlling insects
of the order Lepidoptera and Homoptera.
Formulations
For use in a method according to the present invention, the compounds I can be con-
verted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts,
powders, pastes, granules and directly sprayable solutions. The use form depends on
the particular purpose and application method. Formulations and application methods
are chosen to ensure in each case a fine and uniform distribution of the compound of
the formula I according to the present invention.

The formulations are prepared in a known manner (see e.g. for review US 3,060,084,
EP-A 707 445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engi-
neering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed.,
McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, US 4,172,714,
US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030,
GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and
Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell
Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation tech-
nology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles,
Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publish-
ers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active com-
pound with auxiliaries suitable for the formulation of agrochemicals, such as solvents
and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti-
foaming agents, anti-freezing agents, for seed treatment formulation also optionally
colorants and/or binders and/or gelling agents.
Solvents/carriers, which are suitable, are e.g.:
solvents such as water, aromatic solvents (for example Solvesso products, xy-
lene and the like), paraffins (for example mineral fractions), alcohols (for example
methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone,
gamma-butyrolactone), pyrrolidones (N-metyhl-pyrrolidone (NMP),N-octylpyrrolidone
NOP), acetates (glycol diacetate), alkyl lactates, lactones such as g-butyrolactone,
glycols, fatty acid dimethylamides, fatty acids and fatty acid esters, triglycerides, oils of
vegetable or animal origin and modified oils such as alkylated plant oils. In principle,
solvent mixtures may also be used.
carriers such as ground natural minerals and ground synthetic minerals, such
as silica gels, finely divided silicic acid, silicates, talc, kaolin, attaclay, limestone, lime,
chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium
sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example,
ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and products of
vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal,
cellulose powders and other solid carriers.
Suitable emulsifiers are nonionic and anionic emulsifiers (for example polyoxyethylene
fatty alcohol ethers, alkylsulfonates and arylsulfonates).
Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.
Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of ligno-
sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic
acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty ac-

ids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated
naphthalene and naphthalene derivatives with formaldehyde, condensates of naphtha-
lene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene
octylphenyl ether, ethoxylated isoocty I phenol, octylphenol, nonylphenol, alkylphenyl
polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alky-
laryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxy-
lated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl al-
cohol polyglycol ether acetal, sorbitol esters,
Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bacte-
ricides such as can be added to the formulation.
Suitable antifoaming agents are for example antifoaming agents based on silicon or
magnesium stearate.
Suitable preservatives are for example dichlorophen und benzyl alcohol hemiformal
Suitable thickeners are compounds, which confer a pseudoplastic flow behavior to the
formulation, i.e. high viscosity at rest and low viscosity in the agitated stage. Mention
may be made, in this context, for example, of commercial thickeners based on poly-
saccharides, such as Xanthan Gum® (Kelzan® from Kelco), Rhodopol®23 (Rhone
Poulenc) or Veegum® (from R.T. Vanderbilt), or organic phyllosilicates, such as Atta-
clay® (from Engelhardt). Antifoam agents suitable for the dispersions according to the
invention are, for example, silicone emulsions (such as, for example, Silikon® SRE,
Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, organofluorine
compounds and mixtures thereof. Biocides can be added to stabilize the compositions
according to the invention against attack by microorganisms. Suitable biocides are, for
example, based on isothiazolones such as the compounds marketed under the trade-
marks Proxel® from Avecia (or Arch) or Acticide® RS from Thor Chemie and Kathon®
MK from Rohm & Haas. Suitable antifreeze agents are organic polyols, for example
ethylene glycol, propylene glycol or glycerol. These are usually employed in amounts
of not more than 10% by weight, based on the total weight of the active compound
composition. If appropriate, the active compound compositions according to the inven-
tion may comprise 1 to 5% by weight of buffer, based on the total amount of the formu-
lation prepared, to regulate the pH, the amount and type of the buffer used depending
on the chemical properties of the active compound or the active compounds. Examples
of buffers are alkali metal salts of weak inorganic or organic acids, such as, for exam-
ple, phosphoric acid, boronic acid, acetic acid, propionic acid, citric acid, fumaric acid,
tartaric acid, oxalic acid and succinic acid.
Substances which are suitable for the preparation of directly sprayable solutions, emul-
sions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point,

such as kerosene or diesei oil, furthermore coal tar oils and oils of vegetable or animal
origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraf-
fin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol,
ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar
solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dusts can be prepared by mixing or concomi-
tantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous
granules, can be prepared by binding the active ingredients to solid carriers. Examples
of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay,
limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,
magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as,
for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and
products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nut-
shell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1
to 90% by weight, of the active ingredient. The active ingredients are employed in a
purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
For seed treatment purposes, respective formulations can be diluted 2-10 fold leading
to concentrations in the ready to use preparations of 0,01 to 60% by weight active
compound by weight, preferably 0,1 to 40% by weight.
The compound of formula I can be used as such, in the form of their formulations or
the use forms prepared therefrom, for example in the form of directly sprayable solu-
tions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusta-
ble products, materials for spreading, or granules, by means of spraying, atomizing,
dusting, spreading or pouring. The use forms depend entirely on the intended pur-
poses; they are intended to ensure in each case the finest possible distribution of the
active compounds according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable
powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions,
pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can
be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Al-
ternatively, it is possible to prepare concentrates composed of active substance, wet-
ter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such con-
centrates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can be varied within
relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to
1 % per weight.
The active ingredients may also be used successfully in the ultra-low-volume process
(ULV), it being possible to apply formulations comprising over 95% by weight of active
ingredient, or even to apply the active ingredient without additives.
The following are examples of formulations:
1. Products for dilution with water. For seed treatment purposes, such products may be
applied to the seed diluted or undiluted.
A) Water-soluble concentrates (SL, LS)
10 parts by weight of the active compound is dissolved in 90 parts by weight of water
or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added.
The active compound dissolves upon dilution with water, whereby a formulation with 10
% (w/w) of active compound is obtained.
B) Dispersible concentrates (DC)
20 parts by weight of the active compound is dissolved in 70 parts by weight of cyclo-
hexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyr-
rolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w)
of active compounds is obtained.
C) Emulsifiable concentrates (EC)
15 parts by weight of the active compounds is dissolved in 7 parts by weight of xylene
with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each
case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation
with 15% (w/w) of active compounds is obtained.
D) Emulsions (EW, EO, ES)
25 parts by weight of the active compound is dissolved in 35 parts by weight of xylene
with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each
case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by
means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous
emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w)
of active compound is obtained.

E) Suspensions (SC, OD, FS)
In an agitated ball mill, 20 parts by weight of the active compound is comminuted with
addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water
or of an organic solvent to give a fine active compound suspension. Dilution with water
gives a stable suspension of the active compound, whereby a formulation with 20%
(w/w) of active compound is obtained.
F) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of the active compound is ground finely with addition of 50 parts by
weight of dispersants and wetters and made as water-dispersible or water-soluble
granules by means of technical appliances (for example extrusion, spray tower, fluid-
ized bed). Dilution with water gives a stable dispersion or solution of the active com-
pound, whereby a formulation with 50% (w/w) of active compound is obtained.
G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)
75 parts by weight of the active compound are ground in a rotor-stator mill with addition
of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a
stable dispersion or solution of the active compound, whereby a formulation with 75%
(w/w) of active compound is obtained.
H) Gel-Formulation (GF)
In an agitated ball mill, 20 parts by weight of the active compound is comminuted with
addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters
and 70 parts by weight of water or of an organic solvent to give a fine active compound
suspension. Dilution with water gives a stable suspension of the active compound,
whereby a formulation with 20% (w/w) of active compound is obtained.
2. Products to be applied undiluted for foliar applications. For seed treatment pur-
poses, such products may be applied to the seed diluted or undiluted.
1) Dustable powders (DP, DS)
5 parts by weight of the active compound are ground finely and mixed intimately with
95 parts by weight of finely divided kaolin. This gives a dustable product having 5%
(w/w) of active compound.
J) Granules (GR, FG, GG, MG)

0.5 part by weight of the active compound is ground finely and associated with 95.5
parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound
is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This
gives granules to be applied undiluted for foliar use.
K) ULV solutions (UL)
10 parts by weight of the active compound is dissolved in 90 parts by weight of an or-
ganic solvent, for example xylene. This gives a product having 10% (w/w) of active
compound, which is applied undiluted for foliar use.
Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or
bactericides may be added to the active ingredients, if appropriate just immediately
prior to use (tank mix). These agents usually are admixed with the agents according to
the invention in a weight ratio of 1:10 to 10:1.
The compounds and compositions of the present invention compounds I may be
applied with other active ingredients, for example with other pesticides, insecticides,
herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate,
phytotoxicants and plant growth regulators, safeners and nematicides. These
additional ingredients may be used sequentially or in combination with the above-
described compositions, if appropriate also added only immediately prior to use (tank
mix). For example, the plant(s) may be sprayed with a composition of this invention
either before or after being treated with other active ingredients.
These additional agents can be admixed with the agents used according to the
invention in a weight ratio of 1:10 to 10:1. Mixing the compounds I or the compositions
comprising them in the use form as pesticides with other pesticides frequently results
in a broader pesticidal spectrum of action.
The following list M of pesticides together with which the compounds according to the
invention can be used and with which potential synergistic effects might be produced,
is intended to illustrate the possible combinations, but not to impose any limitation:
M.1. Organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos,
chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate,
disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methi-
dathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon,
parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimi-
phos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazo-
phos, trichlorfon;

M.2. Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran,
carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, pro-
poxur, thiodicarb, triazamate;
M.3. Pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cyperme-
thrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, empen-
thrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-
cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-
fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
M.4. Growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfiuazuron,
diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, te-
flubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine;
b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin;
c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors:
spirodiclofen, spiromesifen, spirotetramat;
M.5. Nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, imi-
dacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid and AKD-1022;
M.6. GABA antagonist compounds: acetoprole, endosulfan, ethiprole, fipronil, va-
niliprole, pyrafluprole, pyriprole, the phenylpyrazole compound of formula r2

M.7. Macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, lepimectin,
spinosad
M.8. METII compounds: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
M.9. METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
M.10. Uncoupler compounds: chlorfenapyr;
M.11. Oxidative phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, fenbu-
tatin oxide, propargite;

M.12. Moulting disruptor compounds: cyromazine;
M.13. Mixed Function Oxidase inhibitor compounds: piperonyl butoxide;
M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone,
M.15. Various: amitraz, benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetro-
zine, sulfur, thiocyclam, flubendiamide, cyenopyrafen, flupyrazofos, cyflumetofen, ami-
doflumet, pyrifluquinazon, the aminoquinazolinone compound of formula I'4

N-R'-2,2-dihalo-1 -R"cyclo-propanecarboxamide-2-(2,6-dichloro- ,, -tri-fluoro-p-
tolyl)hydrazone or N-R'-2,2-di(R'")propionamide-2-(2,6-dichloro- ,, -trifluoro-p-tolyl)-
hydrazone, wherein R' is methyl or ethyl, halo is chloro or bromo, R" is hydrogen or
methyl and R1" is methyl or ethyl, anthranilamide compounds as chlorantraniliprole or
the compound of formula r5

and malononitrile compounds as described in JP 2002 284608, WO 02/89579, WO
02/90320, WO 02/90321, WO 04/06677, WO 04/20399, JP 2004 99597, WO
05/68423, WO 05/68432, or WO 05/63694, especially the malononitrile compounds
CF3(CH2)2C(CN)2CH2(CF2)3CF2H,CF3(CH2)2C(CN)2CH2(CF2)5CF2H,
CF3(CH2)2C(CN)2(CH2)2C(CF3)2F, CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3,
CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H, CF3(CH2)2C(CN)2CH2(CF2)3CF3,
CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H, and CF3CF2CH2C(CN)2CH2(CF2)3CF2H.
The commercially available compounds of the group M may be found in The Pesticide
Manual, 13th Edition, British Crop Protection Council (2003) among other publications.
Thioamides of formula r2 and their preparation have been described in WO 98/28279.
Lepimectin is known from Agro Project, PJB Publications Ltd, November 2004. Ben-
clothiaz and its preparation have been described in EP-A1 454621. Methidathion and
Paraoxon and their preparation have been described in Farm Chemicals Handbook,

Volume 88, Meister Publishing Company, 2001. Acetoprole and its preparation have
been described in WO 98/28277. Metaflumizone and its preparation have been de-
scribed in EP-A1 462 456. Flupyrazofos has been described in Pesticide Science 54,
1988, p.237-243 and in US 4822779. Pyrafluprole and its preparation have been de-
scribed in JP 2002193709 and in WO 01/00614. Pyriprole and its preparation have
been described in WO 98/45274 and in US 6335357. Amidoflumet and its preparation
have been described in US 6221890 and in JP 21010907. Flufenerim and its prepara-
tion have been described in WO 03/007717 and in WO 03/007718. Cyflumetofen and
its preparation have been described in WO 04/080180. The aminoquinazolinone com-
pound of formula r4 has been described in EP A 109 7932.
Anthranilamides of formula T5 and their preparation have been described in
WO 01/70671; WO 02/48137; WO 03/24222, WO 03/15518, WO 04/67528;
WO 04/33468; and WO 05/118552. The malononitrile compounds
CF3(CH2)2C(CN)2CH2(CF2)3CF2H, CF3(CH2)2C(CN)2CH2(CF2)5CF2H,
CF3(CH2)2C(CN)2(CH2)2C(CF3)2F, CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3,
CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H, CF3(CH2)2C(CN)2CH2(CF2)3CF3,
CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H, and CF3CF2CH2C(CN)2CH2(CF2)3CF2H have
been described in WO 05/63694.
Fungicidal mixing partners are those selected from the group F consisting of
F.1 acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl;
F.2 amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph,
fenpropidin, guazatine, iminoctadine, spiroxamin, tridemorph;
F.3 anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl;
F.4 antibiotics such as cycloheximid, griseofulvin, kasugamycin, natamycin, polyoxin or
streptomycin;
F.5 azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole,
dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole,
hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole,
prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizol,
triticonazole, flutriafol;
F.6 dicarboximides such as iprodion, myclozolin, procymidon, vinclozolin;
F.7 dithiocarbamates such as ferbam, nabam, maneb, mancozeb, metam, metiram,
propineb, polycarbamate, thiram, ziram, zineb;
F.8 heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim,
carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadon, fenamidon,
fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol,
probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole,
thifluzamid, thiophanate-methyl, tiadinil, tricyclazole, triforine;

F.9 copper fungicides such as Bordeaux mixture, copper acetate, copper oxychloride,
basic copper suifate;
F.10 nitrophenyl derivatives such as binapacryl, dinocap, dinobuton,
nitrophthalisopropyl;
F.11 phenylpyrroles such as fenpiclonil or fludioxonil;
F.12 strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl,
metominostrobin, orysastrobin, picoxystrobin or trifloxystrobin;
F.13 sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid;
F.14 cinnemamides and analogs such as dimethomorph, flumetover orflumorph;
F.15 sulfur, and other fungicides such as acibenzolar-S-methyl, benthiavalicarb,
carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezin, diclocymet,
diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin-acetate, fenoxanil,
ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene,
metrafenon, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene,
zoxamid.
Applications
The animal pest, i.e. the insects, arachnids and nematodes, the plant, soil or water in
which the plant is growing can be contacted with the present compound(s) I or compo-
sition(s) containing them by any application method known in the art. As such, "con-
tacting" includes both direct contact (applying the compounds/compositions directly on
the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect
contact (applying the compounds/compositions to the locus of the animal pest or
plant).
The compounds of formula I or the pesticidal compositions comprising them may be
used to protect growing plants and crops from attack or infestation by animal pests,
especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally
effective amount of compounds of formula I. The term "crop" refers both to growing
and harvested crops.
Moreover, animal pests may be controlled by contacting the target pest, its food sup-
ply, habitat, breeding ground or its locus with a pesticidally effective amount of com-
pounds of formula I. As such, the application may be carried out before or after the
infection of the locus, growing crops, or harvested crops by the pest.
The compounds of the invention can also be applied preventively to places at which
occurrence of the pests is expected.

The compounds of formula I may be also used to protect growing plants from attack or
infestation by pests by contacting the plant with a pesticidally effective amount of com-
pounds of formula I. As such, "contacting" includes both direct contact (applying the
compounds/compositions directly on the pest and/or plant - typically to the foliage,
stem or roots of the plant) and indirect contact (applying the compounds/compositions
to the locus of the pest and/or plant).
"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environ-
ment in which a pest or parasite is growing or may grow.
In general, "pesticidally effective amount" means the amount of active ingredient
needed to achieve an observable effect on growth, including the effects of necrosis,
death, retardation, prevention, and removal, destruction, or otherwise diminishing the
occurrence and activity of the target organism. The pesticidally effective amount can
vary for the various compounds/compositions used in the invention. A pesticidally ef-
fective amount of the compositions will also vary according to the prevailing conditions
such as desired pesticidal effect and duration, weather, target species, locus, mode of
application, and the like.
The compounds of formula I are effective through both contact (via soil, glass, wall,
bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).
For use against ants, termites, wasps, flies, mosquitos, crickets, or cockroaches, com-
pounds of formula I are preferably used in a bait composition.
The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can
be formed into various shapes and forms suitable to the respective application e.g.
granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure
proper application, e.g. open containers, spray devices, droplet sources, or evapora-
tion sources. Gels can be based on aqueous or oily matrices and can be formulated to
particular necessities in terms of stickyness, moisture retention or aging characteris-
tics.
The bait employed in the composition is a product, which is sufficiently attractive to
incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cock-
roaches to eat it. The attractiveness can be manipulated by using feeding stimulants or
sex pheromones. Food stimulants are chosen, for example, but not exclusively, from
animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from
fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides,
especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even
molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or

specific parts thereof can also serve as a feeding stimulant. Sex pheromones are
known to be more insect specific. Specific pheromones are described in the literature
and are known to those skilled in the art.
Formulations of compounds of formula I as aerosols (e.g in spray cans), oil sprays or
pump sprays are highly suitable for the non-professional user for controlling pests such
as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably com-
posed of the active compound, solvents such as lower alcohols (e.g. methanol, etha-
nol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocar-
bons (e.g. kerosenes) having boiling ranges of approximately 50 to 250°C, dimethyl-
formamide, N-methylpyrrolidone, dimethyl sulphoxide, aromatic hydrocarbons such as
toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol
monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate,
perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols,
aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate,
amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propel-
lants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon diox-
ide, nitrous oxide, or mixtures of these gases.
The oil spray formulations differ from the aerosol recipes in that no propellants are
used.
The compounds of formula I and its respective compositions can also be used in mos-
quito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers
and also in moth papers, moth pads or other heat-independent vaporizer systems.
Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue
and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula I
and its respective compositions also comprise treating surfaces of huts and houses, air
spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or
the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwov-
ens, netting material or foils and tarpaulins preferably comprise a mixture including the
insecticide, optionally a repellent and at least one binder. Suitable repellents for exam-
ple are N,N-Diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-
(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid
lactone, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid
not used for insect control such as {(+/-)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-
trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant ex-
tracts like limonene, eugenol, (+)-Eucamalol (1), (-)-i-epi-eucamalol or crude plant
extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii,
Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders
are selected for example from polymers and copolymers of vinyl esters of aliphatic

acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic es-
ters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate,
mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic
diens, such as butadiene.
The impregnation of curtains and bednets is done in general by dipping the textile ma-
terial into emulsions or dispersions of the insecticide or spraying them onto the nets.
The compounds of formula I and its compositions can be used for protecting wooden
materials such as trees, board fences, sleepers, etc. and buildings such as houses,
outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl
articles, electric wires and cables etc. from ants and/or termites, and for controlling
ants and termites from doing harm to crops or human being (e.g. when the pests in-
vade into houses and public facilities). The compounds of formula I are applied not
only to the surrounding soil surface or into the under-floor soil in order to protect
wooden materials but it can also be applied to lumbered articles such as surfaces of
the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden arti-
cles such as particle boards, half boards, etc. and vinyl articles such as coated electric
wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of ap-
plication against ants doing harm to crops or human beings, the ant controller of the
present invention is applied to the crops or the surrounding soil, or is directly applied to
the nest of ants or the like.
In the case of soil treatment or of application to the pests dwelling place or nest, the
quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from
0.001 to 20 g per 100 m2.
Customary application rates in the protection of materials are, for example, from 0.01 g
to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per
m2.
Insecticidal compositions for use in the impregnation of materials typically contain from
0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1
to 25 weight % of at least one repellent and/or insecticide.
For use in bait compositions, the typical content of active ingredient is from 0.001
weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active
compound.

For use in spray compositions, the content of active ingredient is from 0.001 to 80
weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15
weight %.
For use in treating crop plants, the rate of application of the active ingredients of this
invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to
600 g per hectare, more desirably from 50 g to 500 g per hectare.
Seed treatment
The compounds of formula I are also suitable for the treatment of seeds in order to
protect the seed from insect pest, in particular from soil-living insect pests and the re-
sulting plant's roots and shoots against soil pests and foliar insects.
The compounds of formula I are particularly useful for the protection of the seed from
soil pests and the resulting plant's roots and shoots against soil pests and foliar in-
sects. The protection of the resulting plant's roots and shoots is preferred. More pre-
ferred is the protection of resulting plant's shoots from piercing and sucking insects,
wherein the protection from aphids is most preferred.
The present invention therefore comprises a method for the protection of seeds from
insects, in particular from soil insects and of the seedlings' roots and shoots from in-
sects, in particular from soil and foliar insects, said method comprising contacting the
seeds before sowing and/or after pregermination with a compound of the general for-
mula I or a salt thereof. Particularly preferred is a method, wherein the plant's roots
and shoots are protected, more preferably a method, wherein the plants shoots are
protected form piercing and sucking insects, most preferably aa method, wherein the
plants shoots are protected from aphids.
The term seed embraces seeds and plant propagules of all kinds including but not lim-
ited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings,
cut shoots and the like and means in a preferred embodiment true seeds.
The term seed treatment comprises all suitable seed treatment techniques known in
the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed
pelleting.
The present invention also comprises seeds coated with or containing the active com-
pound.
The term "coated with and/or containing" generally signifies that the active ingredient is
for the most part on the surface of the propagation product at the time of application,
although a greater or lesser part of the ingredient may penetrate into the propagation

product, depending on the method of application. When the said propagation product is
(re)planted, it may absorb the active ingredient.
Suitable seed is seed of cereals, root crops, oil crops, vegetables, spices, ornamentals,
for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize
and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sun-
flowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants,
potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage,
iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas,
garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes,
petunias, geranium/pelargoniums, pansies and impatiens.
In addition, the active compound may also be used for the treatment seeds from
plants, which tolerate the action of herbicides or fungicides or insecticides owing to
breeding, including genetic engineering methods.
For example, the active compound can be employed in treatment of seeds from plants,
which are resistant to herbicides from the group consisting of the sulfonylureas, imida-
zolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous
active substances (see for example, EP-A-0242236, EP-A-242246) (WO 92/00377)
(EP-A-0257993, U.S. Pat. No. 5,013,659) or in transgenic crop plants, for example
cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which
make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259),
Furthermore, the active compound can be used also for the treatment of seeds from
plants, which have modified characteristics in comparison with existing plants consist,
which can be generated for example by traditional breeding methods and/or the gen-
eration of mutants, or by recombinant procedures). For example, a number of cases
have been described of recombinant modifications of crop plants for the purpose of
modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO
91/19806) or of transgenic crop plants having a modified fatty acid composition (WO
91/13972).
The seed treatment application of the active compound is carried out by spraying or by
dusting the seeds before sowing of the plants and before emergence of the plants.
Compositions which are especially useful for seed treatment are e.g.:
A Soluble concentrates (SL, LS)
D Emulsions (EW, EO, ES)
E Suspensions (SC, OD, FS)
F Water-dispersible granules and water-soluble granules (WG, SG)

G Water-dispersible powders and water-soluble powders (WP, SP, WS)
H Gel-Formulations (GF)
I Dustable powders (DP, DS)
Conventional seed treatment formulations include for example flowable concentrates
FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry
treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation
GF. These formulations can be applied to the seed diluted or undiluted. Application to
the seeds is carried out before sowing, either directly on the seeds or after having pre-
germinated the latter
In a preferred embodiment a FS formulation is used for seed treatment. Typcially, a FS
formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200
g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter
of a solvent, preferably water.
Especially preferred FS formulations of compounds of formula I for seed treatment
usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from
0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by
weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by
weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to
15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by
weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from
0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent,
and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an
amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
Seed Treatment formulations may additionally also comprise binders and optionally
colorants.
Binders can be added to improve the adhesion of the active materials on the seeds
after treatment. Suitable binders are block copolymers EO/PO surfactants but also
polyvinylalcoholsl, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybute-
nes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, poly-
ethyleneimines (Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate, ty-
lose and copolymers derived from these polymers.
Optionally, also colorants can be included in the formulation. Suitable colorants or dyes
for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent
Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1,
pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red
48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pig-

ment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white
6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red
14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Examples of a gelling agent is carrageen (Satiagel®)
In the treatment of seed, the application rates of the compounds I are generally from
0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more
preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per
100 kg of seed.
The invention therefore also relates to seed comprising a compound of the formula I, or
an agriculturally useful salt of I, as defined herein. The amount of the compound I or
the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg
of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g
per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
Animal health
The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof
are in particular also suitable for being used for combating parasites in and on animals.
An object of the present invention is therefore also to provide new methods to control
parasites in and on animals. Another object of the invention is to provide safer pesti-
cides for animals. Another object of the invention is further to provide pesticides for
animals that may be used in lower doses than existing pesticides. And another object
of the invention is to provide pesticides for animals, which provide a long residual con-
trol of the parasites.
The invention also relates to compositions containing a parasiticidally effective amount
of compounds of formula I or the enantiomers or veterinarily acceptable salts thereof
and an acceptable carrier, for combating parasites in and on animals.
The present invention also provides a method for treating, controlling, preventing and
protecting animals against infestation and infection by parasites, which comprises
orally, topically or parenterally administering or applying to the animals a parasiticidally
effective amount of a compound of formula I or the enantiomers or veterinarily
acceptable salts thereof or a composition comprising it.
The invention also provides a process for the preparation of a composition for treating,
controlling, preventing or protecting animals against infestation or infection by parasites

which comprises a parasiticidally effective amount of a compound of formula I or the
enantiomers or veterinarily acceptable salts thereof or a composition comprising it.
Activity of compounds against agricultural pests does not suggest their suitability for
control of endo- and ectoparasites in and on animals which requires, for example, low,
non-emetic dosages in the case of oral application, metabolic compatibility with the
animal, low toxicity, and a safe handling.
Surprisingly it has now been found that compounds of formula I are suitable for com-
bating endo- and ectoparasites in and on animals.
Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and
compositions comprising them are preferably used for controlling and preventing infes-
tations and infections animals including warm-blooded animals (including humans) and
fish. They are for example suitable for controlling and preventing infestations and infec-
tions in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry,
rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and
also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens,
geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout,
carp and eels.
Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and
compositions comprising them are preferably used for controlling and preventing infes-
tations and infections in domestic animals, such as dogs or cats.
Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting
lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chig-
gers, gnats, mosquitoes and fleas.
The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof
and compositions comprising them are suitable for systemic and/or non-systemic con-
trol of ecto- and/or endoparasites. They are active against all or some stages of devel-
opment.
The compounds of formula I are especially useful for combating ectoparasites.
The compounds of formula I are especially useful for combating parasites of the follow-
ing orders and species, respectively:
fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla
cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Pe-
riplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuliggi-
nosa, Periplaneta australasiae, and Blatta orientalis,
flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, An-
astrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus,
Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles mini-
mus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya
hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops
atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens,
Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor-
nata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intes-
tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides,
Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Lep-
toconops torrens, Luc/Ha caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis,
Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus ar-
gentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sar-
cophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans,
Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,
lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthi-
ruspubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola
bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.
ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes
holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni,
Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Orni-
thodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Orni-
thonyssus bacoti and Dermanyssus gallinae,
Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella
spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula
spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes
spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes
spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,
Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma
spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,
Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp.,
and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp.,
Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp.,
Trichodectes spp., and Felicola spp,
Roundworms Nematoda:
Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.),
(Trichuridae,) Trichuris spp., Capillaria spp,
Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,
Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necatoramericanus, Bunosto-
mum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia
spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oe-
sophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stepha-
nurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus
spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,
Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioc-
tophyma renale,
Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia
galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara cam's,
Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,
Camallanida, e.g. Dracunculus medinensis (guinea worm)
Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari
spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Hab-
ronema spp.,
Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracantho-
rhynchus hirudinaceus and Oncicola spp,
Planarians (Plathelminthes):
Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicro-
coelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilhar-
zia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,
Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp.,
Ten/a spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp.,

Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra
spp., Anoplocephala spp., and Hymenolepis spp.
The compounds of formula I and compositions containing them are particularly useful
for the control of pests from the orders Diptera, Siphonaptera and Ixodida.
Moreover, the use of the compounds of formula I and compositions containing them for
combating mosquitoes is especially preferred.
The use of the compounds of formula I and compositions containing them for combat-
ing flies is a further preferred embodiment of the present invention.
Furthermore, the use of the compounds of formula I and compositions containing them
for combating fleas is especially preferred.
The use of the compounds of formula I and compositions containing them for combat-
ing ticks is a further preferred embodiment of the present invention.
The compounds of formula I also are especially useful for combating endoparasites
(roundworms nematoda, thorny headed worms and planarians).
Administration can be carried out both prophylactically and therapeutically.
Administration of the active compounds is carried out directly or in the form of suitable
preparations, orally, topically/dermally or parenterally.
For oral administration to warm-blooded animals, the formula I compounds may be
formulated as animal feeds, animal feed premixes, animal feed concentrates, pills,
solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addi-
tion, the formula I compounds may be administered to the animals in their drinking wa-
ter. For oral administration, the dosage form chosen should provide the animal with
0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound,
preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the formula I compounds may be administered to animals parenterally,
for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The
formula I compounds may be dispersed or dissolved in a physiologically acceptable
carrier for subcutaneous injection. Alternatively, the formula I compounds may be for-
mulated into an implant for subcutaneous administration. In addition the formula I com-
pound may be transdermally administered to animals. For parenteral administration,
the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of
animal body weight per day of the formula I compound.

The formula I compounds may also be applied topically to the animals in the form of
dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on for-
mulations and in ointments or oil-in-water or water-in-oil emulsions. For topical applica-
tion, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to
3,000 ppm of the formula I compound. In addition, the formula I compounds may be
formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
- Solutions such as oral solutions, concentrates for oral administration after dilution,
solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or dermal administration; semi-solid prepara-
tions;
- Formulations in which the active compound is processed in an ointment base or in an
oil-in-water or water-in-oil emulsion base;
- Solid preparations such as powders, premixes or concentrates, granules, pellets,
tablets, boluses, capsules; aerosols and inhalants, and active compound-containing
shaped articles.
Compositions suitable for injection are prepared by dissolving the active ingredient in a
suitable solvent and optionally adding further ingredients such as acids, bases, buffer
salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.
Suitable solvents are physiologically tolerable solvents such as water, alkanols such as
ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-
methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.
The active compounds can optionally be dissolved in physiologically tolerable vegeta-
ble or synthetic oils, which are suitable for injection.
Suitable solubilizers are solvents which promote the dissolution of the active compound
in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone,
polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.
Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid es-
ters, and n-butanol.

Oral solutions are administered directly. Concentrates are administered orally after
prior dilution to the use concentration. Oral solutions and concentrates are prepared
according to the state of the art and as described above for injection solutions, sterile
procedures not being necessary.
Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or
sprayed on.
Solutions for use on the skin are prepared according to the state of the art and accord-
ing to what is described above for injection solutions, sterile procedures not being nec-
essary.
Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol,
ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol
alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, me-
thylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylforma-
mide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures
thereof.
It may be advantageous to add thickeners during preparation. Suitable thickeners are
inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate,
organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copoly-
mers, acrylates and methacrylates.
Gels are applied to or spread on the skin or introduced into body cavities. Gels are
prepared by treating solutions which have been prepared as described in the case of
the injection solutions with sufficient thickener that a clear material having an ointment-
like consistency results. The thickeners employed are the thickeners given above.
Pour-on formulations are poured or sprayed onto limited areas of the skin, the active
compound penetrating the skin and acting systemically.
Pour-on formulations are prepared by dissolving, suspending or emulsifying the active
compound in suitable skin-compatible solvents or solvent mixtures. If appropriate,
other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants,
light stabilizers, adhesives are added.
Suitable solvents which are: water, alkanols, glycols, polyethylene glycols, polypropyl-
ene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, pheno-
xyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as
alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene
glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbon-

ates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hy-
drocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones
such as methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, N-
methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-diox- olane and
glycerol formal.
Suitable colorants are all colorants permitted for use on animals and which can be dis-
solved or suspended.
Suitable absorption-promoting substances are, for example, DMSO, spreading oils
such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copoly-
mers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.
Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite,
ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.
Suitable light stabilizers are, for example, novantisolic acid.
Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacry-
lates, natural polymers such as alginates, gelatin.
Emulsions can be administered orally, dermally or as injections.
Emulsions are either of the water-in-oil type or of the oil-in-water type.
They are prepared by dissolving the active compound either in the hydrophobic or in
the hydrophilic phase and homogenizing this with the solvent of the other phase with
the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants,
absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscos-
ity-enhancing substances.
Suitable hydrophobic phases (oils) are:
liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, cas-
tor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture
with vegetable fatty acids of the chain length C8-C12 or other specially selected natural
fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly
also containing hydroxyl groups, mono- and diglycerides of the C8-C10 fatty acids,
fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene
glycol perlargonate, esters of a branched fatty acid of medium chain length with satu-
rated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate,
caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl
stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters

such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and
ester mixtures related to the latter.fatty alcohols such as isotridecyl alcohol, 2-
octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid
and mixtures thereof.
Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol,
sorbitol and mixtures thereof.
Suitable emulsifiers are:
non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monoo-
leate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphe-
nol polyglycol ether;
ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin;
anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mo-
no/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;
cation-active surfactants, such as cetyltrimethylammonium chloride.
Suitable further auxiliaries are: substances which enhance the viscosity and stabilize
the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and
starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone,
polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene
glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.
Suspensions can be administered orally or topically/dermally. They are prepared by
suspending the active compound in a suspending agent, if appropriate with addition of
other auxiliaries such as wetting agents, colorants, bioabsorption-promoting sub-
stances, preservatives, antioxidants, light stabilizers.
Liquid suspending agents are all homogeneous solvents and solvent mixtures.
Suitable wetting agents (dispersants) are the emulsifiers given above.
Other auxiliaries which may be mentioned are those given above.
Semi-solid preparations can be administered orally or topically/dermally. They differ
from the suspensions and emulsions described above only by their higher viscosity.
For the production of solid preparations, the active compound is mixed with suitable
excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
Suitable excipients are all physiologically tolerable solid inert substances. Those used
are inorganic and organic substances. Inorganic substances are, for example, sodium

chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium ox-
ides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or
phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and
feeds such as milk powder, animal meal, grain meals and shreds, starches.
Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been
mentioned above.
Other suitable auxiliaries are lubricants and glidants such as magnesium stearate,
stearic acid, talc, bentonites, disintegration-promoting substances such as starch or
crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyr-
rolidone, and dry binders such as microcrystalline cellulose.
In general, "parasiticidally effective amount" means the amount of active ingredient
needed to achieve an observable effect on growth, including the effects of necrosis,
death, retardation, prevention, and removal, destruction, or otherwise diminishing the
occurrence and activity of the target organism. The parasiticidally effective amount can
vary for the various compounds/compositions used in the invention. A parasiticidally
effective amount of the compositions will also vary according to the prevailing condi-
tions such as desired parasiticidal effect and duration, target species, mode of applica-
tion, and the like.
The compositions which can be used in the invention can comprise generally from
about 0.001 to 95% of the compound of formula I.
Generally it is favorable to apply the compounds of formula I in total amounts of 0.5
mg/kg to 100 mg/kg per day , preferably 1 mg/kg to 50 mg/kg per day.
Ready-to-use preparations contain the compounds acting against parasites, preferably
ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from
0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most
preferably from 5 to 40 per cent by weight.
Preparations which are diluted before use contain the compounds acting against ecto-
parasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per
cent by weight.
Furthermore, the preparations comprise the compounds of formula I against endopara-
sites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per
cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.

In a preferred embodiment of the present invention, the compositions comprising the
compounds of formula I them are applied dermally / topically.
In a further preferred embodiment, the topical application is conducted in the form of
compound-containing shaped articles such as collars, medallions, ear tags, bands for
fixing at body parts, and adhesive strips and foils.
Generally it is favorable to apply solid formulations which release compounds of for-
mula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg,
most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course
of three weeks.
For the preparation of the shaped articles, thermoplastic and flexible plastics as well as
elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers
are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose de-
rivatives, polyamides and polyester which are sufficiently compatible with the com-
pounds of formula I. A detailed list of plastics and elastomers as well as preparation
procedures for the shaped articles is given e.g. in WO 03/086075.
The present invention is now illustrated in further detail by the following examples.
P. Preparation examples:
P.1 Acetic acid 2-[3-(7-bromo-1,2,3,4-tetrahydro-naphthalen-1-yl)-thioureido]-ethyl
ester (compound example 6 of table 1)
To a solution of 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ylamine (0.32 g) in 10 ml
toluene was added acetic acid 2-isothiocyanato-ethyl ester (0.20 g) at RT and stirred
overnight. The reaction mixture was concentrated in vacuo and the residue purified on
silica gel to yield 0.42 g of the product (80%) as an oil.
P.2 Benzoic acid 2-[3-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-1 -yl)-thioureido]-
ethyl ester (compound example 7 of table 1)
To a solution of 5-methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylamine (0.32 g) in 10 ml
toluene was added benzoic acid 2-isothiocyanato-ethyl ester (0.37 g) at RT and stirred
overnight. The reaction mixture was concentrated in vacuo and the residue purified on
silica gel to yield 0.32 g of the product (46%) as a colorless solid, m.p. 135-137 OC.
P.3 Isonicotinic acid 2-(3-indan-1-yl-thioureido)-ethyl ester (compound example 13
of table 1)

To a solution of thiophosgene (4.14 g) in chloroform was added at RT a solution of
13.25 g potassium carbonate in 70 ml of water. To this mixture was added a solution of
indanyl-1-amine (4.00 g) in chloroform (100 ml) and the mixture stirred at RT overnight.
The reaction mixture was washed with water (2 x) and the organic phase dried over
sodium sulfate. Evaporation of the solvent yielded the product (5.20 g, 99%) which was
used for the following step without further purification.
2.97 g of this crude isothiocyanate was dissolved in toluol (70 ml) and treated with
2-aminoethanol for 2 h at 90 °C. The mixture was concentrated in vacuo and the resi-
due titurated with light petrol ether. The solid product was separated by filtration and
dried in vacuo (yield: 3.88 g, 97%) and used without further purification for the next
step.
A solution of 1-(2-hydroxy-ethyl)-3-indan-1-yl-thiourea (0.47 g) and triethyl amine (0.44
g) in THF (20 ml) was treated with a solution of isonicotinyl chloride hydrochloride (0.36
g) in 6 ml THF and the mixture stirred for 4 h at 50 °C. After concentration in vacuo the
mixture was dissolved in ethyl acetate and washed with water, the organic layer dried
separated and dried over sodium sulfate and concentrated in vacuo. The residue was
purified by column chromatography on silica gel yielding a colorless powder (0.27 g) of
the product (39%), m.p. 126-128 °C.
P.4 Methoxy-acetic acid 2-(3-indan-1-yl-thioureido)-ethyl ester (compound example
14 of table 1)
A solution of 1-(2-hydroxy-ethyl)-3-indan-1-yl-thiourea (0.47 g, prepared according to
the procedure described for example 16) and triethyl amine (0.44 g) in THF (20 ml)
was treated at RT with a solution of methoxy acetyl chloride (0.22 g) in THF (6 ml) and
stirred for 10 h at 50 °C. The reaction mixture was concentrated in vacuo, dissolved in
ethyl acetate, washed with water and dried over sodium sulfate. The solvent was
evaporated and the residue purified over silica gel to yield the product (0.36 g) in 58 %
yield.
P.5 (S)-1-lndan-1-yl-3-[2-(thiazol-2-yloxy)-ethyl]-thiourea (compound example 20 of
table 1)
A solution of the S-isomerof 1-(2-hydroxy-ethyl)-3-indan-1-yl-thiourea (0,50 g, pre-
pared according to the procedure described for example 16, starting from enantiomeri-
cally pure (S)-indanyl-1-amine) in dimethylformamide (30 ml) was treated with potas-
sium carbonate (0.37 g) and 2-bromothiazole (0.43 g) and heated at 45 °C for 6 h. Af-
ter additional stirring overnight at RT an additional amount of potassium carbonate
(0.15 g) was added and the solution stirred at 55 °C for 5 h.

Surplus of carbonate was removed by filtration, the filtrate concentrated and the re-
minder purified via chromatography on silica gel. This yielded the product (0.39 g,
58%) as an oil.
C. Compound examples
The compounds of the general formula I can be prepared accordingly. The spectro-
scopical data of these compounds are listed in Table 1.













B. Examples of action against pests
The action of the compounds I against pests was demonstrated by the following
experiments:
The active compounds were formulated
a. for testing the activity against Aphis gossypii, Myzus persicae, and Aphis fabae,
as 50:50 acetone:water solutions amended with 100 ppm Kinetic® (surfactant),
b. for testing the activity against Spodoptera eridania as a 10.000 ppm solution in a
mixture of 35% acetone and water, which was diluted with water, if needed.
After the experiments were completed, in each case the lowest concentration was
determined at which the compound still caused an 75 to 100% inhibition or mortality in
comparison with untreated controls (limit or minimal concentration).
B.1 Cotton Aphid {Aphis gossypii)
Cotton plants in the cotyledon stage (variety 'Delta Pine') are infested with approxi-
mately 100 laboratory-reared aphids by placing infested leaf sections on top of the test
plants. The leaf sections are removed after 24 hr. The cotyledons of the intact plants
are dipped into gradient solutions of the test compound. Aphid mortality on the treated
plants, relative to mortality on check plants, is determined after 5 days.
In this test, compounds of examples nos 1-3, 9-17 and 22-41 at 300 ppm showed over
80% mortality in comparison with untreated controls.
B.2 Green Peach Aphid (Myzus persicae)

Pepper plants in the 2nd leaf-pair stage (variety "California Wonder') are infested with
approximately 40 laboratory-reared aphids by placing infested leaf sections on top of
the test plants. The leaf sections are removed after 24 hr. The leaves of the intact
plants are dipped into gradient solutions of the test compound. Aphid mortality on the
treated plants, relative to mortality on check plants, is determined after 5 days.
In this test, compounds of examples nos. 1-3, 9, 10-15, 17 and 22-41 at 300 ppm
showed over 80% mortality in comparison with untreated controls.
B.3 Bean Aphid (Aphis fabae)
Nasturtium plants in the 1st leaf-pair stage (variety 'Mixed Jewel") are infested with ap-
proximately 25 laboratory-reared aphids by placing infested cut plants on top of the test
plants. The cut plants are removed after 24 hr. The foliage and stem of the test plants
are dipped into gradient solutions of the test compound. Aphid mortality is determined
after 3 days.
In this test, compounds of examples nos. 12-15 at 300 ppm showed over 80%
mortality in comparison with untreated controls.

Claims:
1. A Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I

wherein
n is 1 or 2;
m is 1,2,3 or 4, wherein when m is greater than 1, the radicals R1 may have
the same or different meanings;
R1 is selected from hydrogen, halogen, OH, SH, NH2, SO3H, COOH, cyano,
azido, nitro, formyl, CONH2, CSNH2, CH=N-OH, CH=N-O-(C1-C6)-alkyl,
C(=O)R1c, C(=S)R1c, C1-C6-alkyI, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-
cycloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, d-C8-
alkylthio, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkenylamino, C2-C6-
alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, C2-C6-
alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl,
C2-C6-alkynylsulfonyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl,
(C2-C6-alkynyloxy)-carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-
)carbonyl-oxy or (C2-C6-alkynyl)carbonyloxy, (C2-C6-alkenyl)carbonyl-
amino, wherein the carbon atoms in the aliphatic radicals of the aforemen-
tioned groups may carry any combination of 1, 2 or 3 radicals, independ-
ently of one another selected from the group consisting of halogen, cyano,
nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
C(O)NR1aR1b, (SO2)NR1aR1b, wherein
R1a and R1bare each independently hydrogen, OH, NH2, C1-C6-alkyl, C1-C6-
haloalkyl, C2-C6-alkenyl or C2-C6-alkynyl;
R1c is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-
alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)amino,
di(C1-C6-alkyl)amino, hydrazino, (C1-C6-alkyl)hydrazino, di(Ci-
C6-alkyl)hydrazino, phenyl and heteroaryl, which can be a

mono- or bicyclic 5 to 10 membered heteroaromatic ring, which
contains 1,2,3 or 4 heteroatoms selected from O,S and N;
a radical Y-Ar or a radical Y-Cy, wherein
Y is a single bond, oxygen, sulfur, nitrogen, C1-C6-alkandiyI or C1-C6-
alkandiyloxy;
Ar is phenyl, naphthyl or a mono- or bicyclic 5- to 10-membered het-
eroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected
from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members,
wherein Ar is unsubstituted or may carry any combination of 1 to 5
radicals, independently of one another selected from the group con-
sisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5
radicals, independently of one another selected from the group con-
sisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
and wherein the radical R1 that is bound to adjacent carbon atoms of the
phenyl rings may form, together with said carbon atoms, a fused benzene
ring, a fused saturated or partially unsaturated 5-, 6-, or 7-membered car-
bocycle or a fused 5-, 6- or 7-membered heterocycle, which contains 1,2,3
or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as
ring members, and wherein the fused ring is unsubstituted or may carry 1,
2, 3 or 4 radicals, independently of one another selected from the group
consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-
C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy and C1-C6-alkylthio;
R2 is selected from hydrogen, C(=O)R2d, C(=S)R2d, C1-C6-alkyl, C1-C6-
alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkenyl, C2-C6-alkenylamino, C2-C6-
alkynyl, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkylsulfonyl, C2-
C6-alkenylsulfonyl, C2-C6-alkynylsulfonyl C1-C6-alkylsulfinyl, C2-C6-
alkenylsulfinyl, C2-C6-alkynylsulfinyl, C3-C12-cycloalkyl, P(=O)R2aR2b,
P(=S)R2aR2b, NR2aR2b, SiR2aR2bR2c, N=CR2aR2b, CR2a=NR2b;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem which
may contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen
and which are unsubstituted or substituted with any combination of 1 to 5
groups selected from halogen, cyano, nitro, hydroxy, mercapto, amino, car-
boxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy, or C1-C6-alkylthio; and wherein

R2a, R2b and R2c are selected each independently from hydrogen, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, and wherein
the carbon atoms in these groups may be substituted by 1
to 3 of a substituent selected by halogen, cyano, nitro,
hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-
alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-
Ce-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
R2d is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkynylamino, di(C2-C6-
alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, d-
C6-alkylthio, and wherein the carbon atoms in these groups may be
substituted by 1 to 3 of a substituent selected by halogen, cyano, ni-
tro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-
C6-haloalkoxy, or C1-C6-alkylthio;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem
which may contain 1 to 4 heteroatoms selected from oxygen, sulfur
and nitrogen and which are unsubstituted or substituted with any
combination of 1 to 5 groups selected from halogen, cyano, nitro, hy-
droxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
!3,R4 are selected from hydrogen, cyano, nitro, formyl, C(=O)R3c or
C(=O)R4c, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl,
C1-C6-alkoxy , (C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-
alkylsulfenyl or Ct-C6-alkylsulfonyl wherein the carbon atoms in the
aliphatic radicals of the aforementioned groups may carry any combi-
nation of 1, 2 or 3 radicals, independently of one another selected
from the group consisting of halogen, cyano, nitro, hydroxy, mer-
capto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy,
C2-C6-alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio, C(O)NR3aR3b
or C(O)NR4aR4b, (SO2)NR3aR3b or (SO2)NR4aR4b, phenyl, phenyloxy
or benzyl, each of the last three mentioned radicals may be unsubsti-
tuted or substituted with 1 to 5 radicals, independently of one another
selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-
haloalkyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkoxy and d-
C6-haloalkoxy radicals; and wherein
R3a, R4a and R3b, R4b are each independently selected from hydro-
gen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-
alkenyl, or C2-C6-alkynyl;

R3c, R4c are each independently selected from hydrogen, C1-C6-alkyl,
C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-
alkylthio, C1-C6-alkoxy, (C1-C6-alkyl)amino, di(C1-C6-
alkyl)amino, phenyl and heteroaryl, which can be a mono- or
bicyclic 5 to 10 membered heteroaromatic ring, which con-
tains 1,2,3 or 4 heteroatoms selected from O,S and N;
with the proviso that at least one of R3 and R4 is hydrogen;
or the enantiomers and/or the agriculturally or veterinary acceptable salts
thereof,
with the proviso that compound of formula I is not representing a 3-(1,2,3,4-
tetrahydro-1-naphtyl)-thio-urea derivative, wherein (R1)m,R3 and R4 are hydro-
gens and R2 is hydrogen or R2 is CH3.
An Indanyl-amino-thiourea compound of the formula I as defined in claim 1,
wherein n is 1.
An Tetrahydronaphthyl-amino-thiourea compound of the formula I as defined in
claim 1, wherein n is 2.
An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of formula I ac-
cording to claim 1, wherein m is 1,2 or 3.
An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I
as defined in claim 1, wherein m is 1 or 2.
An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I
as defined in claim 1, wherein m is 1.
An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of formula I ac-
cording to claim 1, wherein
R1 is selected from cyano, azido, halogen, OH, SH, NH2) CONH2l SO3H,
COOH, C(=O)R1c, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-
cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, wherein
the carbon atoms in the aliphatic radicals of the aforementioned groups
may carry any combination of 1, 2 or 3 radicals, independently of one an-
other selected from the group consisting of halogen, cyano, nitro, hydroxy,
amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy;
and wherein

R1c is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl,
C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)amino, di(C1-C6-
alkyl)amino, phenyl and heteroaryl, which can be a mono- or bicyclic
5 to 10 membered heteroaromatic ring, which contains 1,2,3 or 4 het-
eroatoms selected from O,S and N.
An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I
as defined in claim 1, wherein
R2 is selected from C(=O)R2d, C(=S)R2d, C1-C6-alkyl, phenyl or a mono- or bi-
cyclic 5- to 10-membered aromatic ringsystem which may contain 1 to 4
heteroatoms selected from oxygen, sulfur and nitrogen and which are un-
substituted or substituted with any combination of 1 to 5 groups selected
from halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-
alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy,
or C1-C6-alkylthio; and wherein
R2d is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkynylamino, di(C2-C6-
alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, d-
Ce-alkylthio, and wherein the carbon atoms in these groups may be
substituted by 1 to 3 of a substituent selected by halogen, cyano, ni-
tro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-
C6-haloalkoxy, or C1-C6-alkylthio;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem
which may contain 1 to 4 heteroatoms selected from oxygen, sulfur
and nitrogen and which are unsubstituted or substituted with any
combination of 1 to 5 groups selected from halogen, cyano, nitro, hy-
droxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy or C1-C6-alkylthio.
An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I
as defined in claim 1, wherein
R2 is selected from C(=O)R2d, phenyl or a mono- or bicyclic 5- to 10-
membered aromatic ringsystem which may contain 1 to 4 heteroatoms se-
lected from oxygen, sulfur and nitrogen and which are unsubstituted or
substituted with any combination of 1 to 5 groups selected from halogen,
cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy,
C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
and wherein
R2d is selected from C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-
alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkynylamino, di(C2-C6-
alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, d-

Ce-alkylthio, and wherein the carbon atoms in these groups may be
substituted by 1 to 3 of a substituent selected by halogen, cyano, ni-
tro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-
Ce-haloalkoxy, or C1-C6-alkylthio;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem
which may contain 1 to 4 heteroatoms selected from oxygen, sulfur
and nitrogen and which are unsubstituted or substituted with any
combination of 1 to 5 groups selected from halogen, cyano, nitro, hy-
droxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio.
i. An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I
as defined in claim 1, wherein
R2 is selected from C(=O)R2d, phenyl or a mono- or bicyclic 5- to 10-membered
aromatic ringsystem which may contain 1 to 4 heteroatoms selected from
oxygen, sulfur and nitrogen and which are unsubstituted or substituted with
any combination of 1 to 5 groups selected from halogen, cyano, nitro, hy-
droxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
R2d is selected from C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem
which may contain 1 to 4 heteroatoms selected from oxygen, sulfur
and nitrogen and which are unsubstituted or substituted with any
combination of 1 to 5 groups selected from halogen, cyano, nitro, hy-
droxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio.
. An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of formula I ac-
cording to claim 1, wherein
R3, R4 are selected from hydrogen, cyano, C(=O)R3c or C(=O)R4c, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ca-Cs-cycloalkyl, C1-C6-alkoxy ,
(C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl or C1i-
C6-alkylsulfonyl; and wherein
R3c, R4c are each independently selected from hydrogen, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-
alkoxy, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, phenyl
and heteroaryl, which can be a mono- or bicyclic 5 to 10
membered heteroaromatic ring, which contains 1,2,3 or 4
heteroatoms selected from O,S and N;
with the proviso that at least one of R3 and R4 is hydrogen.

12. An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of formula I ac-
cording to claim 1, wherein
R3, R4 are selected from hydrogen, cyano, C(=O)R3c or C(=O)R4, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkinyl; (C1-C6-alkoxy)methylen, C1-C6-
alkylsulfinyl, C1-C6-alkylsulfenyl or C1-C6-alkylsulfonyl; and wherein
R3c, R4c are each independently selected from C1-C6-alkyl C1-C6-
alkoxy, phenyl and heteroaryl, which can be a mono- or
bicyclic 5 to 10 membered heteroaromatic ring, which
contains 1,2,3 or 4 heteroatoms selected from O, S and
N;
with the proviso that at least one of R3 and R4 is hydrogen.
13. An Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of formula I ac-
cording to claim 1, wherein R3 and R4 are both hydrogen.
14. A Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I,

wherein
n is 1 or 2;
m is 1,2 or 3, wherein when m is greater than 1, the radicals R1 may have the
same or different meanings;
R1 is selected from hydrogen, halogen, OH, SH, NH2, SO3H, COOH, cyano,
azido, nitro, formyl, CONH2, CSNH2, CH=N-OH, CH=N-O-(C1-C6)-alkyl,
C(=O)R1c, C(=S)R1c, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-
cycloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C-i-Cs-
alkylthio, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkenylamino, C2-C6-
alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, C2-C6-
alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl,
C2-C6-alkynylsulfonyl, (C1 -C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl,
(C2-C6-alkynyloxy)-carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-
)carbonyl-oxy or (C2-C6-alkynyl-)carbonyloxy, (C2-C6-alkenyl)carbonyl-

amino, wherein the carbon atoms in the aliphatic radicals of the aforemen-
tioned groups may carry any combination of 1, 2 or 3 radicals, independ-
ently of one another selected from the group consisting of halogen, cyano,
nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
C(O)NR1aR1b, (SO2)NR1aR1b, wherein
R1a, R1b are each independently selected from hydrogen, OH, NH2, Cr
Ce-alkyl, C1-C6-haloalkyI, C2-C6-alkenyl or C2-C6-alkynyl.
R1c is selected from hydrogen, CrCe-alkyl, C2-C6-alkenyl, C2-Ce-
alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)amino,
di(C1-C6-alkyl)amino, hydrazino, (C1-C6-alkyl)hydrazino, di(d-
C6-alkyl)hydrazino, phenyl and heteroaryl, which can be a
mono- or bicyclic 5 to 10 membered heteroaromatic ring, which
contains 1,2,3 or 4 heteroatoms selected from O,S and N;
a radical Y-Ar or a radical Y-Cy, wherein
Y is a single bond, oxygen, sulfur, nitrogen, C1-C6-alkandiyl or C1-C6-
alkandiyloxy;
Ar is phenyl, naphthyl or a mono- or bicyclic 5- to 10-membered het-
eroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected
from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members,
wherein Ar is unsubstituted or may carry any combination of 1 to 5
radicals, independently of one another selected from the group con-
sisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5
radicals, independently of one another selected from the group con-
sisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;
and wherein the radical R1 that are bound to adjacent carbon atoms of the
phenyl rings may form, together with said carbon atoms, a fused benzene
ring, a fused saturated or partially unsaturated 5-, 6-, or 7-membered car-
bocycle or a fused 5-, 6- or 7-membered heterocycle, which contains 1,2,3
or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as
ring members, and wherein the fused ring is unsubstituted or may carry 1,
2, 3 or 4 radicals, independently of one another selected from the group
consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-
Ce-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy and C1-C6-alkylthio;

R2 is selected from hydrogen, C(=O)R2d, C(=S)R2d, C1-C6-alkyl, C1-C6-alkylamino,
di(C1-C6-alkyl)amino, C2-C6-alkenyl, C2-C6-alkenylamino, C2-C6-alkynyl, C2-C6-
alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkylsulfonyl, C2-C6-alkenylsulfonyl,
C2-C6-alkynylsulfonyl C1-C6-alkylsulfinyl, C2-C6-alkenyisulfinyl, C2-Ce-
alkynylsulfinyl, C3-C12-cycloalkyl, P(=O)R2aR2b, P(=S)R2aR2b, NR2aR2b,
SiR2aR2bR2c, N=CR2aR2b, CR2a=NR2b;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem which
may contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen and
which are unsubstituted or substituted with any combination of 1 to 5 groups se-
lected from halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-
alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy or Ci-
C6-alkylthio; and wherein
R2a, R2b and R2c are selected each independently from hydrogen, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, and wherein
the carbon atoms in these groups may be substituted by 1
to 3 of a substituent selected by halogen, cyano, nitro,
hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-
alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-
C6-alkynyloxy, C1-C6-haloalkoxy or C1-C6-alkylthio;
R2d is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkynylamino, di(C2-C6-
alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-
C6-alkylthio, and wherein the carbon atoms in these groups may be
substituted by 1 to 3 of a substituent selected by halogen, cyano, ni-
tro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-
C6-haloalkoxy or C1-C6-alkylthio;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem
which may contain 1 to 4 heteroatoms selected from oxygen, sulfur
and nitrogen and which are unsubstituted or substituted with any
combination of 1 to 5 groups selected from halogen, cyano, nitro, hy-
droxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
R3,R4 are selected from hydrogen, cyano, nitro, formyl, C(=O)R3c or
C(=O)R4c, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl,
C1-C6-alkoxy , (C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-
alkylsulfenyl or C1-C6-alkylsulfonyl wherein the carbon atoms in the
aliphatic radicals of the aforementioned groups may carry any combi-
nation of 1, 2 or 3 radicals, independently of one another selected
from the group consisting of halogen, cyano, nitro, hydroxy, mer-

capto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy,
C2-C6-alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio, C(O)NR3aR3b
or C(O)NR4aR4b, (SO2)NR3aR3b or (SO2)NR4aR4b, phenyl, phenyloxy
or benzyl, each of the last three mentioned radicals may be unsubsti-
tuted or substituted with 1 to 5 radicals, independently of one another
selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-
haloalkyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkoxy and Ci-
C6-haloalkoxy; and wherein
R3a, R4a and R3b, R4b are each independently hydrogen, C1-C6-alkyl,
C1-C6-haloalkyl, C2-C6-alkenyl or C2-C6-
alkynyl;
R3c, R40 are selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-
C6-alkinyl, Cs-Ce-cycloalkyl, C1-C6-alkylthio, C1-C6-alkoxy,
(C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, phenyl and het-
eroaryl, which can be a mono- or bicyclic 5 to 10 membered
heteroaromatic ring, which contains 1,2,3 or 4 heteroatoms
selected from O,S and N;
with the proviso that at least one of R3 and R4 is hydrogen;
or the enantiomers and/or the agriculturally or veterinary acceptable salts thereof,
with the proviso that compound of formula I is not representing a 3-(1,2,3,4-
tetrahydro-1-naphtyl)-thio-urea derivative, wherein (R1)m,R3 and R4 are hydro-
gens and R2 is hydrogen or R2 is CH3.
. A Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the formula I,

wherein
n is 1
m is 1 or 2, wherein when m is greater than 1, the radicals R1 may have the
same or different meanings;

R1 is selected from hydrogen, halogen, OH, SH, NH2, SO3H, COOH, cyano,
azido, nitro, formyl, CONH2, CSNH2, CH=N-OH, CH=N-O-(C1-C6)-alkyl,
C(=O)R1c, C(=S)R1c, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-
cycloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, Ci-C8-
alkylthio, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkenylamino, C2-C6-
alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, C2-C6-
alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl,
C2-C6-alkynylsulfonyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl,
(C2-C6-alkynyloxy)-carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-
alkenyl)carbonyl-oxy or (C2-C6-alkynyl)carbonyloxy, (C2-C6-
alkenyl)carbonyl-amino, wherein the carbon atoms in the aliphatic radicals
of the aforementioned groups may carry any combination of 1, 2 or 3 radi-
cals, independently of one another selected from the group consisting of
halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl,
C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy and
C1-C6-alkylthio;
C(O)NR1aR1b, (SO2)NR1aR1b, wherein
R1a and R1bare each independently hydrogen, OH, NH2) C1-C6-alkyl, C1-C6-
haloalkyl, C2-Ce-alkenyl or C2-C6-alkynyl;
R1c is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-Ce-
alkinyl, C3-C3-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)amino,
di(C1-C6-alkyl)amino, hydrazino, (C1-C6-alkyl)hydrazino, di(Ci-
C6-alkyl)hydrazino, phenyl and heteroaryl, which can be a
mono- or bicyclic 5 to 10 membered heteroaromatic ring, which
contains 1,2,3 or 4 heteroatoms selected from O,S and N;
a radical Y-Ar or a radical Y-Cy, wherein
Y is a single bond, oxygen, sulfur, nitrogen, C1-C6-alkandiyl or C1-C6-
alkandiyloxy;
Ar is phenyl, naphthyl or a mono- or bicyclic 5- to 10-membered het-
eroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected
from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members,
wherein Ar is unsubstituted or may carry any combination of 1 to 5
radicals, independently of one another selected from the group con-
sisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloaIkoxy and C1-C6-alkylthio;
Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5
radicals, independently of one another selected from the group con-
sisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-
alkynyloxy, C1-C6-haloalkoxy and C1-C6-alkylthio;

and wherein the radical R1 that are bound to adjacent carbon atoms of the
phenyl rings may form, together with said carbon atoms, a fused benzene
ring, a fused saturated or partially unsaturated 5-, 6-, or 7-membered car-
bocycle or a fused 5-, 6- or 7-membered heterocycle, which contains 1, 2,
3 or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms
as ring members, and wherein the fused ring is unsubstituted or may carry
1, 2, 3 or 4 radicals, independently of one another selected from the group
consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,
C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy and C1-C6-alkylthio;
R2 is selected from hydrogen, C(=O)R2d, C(=S)R2d, C1-C6-alkyl, C1-C6-
alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkenyl, C2-C6-alkenylamino, C2-C6-
alkynyl, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkylsulfonyl, C2-
Ce-alkenylsulfonyl, C2-C6-alkynylsulfonyl C1-C6-alkylsulfinyl, C2-C6-
alkenylsulfinyl, C2-C6-alkynylsulfmyl, C3-C12-cycloalkyl, P(=O)R2aR2b,
P(=S)R2aR2b, NR2aR2b, SiR2aR2bR2c, N=CR2aR2b, CR2a=NR2b;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem which
may contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen
and which are unsubstituted or substituted with any combination of 1 to 5
groups selected from halogen, cyano, nitro, hydroxy, mercapto, amino, car-
boxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-
haloalkoxy, or C1-C6-alkylthio; and wherein
R2a, R2b and R2c are each independently selected from hydrogen, C1-C6-
alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, and wherein
the carbon atoms in these groups may be substituted by 1
to 3 of a substituent selected by halogen, cyano, nitro,
hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-
alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-
C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
R2d is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-Ce-alkynylamino, di(C2-C6-
alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-
C6-alkylthio, and wherein the carbon atoms in these groups may be
substituted by 1 to 3 of a substituent selected by halogen, cyano, ni-
tro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, d-
C6-haloalkoxy or C1-C6-alkylthio;
phenyl or a mono- or bicyclic 5- to 10-membered aromatic ringsystem
which may contain 1 to 4 heteroatoms selected from oxygen, sulfur
and nitrogen and which are unsubstituted or substituted with any

combination of 1 to 5 groups selected from halogen, cyano, nitro, hy-
droxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-
alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, or C1-C6-alkylthio;
R3,R4 are selected from hydrogen, cyano, nitro, formyl, C(=O)R3cor C(=O)R4c,
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkoxy ,
(C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl or C1-C6-
alkylsulfonyl wherein the carbon atoms in the aliphatic radicals of the
aforementioned groups may carry any combination of 1, 2 or 3 radicals, in-
dependently of one another selected from the group consisting of halogen,
cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-
alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-
alkylthio, C(O)NR3aR3b or C(O)NR4aR4b, (SO2)NR3aR3b or (SO2)NR4aR4b,
phenyl, phenyloxy or benzyl, each of the last three mentioned radicals may
be unsubstituted or substituted with 1 to 5 radicals, independently of one
another selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-
haloalkyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkoxy and C1-C6-
haloalkoxy radicals; and wherein
R3a, R4a and R3b, R4b are each independently selected from hydrogen, Cr
Ce-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, orC2-C6-
alkynyl;
R3c, R4c are each independently selected from hydrogen, C1-C6-alkyl,
C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkylthio,
C1-C6-alkoxy, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, phenyl
and heteroaryl, which can be a mono- or bicyclic 5 to 10 mem-
bered heteroaromatic ring, which contains 1,2,3 or 4 heteroa-
toms selected from O,S and N;
with the proviso that at least one of R3 and R4 is hydrogen;
or the enantiomers and/or the agriculturally or veterinary acceptable salts thereof,
with the proviso that compound of formula I is not representing a 3-(1,2,3,4-
tetrahydro-1-naphtyl)-thio-urea derivative, wherein (R1)m,R3 and R4 are hydro-
gens and R2 is hydrogen or R2 is CH3.
An agricultural or veterinary composition comprising at least one Indanyl- and
Tetrahydronaphthyl-amino-thiourea compound of the formula I according to any
one of claims 1-15 or the enantiomers and/or at least one agriculturally or veteri-
nary acceptable salt thereof, and at least one inert liquid and/or solid agronomi-
cally acceptable carrier and, if desired, at least one surfactant.
The use of a Indanyl- and Tetrahydronaphthyl-amino-thiourea compound of the
formula I according to any one of claims 1-15 or the enantiomers and/or at least

one agriculturally or veterinary acceptable salt thereof for combating animal
pests.
A method of combating animal pests which comprises contacting the animal
pests, their habit, breeding ground, food supply, plant, seed, soil, area, material
or environment in which the animal pests are growing or may grow, or the mate-
rials, plants, seeds, soils, surfaces or spaces to be protected from animal attack
or infestation with a pesticidally effective amount of at least one Indanyl- or Tet-
rahydronaphthyl-amino-thiourea compound of the formula I according to any one
of claims 1-15 or the enantiomers and/or at least one agriculturally or veterinary
acceptable salt thereof.
A method for protecting crops from attack or infestation by animal pests, which
comprises contacting a crop with a pesticidally effective amount of at least one
Indanyl- or Tetrahydronaphthyl-amino-thiourea compound of the formula I ac-
cording to any one of claims 1-15 or the enantiomers and/or at least one agricul-
turally acceptable salt thereof.
A method for the protection of seeds from soil insects and of the seedlings'
roots and shoots from insects comprising contacting the seeds before sowing
and/or after pregermination with an Indanyl- and Tetrahydronaphthyl-amino-
thiourea compound of the formula I according to any one of claims 1-15 or the
enantiomers and/or at least one agriculturally acceptable salt thereof in pesti-
cidally effective amounts.
The method according claim to 20, wherein the Indanyl- and Tetrahydronaphthyl-
amino-thiourea compound of formula I is applied in an amount of from 0,1 g to 10
kg per 100 kg of seeds.
The method as defined in claim 18, 19 or 20 wherein the animal pests are in-
sects, arachnids or nematodes.
The method as defined in claim 20, wherein the animal pest are insects like Ho-
moptera or Coleoptera or arachnids of the order of Acarina.
A method according to claim 20, wherein of the resulting plant's roots and shoots
are protected.
A method according to claim 24, wherein the resulting plant's shoots are pro-
tected from aphids.

Seed comprising an Indanyl- and Tetrahydronaphthyl-amino-thiourea compound
of the formula I according to any one of claims 1-15 or the enantiomers and/or at
least one agriculturally salt thereof in an amount of from 0.1 g to 10 kg per 100 kg
of seed.
The use of Indanyl- or Tetrahydronaphthyl-arnino-thiourea compounds of formula
I according to any one of claims 1-15 or the enantiomers and/or at least one vet-
erinary acceptable salt thereof for combating parasites in and on animals.
A method for treating, controlling, preventing or protecting animals against infes-
tation or infection by parasites which comprises orally, topically or parenterally
administering or applying to the animals a parasiticidally effective amount of a In-
danyl- or Tetrahydronaphthyl-amino-thiourea compound of formula I according to
any one of claims 1-15 or the enantiomers and/or at least one veterinary accept-
able salt thereof.
A process for the preparation of a composition for treating, controlling, preventing
or protecting animals against infestation or infection by parasites which com-
prises a parasiticidally effective amount of a Indanyl- or Tetrahydronaphthyl-
amino-thiourea compound of formula I according to any one of claims 1 -15 or the
enantiomers and/or at least one veterinary acceptable salt.

Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds for combating animal pests
The present invention relates to Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula I
wherein the variables R1 to R4 are as in the description.
The invention relates also to methods of combating or controlling insects, arachnids or
nematodes, to methods for protecting growing plants from attack or infestation by insects, arachnids or nematodes, to methods for the protection of seeds from soil insects and of the seedlings' roots and shoots from soil and foliar insects and to methods for treating, controlling, preventing or protecting animals against infestation or infection.

Documents:

01847-kolnp-2008-abstract.pdf

01847-kolnp-2008-claims.pdf

01847-kolnp-2008-correspondence others.pdf

01847-kolnp-2008-description complete.pdf

01847-kolnp-2008-form 1.pdf

01847-kolnp-2008-form 3.pdf

01847-kolnp-2008-form 5.pdf

01847-kolnp-2008-pct priority document notification.pdf

01847-kolnp-2008-pct request form.pdf

1847-KOLNP-2008-(20-11-2012)-CORRESPONDENCE.pdf

1847-KOLNP-2008-(20-11-2012)-FORM 3.pdf

1847-KOLNP-2008-(23-11-2012)-ABSTRACT.pdf

1847-KOLNP-2008-(23-11-2012)-CLAIMS.pdf

1847-KOLNP-2008-(23-11-2012)-CORRESPONDENCE.pdf

1847-KOLNP-2008-(23-11-2012)-DESCRIPTION (COMPLETE).pdf

1847-KOLNP-2008-(23-11-2012)-FORM 2.pdf

1847-KOLNP-2008-(23-11-2012)-FORM 3.pdf

1847-KOLNP-2008-(23-11-2012)-OTHERS.pdf

1847-KOLNP-2008-(23-11-2012)-PETITION UNDER RULE 137-1.1.pdf

1847-KOLNP-2008-(23-11-2012)-PETITION UNDER RULE 137.pdf

1847-KOLNP-2008-ASSIGNMENT.pdf

1847-KOLNP-2008-CORRESPONDENCE 1.1.pdf

1847-kolnp-2008-form 18.pdf

1847-KOLNP-2008-FORM 3.1.pdf

1847-KOLNP-2008-GPA.pdf


Patent Number 255749
Indian Patent Application Number 1847/KOLNP/2008
PG Journal Number 12/2013
Publication Date 22-Mar-2013
Grant Date 20-Mar-2013
Date of Filing 07-May-2008
Name of Patentee BASF SE
Applicant Address 67056 LUDWIGSHAFEN
Inventors:
# Inventor's Name Inventor's Address
1 KORDES MARKUS ROXHEIMERSTRASSE 39, 67240 BOBENHEIM-ROXHEIM
2 CULBERTSON DEBORAH L 6400 VINTAGE RIDGE LANE, FUQUAY VARINA, NC 27526
3 KORADIN CHRISTOPHER RIEDLANGSTR. 15, 67067 LUDWIGSHAFEN
PCT International Classification Number C07C 335/14
PCT International Application Number PCT/EP2006/068480
PCT International Filing date 2006-11-15
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 60/739729 2005-11-25 U.S.A.