Substituted Amino-Thiourea Compounds For Combating Animal Pests

Substituted amino-thiourea compounds of formula I

• wherein
• n is 0, 1, 2, 3 or 4.
• A is CRA.1RA.2, oxygen, NRA.3, sulfur, S(O) or S(O)2,
• wherein
• RA.1, RA.2 are independently of each other selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra;
• C3-C8-cycloalkyl, phenyl and benzyl, wherein each of the last three mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• or
• RA.1 together with RA.2 may also be ═O, ═NRc or ═CRdRe;
• RA.3 is selected from the group consisting of hydrogen, formyl, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg, (SO2)NRfRg,
• phenyl, benzyl, phenoxycarbonyl, 5 or 6 membered hetarylmethyl, 5 or 6 membered hetarylcarbonyl and benzoyl, wherein each of the last six mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetarylcarbonyl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• B is a chemical bond or CH2;
• R1 is hydrogen, C(═O)Rh or C(═S)Rh;
• R2,R3 are selected independently from each other from the group consisting of hydrogen, cyano, nitro, formyl, C(═O)R1, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl and 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, 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, C1-C6-alkylthio, C(O)NRfRg, (SO2)NRfRg, phenyl, phenyloxy and benzyl, each of the last three mentioned radicals may be unsubstituted or substituted with 1, 2, 3, 4 or 5 radicals Rb;
• or
• R2 together with R1 may be C1-C3-alkandiyl, C1-C2-alkandiylcarbonyl, C1-C2-alkandiylthiocarbonyl or a bridging C═O or C═S group.
• R4 is selected from the group consisting of hydrogen, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg,
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, aryl, arylmethyl, aryloxycarbonyl, arylcarbonyl, 5 or 6 membered hetaryl, 5 or 6 membered hetarylmethyl and 5 or 6 membered hetarylcarbonyl, wherein each of the six last mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• R5.1, R5.2 are independently from each other selected from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, carboxy, formyl, formyloxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenoxy, C2-C6-alkynoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkylthio, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, benzyl, 5 or 6 membered hetaryl and 5 or 6 membered hetarylmethyl, wherein each of the last mentioned cyclic radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetaryl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• or
• R5.1 together with R5.2 may also be ═O, ═S, ═NRc or ═CRdRe;
• R6 is selected from the group consisting of halogen, OH, SH, NH2, SO3H, COOH, cyano, azido, nitro, formyl, formyloxy, CONH2, CSNH2, CH═N—OH, CH═N—O—(C1-C6)-alkyl, C(═O)j, C(═S)Rj, 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-alkenyloxy, C2-C6-alkenylamino, di(C1-C6-alkenyl)amino, C2-C6-alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, di(C1-C6-alkynyl)amino, C2-C6-alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl, C2-C6-alkenylsulfoxyl, C2-C6-alkynylsulfonyl, C2-C6-alkynylsulfoxyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl, (C2-C6-alkynyloxy)carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-)carbonyl-oxy, (C2-C6-alkynyl)carbonyloxy, (C1-C6-alkyl)carbonyl-amino, (C2-C6-alkenyl)carbonyl-amino, (C2-C6-alkynyl)carbonyl-amino, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, (SO2)NRfRg,
• a radical Y-Ar, a radical Y-Hc and a radical Y-Cy, wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy group;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Hc is a mono- or bicyclic 5- to 10-membered heteroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members, wherein Hc is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb;
• and wherein the radical(s) R6 that is/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 carbocycle 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 Rb;
• Ra is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C3-C6-cycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl;
• Rb is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, formyloxy, and C1-C6-alkylcarbonyloxy;
• Rc is selected from the group consisting of hydrogen, OH, NH2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, wherein the carbon atoms in these radicals may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, 5 or 6 membered hetaryl, phenylamino, N—(C1-C6-alkyl)-N-phenyl-amino and diphenylamino, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rd, Re are independently of each other selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein the aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rf, Rg are independently of each other selected from the group consisting of hydrogen, hydroxy, amino, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rh is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkandiylamino, C2-C6-alkenylamino, di(C2-C6-alkenyl)amino, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C12-cycloalkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, wherein the carbon atoms in these groups may be substituted with 1, 2, 3, 4 or 5 radicals Ra;
• a radical Y-Ar, a radical Y-Cy and a radical Y-Hc, and wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyloxy, carbonyl or carbonyloxy,
• wherein the aliphatic carbon atoms in these groups may be unsubstituted or substituted with Ra;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb;
• Hc is saturated or partially unsaturated 3 to 8 membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen atoms and/or 1 or 2 heteroaromatic groups selected from the group consisting of S(O) and S(O)2 as ring members, and wherein the ring is unsubstituted or may carry 1, 2, 3 or 4 radicals Rb;
• Ri are each independently selected from the group consisting of 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 contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N;
• Rh is selected from the group consisting of 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 the group consisting of O, S and N;
• or the enantiomers, diastereomers or salts thereof;
• with the provisos that
• i) if B is CH2 and A is CH2, then R1 is different from hydrogen, and
• ii) if B is CH2 and A is C(RA.1)(RA.2) and R1 is hydrogen, then at least one of RA.1 and RA.2 is different than hydrogen, and
• iii) if A is C(RA.1)(RA.2), then at least one of R4, R5.1, R5.2, RA.1 or RA.2 is different than hydrogen.

A method for combating or controlling insects, arachnids or nematodes or for protecting growing plants from attack or infestation by insects, arachnids or nematodes comprising contacting an insect, arachnid or nematode or their food supply, habitat or breeding grounds or contacting a plant, or soil or water in which the plant is growing with a pesticidally effective amount of at least one amino-thiourea compound of the formula I

• wherein
• n is 0, 1, 2, 3 or 4.
• A is CRA.1RA.2, oxygen, NRA.3, sulfur, S(O) or S(O)2,
• wherein
• RA.1, RA.2 are independently of each other selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra,
• C3-C8-cycloalkyl, phenyl and benzyl, wherein each of the last three mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• or
• RA.1 with RA.2 may also be ═O, ═NRc or ═CRdRe;
• RA.3 is selected from the group consisting of hydrogen, formyl, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg, (SO2)NRfRg,
• phenyl, benzyl, phenoxycarbonyl, 5 or 6 membered hetarylmethyl, 5 or 6 membered hetarylcarbonyl and benzoyl, wherein each of the last six mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetarylcarbonyl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• B is a chemical bond or CH2;
• R1 is hydrogen, C(═O)Rh or C(═S)Rh;
• R2,R3 are selected independently from each other from the group consisting of hydrogen, cyano, nitro, formyl, C(═O)Ri, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl and 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, 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, C1-C6-alkylthio, C(O)NRfRg, (SO2)NRfRg, phenyl, phenyloxy and benzyl, each of the last three mentioned radicals may be unsubstituted or substituted with 1, 2, 3,4 or 5 radicals Rb;
• or
• R2 together with R1 may be C1-C3-alkandiyl, C1-C2-alkandiylcarbonyl, C1-C2-alkandiylthiocarbonyl or a bridging C═O or C═S group.
• R4 is selected from the group consisting of hydrogen, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg,
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, aryl, arylmethyl, aryloxycarbonyl, arylcarbonyl, 5 or 6 membered hetaryl, 5 or 6 membered hetarylmethyl and 5 or 6 membered hetarylcarbonyl, wherein each of the six last mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• R5.1 R5.2 are independently from each other selected from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, carboxy, formyl, formyloxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenoxy, C2-C6-alkynoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkylthio, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, benzyl, 5 or 6 membered hetaryl and 5 or 6 membered hetarylmethyl, wherein each of the last mentioned cyclic radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetaryl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• or
• R5.1 together with R5.2 may also be ═O, ═S, ═NRc or ═CRdRe;
• R6 is selected from the group consisting of halogen, OH, SH, NH2, SO3H, COOH, cyano, azido, nitro, formyl, formyloxy, CONH2, CSNH2, CH═N—OH, CH═N—O—(C1-C6)-alkyl, C(═O)Rj, C(═S)Rj, 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-alkenyloxy, C2-C6-alkenylamino, di(C1-C6-alkenyl)amino, C2-C6-alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, di(C1-C6-alkynyl)amino, C2-C6-alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl, C2-C6-alkenylsulfoxyl, C2-C6-alkynylsulfonyl, C2-C6-alkynylsulfoxyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl, (C2-C6-alkynyloxy)carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-)carbonyl-oxy, (C2-C6-alkynyl)carbonyloxy, (C1-C6-alkyl)carbonyl-amino, (C2-C6-alkenyl)carbonyl-amino, (C2-C6-alkynyl)carbonyl-amino, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, (SO2)NRfRg,
• a radical Y-Ar, a radical Y-Hc and a radical Y-Cy, wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy group;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Hc is a mono- or bicyclic 5- to 10-membered heteroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members, wherein He is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb;
• and wherein the radical(s) R6 that is/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 carbocycle 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 Rb;
• Ra is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C3-C6-cycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl;
• Rb is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, formyloxy, and C1-C6-alkylcarbonyloxy;
• Rc is selected from the group consisting of hydrogen, OH, NH2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, wherein the carbon atoms in these radicals may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, 5 or 6 membered hetaryl, phenylamino, N—(C1-C6-alkyl)-N-phenyl-amino and diphenylamino, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rd, Re are independently of each other selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein the aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rf, Rg are independently of each other selected from the group consisting of hydrogen, hydroxy, amino, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rh is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkandiylamino, C2-C6-alkenylamino, di(C2-C6-alkenyl)amino, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C12-cycloalkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, wherein the carbon atoms in these groups may be substituted with 1, 2, 3, 4 or 5 radicals Ra;
• a radical Y-Ar, a radical Y-Cy and a radical Y-Hc, and wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy,
• wherein the aliphatic carbon atoms in these groups may be unsubstituted or substituted with Ra;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb;
• Hc is saturated or partially unsaturated 3 to 8 membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen atoms and/or 1 or 2 heteroaromatic groups selected from the group consisting of S(O) and S(O)2 as ring members, and wherein the ring is unsubstituted or may carry 1, 2, 3 or 4 radicals Rb;
• Ri are each independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, C1-C6-alkylthio, C1-C6-alkoxy, (C1-C6-alkylamino, 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 the group consisting of O, S and N;
• Rj is selected from the group consisting of 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 the group consisting of O, S and N;
• or the enantiomers, diastereomers or salts thereof;
• with the provisos that if A is C(RA.1)(RA.2), then at least one of R4, R5.1, R5.2, RA.1 or RA.2 is different than hydrogen.

A method for the protection of seeds from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one amino-thiourea compound of the formula I

• wherein
• n is 0, 1, 2, 3 or 4.
• A is CRA.1RA.2, oxygen, NRA.3, sulfur, S(O) or S(O)2,
• wherein
• RA.1, RA.2 are independently of each other selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra,
• C3-C8-cycloalkyl, phenyl and benzyl, wherein each of the last three mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• or
• RA.1 together with RA.2 may also be ═O, ═NRc or ═CRdRe;
• RA.3 is selected from the group consisting of hydrogen, formyl, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg, (SO2)NRfRg,
• phenyl, benzyl, phenoxycarbonyl, 5 or 6 membered hetarylmethyl, 5 or 6 membered hetarylcarbonyl and benzoyl, wherein each of the last six mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetarylcarbonyl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• B is a chemical bond or CH2;
• R1 is hydrogen, C(═O)Rh or C(═S)Rh;
• R2,R3 are selected independently from each other from the group consisting of hydrogen, cyano, nitro, formyl, C(═O)Ri, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl and 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, 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, C1-C6-alkylthio, C(O)NRfRg, (SO2)NRfRg, phenyl, phenyloxy and benzyl, each of the last three mentioned radicals may be unsubstituted or substituted with 1, 2, 3, 4 or 5 radicals Rb;
• or
• R2 together with R1 may be C1-C3-alkandiyl, C1-C2-alkandiylcarbonyl, C1-C2-alkandiylthiocarbonyl or a bridging C═O or C═S group.
• R4 is selected from the group consisting of hydrogen, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg,
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, aryl, arylmethyl, aryloxycarbonyl, arylcarbonyl, 5 or 6 membered hetaryl, 5 or 6 membered hetarylmethyl and 5 or 6 membered hetarylcarbonyl, wherein each of the six last mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• R5.1, R5.2 are independently from each other selected from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, carboxy, formyl, formyloxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenoxy, C2-C6-alkynoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkylthio, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, benzyl, 5 or 6 membered hetaryl and 5 or 6 membered hetarylmethyl, wherein each of the last mentioned cyclic radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetaryl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• or
• R5.1 together with R5.2 may also be ═O, ═S, ═NRc or ═CRdRe;
• R6 is selected from the group consisting of halogen, OH, SH, NH2, SO3H, COOH, cyano, azido, nitro, formyl, formyloxy, CONH2, CSNH2, CH═N—OH, CH═N—O—(C1-C6)-alkyl, C(═O)Rj, C(═S)Rj, 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-alkenyloxy, C2-C6-alkenylamino, di(C1-C6-alkenyl)amino, C2-C6-alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, di(C1-C6-alkynyl)amino, C2-C6-alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl, C2-C6-alkenylsulfoxyl, C2-C6-alkynylsulfonyl, C2-C6-alkynylsulfoxyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl, (C2-C6-alkynyloxy)carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-)carbonyl-oxy, (C2-C6-alkynyl)carbonyloxy, (C1-C6-alkyl)carbonyl-amino, (C2-C6-alkenyl)carbonyl-amino, (C2-C6-alkynyl)carbonyl-amino, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, (SO2)NRfRg,
• a radical Y-Ar, a radical Y-Hc and a radical Y-Cy, wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy group;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Hc is a mono- or bicyclic 5- to 10-membered heteroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members, wherein Hc is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb;
• and wherein the radical(s) R6 that is/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 carbocycle 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 Rb;
• Ra is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C3-C6-cycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl;
• Rb is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, formyloxy, and C1-C6-alkylcarbonyloxy;
• Rc is selected from the group consisting of hydrogen, OH, NH2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, wherein the carbon atoms in these radicals may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, 5 or 6 membered hetaryl, phenylamino, N—(C1-C6-alkyl)-N-phenyl-amino and diphenylamino, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rd, Re are independently of each other selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein the aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rf, Rg are independently of each other selected from the group consisting of hydrogen, hydroxy, amino, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rh is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkandiylamino, C2-C6-alkenylamino, di(C2-C6-alkenyl)amino, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C12-cycloalkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, wherein the carbon atoms in these groups may be substituted with 1, 2, 3, 4 or 5 radicals Ra;
• a radical Y-Ar, a radical Y-Cy and a radical Y-Hc, and wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy,
• wherein the aliphatic carbon atoms in these groups may be unsubstituted or substituted with Ra;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb;
• Hc is saturated or partially unsaturated 3 to 8 membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen atoms and/or 1 or 2 heteroaromatic groups selected from the group consisting of S(O) and S(O)2 as ring members, and wherein the ring is unsubstituted or may carry 1, 2, 3 or 4 radicals Rb;
• Ri are each independently selected from the group consisting of 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 contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N;
• Rj is selected from the group consisting of 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 the group consisting of O, S and N;
• or the enantiomers, diastereomers or salts thereof;
• with the provisos that if A is C(RA.1)(RA.2), then at least one of R4, R5.1, R5.2, RA.1 or RA.2 is different than hydrogen.

A seed comprising an amino-thiourea compound of the formula I

• wherein
• n is 0, 1, 2, 3 or 4.
• A is CRA.1RA.2,oxygen, NRA.3, sulfur, S(O) or S(O)2,
• wherein
• RA.1, RA.2 are independently of each other selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra,
• C3-C8-cycloalkyl, phenyl and benzyl, wherein each of the last three mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• or
• RA.1 together with RA.2 may also be ═O, ═NRc or ═CRdRe;
• RA.3 is selected from the group consisting of hydrogen, formyl, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg, (SO2)NRfRg,
• phenyl, benzyl, phenoxycarbonyl, 5 or 6 membered hetarylmethyl, 5 or 6 membered hetarylcarbonyl and benzoyl, wherein each of the last six mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetarylcarbonyl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• B is a chemical bond or CH2;
• R1 is hydrogen, C(═O)Rh or C(═S)Rh;
• R2,R3 are selected independently from each other from the group consisting of hydrogen, cyano, nitro, formyl, C(═O)Ri, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl and 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, 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, C1-C6-alkylthio, C(O)NRfRg, (SO2)NRfRg, phenyl, phenyloxy and benzyl, each of the last three mentioned radicals may be unsubstituted or substituted with 1, 2, 3, 4 or 5 radicals Rb;
• or
• R2 together with R1 may be C1-C3-alkandiyl, C1-C2-alkandiylcarbonyl, C1-C2-alkandiylthiocarbonyl or a bridging C═O or C═S group.
• R4 is selected from the group consisting of hydrogen, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg,
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, aryl, arylmethyl, aryloxycarbonyl, arylcarbonyl, 5 or 6 membered hetaryl, 5 or 6 membered hetarylmethyl and 5 or 6 membered hetarylcarbonyl, wherein each of the six last mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• R5.1, R5.2 are independently from each other selected from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, carboxy, formyl, formyloxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenoxy, C2-C6-alkynoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkylthio, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, benzyl, 5 or 6 membered hetaryl and 5 or 6 membered hetarylmethyl, wherein each of the last mentioned cyclic radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetaryl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• or
• R5.1 together with R5.2 may also be ═O, ═NRc or ═CRdRe;
• R6 is selected from the group consisting of halogen, OH, SH, NH2, SO3H, COOH, cyano, azido, nitro, formyl, formyloxy, CONH2, CSNH2, CH═N—OH, CH═N—O—(C1-C6)-alkyl, C(═O)Rj, C(═S)Rj, 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-alkenyloxy, C2-C6-alkenylamino, di(C1-C6-alkenyl)amino, C2-C6-alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, di(C1-C6-alkynyl)amino, C2-C6-alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl, C2-C6-alkenylsulfoxyl, C2-C6-alkynylsulfonyl, C2-C6-alkynylsulfoxyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl, (C2-C6-alkynyloxy)carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-)carbonyl-oxy, (C2-C6-alkynyl)carbonyloxy, (C1-C6-alkyl)carbonyl-amino, (C2-C6-alkenyl)carbonyl-amino, (C2-C6-alkynyl)carbonyl-amino, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, (SO2)NRfRg,
• a radical Y-Ar, a radical Y-Hc and a radical Y-Cy, wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy group;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Hc is a mono- or bicyclic 5- to 10-membered heteroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members, wherein Hc is unsubstituted or may carry any combination of 1 to 5 radicals Rb
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb
• and wherein the radical(s) R6 that is/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 carbocycle 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 Rb;
• Ra is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C3-C6-cycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl;
• Rb is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, formyloxy, and C1-C6-alkylcarbonyloxy;
• Rc is selected from the group consisting of hydrogen, OH, NH2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, wherein the carbon atoms in these radicals may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, 5 or 6 membered hetaryl, phenylamino, N—(C1-C6-alkyl)-N-phenyl-amino and diphenylamino, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rd, Re are independently of each other selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein the aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rf, Rg are independently of each other selected from the group consisting of hydrogen, hydroxy, amino, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rh is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di(C1-C6-alkyDamino, C2-C6-alkandiylamino, C2-C6-alkenylamino, di(C2-C6-alkenyl)amino, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C12-cycloalkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, wherein the carbon atoms in these groups may be substituted with 1, 2, 3, 4 or 5 radicals Ra;
• a radical Y-Ar, a radical Y-Cy and a radical Y-Hc, and wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy,
• wherein the aliphatic carbon atoms in these groups may be unsubstituted or substituted with Ra;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb;
• Hc is saturated or partially unsaturated 3 to 8 membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen atoms and/or 1 or 2 heteroaromatic groups selected from the group consisting of S(O) and S(O)2 as ring members, and wherein the ring is unsubstituted or may carry 1, 2, 3 or 4 radicals Rb;
• Ri are each independently selected from the group consisting of 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 contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N;
• Rj is selected from the group consisting of 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 the group consisting of O, S and N;
• or the enantiomers, diastereomers or salts thereof;
• with the proviso that if A is C(RA.1)(RA.2) then at least one of R4, R5.1, R5.2, RA.1 or RA.2 is different than hydrogen, or the enatiomers, diastereomers or salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

A method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of an amino-thiourea compound of formula I

• wherein
• n is 0, 1, 2, 3 or 4.
• A is CRA.1RA.2, oxygen, NRA.3, sulfur, S(O) or S(O)2,
• wherein
• RA.1, RA.2 are independently of each other selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, and di-(C1-C6-alkyl)amino, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra,
• C3-C8-cycloalkyl, phenyl and benzyl, wherein each of the last three mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• or
• RA.1 together with RA.2 may also be ═O, ═NRc or ═CRdRe;
• RA.3 is selected from the group consisting of hydrogen, formyl, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg, (SO2)NRfRg,
• phenyl, benzyl, phenoxycarbonyl, 5 or 6 membered hetarylmethyl, 5 or 6 membered hetarylcarbonyl and benzoyl, wherein each of the last six mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetarylcarbonyl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• B is a chemical bond or CH2;
• R1 is hydrogen, C(═O)Rh or C(═S)Rh;
• R2,R3 are selected independently from each other from the group consisting of hydrogen, cyano, nitro, formyl, C(═O)Ri, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C1 -C6-alkoxy)methylen, C1-C6-alkylsulfinyl, C1-C6-alkylsulfenyl and 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, 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, C1-C6-alkylthio, C(O)NRfRg, (SO2)NRfRg, phenyl, phenyloxy and benzyl, each of the last three mentioned radicals may be unsubstituted or substituted with 1, 2, 3, 4 or 5 radicals Rb;
• or
• R2 together with R1 may be C1-C3-alkandiyl, C1-C2-alkandiylcarbonyl, C1-C2-alkandiylthiocarbonyl or a bridging C═O or C═S group.
• R4 is selected from the group consisting of hydrogen, formyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, wherein the carbon atoms in the last 5 mentioned radicals may be unsubstituted or may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, C(S)NRfRg,
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, aryl, arylmethyl, aryloxycarbonyl, arylcarbonyl, 5 or 6 membered hetaryl, 5 or 6 membered hetarylmethyl and 5 or 6 membered hetarylcarbonyl, wherein each of the six last mentioned radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb;
• R5.1, R5.2 are independently from each other selected from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, carboxy, formyl, formyloxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenoxy, C2-C6-alkynoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, and C1-C6-haloalkylthio, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• C3-C8-cycloalkyl, C3-C8-cycloalkenyl, phenyl, benzyl, 5 or 6 membered hetaryl and 5 or 6 membered hetarylmethyl, wherein each of the last mentioned cyclic radicals may be unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals Rb, and wherein the 5 or 6 membered heteroaromatic ring in hetarylmethyl and hetaryl contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members;
• or
• R5.1 together with R5.2 may also be ═O, ═S, ═NRc or ═CRdRe;
• R6 is selected from the group consisting of halogen, OH, SH, NH2, SO3H, COOH, cyano, azido, nitro, formyl, formyloxy, CONH2, CSNH2, CH═N—OH, CH═N—O—(C1-C6)-alkyl, C(═O)Rj, C(═S)Rj, 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-alkenyloxy, C2-C6-alkenylamino, di(C1-C6-alkenyl)amino, C2-C6-alkenylthio, C2-C6-alkynyl, C2-C6-alkynyloxy, C2-C6-alkynylamino, di(C1-C6-alkynyl)amino, C2-C6-alkynylthio, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C2-C6-alkenylsulfonyl, C2-C6-alkenylsulfoxyl, C2-C6-alkynylsulfonyl, C2-C6-alkynylsulfoxyl, (C1-C6-alkoxy)carbonyl, (C2-C6-alkenyloxy)carbonyl, (C2-C6-alkynyloxy)carbonyl, (C1-C6-alkyl)carbonyloxy, (C2-C6-alkenyl-)carbonyl-oxy, (C2-C6-alkynyl)carbonyloxy, (C1-C6-alkyl)carbonyl-amino, (C2-C6-alkenyl)carbonyl-amino, (C2-C6-alkynyl)carbonyl-amino, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals Ra;
• C(O)NRfRg, (SO2)NRfRg,
• a radical Y-Ar, a radical Y-Hc and a radical Y-Cy, wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy group;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb;
• Hc is a mono- or bicyclic 5- to 10-membered heteroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected from 2 oxygen, 2 sulfur and 3 nitrogen atoms as ring members, wherein Hc is unsubstituted or may carry any combination of 1 to 5 radicals Rb
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb
• and wherein the radical(s) R6 that is/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 carbocycle 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 Rb;
• Ra is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C3-C6-cycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl;
• Rb is selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, formyloxy, and C1-C6-alkylcarbonyloxy;
• Rc is selected from the group consisting of hydrogen, OH, NH2, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, wherein the carbon atoms in these radicals may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, 5 or 6 membered hetaryl, phenylamino, N—(C1-C6-alkyl)-N-phenyl-amino and diphenylamino, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rd, Re are independently of each other selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein the aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rf, Rg are independently of each other selected from the group consisting of hydrogen, hydroxy, amino, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals Ra;
• phenyl, benzyl, and 5 or 6 membered hetaryl, wherein aromatic group may be unsubstituted or may carry 1, 2 or 3 substituents Rb;
• Rh is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C2-C6-alkandiylamino, C2-C6-alkenylamino, di(C2-C6-alkenyl)amino, C2-C6-alkynylamino, di(C2-C6-alkynyl)amino, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C12-cycloalkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, wherein the carbon atoms in these groups may be substituted with 1, 2, 3, 4 or 5 radicals Ra;
• a radical Y-Ar, a radical Y-Cy and a radical Y-Hc, and wherein
• Y is a single bond, oxygen, sulfur, nitrogen, NH, NRf, C1-C6-alkandiyl, C1-C6-alkandiyloxy, carbonyl or carbonyloxy,
• wherein the aliphatic carbon atoms in these groups may be unsubstituted or substituted with Ra;
• Ar is phenyl or naphthyl, wherein Ar is unsubstituted or may carry any combination of 1 to 5 radicals Rb
• Cy is C3-C12-cycloalkyl, which is unsubstituted or substituted with 1 to 5 radicals Rb
• Hc is saturated or partially unsaturated 3 to 8 membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen atoms and/or 1 or 2 heteroaromatic groups selected from the group consisting of S(O) and S(O)2 as ring members, and wherein the ring is unsubstituted or may carry 1, 2, 3 or 4 radicals Rb;
• Ri are each independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-Cg-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 the group consisting of O, S and N;
• Rj is selected from the group consisting of 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 the group consisting of O, S and N;
• or the enantiomers, diastereomers or salts thereof;
• with the provisos that if A is C(RA.1)(RA.2), then at least one of R4, R5.1, R5.2, RA.1 or RA.2 is different than hydrogen, or the enantiomers, diastereomers and/or veterinary acceptable salt thereof.