US 8,796,180 B2 · Aminoquinazoline compounds for combating invertebrate pests

Abstract

The invention relates to aminoquinazoline compounds or the enantiomers or veterinarily acceptable salts thereof which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to methods for controlling invertebrate pests by using these compounds and to plant propagation material and to agricultural and veterinary compositions comprising said compounds. wherein A1, A2, A3, A4, R1, R2, R3, R4, R5a, R5b, R5c, R5d and p are defined as in the description.

A method for controlling or combating invertebrate pests attack or infestation which method comprises treating the pests, their food supply, their habitat, their breeding ground, the plant, the plant propagation material, soil, area, material or environment in which the pests are growing or may grow, with a pesticidally effective amount of a compound of the formula (I)

wherein
A1, A2, A3 and A4 are N, NX or CR4 wherein X is a lone pair or O, with the proviso that at most three of A1, A2, A3 and A4 are N or NX;
R1, R2 are selected independently from one another from the group consisting of hydrogen, CN, NO2, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
Si(R11)2R12, OR7, S(O)mR7, NR8R9, N═C(R6)2, C(═O )R6, C(═S)R6, C(═NR8)R6
and a 3-, 4-, 5-, 6- or 7- membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the nitrogen and/or the sulfur atom(s) may be oxidized,
is unsubstituted or substituted with one to five R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;
R3 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5,C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially saturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said heterocyclic ring may be replaced by one or two C═O groups;
each R4 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
or two radicals R4 bound on adjacent carbon atoms together form a group selected from the group consisting of —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above group,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two CH2 groups of the above groups may be replaced by one or two C═O groups;
R5a is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
or R5a may form together with the adjacent carbon atom R5b a 5- or 6-membered ring which is at least substituted with one halogen;
R5b is selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-cycloalkoxy, wherein each mentioned radical
is substituted with at least one halogen,
may be further partially or fully halogenated, and
may be substituted with one to five radicals R6;
or R5b may form together with the adjacent carbon atom R5c or R5a a 5- or 6-membered ring which is substituted with at least one halogen;
R5c is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
Si(R11)2R12, OR7, S(O)mR7, N(R8)R9, N═C(R6)2, C(═O)OR7, C(═S)OR7, C(═NR8)R6, C(═O)N(R8)R9, C(═S)N(R8)R9, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
or R5c may form together with the adjacent carbon atom R5b or R5d a 5- or 6-membered ring which is substituted with at least one halogen in case of R5b being involved;
R5d is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C10-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl,
wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may be unsubstituted or substituted with one or more R6;
Si(R11)2R12, OR7, S(O)mR7, S(O)mN(R8)R9, N(R8)R9, N═C(R6)2, C(═O)R6, C(═S)R6, C(═NR8)R6, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
or R5d may form together with the adjacent carbon atom R5c or with R1 or R2 a 5- or 6-membered ring;
R6 is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;
Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
or two vicinally bound radicals R6 together form a group selected from ═C(Rc)2, ═S(O)mRo, ═S(O)mN(Rn)2, ═NRn and ═NN(Rn)2;
R7 is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;
Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
with the proviso that R7 is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
R8, R9 are selected independently from one another and independently of each occurrence from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;
Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2 phenyl
which may be substituted with 1, 2, 3, 4 or 5 radicals R10;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals R10, and
wherein one or two CH2 groups in said saturated or partially saturated rings may be replaced by one or two C═O groups;
R10 is selected independently from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
wherein the carbon atom of the aforementioned aliphatic and cycloaliphatic radicals may be substituted with one or more Rc;
Si(R11)2R12, ORo, O(CO)Rc, O(CS)Rc, S(O)mRo, S(O)mN(Rn)2, S(CO)Rc, S(CS)Rc, S(C═NRn)Rc, N(Rn)2, N(Rn)C(═O)Rc, N(Rn)C(═S)Rc, NS(O)mRo, N═C(Rc)2, C(═O)Rc, C(═S)Rc, C(═NRn)Rc, C(═O)N(Rn)2, C(═S)N(Rn)2, phenyl
which may be substituted with one to five radicals selected independently from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated or unsaturated,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals selected independently from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
or two radicals R10 bound on adjacent atoms together form a group selected from —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —OCH2CH2CH2—, —OCH═CHCH2—, —CH2OCH2CH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2CH2CH2—, —CH═CHCH2—, —CH2CH2O—, —CH═CHO—, —CH2OCH2—, —CH2C(═O)O—, —C(═O)OCH2—, —O(CH2)O—, —SCH2CH2CH2—, —SCH═CHCH2—, —CH2SCH2CH2—, —SCH2CH2S—, —SCH2SCH2—, —CH2CH2S—, —CH═CHS—, —CH2SCH2—, —CH2C(═S)S—, —C(═S)SCH2—, —S(CH2)S—, —CH2CH2NR8—, —CH2CH═N—, —CH═CH—NR8—, —OCH═N— and —SCH═N—,
wherein in each of the above groups,
one to five hydrogen atoms independently of each other may be replaced by one to five substituents selected from the group consisting of halogen, methyl, halomethyl, hydroxyl, methoxy and halomethoxy, or
one or two or more CH2 groups of the above groups may be replaced by one or two C═O groups;
R11, R12 are selected independently of each other and independently of each occurrence from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl;
Rc is selected independently from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
Ro is selected independently from the group consisting of hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered heterocyclic ring, wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
with the proviso that Ro is not C1-C6-alkoxy or C1-C6-haloalkoxy if it is bound to an oxygen atom;
Rn is selected independently from the group consisting of hydrogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, and a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring,
wherein said heterocyclic ring
is saturated, partially unsaturated or aromatic,
comprises 1, 2 or 3 heteroatoms or heteroatom groups selected from CO, N, O, S, NO, SO and SO2,
is unsubstituted or substituted with one to five radicals, which are selected independently of each other from halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
m is independently 0, 1 or 2;
p is 0, 1, 2, 3 or 4;
or enantiomers or diastereoisomers thereof or their agriculturally or veterinarily acceptable salts, or a composition comprising at least one compound of formula I.

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Aminoquinazoline compounds for combating invertebrate pests

Life of this patent

Aminoquinazoline compounds for combating invertebrate pests

Life of this patent

Abstract

Claims22