N-cyclylamides as nematicides

1. Compounds of the formula I

wherein

Y is O, C═O, or CR12R13;

A is a 5- or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms, each independently selected from oxygen, nitrogen and sulphur, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6;

R6 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C1-4-alkyl or C1-C4-haloalkoxy-C1-C4-alkyl;

R1, R2, R3, R4, R12 and R13, independently of each other, are hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl,

R5 is hydrogen, methoxy or hydroxyl,

B is phenyl substituted by one or more R8,

R8 is, independently of each other, halogen, cyano or a group -L-R9, where each L is independently of each other a bond, —O—, —OC(O)—, —NR7-, —NR7CO—, —NR7S(O)n-, —S(O)n-, —S(O)nNR7-, —COO— or CONR7-,

n is 0, 1 or 2,

R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl and phenyl is unsubstituted or substituted with halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl,

R9 is, independently of each other, C1-C6-alkyl, which is unsubstituted or substituted by one or more R10, C3-C6-cycloalkyl, which is unsubstituted or substituted by one or more R10, C6-C14-bicycloalkyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkenyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkynyl, which is unsubstituted or substituted by one or more R10, phenyl, which is unsubstituted or substituted by R10, or heteroaryl, which is unsubstituted or substituted by one or more R10,

R10 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy,

wherein B and A-CO—NR5 are cis to each other on the four-membered ring,

and tautomers/isomers/enantiomers of these compounds.

2. The compound of according to claim 1 wherein Y is O or CH2;

A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6;

R6 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, or C1-C4-haloalkoxy;

R1, R2, R3, R4, and R5 are each hydrogen;

B is phenyl substituted by one or more R8;

R8 is, independently of each other, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, or C3-C6-cycloalkyl.

3. The compound according to claim 1 wherein A is a 6-membered heteroaromatic ring containing 1 to 2 nitrogen atoms and having 1 to 3 substituents selected from R6, or a phenyl ring having 1 or 3 substitutents selected from R6.

4. The compound according to claim 1 wherein B is a phenyl substituted by 1 to 3 substitutents R8.

5. The compound according to claim 1 wherein B is a phenyl substituted by 1 to 3 substituents, independently selected from fluoro, chloro, trifluoromethyl, cyclopropyl, difluoromethoxy and trifluoromethoxy, A is a phenyl, pyridyl or pyrazinyl, which rings, independently of each other, are unsubstituted or substituted by 1 to 3 substituents, independently selected, from chloro, bromo, fluoro, methyl, cyano, and trifluoromethyl, Y is O or CH2, and R1, R2, R3, R4 and R5 are each hydrogen.

6. A pesticidal composition, which, in addition to comprising formulation adjuvants, comprises a pesticidal effective amount of a compound of the formula I according to claim 1 .

7. The composition according to claim 6 , which further comprises one or more other biologically active agents.

8. A method of controlling damage and/or yield loss caused by a pest and/or fungi which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest and/or fungi or to a plant propagation material an effective amount of a compound of formula (I) as defined in claim 1 .

9. A method for the protecting plant propagation material from damage and/or yield loss caused by a pest and/or fungi which comprises applying to the propagation material or the site, where the propagation material is planted, an effective amount of a compound of formula (I) as defined in claim 1 .

10. The method according to claim 8 wherein the damage or loss is caused by a nematode pest.

11. A treated plant propagation material, wherein adhered to the plant propagation material is an effective amount of a compound of formula (I) as defined in claim 1 .

12. A pharmaceutical composition for the control of helminths, arachnids or arthropodal endo- or ectoparasites which comprises a compound of formula (I) as defined in claim 1 and a physiologically tolerable carrier.

13. The composition according to claim 12 further comprising one or more other biologically active compounds.

14. A method of controlling endo- and ectoparasitic nematode infestations and infections in warm-blooded animals, which comprises injecting, topically applying or orally administering a composition according to claim 12 .

15. Process for the preparation of compounds of the formula I according to claim 1 , which comprises reacting a compound of the formula II

in which B, Y, R 1 , R 2 , R 3 , R 4 and R 5 are as defined in claim 1 , with an acylating agent of formula III

A-C(═O)—R*  (III),

in which A is as defined in claim 1 , and R* is halogen, hydroxyl or C 1-6 alkoxy, in the presence of a base.

16. Compounds of the formula (XIXa)

wherein B, Y, R1, R3 and R4 are as defined in claim 1 , where the compounds of the formulae

are excluded.

17. Compounds of the formula

wherein B, Y, R1, R2, R3, R4 and R5 are as defined in claim 1 , where the compound of the formula

is excluded.

18. The compound according to claim 1 wherein the compound is selected from any one of compounds 1 to 118 of formula (Id)

or a salt or N-oxide thereof;

wherein Y, R9a, R9b, R9c and A are as defined in the following table:

Cpd

no.

Y

R9a,R9b, R9c

A

1

CH 2

4—OCF3

2

CH 2

4—OCF3

3

CH 2

4—OCF3

4

O

4—Cl

5

CH 2

4—Cl

6

CH 2

4—Cl

7

CH 2

4—Cl

8

CH 2

2,4—Cl2

9

CH 2

2,4—Cl2

10

O

4—F

11

CH 2

2,4—Cl2

12

CH 2

2,4—Cl2

13

CH 2

4—Cl

14

CH 2

2—F,4—C1

15

CH 2

2—F,4—C1

16

CH 2

4—OCHF2

17

CH 2

4—OCHF2

18

CH 2

4—Cl

19

CH 2

4—Cl

20

CH 2

4—Cl

21

CH 2

4—Cl

22

CH 2

4—Cl

23

CH 2

4—Cl

24

CH 2

4—Cl

25

CH 2

2,4—Cl2

26

CH 2

2,4—Cl2

27

CH 2

2,4—Cl2

28

CH 2

2,4—Cl2

29

CH 2

2,4—Cl2

30

CH 2

2,4—Cl2

31

CH 2

2,4—Cl2

32

CH 2

4—F

33

CH 2

4—F

34

CH 2

4—Br

35

CH 2

4—Br

36

not tested

4—F

37

CH 2

4—Br

38

CH 2

4—cPr

39

CH 2

4—CN

40

CH 2

4—F

41

CH 2

4—F

42

CH 2

4—F

43

CH 2

4—F

44

CH 2

4—F

45

CH 2

4—Br

46

CH 2

4—Br

47

O

2,4,6—F 3

48

O

4—OCHF 2

49

O

4—CF3

50

O

2—F, 4—CF3

51

O

2,4—F 2

52

O

2,4,6—F 3

53

O

4—F

54

O

4—F

55

O

2,4—F2

56

O

2,4—F2

57

O

2,4,6—F3

58

CH 2

2,4—F2

59

CH 2

2,4—F2

60

CH 2

2,4—F2

61

CH 2

2,4—F2

62

CH 2

2—Cl, 4—CF3

63

CH 2

2—Cl, 4—CF3

64

CH 2

2—Cl, 4—CF3

65

CH 2

2—Cl, 4—CF3

66

CH 2

2—F, 4—CF3

67

CH 2

2—F, 4—CF3

68

CH 2

2—F, 4—CF3

69

CH 2

2—F, 4—CF3

70

CH 2

2,4—Cl2

71

CH 2

2,4—Cl2

72

CH 2

2,4—Cl2

73

CH 2

2,4—Cl2

74

CH 2

2,4—Cl2

75

CH 2

2,4—Cl2

76

CH 2

2,4—Cl2

77

CH 2

2,4—Cl2

78

CH 2

2,4—Cl2

79

CH 2

2,4—Cl2

80

CH 2

2,4—Cl2

81

CH 2

2,4—Cl2

82

CH 2

2,4—Cl2

83

CH 2

2,4—Cl2

84

CH 2

2,4—Cl2

85

CH 2

2,4—Cl2

86

CH 2

2,4—Cl2

87

CH 2

2,4—Cl2

88

CH 2

2,4—Cl2

89

CH 2

2,4—Cl2

90

CH 2

2,4—Cl2

91

CH 2

4—Cl

92

CH 2

4—Cl

93

CH 2

4—Cl

94

CH 2

4—Cl

95

CH 2

4—Cl

96

CH 2

4—Cl

97

CH 2

4—Cl

98

CH 2

4—Cl

99

CH 2

4—Cl

100

CH 2

4—Cl

101

CH 2

4—Cl

102

CH 2

4—Cl

103

CH 2

4—Cl

104

CH 2

4—Cl

105

CH 2

4—Cl

106

CH 2

4—Cl

107

CH 2

4—Cl

108

CH 2

4—Cl

109

CH 2

4—Cl

110

CH 2

4—Cl

111

CH 2

4—Cl

112

CH 2

2—Cl, 4—F

113

CH 2

2—Cl, 4—F

114

CH 2

2—Cl, 4—Br

115

CH 2

2,4—F2

116

CH 2

4—OCF3

117

CH 2

2—F, 4—Cl

118

CH 2

2—Cl, 4—F

and wherein any one of R9a, R9b and R9c is hydrogen unless otherwise defined.

19. The compound, or a salt or N-oxide thereof, according to claim 1 selected from the group consisting of:

N-[(1,2 cis)-2-(4-chlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide;

N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2,6-difluorobenzamide;

N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)benzamide;

N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide;

N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2-(trifluoromethyl)benzamide;

N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide;

N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-3-(trifluoromethyl)pyrazine-2-carboxamide;

N-[(1,2 cis)-2-[2-chloro-4-(trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide;

N-[(1,2 cis)-2-[2-chloro-4-(trifluoromethyl)phenyl]cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide;

N-[(1,2 cis)-2-[2-chloro-4-(trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyrazine-2-carboxamide;

N-[(1,2 cis)-2-[2-fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-2-(trifluoromethyl)benzamide;

N-[(1,2 cis)-2-[2-fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide;

N-[(1,2 cis)-2-[2-fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide;

N-[(1,2 cis)-2-[2-fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyrazine-2-carboxamide;

2-(trifluoromethyl)-N-[(2,3 cis)-2-(2,4,6-trifluorophenyl)oxetan-3-yl]benzamide;

2,6-difluoro-N-[(2,3 cis)-2-(2,4,6-trifluorophenyl)oxetan-3-yl]benzamide;

N-[(2,3 cis)-2-(2,4-difluorophenyl)oxetan-3-yl]-2-(trifluoromethyl)benzamide;

N-[(2,3 cis)-2-(2,4-difluorophenyl)oxetan-3-yl]-2-(trifluoromethyl)pyridine-3-carboxamide;

3-chloro-N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]pyrazine-2-carboxamide;

N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide;

3-chloro-N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]pyridine-2-carboxamide;

N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2-methylpyridine-3-carboxamide;

N-[(1,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-3-methylpyridine-2-carboxamide;

N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide;

2-Chloro-N-[(1,2 cis)-2-(2,4-dichloro-phenyl)-cyclobutyl]-nicotinamide;

N-[(1,2 cis)-2-(2-chloro-4-fluoro-phenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide;

N-[(1,2 cis)-2-(2-chloro-4-fluoro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide;

N-[(1,2 cis)-2-(4-bromo-2-chloro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide;

N-[(1,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide;

N-[(2,3 cis)-2-(2,4-difluorophenyl)oxetan-3-yl]-2-(trifluoromethyl)benzamide;

N-[(1,2 cis)-2-(4-methoxyphenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide;

N-[(1,2 cis)-2-(4-chloro-2-fluoro-phenyl)cyclobutyl]-3-(trifluoromethyl)pyridine-2-carboxamide; and

N-[(1,2 cis)-2-(2-chloro-4-fluoro-phenyl)cyclobutyl]-2-(trifluoromethyl)benzamide.