1. A guide piece for an extraction or coal plough, comprising:
a generally U-shaped guide piece body configured to be inserted into a guide claw of the plough along an insertion direction, the guide piece body including a first leg, a second leg and a connecting portion extending between the first leg and the second leg; and
a recess formed in the guide piece body to extend at an angle with respect to the connecting portion from an outer side of the connecting portion to an outer side of one of the first leg and the second leg, the recess being configured for engagement with a locking mechanism to prevent movement of the guide piece at least in a direction opposite to the insertion direction after installation of the guide piece in the guide claw.
2. The guide piece of claim 1, wherein the recess is configured as a single recess that extends from the outer side of the connecting portion to the outer side of the one of the first leg and the second leg.
3. The guide piece of claim 2, wherein the single recess is formed in a central portion of the guide piece body in a longitudinal direction of the same.
4. The guide piece of claim 1, wherein the recess is formed as groove extending from the outer side of the connecting portion to the outer side of the one of the first leg and the second leg.
5. The guide piece of claim 4, wherein the groove has a generally semi-circular profile.
6. The guide piece of claim 1, wherein the angle is between around 30\xb0 and around 60\xb0.
7. The guide piece of claim 6, wherein the angle is around 45\xb0.
8. The guide piece of claim 1, wherein the recess is a first recess, the guide piece further comprising a second recess formed in the guide piece body to extend at the angle with respect to the connecting portion from the outer side of the connecting portion to an outer side of the other one of the first leg and the second leg.
9. The guide of claim 8, wherein the second recess has a configuration that is substantially the same as that of the first recess.
10. The guide piece of claim 1, further comprising at least one projection formed to project from the guide piece body in the direction of insertion, the at least one projection being configured to support at least in part the guide piece in the guide claw by positive engagement with the same.
11. The guide piece of claim 10, wherein the at least one projection includes at least one of a first projection projecting from a stop formed at one end of the guide piece body to limit at least in part movement of the guide piece in the direction of insertion when the guide piece is inserted into the guide claw, and a second projection formed on the opposite end of the guide piece body to project from the same.
12. A locking mechanism for a guide piece for an extraction or coal plough, the guide piece being configured to be inserted into a guide claw of the plough along an insertion direction, comprising:
a bolt configured to be received in a receiving bore formed in the guide claw and in a recess formed in the guide piece after installation of the guide piece in the guide claw, the bolt including an inner bore and an annular groove disposed adjacent to a first end of the bolt; and
a securing mechanism configured for engagement with the annular groove when the bolt is received in the receiving bore and the recess to secure the bolt in the receiving bore, to thereby prevent movement of the guide piece at least in a direction opposite to the insertion direction.
13. The locking mechanism of claim 12, wherein the securing mechanism includes a locking member and a pin, the locking member being configured to engage with the annular groove of the bolt, the pin being configured to be driven into the inner bore of the bolt to expand the bolt for securing the bolt and the locking member to the guide claw.
14. The locking mechanism of claim 13, wherein the locking member includes a substantially flat base having a cut extending from an outer edge of the base towards a center of the same, the cut having a width corresponding to a diameter of the bolt at the position where the annular groove is formed, and a head portion extending from the base, the head portion including an arcuate outer surface configured to abut against an abutment surface of the guide claw when the locking member engages with the annular groove of the bolt.
15. The locking mechanism of claim 14, wherein the head portion further includes a bottom surface facing the base, the arcuate surface extending from the bottom surface towards a distal end of the head portion, and a tapered surface extending from the distal end of the head portion to the outer edge of the base.
16. The locking mechanism of claim 15, wherein the locking member further includes a locking member inner bore formed at least in the head portion and configured to receive the pin when the pin is driven into the inner bore of the bolt.
17. The locking mechanism of claim 12, wherein the inner bore of the bolt extends through the bolt, allowing the pin to be removed from the bolt via an opening formed in a second end of the bolt opposite to the first end.
18. A guide piece assembly for an extraction or coal plough, comprising:
a guide piece including:
a generally U-shaped guide piece body configured to be inserted into a guide claw of the plough along an insertion direction, the guide piece body including a first leg, a second leg and a connecting portion extending between the first leg and the second leg; and
a recess formed in the guide piece body to extend at an angle with respect to the connecting portion from an outer side of the connecting portion to an outer side of one of the first leg and the second leg; and
a locking mechanism including:
a bolt configured to be received in a receiving bore formed in the guide claw and in the recess formed in the guide piece after installation of the guide piece in the guide claw, the bolt including an inner bore and an annular groove disposed adjacent to a first end of the pin; and
a securing mechanism configured for engagement with the annular groove when the bolt is received in the receiving bore and the recess to secure the bolt in the receiving bore, to thereby prevent movement of the guide piece at least in a direction opposite to the insertion direction.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
What is claimed is:
1. A synergistic insecticidal composition comprising a synergistically effective amount of a neuronal sodium channel antagonist and an arylpyrrole insecticide.
2. The composition according to claim 1 wherein the ratio of the neuronal sodium channel antagonist to the arylpyrrole insecticide is about 1:10 to 1:50.
3. The composition according to claim 2 wherein said neuronal sodium channel antagonist and said arylpyrrole insecticide are dispersed in an inert solid or liquid diluent.
4. The composition according to claim 1 having a neuronal sodium channel antagonist compound of formula
10
11
wherein
A is CR4R5 or NR6;
W is O or S;
X, Y, Z, X, Y and Z are each independently H;
halogen; OH; CN; NO2;
C1-C6alkyl optionally substituted with one or more halogen, C1-C3alkoxy, C1-C3haloalkoxy, C3-C6cycloalkyl, C2-C6alkenyloxy or sulfonyloxy groups;
C1-C6alkoxy optionally substituted with one or more halogen, C1-C3alkoxy or C3-C6cycloalkyl groups;
C1-C6alkoxycarbonyl, C3-C6cycloalkylcarbonyloxy, phenyl optionally substituted with one or more halogen, C1-C4alkyl, or C1-C4alkoxy groups;
aminocarbonyloxy optionally substituted with one or more C1-C3alkyl groups;
C1-C6alkoxycarbonyloxy; C1-C6alkylsulfonyloxy;
C2-C6alkenyl; or NR12R13;
m, p and q are each independently an integer of 1, 2, 3, 4, or 5;
n is an integer of 0, 1 or 2;
r is an integer of 1 or 2;
t is an integer of 1, 2, 3 or 4;
R, R1, R2, R3, R4 and R5 are each independently H or C1-C4alkyl;
R6 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxyalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C1-C6haloalkylthio;
R7 and Re are each independently H; halogen; C1-C6alkyl;
C1-C6alkylcarbonyloxy; or phenyl optionally substituted with one or more halogen, CN, NO2, C1-C6alkyl, C2-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy groups;
R9 and R10 are each independently H, or C1-C4alkyl;
R11 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkylcarbonyl, C1-C6alkoxycarbonyl, or C1-C6haloalkoxycarbonyl;
R12 and R13 are each independently H or C1-C6alkyl;
G is H;
C1-C6alkyl optionally substituted with one or more halogen, C1-C4alkoxy, C1-C6haloalkoxy, CN, NO2S (O)uR14, COR15, CO2R16, phenyl or C3-C6cycloalkyl groups;
C1-C6alkoxy; C1-C6haloalkoxy; CN; NO2; S(O)uR17; COR18; CO2R19;
phenyl optionally substituted with one or more halogen, CN, C1-C3haloalkyl, or C1-C3haloalkoxy groups;
C3-C6cycloalkyl; or phenylthio;
Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO2, S(O)uR20, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxyalkyl, C1-C6alkoxy, C1-C6haloalkoxy, or NR21R22 groups;
u is an integer of 0, 1 or 2;
R14, R15, R16, R18, R19, R21 and R22 are each independently H or C1-C6alkyl;
R17 and R20 are each independently C1-C6alkyl or C1-C6haloalkyl;
R33 is CO2R34;
R34 is H, C1-C6alkyl, C1-C6haloalkyl, phenyl or halophenyl; and
the dotted line configuration represents a double bond or a single bond; or
a stereoisomer thereof.
5. The composition according to claim 4 having a compound of formula I or formula III.
6. The composition according to claim 5 having a compound of formula I or formula III wherein the dotted line configuration represents a double bond.
7. The composition according to claim 6 wherein the formula III compound is in the S-form.
8. The composition according to claim 7 wherein W is O; X is trifluoromethoxy and is in the 4-position; Y is trifluoromethyl and is in the 3-position; Z is CN and is in the 4-position; A is CH2; n is 0; m, p and q are each independently 1; R and R1 are each independently H; Z is Cl; R33 and G are each independently CO2CH3; and Q is p-(trifluoromethoxy)phenyl.
9. The composition according to claim 8 having an arylpyrrole insecticide of formula VI
12
Hal is Cl or Br;
x is an integer of 1, 2, 3, 4, 5 or 6;
D is H,
C1-C6alkyl optionally substituted with one or more halogen, CN, OH, C1-C4alkoxy, C3-C4haloalkoxy, C1-C6alkylthio, C1-C4alkylcarbonyloxy, C1-C4haloalkylthio, C2-C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, halophenoxy, phenyl, halophenyl or C1-C3alkylphenyl groups,
C2-C6alkenyl, C2-C6haloalkenyl, CN, C2-C6alkynyl, C2-C6haloalkynyl, di-(C1-C4alkyl) aminocarbonyl or C3-C6polymethyleneiminocarbonyl;
L is H or halogen;
M and M1 are each independently H, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsufonyl, C1-C4haloalkylsulfonyl, C1-C4alkylcarbonyl, C1-C4haloalkylcarbonyl, NR35R36 or when M and M1 are attached to adjacent carbon atoms, they may be taken together with the carbon atoms to which they are attached to form a ring in which MM1 represents OCH2O, OCF2O or CHCHCHCH;
A is O or S;
R30, R31 and R32 are each independently hydrogen, halogen, NO2, CHO or R31 and R32 may be taken together with the carbon atoms to which they are attached to form a ring in which R31R32 represent
13
L, L, T and V are each independently H, halogen, CN or NO2 with the proviso that no more than two of L, L, T or V are NO2; and
R35 and R36 are each independently H or C1-C4alkyl.
10. The composition according to claim 9 having an arylpyrrole insecticide of formula VI wherein D is H or ethoxymethyl; Ar is phenyl substituted with one or two halogen or halomethyl groups; and x is 1.
11. The composition according to claim 1 having a neuronal sodium channel antagonist compound of formula
14
wherein W is O or S;
X and Y are each independently H; halogen; CN; SCN;
C1-C6alkyl optionally substituted with one or more halogen, NO2, CN, C1-C4alkoxy, C1-C4alkylthio, phenyl, halophenyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, or C1-C4alkoxycarbonyl groups;
C2-C4alkenyl; C2-C4haloalkenyl; C2-C4alkynyl; C2-C4haloalkynyl; C1-C6cycloalkyl; C3-C6halocycloalkyl;
phenyl optionally substituted with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4haloalkylsulfonyl groups;
C1-C4alkylcarbonyl; C1-C4haloalkylcarbonyl; or
NR28R29;
m is an integer of 1, 2, 3, 4 or 5;
G is phenyl optionally substituted with one or more groups which may be the same or different selected from X;
a 5-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0, 1 or 2 nitrogen atoms said 5-membered heteroaromatic ring being attached via carbon and being optionally substituted with one or more groups which may be the same or different selected from X; or
a 6-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0, 1 or 2 nitrogen atoms said 6-membered heteroaromatic ring being attached via carbon and being optionally substituted with one or more groups which may be the same or different selected from X;
Q is H; C1-C6alkyl optionally substituted with one or more halogen, CN, C1-C3alkoxy, C1-C6alkoxycarbonyl, or
phenyl optionally substituted with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylsulfonyl or C1-C4alkylsulfinyl groups;
C2-C6alkenyl; C2-C6alkynyl; or phenyl optionally substituted with one to three groups, which may be the same or different, selected from X;
R23, R24, R25, R26, R27, R28 and R29 are each independently H or C1-C4alkyl; and
the dotted line configuration represents a double bond or a single bond; or
a stereoisomer thereof.
12. The composition according to claim 1 having an arylpyrrole insecticide of formula VI
15
Hal is Cl or Br;
x is an integer of 1, 2, 3, 4, 5 or 6;
D is H,
C1-C6alkyl optionally substituted with one or more halogen, CN, OH, C1-C4alkoxy, C1-C4haloalkoxy, C1-C5alkylthio, C1-C4alkylcarbonyloxy, C1-C4haloalkylthio, C2-C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, halophenoxy, phenyl, halophenyl or C1-C3alkylphenyl groups,
C2-C6alkenyl, C2-C6haloalkenyl, CN, C2-C6alkynyl, C2-C6haloalkynyl, di-(C1-C4alkyl)aminocarbonyl or C3-C6polymethyleneiminocarbonyl;
L is H or halogen;
M and M1 are each independently H, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsufonyl, C1-C4haloalkylsulfonyl, C1-C4alkylcarbonyl, C1-C4haloalkylcarbonyl, NR35R36 or when M and Ml are attached to adjacent carbon atoms, they may be taken together with the carbon atoms to which they are attached to form a ring in which MM1 represents OCH2O, OCF2O or CHCHCHCH;
A is O or S;
R30, R31 and R32 are each independently hydrogen, halogen, NO2, CHO or R31 and R32 may be taken together with the carbon atoms to which they are attached to form a ring in which R31R32 represent
16
L, L, T and V are each independently H, halogen, CN or NO2 with the proviso that no more than two of L, L, T or V are NO2; and
R35 and R36 are each independently H or C1-C4alkyl.
13. The composition according to claim 12 having an arylpyrrole insecticide of formula VI wherein D is H or ethoxymethyl; Ar is phenyl substituted with one or two halogen or halomethyl groups; and x is 1.
14. A method for synergistic insect control which comprises contacting said insect with a synergistically effective amount of a combination of a neuronal sodium channel antagonist and an arylpyrrole insecticide.
15. The method according to claim 14 wherein the neuronal sodium channel antagonist is present in a ratio to the arylpyrrole insecticide of about 1:10 to 1:50.
16. The method according to claim 14 having a neuronal sodium channel antagonist compound of formula
17
18
wherein
A is CR4R5 or NR6;
W is O or S;
X, Y, Z, X, Y and Z are each independently H;
halogen; OH; CN; NO2;
C1-C6alkyl optionally substituted with one or more halogen, C1-C3alkoxy, C1-C3haloalkoxy, C3-C6cycloalkyl, C2-C6alkenyloxy or sulfonyloxy groups;
C1-C6alkoxy optionally substituted with one or more halogen, C1-C3alkoxy or C1-C6cycloalkyl groups;
C1-C6alkoxycarbonyl, C3-C6cycloalkylcarbonyloxy, phenyl optionally substituted with one or more halogen, C1-C4alkyl, or C1-C4alkoxy groups;
aminocarbonyloxy optionally substituted with one or more C1-C3alkyl groups;
C1-C6alkoxycarbonyloxy; C1-C6alkylsulfonyloxy; C2-C6alkenyl; or NR12R13;
m, p and q are each independently an integer of 1, 2, 3, 4, or 5;
n is an integer of 0, 1 or 2;
r is an integer of 1 or 2;
t is an integer of 1, 2, 3 or 4;
R, R1, R2, R3, R4 and R5 are each independently H or C1-C4alkyl;
R6 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxyalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C1-C6haloalkylthio;
R7 and R8 are each independently H; halogen; C1-C6alkyl; C1-C6alkylcarbonyloxy; or phenyl optionally substituted with one or more halogen, CN, NO2, C1-C6alkyl, C2-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy groups;
R9 and R10 are each independently H, or C1-C4alkyl;
R11 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkylcarbonyl, C1-C6alkoxycarbonyl, or C1-C6haloalkoxycarbonyl;
R12 and R13 are each independently H or C1-C6alkyl;
G is H;
C1-C6alkyl optionally substituted with one or more halogen, C1-C4alkoxy, C1-C6haloalkoxy, CN, NO2S(O)uR14, COR15, CO2R16, phenyl or C3-C6cycloalkyl groups;
C1-C6alkoxy; C1-C, haloalkoxy; CN; NO2; S(O)uR17; COR18; CO2R19; phenyl optionally substituted with one or more halogen, CN, C1-C3haloalkyl, or C1-C3haloalkoxy groups;
C3-C6cycloalkyl; or phenylthio;
Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO2, S(O)uR20, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxyalkyl, C1-C6alkoxy, C1-C6haloalkoxy, or NR21R22 groups;
u is an integer of 0, 1 or 2;
R14, R15, R16, R18, R19, R21 and R22 are each independently H or C1-C6alkyl;
R17 and R20 are each independently C1-C6alkyl or C1-C6haloalkyl;
R33 is CO2R34;
R34 is H, C1-C6alkyl, C1-C6haloalkyl, phenyl or halophenyl; and
the dotted line configuration represents a double bond or a single bond; or
a stereoisomer thereof.
17. The method according to claim 16 having a compound of formula I or formula III.
18. The method according to claim 17 having a compound of formula I or formula III wherein the dotted line configuration represents a double bond.
19. The method according to claim 18 wherein the formula III compound is in the S-form.
20. The method according to claim 19 wherein W is O; X is trifluoromethoxy and is in the 4-position; Y is trifluoromethyl and is in the 3-position; Z is CN and is in the 4-position; A is CH2; n is 0; m, p and q are each independently 1; R and R1 are each independently H; Z is Cl; R33 and G are each independently CO2CH3; and Q is p-(trifluoromethoxy)phenyl.
21. The method according to claim 14 having an arylpyrrole insecticide of formula VI
19
Hal is Cl or Br;
x is an integer of 1, 2, 3, 4, 5 or 6;
D is H,
C1-C6alkyl optionally substituted with one or more halogen, CN, OH, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkylcarbonyloxy, C1-C4haloalkylthio, C2-C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, halophenoxy, phenyl , halophenyl or C1-C3alkylphenyl groups,
C2-C6alkenyl, C2-C6haloalkenyl, CN, C2-C6alkynyl, C2-C6haloalkynyl, di-(C1-C4alkyl)aminocarbonyl or C3-C6polymethyleneiminocarbonyl;
L is H or halogen;
M and M1 are each independently H, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsufonyl, C1-C4haloalkylsulfonyl, C1-C4alkylcarbonyl, C1-C4haloalkylcarbonyl, NR35R36 or when M and M1 are attached to adjacent carbon atoms, they may be taken together with the carbon atoms to which they are attached to form a ring in which MM1 represents OCH2O, OCF2O or CHCHCHCH;
A is O or S;
R30, R31 and R32 are each independently hydrogen, halogen, NO2, CHO or R31 and R32 may be taken together with the carbon atoms to which they are attached to form a ring in which R31R32 represent
20
L, L, T and V are each independently H, halogen, CN or NO2 with the proviso that no more than two of L, L, T or V are NO2; and
R35 and R36 are each independently H or C1-C4alkyl.
22. The method according to claim 21 having an arylpyrrole insecticide of formula VI wherein D is H or ethoxymethyl; Ar is phenyl substituted with one or two halogen or halomethyl groups; and x is 1.
23. The method according to claim 14 having a neuronal sodium channel antagonist compound of formula
21
wherein
W is O or S;
X and Y are each independently H; halogen; CN; SCN;
C1-C6alkyl optionally substituted with one or more halogen, NO2, CN, C1-C4alkoxy, C1-C4alkylthio, phenyl, halophenyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, or C1-C4alkoxycarbonyl groups;
C2-C4alkenyl; C2-C4haloalkenyl; C2-C4alkynyl; C2-C4haloalkynyl; C3-C6cycloalkyl; C3-C6halocycloalkyl; phenyl optionally substituted with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4haloalkylsulfonyl groups;
C1-C4alkylcarbonyl; C1-C4haloalkylcarbonyl; or NR28R29;
m is an integer of 1, 2, 3, 4 or 5;
G is phenyl optionally substituted with one or more groups which may be the same or different selected from X;
a 5-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0, 1 or 2 nitrogen atoms said 5-membered heteroaromatic ring being attached via carbon and being optionally substituted with one or more groups which may be the same or different selected from X; or
a 6-membered heteroaromatic ring containing one or two heteroatoms selected from 0 or 1 oxygen, 0 or 1 sulfur and 0, 1 or 2 nitrogen atoms said 6-membered heteroaromatic ring being attached via carbon and being optionally substituted with one or more groups which may be the same or different selected from X;
Q is H;
C1-C6alkyl optionally substituted with one or more halogen, CN, C1-C3alkoxy, C1-C6alkoxycarbonyl, or phenyl optionally substituted with one or more halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylsulfonyl or C1-C4alkylsulfinyl groups;
C2-C6alkenyl; C2-C6alkynyl; or phenyl optionally substituted with one to three groups, which may be the same or different, selected from X;
R23, R24, R25, R26 . R271 R28 and R29 are each independently H or C1-C4alkyl; and
the dotted line configuration represents a double bond or a single bond; or
a stereoisomer thereof.
24. A method for protecting a plant from infestation and attack by insects which comprises applying to the foliage or stem of said plant a synergistically effective amount of a composition according to claim 1.
25. The method according to claim 24 wherein the plant is cotton.
26. The method according to claim 24 wherein the insect is lepidoptera or coleoptera.