This application is the U.S. national stage application of International (PCT) Patent Application Serial No. PCT/GB2018/052078, filed Jul. 23, 2018, which claims the benefit of and priority to GB Application No. 1711839.9, filed Jul. 24, 2017, and GB Application No. 1801491.0, filed Jan. 30, 2018. The entire disclosure of each of these applications is hereby incorporated by reference.

The present invention relates to compounds which are of use in the field of agriculture as herbicides.

Given the global increase in demand for food, there is an international need for new treatments to reduce food crop losses to disease, insects and weeds. Over 40% of crops are lost before harvest worldwide. Losses have actually increased since the mid-1990s.

EP0170191, EP0176101, EP0640600 and WO2010145992 describe benzoxazinone compounds that are useful as herbicides.

It is an aim of certain embodiments of the invention to provide herbicidal compounds that are more active than prior art compounds. It is an aim of certain embodiments of the invention to provide herbicidal compounds that are more selective than prior art compounds, i.e. they may have better, similar or even lower activity than prior art compounds against target plant species but are significantly less active against non-target plant species (e.g. the crops which are being protected).

This invention provides compounds that achieve one or more of the above aims.

SUMMARY OF THE INVENTION

In a first aspect of the invention is provided a compound of formula I:


wherein
X is independently selected from CR6R7, NR8, O, S, S(O) and S(O)2;
Y is independently selected from O and S;
R1is independently a 5- to 7-membered heterocyclyl group; wherein said heterocyclyl group comprises at least one nitrogen atom in the ring; wherein said heterocyclyl group is optionally unsaturated and is optionally fused to either: a second ring selected from benzene, 5- or 6-membered heteroaryl, C3-C6-cycloalkyl and 5- to 7-membered heterocycloalkyl; or a bridged bicyclic ring system; wherein R1is optionally substituted with from 1 to 6 R9groups;
or wherein R1is —N═CR10R11wherein R10and R11together with the carbon atom to which they are attached form a 5- to 9-membered bicyclic or monocyclic heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group comprises at least one nitrogen atom in the ring and is optionally substituted with from 1 to 6 R9groups; R2is independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, OS(O)2R13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R3is selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, 4- to 6-membered heterocycloalkyl, C2-C3-alkylene-OR13aand C1-C3-alkylene-R3a; wherein R3ais selected from: cyano, 3- to 6-membered heterocycloalkyl, C3-C6-cycloalkyl and CO2R13a;
R4and R5together with the carbon atom to which they are attached form a cyclic group selected from C3-C6-cycloalkyl and a 4- to 6-membered heterocycloalkyl, wherein said heterocycloalkyl group comprises at least one heteroatom selected from N, O and S; and wherein said cycloalkyl group and heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups;
R6, R7and R8are each independently selected from H, C1-C6-alkyl and C3-C6-cycloalkyl;
R9is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R12is independently at each occurrence selected from: H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl and 4- to 6-membered heterocycloalkyl;
R13is independently at each occurrence selected from: H, benzyl, C3-C6-cycloalkyl and C1-C6-alkyl;
or where two R13groups are attached to the same nitrogen atom, said R13groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R13ais independently selected from: H, C3-C6-cycloalkyl and C1-C6-alkyl;
R14is independently at each occurrence selected from; H, benzyl, C1-C6-alkyl, C3-C6-cycloalkyl, C(O)—C1-C6-alkyl, S(O)2—C1-C6-alkyl and 4- to 6-membered heterocycloalkyl;
or where a R13group and a R14group are attached to the same nitrogen atom, said R13and R14groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R15is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
p is an integer selected from 0, 1, 2 and 3;
wherein any R2, R3, R6, R7, R8, R9, R12, R13or R14group that is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl (including where two R13groups or an R13group and an R14group together with a nitrogen to which they are attached form a heterocycloalkyl ring), or alkylene-cycloalkyl is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of: ═O; ═NRa, ═NORa, C1-C4-alkyl, halo, nitro, cyano, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, NRaRb, S(O)2Ra, S(O)Ra, S(O)(NRa)Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRaand ORa;
wherein Rais independently selected from H and C1-C4-alkyl; and Rbis independently H, C1-C4-alkyl, C(O)—C1-C4-alkyl, S(O)2—C1-C4-alkyl; or an agronomically acceptable salt or N-oxide thereof.

In another aspect of the invention, is provided a compound of formula II:


wherein
X is independently selected from CR6R7, NR8, O, S, S(O) and S(O)2;
Y is independently selected from O and S;
R1is independently selected from:


and —N═CR10R11; wherein R10and R11together with the carbon atom to which they are attached form a 5- to 9-membered bicyclic or monocyclic heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group comprises at least one nitrogen atom in the ring and is optionally substituted with from 1 to 6 R9groups;
whereinis either a double bond or a single bond;
═Y2is ═O or ═S;
X1is independently absent or is selected from NR19and CR22R22;
X2is independently absent or is CR21;
ring B is a 5- or 6-membered heterocyclyl group; and wherein said heterocyclyl group is optionally fused to a 5- or 6-membered cycloalkyl or heterocycloalkyl ring and wherein the group R1is optionally substituted with from 1 to 5 R9groups;
R2is independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, OS(O)2R13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R3is selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, 4- to 6-membered heterocycloalkyl, C2-C3-alkylene-OR13aand C1-C3-alkylene-R3a; wherein R3ais selected from: cyano, 3- to 6-membered heterocycloalkyl, C3-C6-cycloalkyl and CO2R13a;
R4and R5together with the carbon atom to which they are attached form a cyclic group selected from C3-C6-cycloalkyl and a 4- to 6-membered heterocycloalkyl, wherein said heterocycloalkyl group comprises at least one heteroatom selected from N, O and S; and wherein said cycloalkyl group or heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups;
R6, R7and R8are each independently selected from H, C1-C6-alkyl and C3-C6-cycloalkyl;
R9is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R12is independently at each occurrence selected from: H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl and 4- to 6-membered heterocycloalkyl;
R13is independently at each occurrence selected from: H, benzyl, C3-C6-cycloalkyl and C1-C6-alkyl;
or where two R13groups are attached to the same nitrogen atom, said R13groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R13ais independently selected from: H, C3-C6-cycloalkyl and C1-C6-alkyl;
R14is independently at each occurrence selected from; H, benzyl, C1-C6-alkyl, C3-C6-cycloalkyl, C(O)—C1-C6-alkyl, S(O)2—C1-C6-alkyl and 4- to 6-membered heterocycloalkyl;
or where a R13group and a R14group are attached to the same nitrogen atom, said R13and R14groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring; R15is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R19is independently selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, 4- to 6-membered heterocycloalkyl, C2-C3-alkylene-OR3aand C1-C3-alkylene-R19a; wherein R19ais selected from: cyano, 3- to 6-membered heterocycloalkyl, C3-C6-cycloalkyl and CO2R13a;
R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl;
or two R21groups, together with the carbon atoms to which they are attached form a phenyl ring, a C3-C6-cycloalkyl ring, 5- to 7-membered heterocycloalkyl ring or a 5- or 6-membered bridged bicyclic cycloalkyl or cycloalkenyl ring system, said ring or ring system being optionally substituted with from 1 to 6 R9groups;
or R19and one R21group, together with the nitrogen and carbon atoms to which they are attached form a 5- to 7-membered heterocycloalkyl ring, said ring being optionally substituted with from 1 to 6 R9groups;
R22is independently at each occurrence selected from H and C1-C4-alkyl; and
p is an integer selected from 0, 1, 2 and 3;
wherein any abovementioned alkyl, alkenyl, alkynyl, alkylene, cycloalkyl, heterocycloalkyl (including where two R13groups or an R13group and an R14group together with a nitrogen to which they are attached form a heterocycloalkyl ring) group is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of: ═O; ═NRa, ═NORa, C1-C4-alkyl, halo, nitro, cyano, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, NRaRb, S(O)2Ra, S(O)Ra, S(O)(NRa)Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRaand ORa;
wherein Rais independently selected from H and C1-C4-alkyl; and Rbis independently H, C1-C4-alkyl, C(O)—C1-C4-alkyl, S(O)2—C1-C4-alkyl; or an agronomically acceptable salt or N-oxide thereof.

In an embodiment, the compound of formula I or formula II is a compound of formula III:


wherein R1, R2, R3, R4, R5and p are as described above for compounds of formula I or formula II.

In an embodiment, the compound of formula I or formula II is a compound of formula IV:


wherein R1, R2, R3, R4and R5are as described above for compounds of formula I or formula II.

In an embodiment, the compound of formula I or formula II is a compound of formula V:


wherein R1, R2, R3, R15and p are as described above for compounds of formula I or formula II; wherein x is an integer selected from 0, 1, 2, 3 and 4; and q is an integer selected from 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula VI:


wherein R1, R2, R3and R15are as described above for compounds of formula I or formula II;
wherein x is an integer selected from 0, 1, 2, 3 and 4; and q is an integer selected from 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula VII:


wherein R1, R2, R3, R15and p are as described above for compounds of formula I or formula II; and wherein x is an integer selected from 0, 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula VIII:


wherein R1, R2, R3and R15are as described above for compounds of formula I or formula II; and wherein x is an integer selected from 0, 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula IX:


wherein R1, R2, R3, R15and p are as described above for compounds of formula I or formula II; and wherein Z is independently selected from —NR16—, —O—, —S(O)—, —S(O)2—, —S(O)NR17— and —S—; R16is independently selected from H, C1-C4-alkyl, S(O)2R13, C(O)R13, C3-C4-alkenyl and C3-C4-alkynyl; R17is independently selected from H, C1-C4-alkyl, C3-C4-alkenyl and C3-C4-alkynyl; y is an integer selected from 0, 1, 2 and 3; r and s are each an integer selected from 1, 2 and 3; and wherein the sum of r and s is 2, 3 or 4.

In an embodiment, the compound of formula I or formula II is a compound of formula X:


wherein R1, R2, R3and R15are as described above for compounds of formula I or formula II; and wherein Z is independently selected from —NR6—, —O—, —S(O)—, —S(O)2—, —S(O)NR17— and —S—; R16is independently selected from H, C1-C4-alkyl, S(O)2R13C(O)R13, C3-C4-alkenyl and C3-C4-alkynyl; R17is independently selected from H, C1-C4-alkyl, C3-C4-alkenyl and C3-C4-alkynyl; y is an integer selected from 0, 1, 2 and 3; r and s are each an integer selected from 1, 2 and 3; and wherein the sum of r and s is 2, 3 or 4.

In an embodiment, the compound of formula I or formula II is a compound of formula XI:


wherein R1, R2, R3, R15, X, Y and p are as described above for compounds of formula I or formula II; wherein x is an integer selected from 0, 1, 2, 3 and 4; and q is an integer selected from 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula XII:


wherein R1, R2, R3, R15, X and Y are as described above for compounds of formula I or formula II; wherein x is an integer selected from 0, 1, 2, 3 and 4; and q is an integer selected from 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula XIII:


wherein R1, R2, R3, R15, X, Y and p are as described above for compounds of formula I or formula II; and wherein x is an integer selected from 0, 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula XIV:


wherein R1, R2, R3, R15, X and Y are as described above for compounds of formula I or formula II; and wherein x is an integer selected from 0, 1, 2, 3 and 4.

In an embodiment, the compound of formula I or formula II is a compound of formula XV:


wherein R1, R2, R3, R15, X, Y and p are as described above for compounds of formula I or formula II; and wherein Z is independently selected from —NR6—, —O—, —S(O)—, —S(O)2—, —S(O)NR17and —S—; R16is independently selected from H, C1-C4-alkyl, S(O)2R13, C(O)R13, C3-C4-alkenyl and C3-C4-alkynyl; R17is independently selected from H, C1-C4-alkyl, C3-C4-alkenyl and C3-C4-alkynyl; y is an integer selected from 0, 1, 2 and 3; r and s are each an integer selected from 1, 2 and 3; and wherein the sum of r and s is 2, 3 or 4.

In an embodiment, the compound of formula I or formula II is a compound of formula XVI:


wherein R1, R2, R3, R15, X and Y are as described above for compounds of formula I or formula II; and wherein Z is independently selected from —NR6—, —O—, —S(O)—, —S(O)2—, —S(O)NR17and —S—; R16is independently selected from H, C1-C4-alkyl, S(O)2R13, C(O)R13, C3-C4-alkenyl and C3-C4-alkynyl; R17is independently selected from H, C1-C4-alkyl, C3-C4-alkenyl and C3-C4-alkynyl; y is an integer selected from 0, 1, 2 and 3; r and s are each an integer selected from 1, 2 and 3; and wherein the sum of r and s is 2, 3 or 4.

The following embodiments apply to compounds of any of formulae (I)-(XVI). These embodiments are independent and interchangeable. Any one embodiment may be combined with any other embodiment, where chemically allowed. In other words, any of the features described in the following embodiments may (where chemically allowable) be combined with the features described in one or more other embodiments. In particular, where a compound is exemplified or illustrated in this specification, any two or more of the embodiments listed below, expressed at any level of generality, which encompass that compound may be combined to provide a further embodiment which forms part of the present disclosure.

It may be that R1is independently a 5- to 7-membered heterocyclyl group; wherein said heterocyclyl group is comprises at least one nitrogen atom in the ring; wherein said heterocyclyl group is optionally unsaturated and is optionally fused to a second ring selected from benzene, 5- or 6-membered heteroaryl, C5-C6-cycloalkyl and 5- to 7-membered heterocycloalkyl; wherein R1is optionally substituted with from 1 to 6 R9groups. It may be that the 5- to 7-membered heterocyclyl group is attached to the rest of the molecule via a nitrogen atom in the ring (where there is more than one nitrogen atom in the ring) or the nitrogen atom in the ring (where there is a single nitrogen atom in the ring).

R1may have the structure:


wherein ring A is a 5- or 6-membered heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated and is optionally fused to a 5- or 6-membered cycloalkyl, benzene or 5- or 6-heterocycloalkyl ring; ═Y2is ═O or ═S and wherein the group R1is optionally substituted with from 1 to 4 R9groups. Ring A may be a 5- or 6-membered heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein the group R1is optionally substituted with from 1 to 4 R9groups. ═Y2may be ═O.

R1may have the structure:


wherein =A1is independently selected from ═O, ═S; and R20is independently at each occurrence selected from H and C1-C4-alkyl.
=A1may be ═O. =A1may be ═S. R20may be at both occurrences C1-C4-alkyl, e.g. Me.

In certain illustrative examples, R1may be:



Preferably, however, R1does not have the structure:



R1may have the structure:


whereinis either a double bond or a single bond; ═Y2is ═O or ═S; X1is independently absent or is selected from NR19and CR22R22; X2is independently absent or is CR21; R19is independently selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, 4- to 6-membered heterocycloalkyl, C2-C3-alkylene-OR13aand C1-C3-alkylene-R19a; wherein R19ais selected from: cyano, 3- to 6-membered heterocycloalkyl, C3-C6-cycloalkyl and CO2R13a; R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl; or two R21groups, together with the carbon atoms to which they are attached form a phenyl ring, a C3-C6-cycloalkyl ring, 5- to 7-membered heterocycloalkyl ring or a 5- or 6-membered bridged bicyclic cycloalkyl ring system, said ring or ring system being optionally substituted with from 1 to 6 R9groups; or R19and one R21group, together with the nitrogen and carbon atoms to which they are attached form a 5- to 7-membered heterocycloalkyl ring, said ring being optionally substituted with from 1 to 6 R9groups; and R22is independently at each occurrence selected from H and C1-C4-alkyl.

R1may have the structure:


whereinis either a carbon-carbon double bond or a carbon-carbon single bond; ═Y2is ═O or ═S; X1is independently absent or is selected from NR19and CR22R22; R19is independently selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, 4- to 6-membered heterocycloalkyl, C2-C3-alkylene-OR3aand C1-C3-alkylene-R19a; wherein R19ais selected from: cyano, 3- to 6-membered heterocycloalkyl, C3-C6-cycloalkyl and CO2R13a; R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl; or two R21groups, together with the carbon atoms to which they are attached form a phenyl ring, a C3-C6-cycloalkyl ring, 5- to 7-membered heterocycloalkyl ring or a 5- or 6-membered bridged bicyclic cycloalkyl ring system, said ring or ring system being optionally substituted with from 1 to 6 R9groups; or R19and one R21group, together with the nitrogen and carbon atoms to which they are attached form a 5- to 7-membered heterocycloalkyl ring, said ring being optionally substituted with from 1 to 6 R9groups; and R22is independently at each occurrence selected from H and C1-C4-alkyl.

R1may have the structure:


whereinis either a carbon-carbon double bond or a carbon-carbon single bond; ═Y2is ═O or ═S; X1is independently absent or is selected from NR19and CR22R22; R19is independently selected from H and C1-C4-alkyl; R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl or the two R21groups, together with the carbons to which they are attached form a phenyl ring or a C3-C6-cycloalkyl ring, said phenyl or cyclohexyl ring being optionally substituted with from 1 to 6 R9groups; and R22is independently at each occurrence selected from H and C1-C4-alkyl. ═Y2may be ═O. X1may be absent.

R1may be


wherein R18is independently at each occurrence selected from C1-C4-alkyl, C1-C4-haloalkyl, halogen, nitro, OR12, SR13, cyano, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl and NR13R14; R19is independently selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, 4- to 6-membered heterocycloalkyl, C2-C3-alkylene-OR13aand C1-C3-alkylene-R19a; wherein R19ais selected from: cyano, 3- to 6-membered heterocycloalkyl, C3-C6-cycloalkyl and CO2R13a; and n is an integer independently selected from 0, 1 and 2; wherein where n is 2, the two R18groups may together with the carbon atoms to which they are attached form a benzene ring.

It may be that R18is independently at each occurrence selected from C1-C4-alkyl, C1-C4-haloalkyl, halogen, nitro, OR12, SR13, cyano, C2-C4-alkenyl, C2-C4-alkynyl, and NR13R14; R19is independently selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, 4- to 6-membered heterocycloalkyl, C2-C3-alkylene-OR13aand C1-C3-alkylene-R19a; wherein R19ais selected from: cyano and CO2R13a; and n is an integer independently selected from 0, 1 and 2; wherein where n is 2, the two R18groups may together with the carbon atoms to which they are attached form a benzene ring.

It may be that n is 1. R18may be independently at each occurrence selected from: C1-C4-alkyl, C1-C4-haloalkyl and halogen. R18may be independently at each occurrence selected from: C1-C4-alkyl and C1-C4-haloalkyl. Thus, R18may be C1-C4-haloalkyl, e.g. CF3.

It may be that n is 2 and the two R18groups may together with the carbon atoms to which they are attached form a benzene ring.

R19may be independently selected from C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkynyl and C1-C3-alkylene-R19a. R19amay be CO2R13a. R19may independently selected from H and C1-C4-alkyl. R19may be C1-C4-alkyl. Preferably, R19is methyl.

In certain illustrative examples, R1may be selected from:



R1may have the structure:


whereinis either a carbon-carbon double bond or a carbon-carbon single bond; ═Y2is ═O or ═S; and R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl or the two R21groups, together with the carbons to which they are attached form a ring selected from phenyl ring, C3-C6-cycloalkyl, 5- or 6-membered heterocycloalkyl, said ring being optionally substituted with from 1 to 6 R9groups. ═Y2may be ═O.

R1may have the structure:


wherein ═Y2is ═O or ═S; and R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl or the two R21groups, together with the carbons to which they are attached form a phenyl ring, said phenyl being optionally substituted with from 1 to 6 R9groups. ═Y2may be ═O.

R1may have the structure:


wherein ═Y2is ═O or ═S; and R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl. ═Y2may be ═O.

R1may have the structure:


wherein ═Y2is ═O or ═S; and wherein z is an integer selected from 0 to 4. ═Y2may be ═O. In these embodiments, R9may be independently at each occurrence selected from halo, OR12, C1-C4-alkyl and C1-C4-haloalkyl. In these embodiments, z may be selected from 1 and 2. z may be 1.

In certain illustrative examples, R1may be:



R1may have the structure:


wherein ═Y2is ═O or ═S; and ring D is a 5- to 7-membered heterocycloalkyl ring, said ring being optionally substituted with from 1 to 6 R9groups. ═Y2may be ═O.

Ring D may be a heterocycle selected from piperidine, pyrrolidine, morpholine and thiomorpholine.

Ring D may be unsubstituted.

In certain illustrative examples, R1may be:



Other illustrative examples of R1include:



R1may have the structure:


wherein ring B is a 5- or 6-membered heterocyclyl group; and wherein said heterocyclyl group is optionally fused to a 5- or 6-membered cycloalkyl or heterocycloalkyl ring and wherein the group R1is optionally substituted with from 1 to 5 R9groups. Ring B may be a 5- or 6-membered heterocyclyl group; and wherein said heterocyclyl group is optionally substituted with from 1 to 5 R9groups.

Illustrative examples of R1include:



R1may be —N═CR10R11wherein R10and R11together with the carbon atom to which they are attached form a 5- to 9-membered bicyclic or monocyclic heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group comprises at least one nitrogen atom in the ring and is optionally substituted with from 1 to 6 R9groups.

R1may have the structure:


wherein ring C is a 5- or 6-membered heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group is optionally fused to a 5- or 6-membered cycloalkyl or heterocycloalkyl ring and wherein the group R1is optionally substituted with from 1 to 5 R9groups. It may be that ring C is a 5- or 6-membered heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group is fused to a 5- or 6-membered cycloalkyl or heterocycloalkyl ring and wherein the group R1is optionally substituted with from 1 to 5 R9groups.

Illustrative examples of R1include:



R3may be selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C3-alkylene-C3-C6-cycloalkyl, C1-C3-alkylene-CO2R13a, C2-C3-alkylene-OR13a, C3-C6-alkenyl, C3-C6-alkynyl and 4- to 6-membered heterocycloalkyl.

R3may be selected from C1-C6-alkyl, C3-C6-cycloalkyl, C1-C3-alkylene-C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl and 4- to 6-membered heterocycloalkyl. R3may be unsubstituted. R3may be selected from C1-C4-alkyl, C1-alkylene-C3-cycloalkyl, C3-C5-alkenyl and C3-C4-alkynyl. R3may be selected from C3-C5-alkenyl and C3-C4-alkynyl. R3may be selected from allyl, prenyl and propargyl. R3may be C3-C4-alkynyl. R3may be propargyl, which may be terminally substituted (e.g. with a halo group) or unsubstituted. R3may be unsubstituted propargyl. R3may be selected from C1-C6-alkyl, C3-C6-cycloalkyl, C1-C3-alkylene-CO2R13a, C2-C3-alkylene-OR13a, C1-C3-alkylene-C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl and 4- to 6-membered heterocycloalkyl. R3may be unsubstituted. R3may be selected from C1-C4-alkyl, C1-alkylene-C3-C4-cycloalkyl, C3-C5-alkenyl and C3-C4-alkynyl.

R3may be C1-C3-alkylene-CO2R13a. R3may be C1-alkylene-CO2R13a. R3may be CH(Me)-CO2—R13a.

R3may be C2-C3-alkylene-OR13a. R3may be C2-alkylene-OR13a. R13amay be C1-C4-alkyl. R13amay be methyl or ethyl.

R3may be C1-alkylene-C3-C4-cycloalkyl. R3may be C1-alkylene-cyclopropyl. R3may be C1-alkylene-cyclobutyl. In these embodiments, R3may be unsubstituted.

R3may be C1-C3-alkylene-CN. R3may be C1-alkylene-CN. R3may be CH2CN.

R4and R5may, together with the carbon atom to which they are attached, form a C3-C6-cycloalkyl group; wherein the cycloalkyl group is optionally substituted with from 1 to 4 R15groups. Thus, R4and R5may together with the carbon atom to which they are attached form a cyclopropyl group; wherein the cyclopropyl group is optionally substituted with from 1 to 4 R15groups. R4and R5may together with the carbon atom to which they are attached form an unsubstituted cyclopropyl group.

R4and R5may together with the carbon atom to which they are attached form a cyclobutyl group; wherein the cyclobutyl group is optionally substituted with from 1 to 4 R15groups. R4and R5may together with the carbon atom to which they are attached form an unsubstituted cyclobutyl group.

R4and R5may together with the carbon atom to which they are attached form a cyclopentyl group; wherein the cyclopentyl group is optionally substituted with from 1 to 4 R15groups. R4and R5may together with the carbon atom to which they are attached form an unsubstituted cyclopentyl group.

R4and R5may together with the carbon atom to which they are attached form a cyclohexyl group; wherein the cyclohexyl group is optionally substituted with from 1 to 4 R15groups. R4and R5may together with the carbon atom to which they are attached form an unsubstituted cyclohexyl group.

R4and R5together with the carbon atom to which they are attached may form a 4- to 6-membered heterocycloalkyl group; wherein the heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups.

R4and R5may, together with the carbon to which they are attached have the structure:


wherein Z is independently selected from —NR16—, —O—, —S(O)—, —S(O)2—, —S(O)NR17— and —S—; R16is independently selected from H, C1-C4-alkyl, S(O)2R13, C(O)R13, C3-C4-alkenyl and C3-C4-alkynyl; R17is independently selected from H, C1-C4-alkyl, C3-C4-alkenyl and C3-C4-alkynyl; y is an integer selected from 0, 1, 2 and 3; r and s are each an integer selected from 1, 2 and 3; and wherein the sum of r and s is 2, 3 or 4.

R4and R5together with the carbon atom to which they are attached may form a 4-membered heterocycloalkyl group; wherein the heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups. Thus, it may be that r is 1 and s is 1.

R4and R5together with the carbon atom to which they are attached may form a 5-membered heterocycloalkyl group; wherein the heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups. Thus, it may be that r is 1 and s is 2.

R4and R5together with the carbon atom to which they are attached may form a 6-membered heterocycloalkyl group; wherein the heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups. It may be that r is 2 and s is 2. It may be that r is 1 and s is 3.

It may be that Z is NR16. It may be that Z is NR16, r is 1 and s is 1. It may be that Z is NR16, r is 1 and s is 2. It may be that Z is NR16, r is 2 and s is 2. It may be that Z is NR16, r is 1 and s is 3. It may be that R16is selected from H and C1-C4-alkyl. It may be that R16is H. It may be that R16is C1-C4-alkyl, e.g. Me.

It may be that Z is O or S. It may be that Z is O. It may be that Z is S. It may be that Z is O, r is 1 and s is 1. It may be that Z is O, r is 1 and s is 2. It may be that Z is O, r is 2 and s is 2. It may be that Z is O, r is 1 and s is 3. It may be that Z is S, r is 1 and s is 1. It may be that Z is S, r is 1 and s is 2. It may be that Z is S, r is 2 and s is 2. It may be that Z is S, r is 1 and s is 3.

It may be that Z is SO2. It may be that Z is SO2, r is 1 and s is 1. It may be that Z is SO2, r is 1 and s is 2. It may be that Z is SO2, r is 2 and s is 2. It may be that Z is SO2, r is 1 and s is 3. y may be 0. y may be 1.

R9may be independently at each occurrence selected from: ═O, ═S, C1-C4-alkyl, C1-C4-haloalkyl and halogen. R9may be independently at each occurrence selected from: ═O, ═S, C1-C4-alkyl and C1-C4-haloalkyl. R9may be independently at each occurrence selected from: C1-C4-alkyl, C1-C4-haloalkyl and halogen.

p may be 1 or p may be 2. R2may be independently at each occurrence selected from: C1-C4-alkyl, C1-C4-haloalkyl and halogen. It may be that R2is at each occurrence halogen. It may be that R2is at each occurrence F. Said halogen substituents may be the same or different. If, for example, p is 2, R2may be at both occurrences F. As another example, if p is 2, R2may be at one occurrence Cl and at the other occurrence F. Preferably, p is 1 and the single R2substituent is situated para to the nitrogen that is also attached to R3. In these embodiments, the single R2may be halogen, e.g. fluoro. Further preferably, p is 1 and the single R2substituent is fluoro and is situated para to the nitrogen that is also attached to R3.

It may be that R12is independently at each occurrence selected from: H, C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl; R13is independently at each occurrence selected from: H, C3-C6-cycloalkyl and C1-C6-alkyl; and R14is independently at each occurrence selected from; H, C1-C6-alkyl, C3-C6-cycloalkyl, C(O)—C1-C6-alkyl and S(O)2—C1-C6-alkyl.

It may be that R12is independently at each occurrence selected from: H, C1-C4-alkyl and C1-C4-haloalkyl; R13is independently at each occurrence selected from: H and C1-C4-alkyl; and R14is independently at each occurrence selected from; H, C1-C4-alkyl, C(O)—C1-C4-alkyl and S(O)2—C1-C4-alkyl.

R15may be independently at each occurrence be selected from ═O, OR12, NR13R14, C1-C4-alkyl and C1-C4-haloalkyl. R15may be independently at each occurrence be selected from C1-C4-alkyl and C1-C4-haloalkyl.

It may be that X is independently selected from O, S, S(O) and S(O)2. Preferably, X is O.

It may be that Y is O.

It may be that X is independently selected from O, S, S(O) and S(O)2and Y is O. Preferably, X is O and Y is O.

It may be that X is independently selected from O, S, S(O) and S(O)2; Y is O; R2is fluoro; p is 1 and R2is situated para to the nitrogen that is also attached to R3. Preferably, X is O; Y is O and R2is fluoro; p is 1 and R2is situated para to the nitrogen that is also attached to R3.

It may be that X is independently selected from O, S, S(O) and S(O)2; Y is O and R3is propargyl. Preferably, X is O; Y is O and R3is propargyl.

It may be that X is independently selected from O, S, S(O) and S(O)2; Y is O; R2is F; p is 1 and R4and R5together with the carbon atom to which they are attached form a cyclic group selected from C3-C6-cycloalkyl. Preferably X is O; Y is O; R2is F; p is 1 and R4and R5together with the carbon atom to which they are attached form cyclopropyl.

It may be that X is independently selected from O, S, S(O) and S(O)2; Y is O; R2is F; p is 1; R3is propargyl and R4and R5together with the carbon atom to which they are attached form a cyclic group selected from C3-C6-cycloalkyl. Preferably X is O; Y is O; R2is F; p is 1; R3is propargyl and R4and R5together with the carbon atom to which they are attached form cyclopropyl.

The compound of formula I or formula II may be selected from:



The invention is also described in the following numbered paragraphs:1. A compound of formula Ia:


wherein
X is independently selected from CR6R7, NR8, O, S, S(O) and S(O)2;
Y is independently selected from O and S;
R1is independently a 5- to 7-membered heterocyclyl group; wherein said heterocyclyl group comprises at least one nitrogen atom in the ring; wherein said heterocyclyl group is optionally unsaturated and is optionally fused to a second ring selected from benzene, 5- or 6-membered heteroaryl, C5-C6-cycloalkyl and 5- to 7-membered heterocycloalkyl; wherein R1is optionally substituted with from 1 to 6 R9groups;
or wherein R1is —N═CR10R11wherein R10and R11together with the carbon atom to which they are attached form a 5- to 9-membered bicyclic or monocyclic heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group comprises at least one nitrogen atom in the ring and is optionally substituted with from 1 to 6 R9groups; R2is independently at each occurrence selected from C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, OS(O)2R13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R3is selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C3-alkylene-C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl and 4- to 6-membered heterocycloalkyl;
R4and R5together with the carbon atom to which they are attached form a cyclic group selected from C3-C6-cycloalkyl and a 4- to 6-membered heterocycloalkyl, wherein said heterocycloalkyl group comprises at least one heteroatom selected from N, O and S; and wherein said cycloalkyl group and heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups;
R6, R7and R8are each independently selected from H, C1-C6-alkyl and C3-C6-cycloalkyl;
R9is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C4-alkenyl, C2-C4-alkynyl, and NR13R14;
R12is independently at each occurrence selected from: H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl and 4- to 6-membered heterocycloalkyl;
R13is independently at each occurrence selected from: H, C3-C6-cycloalkyl and C1-C6-alkyl; or where two R13groups are attached to the same nitrogen atom, said R13groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R14is independently at each occurrence selected from; H, C1-C6-alkyl, C3-C6-cycloalkyl, C(O)—C1-C6-alkyl, S(O)2—C1-C6-alkyl and 4- to 6-membered heterocycloalkyl;
or where a R13group and a R14group are attached to the same nitrogen atom, said R13and R14groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R15is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C4-alkenyl, C2-C4-alkynyl, and NR13R14;
p is an integer selected from 0, 1, 2 and 3;
wherein any R2, R3, R6, R7, R8, R9, R12, R13or R14group that is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl (including where two R13groups or an R13group and an R14group together with a nitrogen to which they are attached form a heterocycloalkyl ring), or alkylene-cycloalkyl is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of: ═O; ═NRa, ═NORa, C1-C4-alkyl, halo, nitro, cyano, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, NRaRb, S(O)2Ra, S(O)Ra, S(O)(NRa)Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRaand ORa;
wherein Rais independently selected from H and C1-C4-alkyl; and Rbis independently H, C1-C4-alkyl, C(O)—C1-C4-alkyl, S(O)2—C1-C4-alkyl; or an agronomically acceptable salt or N-oxide thereof.2. A compound of paragraph 1 wherein X is selected from O and S.3. A compound of paragraph 1 or paragraph 2, wherein Y is O.4. A compound of any one of paragraphs 1 to 3, wherein R1has the structure:


wherein ring A is a 5- or 6-membered heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated and is optionally fused to a 5- or 6-membered cycloalkyl, benzene or 5- or 6-heterocycloalkyl ring; ═Y2is ═O or ═S and wherein the group R1is optionally substituted with from 1 to 4 R9groups.5. A compound of any one of paragraphs 1 to 3, wherein R1has the structure:


wherein ring B is a 5- or 6-membered heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group is optionally fused to a 5- or 6-membered cycloalkyl or heterocycloalkyl ring and wherein the group R1is optionally substituted with from 1 to 5 R9groups.6. A compound of any one of paragraphs 1 to 5, wherein R3is selected from C1-C4-alkyl, C1-alkylene-C3-cycloalkyl, C3-C4-alkenyl and C3-C4-alkynyl.7. A compound of claim6, wherein R3is propargyl.8. A compound of any one of paragraphs 1 to 7, wherein R4and R5may together with the carbon atom to which they are attached form a C3-C6-cycloalkyl group; wherein the cycloalkyl group is optionally substituted with from 1 to 4 R15groups.9. A compound of paragraph 8, wherein R4and R5together with the carbon atom to which they are attached form a cyclopropyl group; wherein the cyclopropyl group is optionally substituted with from 1 to 4 R15groups.10. A compound of any one of paragraphs 1 to 7, wherein R4and R5may, together with the carbon to which they are attached have the structure:


wherein Z is independently selected from —NR16—, —O—, —S(O)—, —S(O)2—, —S(O)NR17— and —S—; R16is independently selected from C1-C4-alkyl, S(O)2R13C(O)R13, C3-C4-alkenyl and C3-C4-alkynyl; R17is independently selected from H, C1-C4-alkyl, C3-C4-alkenyl and C3-C4-alkynyl; y is an integer selected from 0, 1, 2 and 3; r and s are each an integer selected from 1, 2 and 3; and wherein the sum of r and s is 2, 3 or 4.11. A compound of paragraph 10, wherein Z is NR16.12. A compound of paragraph 10, wherein Z is O.13. A compound of any one of paragraphs 10 to 12, wherein the sum of r and s is 2.14. A compound of any one of paragraphs 10 to 12, wherein the sum of r and s is 3.15. A compound of any one of paragraphs 10 to 12, wherein the sum of r and s is 4.16. A compound of any one of paragraphs 1 to 3, wherein p is 1 and the single R2substituent is situated para to the nitrogen that is also attached to R3.17. A compound of formula II:


wherein
X is independently selected from CR6R7, NR8, O, S, S(O) and S(O)2;
Y is independently selected from O and S;
R1is independently selected from:


and —N═CR10R11; wherein R10and R11together with the carbon atom to which they are attached form a 5- to 9-membered bicyclic or monocyclic heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group comprises at least one nitrogen atom in the ring and is optionally substituted with from 1 to 6 R9groups;
whereinis either a carbon-carbon double bond or a carbon-carbon single bond;
═Y2is ═O or ═S;
X1is independently absent or is selected from NR19and CR22R22;
ring B is a 5- or 6-membered heterocyclyl group, wherein said heterocyclyl group is optionally unsaturated; and wherein said heterocyclyl group is optionally fused to a 5- or 6-membered cycloalkyl or heterocycloalkyl ring and wherein the group R1is optionally substituted with from 1 to 5 R9groups;
R3is selected from C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C3-alkylene-C3-C6-cycloalkyl, C1-C3-alkylene-CO2R13a, C2-C3-alkylene-OR13a, C3-C6-alkenyl, C3-C6-alkynyl and 4- to 6-membered heterocycloalkyl;
R4and R5together with the carbon atom to which they are attached form a cyclic group selected from C3-C6-cycloalkyl and a 4- to 6-membered heterocycloalkyl, wherein said heterocycloalkyl group comprises at least one heteroatom selected from N, O and S; and wherein said cycloalkyl group and heterocycloalkyl group is optionally substituted with from 1 to 4 R15groups;
R6, R7and R8are each independently selected from H, C1-C6-alkyl and C3-C6-cycloalkyl;
R9is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R12is independently at each occurrence selected from: H, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl and 4- to 6-membered heterocycloalkyl;
R13is independently at each occurrence selected from: H, C3-C6-cycloalkyl and C1-C6-alkyl;
or where two R13groups are attached to the same nitrogen atom, said R13groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring;
R13ais independently selected from: H, C3-C6-cycloalkyl and C1-C6-alkyl;
R14is independently at each occurrence selected from; H, C1-C6-alkyl, C3-C6-cycloalkyl, C(O)—C1-C6-alkyl, S(O)2—C1-C6-alkyl and 4- to 6-membered heterocycloalkyl;
or where a R13group and a R14group are attached to the same nitrogen atom, said R13and R14groups, together with said nitrogen atom form a 4-, 5-, 6- or 7-membered heterocycloalkyl ring; R15is independently at each occurrence selected from: ═O, ═S, ═NR13, C1-C6-alkyl, C1-C6-haloalkyl, halogen, nitro, OR12, SR13, S(O)2R13, S(O)2NR13R13, S(O)(NR13)R13, S(O)R13, C(O)R13, C(O)NR13R13, C(O)OR13, cyano, C2-C6-alkenyl, C2-C6-alkynyl, and NR13R14;
R21is independently selected from H, halo, C1-C4-alkyl and C1-C4-haloalkyl or two R21groups, together with the carbons to which they are attached form a phenyl ring, a C3-C6-cycloalkyl ring or a 5- or 6-membered bridged bicyclic cycloalkyl ring system, said phenyl or cyclohexyl ring or ring system being optionally substituted with from 1 to 6 R9groups;
R22is independently at each occurrence selected from H and C1-C4-alkyl; and
p is an integer selected from 0, 1, 2 and 3;
wherein any R2, R3, R6, R7, R8, R9, R12, R13or R14group that is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl (including where two R13groups or an R13group and an R14group together with a nitrogen to which they are attached form a heterocycloalkyl ring), or alkylene-cycloalkyl is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of: ═O; ═NRa, ═NORa, C1-C4-alkyl, halo, nitro, cyano, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, NRaRb, S(O)2Ra, S(O)Ra, S(O)(NRa)Ra, S(O)2NRaRa, CO2Ra, C(O)Ra, CONRaRaand ORa;
wherein Rais independently selected from H and C1-C4-alkyl; and Rbis independently H, C1-C4-alkyl, C(O)—C1-C4-alkyl, S(O)2—C1-C4-alkyl; or an agronomically acceptable salt or N-oxide thereof.18. A compound of paragraph 17 wherein X is selected from O and S.19. A compound of paragraph 17 or paragraph 18, wherein Y is O.20. A compound of any one of paragraphs 17 to 19, wherein R1has the structure:

21. A compound of any one of paragraphs 17 to 19, wherein R1has the structure:

22. A compound of any one of paragraphs 17 to 19, wherein R1has the structure:

23. A compound of any one of paragraphs 17 to 22, wherein R3is selected from C1-C4-alkyl, C1-alkylene-C3-C4-cycloalkyl, C1-C3-alkylene-CO2R13a, C2-C3-alkylene-OR13a, C3-C4-alkenyl and C3-C4-alkynyl.24. A compound of paragraph 23, wherein R3is propargyl.25. A compound of any one of paragraphs 17 to 24, wherein R4and R5may together with the carbon atom to which they are attached form a C3-C6-cycloalkyl group; wherein the cycloalkyl group is optionally substituted with from 1 to 4 R15groups.26. A compound of paragraph 25, wherein R4and R5together with the carbon atom to which they are attached form a cyclopropyl group; wherein the cyclopropyl group is optionally substituted with from 1 to 4 R15groups.27. A compound of any one of paragraphs 17 to 24, wherein R4and R5may, together with the carbon to which they are attached have the structure:


wherein Z is independently selected from —NR16—, —O—, —S(O)—, —S(O)2—, —S(O)NR17— and —S—; R16is independently selected from C1-C4-alkyl, S(O)2R13, C(O)R13, C3-C4-alkenyl and C3-C4-alkynyl; R17is independently selected from H, C1-C4-alkyl, C3-C4-alkenyl and C3-C4-alkynyl; y is an integer selected from 0, 1, 2 and 3; r and s are each an integer selected from 1, 2 and 3; and wherein the sum of r and s is 2, 3 or 4.28. A compound of paragraph 27, wherein Z is NR1629. A compound of paragraph 27, wherein Z is O.30. A compound of any one of paragraphs 27 to 29, wherein the sum of r and s is 2.31. A compound of any one of paragraphs 27 to 29, wherein the sum of r and s is 3.32. A compound of any one of paragraphs 27 to 29, wherein the sum of r and s is 4.33. A compound of any one of paragraphs 17 to 32, wherein p is 1 and the single R2substituent is situated para to the nitrogen that is also attached to R3.34. A method for controlling weeds, the method comprising applying a compound of any one of paragraphs 1 to 33 to the plants themselves or to the area where it is intended that the plants will grow.35. Use of a compound of any one of paragraphs 1 to 33 as a herbicide.36. A herbicidal composition comprising an effective amount of an active compound of any one of paragraphs 1 to 33.

