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1. WO2020109039 - PESTICIDAL COMPOUNDS

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

We claim:

1 . Compounds of the formula I


wherein

A1 is N or CRA1;

A2 is N or CRA2;

A3 is N or CRA3;

wherein at least one of the A1, A2, A3 is N;

B1 is CRB1;

B2 is CRB2;

B3 is CRB3;

RA1, RA2 , and RA3 independently of each other are selected from H, halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-C6-alkenyl, tri-Ci-Ce- alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3- C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, Ci-C4-alkyl-C3-C6- cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-0Ra, NRbRc, Ci-C6-alkylene-NRbRc, 0-Ci-C6-alkyiene-NRbRc, Ci-C6- alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=0)-NRbRc, C(=0)-Rd, S02NRbRc, or S(=0)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

RB1, RB2, and RB3, independently of each other are H, halogen, N3, OH, CN, NO2, - SCN, -SF5, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6- alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, Ci-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-0Ra, NRbRc, Ci-C6-alkylene-NRbRc, 0-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene- CN, NH-Ci-C6-alkylene-NRbRc, C(=0)-NRbRc, C(=0)-Rd, S02NRbRc, or S(=0)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Q is -N=C(X)-, -N(R2)-C(=NR)-, or -N(R2)-C(=S)-, -C(R4R5)-0-, -C(=0)-0-, - S(=0)m-C(R7R8)-, -N(R2)-S(=0)m-, -N(R2)-C(R9R10)-, -C(=0)-C(R19R20)-, -N(R2)- C(=0)-, -C(R13R14)-C(R15R16)-, or -C(R17)=C(R18)-; wherein Ar is bound to either side of Q;

X is identical or different, H, halogen, SR7, OR8, N(R3)2, -CR4=N(OCH3), CN, Ci-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted or substituted with halogen; phenyl, or -Chh-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

R is identical or different, H, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6- cycloalkyl, wherein the alkyl, alkenyl, alkynyl and cycloalkyl moieties are unsubstituted or substituted with halogen,

SR7, OR8, N(R3)2, phenyl, or -Chh-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

R2 is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(0)-0Ra, Ci-C6-alkylen-NRbRc, Ci-C6-alkylen-CN, C(0)-NRbRc, C(0)-Rd, S02NRbRc, S(=0)mRe, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

R3 is H, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4- alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, or C3-C6-cycloalkoxy-Ci-C4- alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

Ci-C6-alkylene-CN, phenyl, or -Chh-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

R4, R5, R7, R8, R9, R10, R13, R14, R15, R16, R17, R18, R19, R20 are, identical or different, H, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-0Ra, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=0)-NRbRc, C(=0)-Rd, S02NRbRc, S(=0)mRe, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

R6 is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein

the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-0Ra, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=0)-NRbRc, C(=0)-Rd, S02NRbRc, S(=0)mRe, phenyl, -CH2-C(=0)-0Ra, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with RAr, wherein

RAr is halogen, N3, OH, CN, NO2, -SON, -SF5, Ci-Ce-alkyl, Ci-Ce-alkoxy, C2-C6- alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy- Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen, C(=0)-0Ra, NRbRc, Ci-C6-alkylene-NRbRc, 0-Ci-C6-aikylene-NRbRc, Ci-C6- alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=0)-NRbRc, C(=0)-Rd, S02NRbRc, or S(=0)mRe, phenyl, phenoxy, phenylcarbonyl, phenylthio or -CH2-phenyl, wherein phenyl rings are unsubstituted or substituted with Rf;

R1 is a moiety of formula Y-Z-T-R11 or Y-Z-T-R12; wherein

Y is -CRya=N-, wherein the N is bound to Z;

-NRyc-C(=0)-, wherein C(=0) is bound to Z; or

-NRyc-C(=S)-, wherein C(=S) is bound to Z;

Z is a single bond;

-NRzc-C(=0)-, wherein C(=0) is bound to T;

-NRZC-C(=S)-, wherein C(=S) is bound to T;

-N=C(S-Rza)-, wherein T is bound to the carbon atom;

-0-C(=0)-, wherein T is bound to the carbon atom; or

-NRzc-C(S-Rza)=, wherein T is bound to the carbon atom;

T is O, N or N-RT;

R1 1 is Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, Ci-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=0)-NRbRc, C(=0)-Rd, aryl, aryl-carbonyl, aryl-Ci-C4-alkyl, aryloxy-Ci-C4-alkyl, heteroaryl, carbonyl- heteroaryl, heteroaryl-Ci-C4-alkyl or heteroaryloxy-Ci-C4-alkyl, wherein the phenyl rings are unsubstituted or substituted with R9 and wherein the heteroaryl is a 5- or 6-membered monocyclic heteroaryl or a 8-, 9- or 10- membered bicyclic heteroaryl;

R12 is a radical of the formula A1;

191 122

123

(A1)


wherein # indicates the point of attachment to T ;

R121, R122, R123 are, identical or different, H, halogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy, C2-C6-al- kenyloxy, C2-C6-alkynyloxy, Ci-C6-alkoxy-Ci-C4-alkoxy, C1-C6- alkylcarbonlyoxy, Ci-C6-alkenylcarbonlyoxy, C3-C6- cycloalkylcarbonlyoxy, wherein the alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and cycloalkyl moieties are unsubstituted or substituted with halogen, or NRbRc, or one of R121, R122, R123 may also be oxo;

R124 is H, Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy, or C2-C6- alkenyloxy, wherein the alkyl, alkoxy, alkenyl and alkenyloxy moieties are unsubstituted or substituted with halogen;

and where

Rya is H, halogen, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, Ci- C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, C1-C4- alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-ORa, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=0)-NRbRc, C(=0)-Rd, SC>2NRbRc, S(=0)mRe, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Ryc, Rzc are, identical or different, H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkyl-Ci-C6-alkoxy, C3-C6-cycloalkyl, Ci-C4-alkyl-C3-C6-cycloalkyl, or Ci-C4-alkyl-C3-C6-cycloalkoxy, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen;

RT is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkyl-Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-ORa, Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=0)-NRbRc,

C(=0)-Rd, SC>2NRbRc, S(=0)mRe, phenyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Rzc together with RT if present, may form Ci-C6-alkylene or a linear C2-C6- alkenylene group, where in the linear Ci-C6-alkylene and the linear C2-C6- alkenylene a CH2 moiety may be replaced by a carbonyl or a C=N-R' and/or wherein 1 or 2 CH2 moieties may be replaced by O or S and/or wherein the linear Ci-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;

Rza is H, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6- alkynyl, Ci-C4-alkyl-Ci-C6-alkoxy, C3-C6-cycloalkyl, Ci-C4-alkyl-C3-C6- cycloalkoxy, Ci-C4-alkyl-C3-C6-cycloalkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, C(=0)-NRbRc, C(=0)-Rd, phenyl, phenylcarbonyl, or -CH2-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Rza together with RT if present, may form Ci-C6-alkylene or a linear C2-C6- alkenylene group, where in the linear Ci-C6-alkylene and the linear C2-C6- alkenylene a CH2 moiety may be replaced by a carbonyl or a C=N-R' and/or wherein 1 or 2 CH2 moieties may be replaced by O or S and/or wherein the linear Ci-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;

Ra, Rb and Rc are, identical or different, H, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are

unsubstituted or substituted with halogen,

Ci-C6-alkylene-CN, phenyl, or -Chh-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Rb and Rc together with the nitrogen they are attached may form 5- or 6- membered saturated, partially or fully unsaturated heterocyclic ring;

Rd is H, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3- C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

phenyl, or -Chh-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Re is Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, wherein the alkyl, cycloalkyl moieties are unsubstituted or substituted with halogen, phenyl and -Chh-phenyl, wherein the phenyl rings are unsubstituted or substituted with Rf;

Rf is halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6- alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C1-C6- alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl- Ci-C4-alkyl, C3-C6-cycloalkoxyx-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, 0-Ci-C6-alkyiene-NRbRc, Ci-C6-alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=0)-NRbRc, C(=0)-Rd, S02NRbRc, or S(=0)mRe;

R9 is halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6- alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C1-C6- alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl- Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl and cycloalkoxy moieties are unsubstituted or substituted with halogen,

C(=0)-ORa, NRbRc, Ci-C6-alkylene-NRbRc, 0-Ci-C6-alkylene-NRbRc, Ci-C6-alkylene-CN, NH-Ci-C6-alkylene-NRbRc, C(=0)-NRbRc, C(=0)-Rd, S02NRbRc, or S(=0)mRe;

Rh is halogen, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, or CN;

m is 0,1 , or 2;

and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.

2. The compounds of formula I according to claim 1 , wherein A1 is CRA1, A2 is CRA2, A3 is N.

3. The compounds of formula I according to claim 1 , wherein A1 is CRA1, A2 is N, A3 is CRA3.

4. The compounds of formula I according to claim 1 , wherein A1 is CRA1, A2 is N, A3 is N. 5. The compounds of formula I according to any of the preseeding claim, wherein RB1, RB2, and RB3, independently of each other are H, halogen, or Ci-C6-alkyl.

6. The compounds of formula I according to any of claim 1 to claim 5, wherein R1 are

formulas YZT-1 to YZT-9, wherein V denotes attachment to the 10 membered hetaryl;


wherein R11, R12, RT, Rya, Ryc, Rza and Rzc are as defined in claim 1.

7. The compounds of formula I according to any of claim 1 to claim 6, wherein Ar are

formulas Ar-1 to Ar-20

8. A composition, comprising one compound of formula I according to any of claims 1 to 7, an N-oxide or an agriculturally acceptable salt thereof, and a further active sub stance.

9. A method for combating or controlling invertebrate pests, which method comprises con tacting said pest or its food supply, habitat or breeding grounds with a pesticidally ef fective amount of at least one compound according to any of claims 1 to 7 or the com- position according to claim 8.

10. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water wherein the plant is grow ing, with a pesticidally effective amount of at least one compound according to any of claims 1 to 7 or the composition according to claim 8.

1 1. Seed comprising a compound according to any of claims 1 to 7, or the enantiomers, di- astereomers or salts thereof or comprising a composition according to claim 8, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

12. A use of a compound of the formula I according to any of claims 1 to 7, and of an agri culturally acceptable salt thereof or of the compositions according to claim 8, for pro tecting growing plants from attack or infestation by invertebrate pests.

13. A method for treating or protecting an animal from infestation or infection by inverte brate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I according to any of claims 1 to 7, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.